MiMeDB: Showing metabocard for Bilirubin (MMDBc0000328)

Human

Plant

Animal

Xenobiotic

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:28:49 UTC

Update Date

2024-09-27 20:55:55 UTC

Metabolite ID

MMDBc0000328

Metabolite Identification

Common Name

Bilirubin

Description

Bilirubin is a yellow bile pigment that is a degradation product of heme. It occurs in the normal catabolic pathway that breaks down heme in vertebrates. This catabolism is a necessary process in the body's clearance of waste products that arise from the destruction of aged or abnormal red blood cells. Bilirubin has been found in all vertebrates and in certain plants including Strelitzia nicolai (PMID: 28573242 ). Bilirubin levels in humans are elevated in certain diseases such as jaundice and liver disease and it is responsible for the yellow color of bruises and the yellow discoloration in jaundice. Bilirubin breakdown products, such as stercobilin, cause the brown color of feces. A different breakdown product, urobilin, is the main component of the straw-yellow color in urine. Bilirubin consists of an open chain of four pyrroles (tetrapyrrole). It is formed by oxidative cleavage of a porphyrin in heme, which leads to biliverdin, a green tetrapyrrolic bile pigment that is also a product of heme catabolism. Biliverdin is then reduced to bilirubin via biliverdin reductase. After conjugation with glucuronic acid, bilirubin can be excreted in the urine. Bilirubin is structurally similar to the pigment phycobilin used by certain algae to capture light energy, and to the pigment phytochrome used by plants to sense light. Elevated bilirubin levels in humans are associated with Crigler-Najjar syndrome type I, which is an inborn error of metabolism. Crigler-Najjar syndrome is a rare genetic disorder characterized by an inability to properly convert and clear bilirubin from the body. Affected individuals cannot convert unconjugated bilirubin to the conjugated form because they lack a specific liver enzyme required to break down (metabolize) bilirubin. Since they cannot convert bilirubin, they develop abnormally high levels of unconjugated bilirubin in the blood (hyperbilirubinemia). Crigler-Najjar syndrome is caused by mutations in the UGT1A1 gene. The hallmark finding of Crigler-Najjar syndrome is a persistent yellowing of the skin, mucous membranes and whites of the eyes (jaundice). Elevation of both alanine aminotransferase and bilirubin levels in serum or plasma can be indicative of serious liver injury. High levels of bilirubin are indicative of jaundice, which is easily recognizable due to a yellowing of the skin and eyes. Bilirubin is also an antioxidant. Bilirubin's antioxidant activity may be particularly important in the brain, where it prevents excitotoxicity and neuronal death by scavenging superoxide during N-methyl-D-aspartic acid neurotransmission (PMID: 31353321 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652303182019232D          

 43 46  0  0  0  0            999 V2000
   -1.8645   -1.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0395   -1.3329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1195   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1207    1.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4264    0.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2469    0.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5824    1.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4062    1.4927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1195   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9042   -2.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 37  1  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  6  2  2  0  0  0  0
  3  2  1  0  0  0  0
  2 27  1  0  0  0  0
  4  6  1  0  0  0  0
  4  5  1  0  0  0  0
  6 39  1  0  0  0  0
 15  7  2  0  0  0  0
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 10  7  1  0  0  0  0
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 39 40  1  0  0  0  0
 40 42  1  0  0  0  0
 42 41  2  0  0  0  0
 42 43  1  0  0  0  0
M  END

HMDB0000054
     RDKit          3D
Bilirubin
 79 82  0  0  0  0  0  0  0  0999 V2000
   -9.3811    3.3987   -0.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3929    2.7185    0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2364    1.9224    0.1676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3549    1.8953   -0.8881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5131    2.6246   -2.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2223    1.0212   -0.5338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2542    0.7063   -1.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1414   -0.1633   -1.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8594    0.1075   -1.3868 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0346   -0.9606   -1.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6648    1.0322   -0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7496    2.2742    0.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6024    3.0600    0.3953 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0297    4.3927    0.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3325    5.3928    0.9803 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3716   -1.8146   -0.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5760   -6.0990   -1.0253 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8538   -1.8698   -0.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9866    1.1764   -1.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6234    0.5512   -0.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6390    2.6994    0.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9713    5.7768   -0.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9185    5.5520    1.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6961    6.5552    0.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9528    3.8260   -0.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5386    0.8984   -0.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9774    1.9581   -0.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4339   -0.9406    1.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3785   -2.1856    1.8469 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2606   -2.5002    0.2756 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9445   -3.5187    0.9430 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2904   -3.6440    0.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2769   -3.7796   -2.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8904   -3.8731   -1.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6610   -5.7236   -0.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3866   -3.8229    0.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7897   -3.7388   -0.4685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0854   -2.2523    1.6041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6842   -3.9369    1.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0204   -0.3022    2.0335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2066   -3.3006   -0.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5004   -2.3223    1.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2203   -1.8801   -0.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8154   -0.0528    1.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
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 22 23  1  0
 23 24  2  3
 14 25  2  0
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 27 28  1  0
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 34 35  1  0
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 36 38  1  0
 33 39  1  0
 39 40  1  0
  6 41  1  0
 41 42  1  0
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 39  8  2  0
 27 12  2  0
 22 16  1  0
  1 44  1  0
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  5 47  1  0
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  7 50  1  0
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 34 72  1  0
 35 73  1  0
 35 74  1  0
 38 75  1  0
 40 76  1  0
 40 77  1  0
 40 78  1  0
 41 79  1  0
M  END


  Mrv1652303182019232D          

 43 46  0  0  0  0            999 V2000
   -1.8645   -1.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0395   -1.3329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1195   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9041   -2.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4520   -2.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1207    1.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0139    0.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2069    0.2597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8744    1.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0459    2.2227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4264    0.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2469    0.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5824    1.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4062    1.4927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8646   -1.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0396   -1.3329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1195   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9042   -2.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4521   -2.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4521   -3.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1666   -3.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4521   -5.0775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1666   -4.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8809   -5.0775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0139    0.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4265    0.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2469    0.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8744    1.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0460    2.2227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8306    2.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2070    0.2597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1207    1.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4063    1.4927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3495   -0.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3495   -0.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4520   -3.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1665   -3.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8809   -5.0775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1665   -4.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4520   -5.0775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 37  1  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  6  2  2  0  0  0  0
  3  2  1  0  0  0  0
  2 27  1  0  0  0  0
  4  6  1  0  0  0  0
  4  5  1  0  0  0  0
  6 39  1  0  0  0  0
 15  7  2  0  0  0  0
  7  9  1  0  0  0  0
 10  7  1  0  0  0  0
  8 37  2  0  0  0  0
  9  8  1  0  0  0  0
 12  8  1  0  0  0  0
 10 12  2  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 16 27  1  0  0  0  0
 18 16  1  0  0  0  0
 21 16  2  0  0  0  0
 38 17  1  0  0  0  0
 18 17  1  0  0  0  0
 19 17  2  0  0  0  0
 19 21  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 25  1  0  0  0  0
 25 24  2  0  0  0  0
 25 26  1  0  0  0  0
 28 34  1  0  0  0  0
 29 28  1  0  0  0  0
 38 28  2  0  0  0  0
 31 29  2  0  0  0  0
 29 30  1  0  0  0  0
 31 35  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 39 40  1  0  0  0  0
 40 42  1  0  0  0  0
 42 41  2  0  0  0  0
 42 43  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000328

> <DATABASE_NAME>
MIME

> <SMILES>
CC1=C(C=C)\C(NC1=O)=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(CCC(O)=O)C(C)=C(N2)\C=C2/NC(=O)C(C=C)=C2C)N1

> <INCHI_IDENTIFIER>
InChI=1S/C33H36N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h7-8,13-14,34-35H,1-2,9-12,15H2,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b26-13-,27-14-

> <INCHI_KEY>
BPYKTIZUTYGOLE-IFADSCNNSA-N

> <FORMULA>
C33H36N4O6

> <MOLECULAR_WEIGHT>
584.6621

> <EXACT_MASS>
584.263484904

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
66.1582703894841

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(2-{[3-(2-carboxyethyl)-5-{[(2Z)-4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid

