MiMeDB: Showing metabocard for Reduced riboflavin (MMDBc0030337)

Microbial

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 00:04:07 UTC

Update Date

2022-08-31 17:43:53 UTC

Metabolite ID

MMDBc0030337

Metabolite Identification

Common Name

Reduced riboflavin

Description

Reduced riboflavin is a member of the chemical class known as Quinoxalines. These are compounds containing a quinoxaline moiety, a bicyclic heterocycle made up of a benzene ring fused to a pyrazine ring. Compared to riboflavin, reduced riboflavin has one extra hydrogen attached to an oxygen on its ring structure. Riboflavin, also known as vitamin B2, is the central component of the cofactors FAD and FMN, and is therefore required by all flavoproteins. As such, vitamin B2 is required for a wide variety of cellular processes. It plays a key role in energy metabolism, and for the metabolism of fats, ketone bodies, carbohydrates, and proteins. The reduced form, which occurs in metabolism along with the oxidized form, is colorless. (Wikipedia)

Structure

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

Untitled Document-1
  Mrv1652304202019272D          

 25 27  0  0  0  0            999 V2000
   -2.5006   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -2.2688    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.6188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -1.8563    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.6188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -3.0938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.6188    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0717    1.4437    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7862    1.8563    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7862    2.6812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    3.0938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  5  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14  9  2  0  0  0  0
 11 15  2  0  0  0  0
 13 16  2  0  0  0  0
 17 10  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 18 23  1  1  0  0  0
 19 24  1  6  0  0  0
 20 25  1  6  0  0  0
M  END

HMDB0001557
     RDKit          3D
Riboflavin reduced
 41 43  0  0  0  0  0  0  0  0999 V2000
    1.2244   -2.6161   -3.9561 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8396   -1.9698   -3.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1485   -1.2075   -2.1710 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8210   -0.5460   -1.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1001    0.2228   -0.3539 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3311    0.3108   -0.4680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0762   -0.7553    0.2950 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8701   -0.7877    1.6385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5299   -0.6978   -0.1010 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2597   -1.7979    0.3596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2416    0.5461    0.3084 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3959    0.6810    1.6735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6288    0.4875   -0.3453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3366   -0.5867    0.1449 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7813    0.8785    0.5883 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1215    1.6775    1.4951 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8309    2.3416    2.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1967    2.2532    2.5483 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8914    1.4668    1.6620 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1757    0.7923    0.6968 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933    0.0272   -0.1665 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2660   -0.6520   -1.1310 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9361   -1.4437   -2.0361 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2029   -1.5667   -1.9947 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1786   -2.0702   -2.9538 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7517    1.3221   -0.3718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5497    0.0569   -1.5582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6931   -1.7298   -0.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2670   -0.0987    2.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6250   -0.7535   -1.2267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2456   -2.5455   -0.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7683    1.4591   -0.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6640   -0.1519    2.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1747    1.4504   -0.1464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5329    0.4042   -1.4400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4048   -0.6018    1.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0352    1.7496    1.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3162    2.9683    3.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7548    2.7986    3.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9685    1.3698    1.7079 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6641   -2.6857   -3.6631 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
  5 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25  2  1  0
 22  4  1  0
 20 15  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  6
  8 29  1  0
  9 30  1  6
 10 31  1  0
 11 32  1  6
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 25 41  1  0
M  END

Untitled Document-1
  Mrv1652304202019272D          

 25 27  0  0  0  0            999 V2000
   -2.5006   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -2.2688    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.6188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -1.8563    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.6188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -3.0938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.6188    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0717    1.4437    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7862    1.8563    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7862    2.6812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    3.0938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  5  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14  9  2  0  0  0  0
 11 15  2  0  0  0  0
 13 16  2  0  0  0  0
 17 10  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 18 23  1  1  0  0  0
 19 24  1  6  0  0  0
 20 25  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0030337

> <DATABASE_NAME>
MIME

> <SMILES>
OC[C@@H](O)[C@H](O)[C@H](O)CN1C2=CC=CC=C2N=C2C(=O)NC(=O)N=C12

> <INCHI_IDENTIFIER>
InChI=1S/C15H16N4O6/c20-6-10(22)12(23)9(21)5-19-8-4-2-1-3-7(8)16-11-13(19)17-15(25)18-14(11)24/h1-4,9-10,12,20-23H,5-6H2,(H,18,24,25)/t9-,10-,12-/m1/s1