> <ALOGPS_LOGP>
3.22

> <JCHEM_LOGP>
3.119106452999999

> <ALOGPS_LOGS>
-4.78

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.630728870728111

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.027490824017337

> <JCHEM_PKA_STRONGEST_BASIC>
-2.754561928374644

> <JCHEM_POLAR_SURFACE_AREA>
164.37999999999997

> <JCHEM_REFRACTIVITY>
168.89600000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.64e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bilirubin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000054
     RDKit          3D
Bilirubin
 79 82  0  0  0  0  0  0  0  0999 V2000
   -9.3811    3.3987   -0.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3929    2.7185    0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2364    1.9224    0.1676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3549    1.8953   -0.8881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5131    2.6246   -2.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2223    1.0212   -0.5338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2542    0.7063   -1.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1414   -0.1633   -1.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8594    0.1075   -1.3868 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0346   -0.9606   -1.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3297   -0.9988   -1.5120 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5856   -0.8971   -0.8432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3193    0.2944   -0.9184 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5081    0.1525   -0.3420 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6648    1.0322   -0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7496    2.2742    0.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6024    3.0600    0.3953 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0297    4.3927    0.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3325    5.3928    0.9803 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4513    4.4268    0.3765 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3119    5.6543    0.5114 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8817    3.1801    0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2503    2.9293   -0.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8749    1.8697   -0.6675 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5564   -1.1255    0.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7080   -1.7266    0.8618 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3716   -1.8146   -0.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2324   -3.2660    0.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7795   -4.0694   -1.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6336   -5.5123   -0.8617 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5760   -6.0990   -1.0253 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7672   -6.2305   -0.4374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8538   -1.8698   -0.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4827   -3.1529    0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9678   -2.9509    1.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0083   -2.4041    2.4523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8307   -3.1799    3.0521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1378   -1.0539    2.6731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1749   -1.3932   -0.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3245   -2.2311    0.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4373    0.5387    0.7706 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6784    1.0880    1.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1755    0.8429    2.3559 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2168    3.9181   -0.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0050    3.9725   -1.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9904    2.2043    1.1750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7853    3.6976   -1.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5081    2.7100   -2.6901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1889    2.1286   -2.8867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2984    1.1357   -2.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5803    0.9918   -1.8409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4130   -2.0492   -2.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3749   -0.3520   -2.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9866    1.1764   -1.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6234    0.5512   -0.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6390    2.6994    0.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9713    5.7768   -0.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9185    5.5520    1.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6961    6.5552    0.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9528    3.8260   -0.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5386    0.8984   -0.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9774    1.9581   -0.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4339   -0.9406    1.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3785   -2.1856    1.8469 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2606   -2.5002    0.2756 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9445   -3.5187    0.9430 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2904   -3.6440    0.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2769   -3.7796   -2.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8904   -3.8731   -1.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6610   -5.7236   -0.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3866   -3.8229    0.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7897   -3.7388   -0.4685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0854   -2.2523    1.6041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6842   -3.9369    1.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0204   -0.3022    2.0335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2066   -3.3006   -0.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5004   -2.3223    1.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2203   -1.8801   -0.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8154   -0.0528    1.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  3
 14 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 10 33  2  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 36 38  1  0
 33 39  1  0
 39 40  1  0
  6 41  1  0
 41 42  1  0
 42 43  2  0
 42  3  1  0
 39  8  2  0
 27 12  2  0
 22 16  1  0
  1 44  1  0
  1 45  1  0
  2 46  1  0
  5 47  1  0
  5 48  1  0
  5 49  1  0
  7 50  1  0
  9 51  1  0
 11 52  1  0
 11 53  1  0
 13 54  1  0
 15 55  1  0
 17 56  1  0
 21 57  1  0
 21 58  1  0
 21 59  1  0
 23 60  1  0
 24 61  1  0
 24 62  1  0
 26 63  1  0
 26 64  1  0
 26 65  1  0
 28 66  1  0
 28 67  1  0
 29 68  1  0
 29 69  1  0
 32 70  1  0
 34 71  1  0
 34 72  1  0
 35 73  1  0
 35 74  1  0
 38 75  1  0
 40 76  1  0
 40 77  1  0
 40 78  1  0
 41 79  1  0
M  END

HEADER    PROTEIN                                 18-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-MAR-20         0                                  
HETATM    1  C   UNK     0      -3.480  -2.488   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.465  -3.953   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -1.940  -2.488   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -3.956  -3.953   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.421  -4.429   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.710  -4.858   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.092   2.016   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.759   0.165   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -2.253   0.485   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -3.499   2.642   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.819   4.149   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.529   1.498   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.061   1.659   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.687   3.066   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.758   2.786   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.465  -3.953   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.481  -2.488   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       1.941  -2.488   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       3.956  -3.953   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.421  -4.429   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.711  -4.858   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.711  -6.398   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.044  -7.168   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.711  -9.478   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.044  -8.708   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.378  -9.478   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.000  -4.429   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.759   0.165   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.529   1.498   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.061   1.659   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.499   2.642   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.819   4.149   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.284   4.625   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0       2.253   0.485   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0       2.092   2.016   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       0.758   2.786   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -4.386  -1.242   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.386  -1.242   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -2.710  -6.398   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -4.044  -7.168   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -5.378  -9.478   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -4.044  -8.708   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -2.710  -9.478   0.000  0.00  0.00           O+0
CONECT    1   37    3    4                                                  
CONECT    2    6    3   27                                                  
CONECT    3    1    2                                                       
CONECT    4    1    6    5                                                  
CONECT    5    4                                                            
CONECT    6    2    4   39                                                  
CONECT    7   15    9   10                                                  
CONECT    8   37    9   12                                                  
CONECT    9    7    8                                                       
CONECT   10    7   12   11                                                  
CONECT   11   10                                                            
CONECT   12    8   10   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15    7                                                            
CONECT   16   27   18   21                                                  
CONECT   17   38   18   19                                                  
CONECT   18   16   17                                                       
CONECT   19   17   21   20                                                  
CONECT   20   19                                                            
CONECT   21   16   19   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   25                                                       
CONECT   24   25                                                            
CONECT   25   23   24   26                                                  
CONECT   26   25                                                            
CONECT   27    2   16                                                       
CONECT   28   34   29   38                                                  
CONECT   29   28   31   30                                                  
CONECT   30   29                                                            
CONECT   31   29   35   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
CONECT   34   28   35                                                       
CONECT   35   31   34   36                                                  
CONECT   36   35                                                            
CONECT   37    1    8                                                       
CONECT   38   17   28                                                       
CONECT   39    6   40                                                       
CONECT   40   39   42                                                       
CONECT   41   42                                                            
CONECT   42   40   41   43                                                  
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   92    0
END

COMPND    HMDB0000054
HETATM    1  C1  UNL     1      -9.381   3.399  -0.124  1.00  0.00           C  
HETATM    2  C2  UNL     1      -8.393   2.718   0.011  1.00  0.00           C  
HETATM    3  C3  UNL     1      -7.236   1.922   0.168  1.00  0.00           C  
HETATM    4  C4  UNL     1      -6.355   1.895  -0.888  1.00  0.00           C  
HETATM    5  C5  UNL     1      -6.513   2.625  -2.170  1.00  0.00           C  
HETATM    6  C6  UNL     1      -5.222   1.021  -0.534  1.00  0.00           C  
HETATM    7  C7  UNL     1      -4.254   0.706  -1.350  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.141  -0.163  -1.018  1.00  0.00           C  
HETATM    9  N1  UNL     1      -1.859   0.108  -1.387  1.00  0.00           N  
HETATM   10  C9  UNL     1      -1.035  -0.961  -1.050  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.330  -0.999  -1.512  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.586  -0.897  -0.843  1.00  0.00           C  
HETATM   13  N2  UNL     1       2.319   0.294  -0.918  1.00  0.00           N  
HETATM   14  C12 UNL     1       3.508   0.153  -0.342  1.00  0.00           C  
HETATM   15  C13 UNL     1       4.665   1.032  -0.299  1.00  0.00           C  
HETATM   16  C14 UNL     1       4.750   2.274   0.005  1.00  0.00           C  
HETATM   17  N3  UNL     1       3.602   3.060   0.395  1.00  0.00           N  
HETATM   18  C15 UNL     1       4.030   4.393   0.625  1.00  0.00           C  
HETATM   19  O1  UNL     1       3.333   5.393   0.980  1.00  0.00           O  
HETATM   20  C16 UNL     1       5.451   4.427   0.377  1.00  0.00           C  
HETATM   21  C17 UNL     1       6.312   5.654   0.511  1.00  0.00           C  
HETATM   22  C18 UNL     1       5.882   3.180   0.011  1.00  0.00           C  
HETATM   23  C19 UNL     1       7.250   2.929  -0.321  1.00  0.00           C  
HETATM   24  C20 UNL     1       7.875   1.870  -0.668  1.00  0.00           C  
HETATM   25  C21 UNL     1       3.556  -1.126   0.124  1.00  0.00           C  
HETATM   26  C22 UNL     1       4.708  -1.727   0.862  1.00  0.00           C  
HETATM   27  C23 UNL     1       2.372  -1.815  -0.175  1.00  0.00           C  
HETATM   28  C24 UNL     1       2.232  -3.266   0.084  1.00  0.00           C  
HETATM   29  C25 UNL     1       2.780  -4.069  -1.095  1.00  0.00           C  
HETATM   30  C26 UNL     1       2.634  -5.512  -0.862  1.00  0.00           C  
HETATM   31  O2  UNL     1       1.576  -6.099  -1.025  1.00  0.00           O  
HETATM   32  O3  UNL     1       3.767  -6.230  -0.437  1.00  0.00           O  
HETATM   33  C27 UNL     1      -1.854  -1.870  -0.455  1.00  0.00           C  
HETATM   34  C28 UNL     1      -1.483  -3.153   0.153  1.00  0.00           C  
HETATM   35  C29 UNL     1      -0.968  -2.951   1.554  1.00  0.00           C  
HETATM   36  C30 UNL     1      -2.008  -2.404   2.452  1.00  0.00           C  
HETATM   37  O4  UNL     1      -2.831  -3.180   3.052  1.00  0.00           O  
HETATM   38  O5  UNL     1      -2.138  -1.054   2.673  1.00  0.00           O  
HETATM   39  C31 UNL     1      -3.175  -1.393  -0.433  1.00  0.00           C  
HETATM   40  C32 UNL     1      -4.325  -2.231   0.002  1.00  0.00           C  
HETATM   41  N4  UNL     1      -5.437   0.539   0.771  1.00  0.00           N  
HETATM   42  C33 UNL     1      -6.678   1.088   1.202  1.00  0.00           C  
HETATM   43  O6  UNL     1      -7.175   0.843   2.356  1.00  0.00           O  
HETATM   44  H1  UNL     1     -10.217   3.918  -0.149  1.00  0.00           H  
HETATM   45  H2  UNL     1      -9.005   3.972  -1.301  1.00  0.00           H  
HETATM   46  H3  UNL     1      -8.990   2.204   1.175  1.00  0.00           H  
HETATM   47  H4  UNL     1      -6.785   3.698  -1.968  1.00  0.00           H  
HETATM   48  H5  UNL     1      -5.508   2.710  -2.690  1.00  0.00           H  
HETATM   49  H6  UNL     1      -7.189   2.129  -2.887  1.00  0.00           H  
HETATM   50  H7  UNL     1      -4.298   1.136  -2.383  1.00  0.00           H  
HETATM   51  H8  UNL     1      -1.580   0.992  -1.841  1.00  0.00           H  
HETATM   52  H9  UNL     1       0.413  -2.049  -2.135  1.00  0.00           H  
HETATM   53  H10 UNL     1       0.375  -0.352  -2.510  1.00  0.00           H  
HETATM   54  H11 UNL     1       1.987   1.176  -1.350  1.00  0.00           H  
HETATM   55  H12 UNL     1       5.623   0.551  -0.586  1.00  0.00           H  
HETATM   56  H13 UNL     1       2.639   2.699   0.495  1.00  0.00           H  
HETATM   57  H14 UNL     1       6.971   5.777  -0.364  1.00  0.00           H  
HETATM   58  H15 UNL     1       6.918   5.552   1.445  1.00  0.00           H  
HETATM   59  H16 UNL     1       5.696   6.555   0.631  1.00  0.00           H  
HETATM   60  H17 UNL     1       7.953   3.826  -0.283  1.00  0.00           H  
HETATM   61  H18 UNL     1       7.539   0.898  -0.801  1.00  0.00           H  
HETATM   62  H19 UNL     1       8.977   1.958  -0.888  1.00  0.00           H  
HETATM   63  H20 UNL     1       5.434  -0.941   1.116  1.00  0.00           H  
HETATM   64  H21 UNL     1       4.378  -2.186   1.847  1.00  0.00           H  
HETATM   65  H22 UNL     1       5.261  -2.500   0.276  1.00  0.00           H  
HETATM   66  H23 UNL     1       2.944  -3.519   0.943  1.00  0.00           H  
HETATM   67  H24 UNL     1       1.290  -3.644   0.386  1.00  0.00           H  
HETATM   68  H25 UNL     1       2.277  -3.780  -2.008  1.00  0.00           H  
HETATM   69  H26 UNL     1       3.890  -3.873  -1.152  1.00  0.00           H  
HETATM   70  H27 UNL     1       4.661  -5.724  -0.302  1.00  0.00           H  
HETATM   71  H28 UNL     1      -2.387  -3.823   0.279  1.00  0.00           H  
HETATM   72  H29 UNL     1      -0.790  -3.739  -0.468  1.00  0.00           H  
HETATM   73  H30 UNL     1      -0.085  -2.252   1.604  1.00  0.00           H  
HETATM   74  H31 UNL     1      -0.684  -3.937   1.968  1.00  0.00           H  
HETATM   75  H32 UNL     1      -2.020  -0.302   2.034  1.00  0.00           H  
HETATM   76  H33 UNL     1      -4.207  -3.301  -0.396  1.00  0.00           H  
HETATM   77  H34 UNL     1      -4.500  -2.322   1.060  1.00  0.00           H  
HETATM   78  H35 UNL     1      -5.220  -1.880  -0.589  1.00  0.00           H  
HETATM   79  H36 UNL     1      -4.815  -0.053   1.351  1.00  0.00           H  
CONECT    1    2    2   44   45
CONECT    2    3   46
CONECT    3    4    4   42
CONECT    4    5    6
CONECT    5   47   48   49
CONECT    6    7    7   41
CONECT    7    8   50
CONECT    8    9   39   39
CONECT    9   10   51
CONECT   10   11   33   33
CONECT   11   12   52   53
CONECT   12   13   27   27
CONECT   13   14   54
CONECT   14   15   25   25
CONECT   15   16   16   55
CONECT   16   17   22
CONECT   17   18   56
CONECT   18   19   19   20
CONECT   20   21   22   22
CONECT   21   57   58   59
CONECT   22   23
CONECT   23   24   24   60
CONECT   24   61   62
CONECT   25   26   27
CONECT   26   63   64   65
CONECT   27   28
CONECT   28   29   66   67
CONECT   29   30   68   69
CONECT   30   31   31   32
CONECT   32   70
CONECT   33   34   39
CONECT   34   35   71   72
CONECT   35   36   73   74
CONECT   36   37   37   38
CONECT   38   75
CONECT   39   40
CONECT   40   76   77   78
CONECT   41   42   79
CONECT   42   43   43
END

HMDB0000054
     RDKit          3D
Bilirubin
 79 82  0  0  0  0  0  0  0  0999 V2000
   -9.3811    3.3987   -0.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3929    2.7185    0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2364    1.9224    0.1676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3549    1.8953   -0.8881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5131    2.6246   -2.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2223    1.0212   -0.5338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2542    0.7063   -1.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1414   -0.1633   -1.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8594    0.1075   -1.3868 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0346   -0.9606   -1.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3297   -0.9988   -1.5120 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5856   -0.8971   -0.8432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3193    0.2944   -0.9184 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5081    0.1525   -0.3420 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6648    1.0322   -0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7496    2.2742    0.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6024    3.0600    0.3953 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0297    4.3927    0.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3325    5.3928    0.9803 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4513    4.4268    0.3765 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3119    5.6543    0.5114 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8817    3.1801    0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2503    2.9293   -0.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8749    1.8697   -0.6675 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5564   -1.1255    0.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7080   -1.7266    0.8618 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3716   -1.8146   -0.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2324   -3.2660    0.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7795   -4.0694   -1.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6336   -5.5123   -0.8617 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5760   -6.0990   -1.0253 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7672   -6.2305   -0.4374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8538   -1.8698   -0.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4827   -3.1529    0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9678   -2.9509    1.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0083   -2.4041    2.4523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8307   -3.1799    3.0521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1378   -1.0539    2.6731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1749   -1.3932   -0.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3245   -2.2311    0.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4373    0.5387    0.7706 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6784    1.0880    1.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1755    0.8429    2.3559 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2168    3.9181   -0.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0050    3.9725   -1.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9904    2.2043    1.1750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7853    3.6976   -1.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5081    2.7100   -2.6901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1889    2.1286   -2.8867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2984    1.1357   -2.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5803    0.9918   -1.8409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4130   -2.0492   -2.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3749   -0.3520   -2.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9866    1.1764   -1.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6234    0.5512   -0.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6390    2.6994    0.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9713    5.7768   -0.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9185    5.5520    1.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6961    6.5552    0.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9528    3.8260   -0.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5386    0.8984   -0.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9774    1.9581   -0.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4339   -0.9406    1.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3785   -2.1856    1.8469 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2606   -2.5002    0.2756 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9445   -3.5187    0.9430 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2904   -3.6440    0.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2769   -3.7796   -2.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8904   -3.8731   -1.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6610   -5.7236   -0.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3866   -3.8229    0.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7897   -3.7388   -0.4685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0854   -2.2523    1.6041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6842   -3.9369    1.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0204   -0.3022    2.0335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2066   -3.3006   -0.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5004   -2.3223    1.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2203   -1.8801   -0.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8154   -0.0528    1.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  3
 14 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 10 33  2  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 36 38  1  0
 33 39  1  0
 39 40  1  0
  6 41  1  0
 41 42  1  0
 42 43  2  0
 42  3  1  0
 39  8  2  0
 27 12  2  0
 22 16  1  0
  1 44  1  0
  1 45  1  0
  2 46  1  0
  5 47  1  0
  5 48  1  0
  5 49  1  0
  7 50  1  0
  9 51  1  0
 11 52  1  0
 11 53  1  0
 13 54  1  0
 15 55  1  0
 17 56  1  0
 21 57  1  0
 21 58  1  0
 21 59  1  0
 23 60  1  0
 24 61  1  0
 24 62  1  0
 26 63  1  0
 26 64  1  0
 26 65  1  0
 28 66  1  0
 28 67  1  0
 29 68  1  0
 29 69  1  0
 32 70  1  0
 34 71  1  0
 34 72  1  0
 35 73  1  0
 35 74  1  0
 38 75  1  0
 40 76  1  0
 40 77  1  0
 40 78  1  0
 41 79  1  0
M  END