> <INCHI_KEY>
ATANIONNQLTUND-CKYFFXLPSA-N

> <FORMULA>
C15H16N4O6

> <MOLECULAR_WEIGHT>
348.3107

> <EXACT_MASS>
348.106984264

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
33.23818558641372

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
10-[(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl]-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione

> <ALOGPS_LOGP>
-1.64

> <JCHEM_LOGP>
-1.9433830386666664

> <ALOGPS_LOGS>
-2.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.852833325035373

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.969939673882121

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9741788041843122

> <JCHEM_POLAR_SURFACE_AREA>
155.04999999999998

> <JCHEM_REFRACTIVITY>
86.18599999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.76e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-[(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl]-3H-benzo[g]pteridine-2,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001557
     RDKit          3D
Riboflavin reduced
 41 43  0  0  0  0  0  0  0  0999 V2000
    1.2244   -2.6161   -3.9561 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8396   -1.9698   -3.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1485   -1.2075   -2.1710 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8210   -0.5460   -1.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1001    0.2228   -0.3539 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3311    0.3108   -0.4680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0762   -0.7553    0.2950 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8701   -0.7877    1.6385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5299   -0.6978   -0.1010 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2597   -1.7979    0.3596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2416    0.5461    0.3084 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3959    0.6810    1.6735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6288    0.4875   -0.3453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3366   -0.5867    0.1449 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7813    0.8785    0.5883 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1215    1.6775    1.4951 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8309    2.3416    2.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1967    2.2532    2.5483 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8914    1.4668    1.6620 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1757    0.7923    0.6968 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933    0.0272   -0.1665 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2660   -0.6520   -1.1310 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9361   -1.4437   -2.0361 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2029   -1.5667   -1.9947 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1786   -2.0702   -2.9538 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7517    1.3221   -0.3718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5497    0.0569   -1.5582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6931   -1.7298   -0.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2670   -0.0987    2.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6250   -0.7535   -1.2267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2456   -2.5455   -0.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7683    1.4591   -0.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6640   -0.1519    2.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1747    1.4504   -0.1464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5329    0.4042   -1.4400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4048   -0.6018    1.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0352    1.7496    1.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3162    2.9683    3.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7548    2.7986    3.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9685    1.3698    1.7079 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6641   -2.6857   -3.6631 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
  5 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25  2  1  0
 22  4  1  0
 20 15  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  6
  8 29  1  0
  9 30  1  6
 10 31  1  0
 11 32  1  6
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 25 41  1  0
M  END