Synonyms

Value	Source
1,10,19,22,23,24-Hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinylbiline-8,12-dipropionic acid	ChEBI
2,17-Diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acid	ChEBI
2,7,13,17-Tetramethyl-1,19-dioxo-3,18-divinyl-1,10,19,22,23,24-hexahydro-21H-biline-8,12-dipropanoic acid	ChEBI
8,12-Bis(2-carboxyethyl)-2,7,13,17-tetramethyl-3,18-divinylbiladiene-ac-1,19(21H,24H)-dione	ChEBI
Bilirubin(Z,Z)	ChEBI
Bilirubin-ixalpha	ChEBI
1,10,19,22,23,24-Hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinylbiline-8,12-dipropionate	Generator
2,17-Diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoate	Generator
2,7,13,17-Tetramethyl-1,19-dioxo-3,18-divinyl-1,10,19,22,23,24-hexahydro-21H-biline-8,12-dipropanoate	Generator
Bilirubin ixalpha	HMDB
(4Z,15Z)-Bilirubin ixa	HMDB
(Z,Z)-Bilirubin ixa	HMDB
1,10,19,22,23,24-Hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-biline-8,12-dipropionate	HMDB
1,10,19,22,23,24-Hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-biline-8,12-dipropionic acid	HMDB
3-(2-((3-(2-Carboxyethyl)-4-methyl-5-((3-methyl-5-oxo-4-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl)-1H-pyrrol-2-yl)methyl)-4-methyl-5-((4-methyl-5-oxo-3-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl)-1H-pyrrol-3-yl)propanoate	HMDB
3-(2-((3-(2-Carboxyethyl)-4-methyl-5-((3-methyl-5-oxo-4-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl)-1H-pyrrol-2-yl)methyl)-4-methyl-5-((4-methyl-5-oxo-3-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl)-1H-pyrrol-3-yl)propanoic acid	HMDB
3-(2-((3-(2-Carboxyethyl)-4-methyl-5-[(Z)-(3-methyl-5-oxo-4-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl]-1H-pyrrol-2-yl)methyl)-4-methyl-5-[(Z)-(4-methyl-5-oxo-3-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene	HMDB
3-[2-[[3-(2-Carboxyethyl)-5-[(3-ethenyl-4-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(4-ethenyl-3-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoate	HMDB
3-[2-[[3-(2-Carboxyethyl)-5-[(3-ethenyl-4-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(4-ethenyl-3-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid	HMDB
3-[2-[[3-(2-Carboxyethyl)-5-[(Z)-(3-ethenyl-4-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(Z)-(4-ethenyl-3-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoate	HMDB
3-[2-[[3-(2-Carboxyethyl)-5-[(Z)-(3-ethenyl-4-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(Z)-(4-ethenyl-3-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid	HMDB
Bilirubin IX-alpha	HMDB
Cholerythrin	HMDB
Hematoidin	HMDB
Bilirubin IX alpha	HMDB

Molecular Formula

C₃₃H₃₆N₄O₆

Average Mass

584.6621

Monoisotopic Mass

584.263484904

IUPAC Name

3-(2-{[3-(2-carboxyethyl)-5-{[(2Z)-4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid

Traditional Name

bilirubin

CAS Registry Number

Not Available

SMILES

CC1=C(C=C)\C(NC1=O)=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(CCC(O)=O)C(C)=C(N2)\C=C2/NC(=O)C(C=C)=C2C)N1

InChI Identifier

InChI=1S/C33H36N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h7-8,13-14,34-35H,1-2,9-12,15H2,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b26-13-,27-14-

InChI Key

BPYKTIZUTYGOLE-IFADSCNNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bilirubins. These are organic compounds containing a dicarboxylic acyclic tetrapyrrole derivative.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrapyrroles and derivatives

Sub Class

Bilirubins

Direct Parent

Bilirubins

Alternative Parents

Substituents

Bilirubin skeleton
Dicarboxylic acid or derivatives
Substituted pyrrole
Pyrrole
Pyrroline
Heteroaromatic compound
Secondary carboxylic acid amide
Lactam
Carboxamide group
Azacycle
Carboxylic acid
Carboxylic acid derivative
Organopnictogen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

dicarboxylic acid (CHEBI:16990 )
biladienes (CHEBI:16990 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0096 g/L	ALOGPS
logP	3.22	ALOGPS
logP	3.12	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	4.03	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	164.38 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	168.9 m³·mol⁻¹	ChemAxon
Polarizability	66.16 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00vr-0100090000-d19585e898437e8be1d5	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-01vn-3100069000-c39a7113e7f8eb3fa22a	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("Bilirubin,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-000i-0090000000-50ff729317f07f6120b5	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0002-0090000000-83d0d13757dcbce35604	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0002-0090000000-491b2676042d62727784	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-01p9-1090000000-1d547122826037e04cfb	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-000i-1090000000-30f7fa38dcf8706b38c6	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-001i-1030090000-dea3b39afc072d2855c5	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000i-1090010000-369d79a300efec3a6c78	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0091050000-78e3736d034dec9b8fa9	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0002-0091000000-cc507e875cc295800fa0	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0090000000-679d7d93f8aeb5b1c0d1	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0090020000-ea54f49e76225d251990	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0002-0091000000-24657f467af3adfa1e8c	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-000i-0020090000-5bcce058438671178ee4	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0092030000-24054054aef5b235a850	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-000i-0030090000-b525a9b7bb66406e6afc	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00ks-0000090000-ddf9acb7f968b9079764	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00g0-0110290000-ae6f323e9f5e9e26199c	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uml-1102910000-df5146b3612e4fb4ce5e	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000090000-6deb1aed1a9c3839e2a9	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-053i-1010190000-7435a4388bade8e83d10	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9010240000-cc90fff0581c6bcefd0d	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kr-0010090000-d21be2c11a0dfd17c6e9	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-0030190000-749f82b203e182b3e46f	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0kac-0291230000-962a583eff6dd8d5cf73	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0010090000-467141ca1354a02b0aef	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C, experimental)		2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, DMSO, experimental)		2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, DMSO, experimental)		2016-10-22	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)		2012-12-04	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (void)	2025-10-23	157.0
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (void)	2025-10-23	41.6
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	725.3
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	816.2
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	665.3
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	223.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (retained)	2025-10-23	3318.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	94.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	393.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	598.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	179.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	168.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	226.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (void)	2025-10-23	8.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	185.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (retained)	2025-10-23	173.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	490.7
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	2094.4
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	1535.9