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Untitled Document-1                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  C   UNK     0      -4.668  -1.925   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.668  -3.465   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.334  -4.235   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.001  -3.465   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.001  -1.925   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.334  -1.155   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -0.667  -4.235   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       0.667  -3.465   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.667  -1.925   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -0.667  -1.155   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       2.001  -4.235   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       3.334  -3.465   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       3.334  -1.925   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       2.001  -1.155   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       2.001  -5.775   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       4.668  -1.155   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.667   0.385   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.001   1.155   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.001   2.695   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.334   3.465   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.334   5.005   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.668   5.775   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -3.334   0.385   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -0.667   3.465   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -4.668   2.695   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9    5   17                                                  
CONECT   11    8   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13    9                                                       
CONECT   15   11                                                            
CONECT   16   13                                                            
CONECT   17   10   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20   24                                                  
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   18                                                            
CONECT   24   19                                                            
CONECT   25   20                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0001557
HETATM    1  O1  UNL     1       1.224  -2.616  -3.956  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.840  -1.970  -3.035  1.00  0.00           C  
HETATM    3  N1  UNL     1       1.148  -1.207  -2.171  1.00  0.00           N  
HETATM    4  C2  UNL     1       1.821  -0.546  -1.222  1.00  0.00           C  
HETATM    5  N2  UNL     1       1.100   0.223  -0.354  1.00  0.00           N  
HETATM    6  C3  UNL     1      -0.331   0.311  -0.468  1.00  0.00           C  
HETATM    7  C4  UNL     1      -1.076  -0.755   0.295  1.00  0.00           C  
HETATM    8  O2  UNL     1      -0.870  -0.788   1.639  1.00  0.00           O  
HETATM    9  C5  UNL     1      -2.530  -0.698  -0.101  1.00  0.00           C  
HETATM   10  O3  UNL     1      -3.260  -1.798   0.360  1.00  0.00           O  
HETATM   11  C6  UNL     1      -3.242   0.546   0.308  1.00  0.00           C  
HETATM   12  O4  UNL     1      -3.396   0.681   1.673  1.00  0.00           O  
HETATM   13  C7  UNL     1      -4.629   0.488  -0.345  1.00  0.00           C  
HETATM   14  O5  UNL     1      -5.337  -0.587   0.145  1.00  0.00           O  
HETATM   15  C8  UNL     1       1.781   0.878   0.588  1.00  0.00           C  
HETATM   16  C9  UNL     1       1.122   1.677   1.495  1.00  0.00           C  
HETATM   17  C10 UNL     1       1.831   2.342   2.446  1.00  0.00           C  
HETATM   18  C11 UNL     1       3.197   2.253   2.548  1.00  0.00           C  
HETATM   19  C12 UNL     1       3.891   1.467   1.662  1.00  0.00           C  
HETATM   20  C13 UNL     1       3.176   0.792   0.697  1.00  0.00           C  
HETATM   21  N3  UNL     1       3.893   0.027  -0.166  1.00  0.00           N  
HETATM   22  C14 UNL     1       3.266  -0.652  -1.131  1.00  0.00           C  
HETATM   23  C15 UNL     1       3.936  -1.444  -2.036  1.00  0.00           C  
HETATM   24  O6  UNL     1       5.203  -1.567  -1.995  1.00  0.00           O  
HETATM   25  N4  UNL     1       3.179  -2.070  -2.954  1.00  0.00           N  
HETATM   26  H1  UNL     1      -0.752   1.322  -0.372  1.00  0.00           H  
HETATM   27  H2  UNL     1      -0.550   0.057  -1.558  1.00  0.00           H  
HETATM   28  H3  UNL     1      -0.693  -1.730  -0.115  1.00  0.00           H  
HETATM   29  H4  UNL     1      -1.267  -0.099   2.187  1.00  0.00           H  
HETATM   30  H5  UNL     1      -2.625  -0.753  -1.227  1.00  0.00           H  
HETATM   31  H6  UNL     1      -3.246  -2.546  -0.270  1.00  0.00           H  
HETATM   32  H7  UNL     1      -2.768   1.459  -0.132  1.00  0.00           H  
HETATM   33  H8  UNL     1      -3.664  -0.152   2.100  1.00  0.00           H  
HETATM   34  H9  UNL     1      -5.175   1.450  -0.146  1.00  0.00           H  
HETATM   35  H10 UNL     1      -4.533   0.404  -1.440  1.00  0.00           H  
HETATM   36  H11 UNL     1      -5.405  -0.602   1.116  1.00  0.00           H  
HETATM   37  H12 UNL     1       0.035   1.750   1.407  1.00  0.00           H  
HETATM   38  H13 UNL     1       1.316   2.968   3.158  1.00  0.00           H  
HETATM   39  H14 UNL     1       3.755   2.799   3.326  1.00  0.00           H  
HETATM   40  H15 UNL     1       4.969   1.370   1.708  1.00  0.00           H  
HETATM   41  H16 UNL     1       3.664  -2.686  -3.663  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   25
CONECT    3    4    4
CONECT    4    5   22
CONECT    5    6   15
CONECT    6    7   26   27
CONECT    7    8    9   28
CONECT    8   29
CONECT    9   10   11   30
CONECT   10   31
CONECT   11   12   13   32
CONECT   12   33
CONECT   13   14   34   35
CONECT   14   36
CONECT   15   16   16   20
CONECT   16   17   37
CONECT   17   18   18   38
CONECT   18   19   39
CONECT   19   20   20   40
CONECT   20   21
CONECT   21   22   22
CONECT   22   23
CONECT   23   24   24   25
CONECT   25   41
END

HMDB0001557
     RDKit          3D
Riboflavin reduced
 41 43  0  0  0  0  0  0  0  0999 V2000
    1.2244   -2.6161   -3.9561 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8396   -1.9698   -3.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1485   -1.2075   -2.1710 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8210   -0.5460   -1.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1001    0.2228   -0.3539 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3311    0.3108   -0.4680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0762   -0.7553    0.2950 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8701   -0.7877    1.6385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5299   -0.6978   -0.1010 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2597   -1.7979    0.3596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2416    0.5461    0.3084 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3959    0.6810    1.6735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6288    0.4875   -0.3453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3366   -0.5867    0.1449 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7813    0.8785    0.5883 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1215    1.6775    1.4951 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8309    2.3416    2.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1967    2.2532    2.5483 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8914    1.4668    1.6620 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1757    0.7923    0.6968 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933    0.0272   -0.1665 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2660   -0.6520   -1.1310 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9361   -1.4437   -2.0361 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2029   -1.5667   -1.9947 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1786   -2.0702   -2.9538 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7517    1.3221   -0.3718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5497    0.0569   -1.5582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6931   -1.7298   -0.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2670   -0.0987    2.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6250   -0.7535   -1.2267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2456   -2.5455   -0.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7683    1.4591   -0.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6640   -0.1519    2.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1747    1.4504   -0.1464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5329    0.4042   -1.4400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4048   -0.6018    1.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0352    1.7496    1.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3162    2.9683    3.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7548    2.7986    3.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9685    1.3698    1.7079 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6641   -2.6857   -3.6631 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
  5 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25  2  1  0
 22  4  1  0
 20 15  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  6
  8 29  1  0
  9 30  1  6
 10 31  1  0
 11 32  1  6
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 25 41  1  0
M  END

Synonyms

Value	Source
4a,5-Dihydroriboflavin	HMDB
4a,5-Dihydroriboflavine	HMDB
7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)-4a,5-dihydroisoalloxazine	HMDB
7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)-5,10-dihydrobenzo[g]pteridine-2,4(3H,4ah)-dione	HMDB
Reduced riboflavin	HMDB

Molecular Formula

C₁₅H₁₆N₄O₆

Average Mass

348.3107

Monoisotopic Mass

348.106984264

IUPAC Name

10-[(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl]-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione

Traditional Name

10-[(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl]-3H-benzo[g]pteridine-2,4-dione

CAS Registry Number

Not Available

SMILES

OC[C@@H](O)[C@H](O)[C@H](O)CN1C2=CC=CC=C2N=C2C(=O)NC(=O)N=C12

InChI Identifier

InChI=1S/C15H16N4O6/c20-6-10(22)12(23)9(21)5-19-8-4-2-1-3-7(8)16-11-13(19)17-15(25)18-14(11)24/h1-4,9-10,12,20-23H,5-6H2,(H,18,24,25)/t9-,10-,12-/m1/s1

InChI Key

ATANIONNQLTUND-CKYFFXLPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alloxazines and isoalloxazines. These are organic compounds comprising the (iso)alloxazine structure (Benzo[g]pteridine-2,4-dione).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Alloxazines and isoalloxazines

Direct Parent

Alloxazines and isoalloxazines

Alternative Parents

Substituents

Isoalloxazine
Diazanaphthalene
Quinoxaline
Pyrimidone
Pyrazine
Pyrimidine
Benzenoid
Heteroaromatic compound
Vinylogous amide
Secondary alcohol
Lactam
Polyol
Azacycle
Alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.48 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-1.9	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	5.97	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	155.05 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	86.19 m³·mol⁻¹	ChemAxon
Polarizability	33.24 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0bwi-8094000000-f43f7112ee283826153b	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-00di-3042269000-7f5ae8c8ce0af8c53f55	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_7) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_4_1) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_4_5) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("Riboflavin reduced,3TBDMS,#7" TMS) - 70eV, Positive	Not Available	2021-10-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000t-0029000000-bc104c9d050e033b69d4	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01t9-4091000000-afc0f707ee1ce75b867c	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-2190000000-570c6cbcf04a46a68c76	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udl-4097000000-b676ae8b47eab2fb18c7	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-f5254591b51a0d846765	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9010000000-0abc9b0d47dd58c290bd	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0029000000-01cbdc02a72aeccc6223	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ta-0098000000-708769959f1af25b7e78	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00b9-0590000000-bc32c00ac0788074d256	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0092000000-f9ec2194483db51c8410	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03fr-1090000000-71092bfa8904438a88ac	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ffx-6590000000-eca89bd048fc24f150a8	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	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 (eluted)	2025-10-23	345.4
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	187.3
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	178.7
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	382.1
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	319.8
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	259.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	1211.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	349.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	879.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	163.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	214.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	165.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	47.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	296.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	588.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	138.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	242.2
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1298.5
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	666.1