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Bilirubin_TMS_1	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)[NH]3)[NH]2)NC1=O	standard non polar	2025-10-23	2437.03
Gas Chromatography	Bilirubin_TMS_2	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)[NH]3)[NH]2)NC1=O	standard non polar	2025-10-23	1473.47
Gas Chromatography	Bilirubin_TMS_3	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)[NH]2)NC1=O	standard non polar	2025-10-23	1095.98
Gas Chromatography	Bilirubin_TMS_4	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)[NH]3)N2[Si](C)(C)C)NC1=O	standard non polar	2025-10-23	986.004
Gas Chromatography	Bilirubin_TMS_5	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)[NH]3)[NH]2)N([Si](C)(C)C)C1=O	standard non polar	2025-10-23	1684.08
Gas Chromatography	Bilirubin_TMS_6	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)N3[Si](C)(C)C)[NH]2)NC1=O	standard non polar	2025-10-23	2011.41
Gas Chromatography	Bilirubin_TMS_7	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)[NH]3)[NH]2)NC1=O	standard non polar	2025-10-23	2209.81
Gas Chromatography	Bilirubin_TMS_8	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)[NH]3)N2[Si](C)(C)C)NC1=O	standard non polar	2025-10-23	1676.6
Gas Chromatography	Bilirubin_TMS_9	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)N3[Si](C)(C)C)[NH]2)NC1=O	standard non polar	2025-10-23	3259.77
Gas Chromatography	Bilirubin_TMS_10	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)[NH]2)NC1=O	standard non polar	2025-10-23	1683.01
Gas Chromatography	Bilirubin_TMS_11	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)[NH]3)[NH]2)N([Si](C)(C)C)C1=O	standard non polar	2025-10-23	1812.64
Gas Chromatography	Bilirubin_TMS_12	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)[NH]3)N2[Si](C)(C)C)NC1=O	standard non polar	2025-10-23	1560.93
Gas Chromatography	Bilirubin_TMS_13	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)N3[Si](C)(C)C)[NH]2)NC1=O	standard non polar	2025-10-23	2025.8
Gas Chromatography	Bilirubin_TMS_14	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)[NH]2)NC1=O	standard non polar	2025-10-23	2818.87
Gas Chromatography	Bilirubin_TMS_15	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)[NH]3)[NH]2)N([Si](C)(C)C)C1=O	standard non polar	2025-10-23	1777.14
Gas Chromatography	Bilirubin_TMS_16	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)N2[Si](C)(C)C)NC1=O	standard non polar	2025-10-23	2661.25
Gas Chromatography	Bilirubin_TMS_17	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)[NH]2)NC1=O	standard non polar	2025-10-23	1044.94
Gas Chromatography	Bilirubin_TMS_18	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)[NH]2)N([Si](C)(C)C)C1=O	standard non polar	2025-10-23	2069.41
Gas Chromatography	Bilirubin_TMS_19	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)N3[Si](C)(C)C)N2[Si](C)(C)C)NC1=O	standard non polar	2025-10-23	764.103
Gas Chromatography	Bilirubin_TMS_20	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)[NH]3)N2[Si](C)(C)C)N([Si](C)(C)C)C1=O	standard non polar	2025-10-23	1645.46
Gas Chromatography	Bilirubin_TMS_21	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)N3[Si](C)(C)C)[NH]2)N([Si](C)(C)C)C1=O	standard non polar	2025-10-23	993.603
Gas Chromatography	Bilirubin_TMS_22	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)[NH]3)N2[Si](C)(C)C)NC1=O	standard non polar	2025-10-23	3179.65
Gas Chromatography	Bilirubin_TMS_23	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)N3[Si](C)(C)C)[NH]2)NC1=O	standard non polar	2025-10-23	1487.15
Gas Chromatography	Bilirubin_TMS_24	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)[NH]2)NC1=O	standard non polar	2025-10-23	1936.0
Gas Chromatography	Bilirubin_TMS_25	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)[NH]3)[NH]2)N([Si](C)(C)C)C1=O	standard non polar	2025-10-23	1483.14
Gas Chromatography	Bilirubin_TMS_26	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)N3[Si](C)(C)C)N2[Si](C)(C)C)NC1=O	standard non polar	2025-10-23	3334.99
Gas Chromatography	Bilirubin_TMS_27	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)N2[Si](C)(C)C)NC1=O	standard non polar	2025-10-23	2427.79
Gas Chromatography	Bilirubin_TMS_28	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)[NH]3)N2[Si](C)(C)C)N([Si](C)(C)C)C1=O	standard non polar	2025-10-23	2366.84
Gas Chromatography	Bilirubin_TMS_29	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)[NH]2)NC1=O	standard non polar	2025-10-23	494.692
Gas Chromatography	Bilirubin_TMS_30	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)N3[Si](C)(C)C)[NH]2)N([Si](C)(C)C)C1=O	standard non polar	2025-10-23	925.872
Gas Chromatography	Bilirubin_TMS_31	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)[NH]2)N([Si](C)(C)C)C1=O	standard non polar	2025-10-23	2822.09
Gas Chromatography	Bilirubin_TMS_32	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)N3[Si](C)(C)C)N2[Si](C)(C)C)NC1=O	standard non polar	2025-10-23	483.183
Gas Chromatography	Bilirubin_TMS_33	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)N2[Si](C)(C)C)NC1=O	standard non polar	2025-10-23	2740.98
Gas Chromatography	Bilirubin_TMS_34	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)[NH]3)N2[Si](C)(C)C)N([Si](C)(C)C)C1=O	standard non polar	2025-10-23	2511.26
Gas Chromatography	Bilirubin_TMS_35	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)[NH]2)NC1=O	standard non polar	2025-10-23	987.126
Gas Chromatography	Bilirubin_TMS_36	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)N3[Si](C)(C)C)[NH]2)N([Si](C)(C)C)C1=O	standard non polar	2025-10-23	1809.06
Gas Chromatography	Bilirubin_TMS_37	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)[NH]2)N([Si](C)(C)C)C1=O	standard non polar	2025-10-23	1176.2
Gas Chromatography	Bilirubin_TMS_38	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)N2[Si](C)(C)C)NC1=O	standard non polar	2025-10-23	2682.73
Gas Chromatography	Bilirubin_TMS_39	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)N2[Si](C)(C)C)N([Si](C)(C)C)C1=O	standard non polar	2025-10-23	1900.25
Gas Chromatography	Bilirubin_TMS_40	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)[NH]2)N([Si](C)(C)C)C1=O	standard non polar	2025-10-23	1338.0
Gas Chromatography	Bilirubin_TMS_41	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)N3[Si](C)(C)C)N2[Si](C)(C)C)N([Si](C)(C)C)C1=O	standard non polar	2025-10-23	3931.62
Gas Chromatography	Bilirubin_TMS_42	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)N3[Si](C)(C)C)N2[Si](C)(C)C)NC1=O	standard non polar	2025-10-23	2576.17
Gas Chromatography	Bilirubin_TMS_43	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)N2[Si](C)(C)C)NC1=O	standard non polar	2025-10-23	1603.95
Gas Chromatography	Bilirubin_TMS_44	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)[NH]3)N2[Si](C)(C)C)N([Si](C)(C)C)C1=O	standard non polar	2025-10-23	1599.05
Gas Chromatography	Bilirubin_TMS_45	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)[NH]2)NC1=O	standard non polar	2025-10-23	1292.84
Gas Chromatography	Bilirubin_TMS_46	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)N3[Si](C)(C)C)[NH]2)N([Si](C)(C)C)C1=O	standard non polar	2025-10-23	483.617
Gas Chromatography	Bilirubin_TMS_47	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)[NH]2)N([Si](C)(C)C)C1=O	standard non polar	2025-10-23	2212.21
Gas Chromatography	Bilirubin_TMS_48	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)N2[Si](C)(C)C)NC1=O	standard non polar	2025-10-23	1912.97
Gas Chromatography	Bilirubin_TMS_49	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)N3[Si](C)(C)C)N2[Si](C)(C)C)N([Si](C)(C)C)C1=O	standard non polar	2025-10-23	303.563
Gas Chromatography	Bilirubin_TMS_50	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)N2[Si](C)(C)C)N([Si](C)(C)C)C1=O	standard non polar	2025-10-23	457.422
Gas Chromatography	Bilirubin_TMS_51	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)[NH]2)N([Si](C)(C)C)C1=O	standard non polar	2025-10-23	2761.51
Gas Chromatography	Bilirubin_TMS_52	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)N2[Si](C)(C)C)NC1=O	standard non polar	2025-10-23	2978.74
Gas Chromatography	Bilirubin_TMS_53	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)N3[Si](C)(C)C)N2[Si](C)(C)C)N([Si](C)(C)C)C1=O	standard non polar	2025-10-23	1695.21
Gas Chromatography	Bilirubin_TMS_54	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)N2[Si](C)(C)C)N([Si](C)(C)C)C1=O	standard non polar	2025-10-23	1360.8
Gas Chromatography	Bilirubin_TMS_55	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)[NH]2)N([Si](C)(C)C)C1=O	standard non polar	2025-10-23	1634.5
Gas Chromatography	Bilirubin_TMS_56	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)N2[Si](C)(C)C)N([Si](C)(C)C)C1=O	standard non polar	2025-10-23	1606.6
Gas Chromatography	Bilirubin_TMS_1	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)[NH]3)[NH]2)NC1=O	standard polar	2025-10-23	1618.06
Gas Chromatography	Bilirubin_TMS_2	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)[NH]3)[NH]2)NC1=O	standard polar	2025-10-23	354.294
Gas Chromatography	Bilirubin_TMS_3	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)[NH]2)NC1=O	standard polar	2025-10-23	2290.8
Gas Chromatography	Bilirubin_TMS_4	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)[NH]3)N2[Si](C)(C)C)NC1=O	standard polar	2025-10-23	2375.43
Gas Chromatography	Bilirubin_TMS_5	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)[NH]3)[NH]2)N([Si](C)(C)C)C1=O	standard polar	2025-10-23	3399.26
Gas Chromatography	Bilirubin_TMS_6	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)N3[Si](C)(C)C)[NH]2)NC1=O	standard polar	2025-10-23	602.018
Gas Chromatography	Bilirubin_TMS_7	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)[NH]3)[NH]2)NC1=O	standard polar	2025-10-23	1724.4
Gas Chromatography	Bilirubin_TMS_8	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)[NH]3)N2[Si](C)(C)C)NC1=O	standard polar	2025-10-23	2506.12
Gas Chromatography	Bilirubin_TMS_9	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)N3[Si](C)(C)C)[NH]2)NC1=O	standard polar	2025-10-23	1656.87
Gas Chromatography	Bilirubin_TMS_10	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)[NH]2)NC1=O	standard polar	2025-10-23	1247.46
Gas Chromatography	Bilirubin_TMS_11	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)[NH]3)[NH]2)N([Si](C)(C)C)C1=O	standard polar	2025-10-23	326.762
Gas Chromatography	Bilirubin_TMS_12	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)[NH]3)N2[Si](C)(C)C)NC1=O	standard polar	2025-10-23	2681.34
Gas Chromatography	Bilirubin_TMS_13	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)N3[Si](C)(C)C)[NH]2)NC1=O	standard polar	2025-10-23	2483.84
Gas Chromatography	Bilirubin_TMS_14	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)[NH]2)NC1=O	standard polar	2025-10-23	1098.25
Gas Chromatography	Bilirubin_TMS_15	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)[NH]3)[NH]2)N([Si](C)(C)C)C1=O	standard polar	2025-10-23	437.851
Gas Chromatography	Bilirubin_TMS_16	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)N2[Si](C)(C)C)NC1=O	standard polar	2025-10-23	1920.8
Gas Chromatography	Bilirubin_TMS_17	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)[NH]2)NC1=O	standard polar	2025-10-23	1657.63
Gas Chromatography	Bilirubin_TMS_18	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)[NH]2)N([Si](C)(C)C)C1=O	standard polar	2025-10-23	2479.63
Gas Chromatography	Bilirubin_TMS_19	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)N3[Si](C)(C)C)N2[Si](C)(C)C)NC1=O	standard polar	2025-10-23	3238.43
Gas Chromatography	Bilirubin_TMS_20	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)[NH]3)N2[Si](C)(C)C)N([Si](C)(C)C)C1=O	standard polar	2025-10-23	1390.93
Gas Chromatography	Bilirubin_TMS_21	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)N3[Si](C)(C)C)[NH]2)N([Si](C)(C)C)C1=O	standard polar	2025-10-23	3687.43
Gas Chromatography	Bilirubin_TMS_22	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)[NH]3)N2[Si](C)(C)C)NC1=O	standard polar	2025-10-23	1419.62
Gas Chromatography	Bilirubin_TMS_23	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)N3[Si](C)(C)C)[NH]2)NC1=O	standard polar	2025-10-23	1138.12
Gas Chromatography	Bilirubin_TMS_24	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)[NH]2)NC1=O	standard polar	2025-10-23	2318.58
Gas Chromatography	Bilirubin_TMS_25	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)[NH]3)[NH]2)N([Si](C)(C)C)C1=O	standard polar	2025-10-23	2038.98
Gas Chromatography	Bilirubin_TMS_26	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)N3[Si](C)(C)C)N2[Si](C)(C)C)NC1=O	standard polar	2025-10-23	3983.66
Gas Chromatography	Bilirubin_TMS_27	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)N2[Si](C)(C)C)NC1=O	standard polar	2025-10-23	2495.61
Gas Chromatography	Bilirubin_TMS_28	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)[NH]3)N2[Si](C)(C)C)N([Si](C)(C)C)C1=O	standard polar	2025-10-23	1589.26
Gas Chromatography	Bilirubin_TMS_29	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)[NH]2)NC1=O	standard polar	2025-10-23	2480.04
Gas Chromatography	Bilirubin_TMS_30	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)N3[Si](C)(C)C)[NH]2)N([Si](C)(C)C)C1=O	standard polar	2025-10-23	1826.17
Gas Chromatography	Bilirubin_TMS_31	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)[NH]2)N([Si](C)(C)C)C1=O	standard polar	2025-10-23	1907.29
Gas Chromatography	Bilirubin_TMS_32	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)N3[Si](C)(C)C)N2[Si](C)(C)C)NC1=O	standard polar	2025-10-23	642.217
Gas Chromatography	Bilirubin_TMS_33	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)N2[Si](C)(C)C)NC1=O	standard polar	2025-10-23	1893.45
Gas Chromatography	Bilirubin_TMS_34	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)[NH]3)N2[Si](C)(C)C)N([Si](C)(C)C)C1=O	standard polar	2025-10-23	2581.89
Gas Chromatography	Bilirubin_TMS_35	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)[NH]2)NC1=O	standard polar	2025-10-23	92.3146
Gas Chromatography	Bilirubin_TMS_36	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)N3[Si](C)(C)C)[NH]2)N([Si](C)(C)C)C1=O	standard polar	2025-10-23	2149.68
Gas Chromatography	Bilirubin_TMS_37	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)[NH]2)N([Si](C)(C)C)C1=O	standard polar	2025-10-23	3504.98
Gas Chromatography	Bilirubin_TMS_38	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)N2[Si](C)(C)C)NC1=O	standard polar	2025-10-23	2961.8
Gas Chromatography	Bilirubin_TMS_39	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)N2[Si](C)(C)C)N([Si](C)(C)C)C1=O	standard polar	2025-10-23	2625.45
Gas Chromatography	Bilirubin_TMS_40	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)[NH]2)N([Si](C)(C)C)C1=O	standard polar	2025-10-23	2167.98
Gas Chromatography	Bilirubin_TMS_41	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)N3[Si](C)(C)C)N2[Si](C)(C)C)N([Si](C)(C)C)C1=O	standard polar	2025-10-23	2232.27
Gas Chromatography	Bilirubin_TMS_42	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)N3[Si](C)(C)C)N2[Si](C)(C)C)NC1=O	standard polar	2025-10-23	1021.31
Gas Chromatography	Bilirubin_TMS_43	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)N2[Si](C)(C)C)NC1=O	standard polar	2025-10-23	3123.13
Gas Chromatography	Bilirubin_TMS_44	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)[NH]3)N2[Si](C)(C)C)N([Si](C)(C)C)C1=O	standard polar	2025-10-23	771.609
Gas Chromatography	Bilirubin_TMS_45	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)[NH]2)NC1=O	standard polar	2025-10-23	2243.45
Gas Chromatography	Bilirubin_TMS_46	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)N3[Si](C)(C)C)[NH]2)N([Si](C)(C)C)C1=O	standard polar	2025-10-23	2343.16
Gas Chromatography	Bilirubin_TMS_47	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)[NH]2)N([Si](C)(C)C)C1=O	standard polar	2025-10-23	2178.66
Gas Chromatography	Bilirubin_TMS_48	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)N2[Si](C)(C)C)NC1=O	standard polar	2025-10-23	3207.23
Gas Chromatography	Bilirubin_TMS_49	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)N3[Si](C)(C)C)N2[Si](C)(C)C)N([Si](C)(C)C)C1=O	standard polar	2025-10-23	2063.2
Gas Chromatography	Bilirubin_TMS_50	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)N2[Si](C)(C)C)N([Si](C)(C)C)C1=O	standard polar	2025-10-23	856.97
Gas Chromatography	Bilirubin_TMS_51	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)[NH]2)N([Si](C)(C)C)C1=O	standard polar	2025-10-23	3053.11
Gas Chromatography	Bilirubin_TMS_52	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)N2[Si](C)(C)C)NC1=O	standard polar	2025-10-23	2533.21
Gas Chromatography	Bilirubin_TMS_53	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)N3[Si](C)(C)C)N2[Si](C)(C)C)N([Si](C)(C)C)C1=O	standard polar	2025-10-23	1164.02
Gas Chromatography	Bilirubin_TMS_54	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)N2[Si](C)(C)C)N([Si](C)(C)C)C1=O	standard polar	2025-10-23	2863.22
Gas Chromatography	Bilirubin_TMS_55	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)[NH]2)N([Si](C)(C)C)C1=O	standard polar	2025-10-23	2205.04
Gas Chromatography	Bilirubin_TMS_56	C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4/C(C=C)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)N2[Si](C)(C)C)N([Si](C)(C)C)C1=O	standard polar	2025-10-23	2258.1

Biological Properties

Cellular Locations

Cytoplasm
Endoplasmic reticulum
Extracellular
Membrane

Biospecimen Locations

Bile
Blood
Bone Marrow
Brain
Cerebrospinal Fluid (CSF)
Epidermis
Erythrocyte
Feces
Fibroblasts
Intestine
Kidney
Liver
Neuron
Pancreas
Placenta
Platelet
Skeletal Muscle
Spleen
Thyroid Gland
Urine

Tissue Locations

Bile
Bone Marrow
Brain
Epidermis
Erythrocyte
Fibroblasts
Intestine
Kidney
Liver
Neuron
Pancreas
Placenta
Platelet
Skeletal Muscle
Spleen
Thyroid Gland

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191869	Heme oxygenase 1	Unknown	P09601	Homo sapiens
MMDBp0192111	UDP-glucuronosyltransferase 2B28	Enzyme	Q9BY64	Homo sapiens
MMDBp0192115	Solute carrier organic anion transporter family member 1B1	Transporter	Q9Y6L6	Homo sapiens
MMDBp0192118	UDP-glucuronosyltransferase 2B4	Enzyme	P06133	Homo sapiens
MMDBp0192135	UDP-glucuronosyltransferase 1-4	Enzyme	P22310	Homo sapiens
MMDBp0192136	UDP-glucuronosyltransferase 2B10	Enzyme	P36537	Homo sapiens
MMDBp0192137	UDP-glucuronosyltransferase 2B7	Enzyme	P16662	Homo sapiens
MMDBp0192138	UDP-glucuronosyltransferase 2B15	Enzyme	P54855	Homo sapiens
MMDBp0192139	UDP-glucuronosyltransferase 2A1	Enzyme	Q9Y4X1	Homo sapiens
MMDBp0192140	UDP-glucuronosyltransferase 1-1	Enzyme	P22309	Homo sapiens
MMDBp0192141	UDP-glucuronosyltransferase 1-9	Enzyme	O60656	Homo sapiens
MMDBp0192142	UDP-glucuronosyltransferase 1-8	Enzyme	Q9HAW9	Homo sapiens
MMDBp0192143	UDP-glucuronosyltransferase 1-3	Enzyme	P35503	Homo sapiens
MMDBp0192144	UDP-glucuronosyltransferase 1-10	Enzyme	Q9HAW8	Homo sapiens
MMDBp0192145	UDP-glucuronosyltransferase 2B17	Enzyme	O75795	Homo sapiens
MMDBp0192146	UDP-glucuronosyltransferase 1-6	Enzyme	P19224	Homo sapiens
MMDBp0192147	UDP-glucuronosyltransferase 1-5	Enzyme	P35504	Homo sapiens
MMDBp0192148	UDP-glucuronosyltransferase 2B11	Enzyme	O75310	Homo sapiens
MMDBp0192151	UDP-glucuronosyltransferase 1-7	Enzyme	Q9HAW7	Homo sapiens
MMDBp0192339	Biliverdin reductase A	Unknown	P53004	Homo sapiens
MMDBp0192340	Flavin reductase (NADPH)	Unknown	P30043	Homo sapiens
MMDBp0193190	Canalicular multispecific organic anion transporter 1	Transporter	Q92887	Homo sapiens
MMDBp0193303	Aryl hydrocarbon receptor	Unknown	P35869	Homo sapiens
MMDBp0193408	Serum albumin	Unknown	P02768	Homo sapiens
MMDBp0193518	Alpha-fetoprotein	Unknown	P02771	Homo sapiens
MMDBp0194142	UDP-glucuronosyltransferase 2A3	Enzyme	Q6UWM9	Homo sapiens
MMDBp0195932	HCG2039726, isoform CRA_f	Enzyme	Q5DT02	Homo sapiens
MMDBp0195933	HCG2039726, isoform CRA_e	Enzyme	Q5DSZ6	Homo sapiens
MMDBp0195934	UDP glycosyltransferase 1 family polypeptide A7	Enzyme	Q5DSZ7	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0019751	Biliverdin	Bilirubin	Unknown Protein		PathBank	31602464
MMDBr0019752	Bilirubin	Uridine 5'-diphosphate	Unknown Protein		PathBank	31602464
MMDBr0025585	Bilirubin	biliverdin IXalpha	F420H(2)-dependent biliverdin reductase	Reduction	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Cerebral vasospasm	Increased	Association	Human Cerebrospinal Fluid (CSF)	HMDB	15789034
Crigler-najjar syndrome type i		Association	Human Blood	HMDB	6814411
Crohn's disease		Association	Human Bile	HMDB	16440420
Gallbladder disease		Association	Human Bile	HMDB	16440420
Growth hormone deficiency		Association	Human Blood	HMDB	16384844
Primary hypomagnesemia		Association	Human Blood	HMDB	10337938
Crigler-najjar syndrome type i		Association	Human Blood	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Actinobacteria	1	Human ; Human feces; Human sputum; Human saliva; Human supragingival plaque; Human subgingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria/Eubacteria	Firmicutes	3	Human feces; Human urine; Human sputum	Indirect association between microbiota composition and metabolites measured in host biospecimen
Eukaryota/Fungi	Ascomycota	2	Human feces; Human saliva	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Blood	Detected and Quantified			25.656	78.678	uM	Adult (>18 years old)	Both	Anemia, congenital dyserythropoietic, type II	HMDB	19621418
Human Blood	Detected and Quantified	106				uM	Infant (0-1 year old)	Female	Bile Acid Synthesis Defect, Congenital, 1	HMDB	26712441
Human Cerebrospinal fluid (csf)	Detected and Quantified	17.3	12.4			uM	Adult (>18 years old)	Both	Cerebral Vasospasm	HMDB	15789034
Human Blood	Detected and Quantified			18.814	518.248	uM	Adult (>18 years old)	Male	Cholestasis, progressive familial intrahepatic, 1	HMDB	15448432
Human Blood	Detected and Quantified	41		6	381	uM	Children (1-13 years old)	Both	Cholestasis, progressive familial intrahepatic, 1	HMDB	22424345
Human Blood	Detected and Quantified			42.760	141.962	uM	Children (1-13 years old)	Female	Cholestasis, progressive familial intrahepatic, 1	HMDB	15448432
Human Blood	Detected and Quantified			22	41	uM	Newborn (0-30 days old)	Both	Citrullinemia type II, neonatal-onset	HMDB	11281457
Human Blood	Detected and Quantified			41	101	uM	Newborn (0-30 days old)	Both	Citrullinemia type II, neonatal-onset	HMDB	11281457
Human Blood	Detected and Quantified	650				uM	Adolescent (13-18 years old)	Male	Crigler-Najjar syndrome Type I	HMDB	6814411
Human Bile	Detected and Quantified	4600		3900	5300	uM	Adult (>18 years old)	Both	Crohn's disease	HMDB	16440420
Human Bile	Detected and Quantified	5000		4300	5700	uM	Adult (>18 years old)	Both	Crohn's disease	HMDB	16440420
Human Bile	Detected and Quantified	5900		4300	7500	uM	Adult (>18 years old)	Both	Crohn's disease	HMDB	16440420
Human Blood	Detected and Quantified	78.678				uM	Newborn (0-30 days old)	Male	Donohue Syndrome	HMDB	26871809
Human Blood	Detected and Quantified	111.175				uM	Newborn (0-30 days old)	Male	Donohue Syndrome	HMDB	26871809
Human Bile	Detected and Quantified	2600		2400	2800	uM	Adult (>18 years old)	Both	Gallstone disease	HMDB	16440420
Human Blood	Detected and Quantified	380.733	142.989			uM	Newborn (0-30 days old)	Both	Glucose-6-phosphate dehydrogenase deficiency	HMDB	14703221
Human Blood	Detected and Quantified	14.6	2.5			uM	Adult (>18 years old)	Both	Growth hormone deficiency	HMDB	16384844
Human Blood	Detected and Quantified	8.80	1.22			uM	Adult (>18 years old)	Both	Growth hormone deficiency	HMDB	16384844
Human Blood	Detected and Quantified			28.7	170	uM	Children (1-13 years old)	Both	Infantile Liver Failure Syndrome 2	HMDB	26541327
Human Blood	Detected and Quantified			46.9	233	uM	Children (1-13 years old)	Both	Infantile Liver Failure Syndrome 2	HMDB	26541327
Human Blood	Detected and Quantified			73.1	85.0	uM	Infant (0-1 year old)	Female	Infantile Liver Failure Syndrome 2	HMDB	26541327
Human Blood	Detected and Quantified	29.59				uM	Newborn (0-30 days old)	Male	Lathosterolosis	HMDB	12189593
Human Blood	Detected and Quantified	42.247				uM	Newborn (0-30 days old)	Male	Lathosterolosis	HMDB	12189593
Human Blood	Detected and Quantified	24.5				uM	Adult (>18 years old)	Female	Lecithin:cholesterol Acyltransferase Deficiency	HMDB	16051254
Human Blood	Detected and Quantified			6.842	20.525	uM	Adult (>18 years old)	Male	Primary Hypomagnesemia	HMDB	10337938
Human Blood	Detected and Quantified			3	21	uM	Newborn (0-30 days old)	Not Specified	Normal	HMDB	11281457
Human Blood	Detected and Quantified	<12				uM	Newborn (0-30 days old)	Not Specified	Normal	HMDB	11281457
Human Blood	Detected and Quantified	<12.828				uM	Adult (>18 years old)	Both	Normal	HMDB	19621418
Human Blood	Detected and Quantified	<20				uM	Children (1-13 years old)	Not Specified	Normal	HMDB	26541327
Human Blood	Detected and Quantified	<3.4				uM	Children (1-13 years old)	Not Specified	Normal	HMDB	26541327
Human Blood	Detected and Quantified	15.2	2.0			uM	Adult (>18 years old)	Both	Normal	HMDB	16384844
Human Blood	Detected and Quantified	310.265	65.850			uM	Newborn (0-30 days old)	Not Specified	Normal	HMDB	14703221
Human Blood	Detected and Quantified			6.842	20.525	uM	Children (1-13 years old)	Not Specified	Normal	HMDB	15448432
Human Blood	Detected and Quantified	8.0	0.9			uM	Adult (>18 years old)	Both	Normal	HMDB	16384844
Human Blood	Detected and Quantified	573.0		291.0	855.0	uM	Children (1-13 years old)	Both	Crigler-Najjar syndrome Type I	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Human Blood	Detected and Quantified	59.2				uM	Infant (0-1 year old)	Female	Wolcott-Rallison syndrome	HMDB	Neonatal diabetes in Wolcott-Rallison syndrome: a case report
Human Urine	Detected and Quantified			0.51	5.13	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	David F. Putnam Composition and Concentrative Properties of Human Urine. NASA Contractor Report. July 1971
Human Cerebrospinal fluid (csf)	Detected and Quantified			0	0.2	uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	0.032		0.0019	0.21	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	8.500	4			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	<17				uM	Children (1 - 13 years old)		Normal	HMDB	Hereditary Jaundice and Disorders of Bilirubin Metabolism. In: Valle D, Beaudet AL, Vogelstein B, Kinzler KW, Antonarakis SE, Ballabio A, Gibson K, Mitchell G. eds. The Online Metabolic and Molecular Bases of Inherited Disease New York, NY. http://ommbid.mhmedical.com.login.ezproxy.library.ualberta.ca/content.aspx?bookid=971&sectionid=62639411
Human Blood	Detected and Quantified	13.0		5.0	21.0	uM	Adult (>18 years old)	Both	Normal	HMDB	Louise M. Malarkey, Mary Ellen McMorrow. Saunders Nursing Guide to Diagnostic and Laboratory Tests. Elsevier Health Sciences, Nov 1, 2011.
Human Urine	Detected and Quantified	< 0.1				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	Tietz Clinical Guide to Laboratory Tests 4th Ed., 2006.
Human Blood	Detected and Quantified			5.10	18.0	uM	Adult (>18 years old)	Both	Normal	HMDB	Vancouver Coastal Health Lab (http://www.vch.ca/Locations-Services/result?res_id=601)
Human Blood	Detected and Quantified			5.131	17.104	uM	Adult (>18 years old)	Both	Normal	HMDB	Vancouver Coastal Health Lab (http://www.vch.ca/Locations-Services/result?res_id=601)
Human Bile	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Bone marrow	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Brain	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Epidermis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Erythrocyte	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Kidney	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Pancreas	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Skeletal muscle	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Spleen	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Thyroid gland	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24740205
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0000054

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

5280352

PDB ID

Not Available

ChEBI ID

16990

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Bayes Garcia R, Maldonado Lozano J, Molina Font JA: [Interrelation of bilirubin and free fatty acids in newborn infants with pathologic conditions]. An Esp Pediatr. 1989 Jan;30(1):27-31. [PubMed:2648917 ]
Tiribelli C, Ostrow JD: New concepts in bilirubin and jaundice: report of the Third International Bilirubin Workshop, April 6-8, 1995, Trieste, Italy. Hepatology. 1996 Nov;24(5):1296-311. doi: 10.1002/hep.510240551. [PubMed:8903413 ]
Kotal P, Van der Veere CN, Sinaasappel M, Elferink RO, Vitek L, Brodanova M, Jansen PL, Fevery J: Intestinal excretion of unconjugated bilirubin in man and rats with inherited unconjugated hyperbilirubinemia. Pediatr Res. 1997 Aug;42(2):195-200. doi: 10.1203/00006450-199708000-00011. [PubMed:9262222 ]
Kikuchi S, Hata M, Fukumoto K, Yamane Y, Matsui T, Tamura A, Yonemura S, Yamagishi H, Keppler D, Tsukita S, Tsukita S: Radixin deficiency causes conjugated hyperbilirubinemia with loss of Mrp2 from bile canalicular membranes. Nat Genet. 2002 Jul;31(3):320-5. doi: 10.1038/ng905. Epub 2002 Jun 17. [PubMed:12068294 ]
Lin JM, Jiang CQ: [Clinical manifestation and ultrasonic characteristics of five patients with acute arsenic poisoning]. Zhonghua Lao Dong Wei Sheng Zhi Ye Bing Za Zhi. 2003 Dec;21(6):420-2. [PubMed:14761351 ]
Sikkel E, Pasman SA, Oepkes D, Kanhai HH, Vandenbussche FP: On the origin of amniotic fluid bilirubin. Placenta. 2004 May;25(5):463-8. doi: 10.1016/j.placenta.2003.10.015. [PubMed:15081641 ]
Slusher TM, Angyo IA, Bode-Thomas F, Akor F, Pam SD, Adetunji AA, McLaren DW, Wong RJ, Vreman HJ, Stevenson DK: Transcutaneous bilirubin measurements and serum total bilirubin levels in indigenous African infants. Pediatrics. 2004 Jun;113(6):1636-41. doi: 10.1542/peds.113.6.1636. [PubMed:15173484 ]
Zhan X, Wang SY, Wang L, Qu P: [Decreased peripheral nerve conduction velocity may be associated with lower-serum level of vitamin E in patients with infantile hepatitis syndrome]. Zhonghua Er Ke Za Zhi. 2004 May;42(5):362-6. [PubMed:15189696 ]
Kabicek P: Importance of serum bile acids determination in adolescents with juvenile hyperbilirubinaemia. Cent Eur J Public Health. 2004 Jun;12(2):102-9. [PubMed:15242029 ]
Yamamoto S, Kubo S, Hai S, Uenishi T, Yamamoto T, Shuto T, Takemura S, Tanaka H, Yamazaki O, Hirohashi K, Tanaka T: Hepatitis C virus infection as a likely etiology of intrahepatic cholangiocarcinoma. Cancer Sci. 2004 Jul;95(7):592-5. doi: 10.1111/j.1349-7006.2004.tb02492.x. [PubMed:15245596 ]
Schmidt CM, Powell ES, Yiannoutsos CT, Howard TJ, Wiebke EA, Wiesenauer CA, Baumgardner JA, Cummings OW, Jacobson LE, Broadie TA, Canal DF, Goulet RJ Jr, Curie EA, Cardenes H, Watkins JM, Loehrer PJ, Lillemoe KD, Madura JA: Pancreaticoduodenectomy: a 20-year experience in 516 patients. Arch Surg. 2004 Jul;139(7):718-25; discussion 725-7. doi: 10.1001/archsurg.139.7.718. [PubMed:15249403 ]
Danko I, Jia Z, Zhang G: Nonviral gene transfer into liver and muscle for treatment of hyperbilirubinemia in the gunn rat. Hum Gene Ther. 2004 Dec;15(12):1279-86. doi: 10.1089/hum.2004.15.1279. [PubMed:15684703 ]
Azer SA: A multimedia CD-ROM tool to improve student understanding of bile salts and bilirubin metabolism: evaluation of its use in a medical hybrid PBL course. Adv Physiol Educ. 2005 Mar;29(1):40-50. doi: 10.1152/advan.00015.2004. [PubMed:15718382 ]
Nanjundaswamy S, Petrova A, Mehta R, Hegyi T: Transcutaneous bilirubinometry in preterm infants receiving phototherapy. Am J Perinatol. 2005 Apr;22(3):127-31. doi: 10.1055/s-2005-863785. [PubMed:15838745 ]
Randeberg LL, Roll EB, Nilsen LT, Christensen T, Svaasand LO: In vivo spectroscopy of jaundiced newborn skin reveals more than a bilirubin index. Acta Paediatr. 2005 Jan;94(1):65-71. doi: 10.1111/j.1651-2227.2005.tb01790.x. [PubMed:15858963 ]
Deja M, Hildebrandt B, Ahlers O, Riess H, Wust P, Gerlach H, Kerner T: Goal-directed therapy of cardiac preload in induced whole-body hyperthermia. Chest. 2005 Aug;128(2):580-6. doi: 10.1378/chest.128.2.580. [PubMed:16100141 ]
Sando M, Sato Y, Iwata S, Akita H, Sunakawa K: In vitro protein binding of teicoplanin to neonatal serum. J Infect Chemother. 2004 Oct;10(5):280-3. doi: 10.1007/s10156-004-0339-x. [PubMed:16163462 ]
Ciszowski K, Gomolka E, Jenner B: [The influence of the dose, time since ingestion and concentration of the xenobiotic on the clinical state and severity of liver damage with patients intoxicated with paracetamol]. Przegl Lek. 2005;62(6):456-61. [PubMed:16225094 ]
Lapidus A, Akerlund JE, Einarsson C: Gallbladder bile composition in patients with Crohn 's disease. World J Gastroenterol. 2006 Jan 7;12(1):70-4. doi: 10.3748/wjg.v12.i1.70. [PubMed:16440420 ]
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Showing metabocard for Bilirubin (MMDBc0000328)

MOL for #<Metabolite:0x00007f2e4c054ca0>

3D MOL for #<Metabolite:0x00007f2e4c054ca0>

3D SDF for #<Metabolite:0x00007f2e4c054ca0>

3D-SDF for #<Metabolite:0x00007f2e4c054ca0>

PDB for #<Metabolite:0x00007f2e4c054ca0>

3D PDB for #<Metabolite:0x00007f2e4c054ca0>

SMILES for #<Metabolite:0x00007f2e4c054ca0>

INCHI for #<Metabolite:0x00007f2e4c054ca0>

Structure for #<Metabolite:0x00007f2e4c054ca0>

3D Structure for #<Metabolite:0x00007f2e4c054ca0>