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Reduced riboflavin_TMS_1	C[Si](C)(C)OC[C@@H](O)[C@H](O)[C@H](O)CN1C2=NC(=O)[NH]C(=O)C2=NC2=CC=CC=C21	standard non polar	2025-10-24	2341.25
Gas Chromatography	Reduced riboflavin_TMS_2	C[Si](C)(C)O[C@H](CO)[C@H](O)[C@H](O)CN1C2=NC(=O)[NH]C(=O)C2=NC2=CC=CC=C21	standard non polar	2025-10-24	1917.9
Gas Chromatography	Reduced riboflavin_TMS_3	C[Si](C)(C)O[C@@H]([C@H](O)CO)[C@H](O)CN1C2=NC(=O)[NH]C(=O)C2=NC2=CC=CC=C21	standard non polar	2025-10-24	2284.01
Gas Chromatography	Reduced riboflavin_TMS_4	C[Si](C)(C)O[C@H](CN1C2=NC(=O)[NH]C(=O)C2=NC2=CC=CC=C21)[C@@H](O)[C@H](O)CO	standard non polar	2025-10-24	1119.53
Gas Chromatography	Reduced riboflavin_TMS_5	C[Si](C)(C)N1C(=O)N=C2C(=NC3=CC=CC=C3N2C[C@@H](O)[C@@H](O)[C@H](O)CO)C1=O	standard non polar	2025-10-24	1913.33
Gas Chromatography	Reduced riboflavin_TMS_6	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O)[C@H](O)CN1C2=NC(=O)[NH]C(=O)C2=NC2=CC=CC=C21	standard non polar	2025-10-24	2041.77
Gas Chromatography	Reduced riboflavin_TMS_7	C[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C)[C@H](O)CN1C2=NC(=O)[NH]C(=O)C2=NC2=CC=CC=C21	standard non polar	2025-10-24	1285.08
Gas Chromatography	Reduced riboflavin_TMS_8	C[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](CN1C2=NC(=O)[NH]C(=O)C2=NC2=CC=CC=C21)O[Si](C)(C)C	standard non polar	2025-10-24	1467.17
Gas Chromatography	Reduced riboflavin_TMS_9	C[Si](C)(C)OC[C@@H](O)[C@H](O)[C@H](O)CN1C2=NC(=O)N([Si](C)(C)C)C(=O)C2=NC2=CC=CC=C21	standard non polar	2025-10-24	1956.82
Gas Chromatography	Reduced riboflavin_TMS_10	C[Si](C)(C)O[C@H](CO)[C@H](O[Si](C)(C)C)[C@H](O)CN1C2=NC(=O)[NH]C(=O)C2=NC2=CC=CC=C21	standard non polar	2025-10-24	1587.55
Gas Chromatography	Reduced riboflavin_TMS_11	C[Si](C)(C)O[C@H](CO)[C@H](O)[C@@H](CN1C2=NC(=O)[NH]C(=O)C2=NC2=CC=CC=C21)O[Si](C)(C)C	standard non polar	2025-10-24	2841.1
Gas Chromatography	Reduced riboflavin_TMS_12	C[Si](C)(C)O[C@H](CO)[C@H](O)[C@H](O)CN1C2=NC(=O)N([Si](C)(C)C)C(=O)C2=NC2=CC=CC=C21	standard non polar	2025-10-24	1814.19
Gas Chromatography	Reduced riboflavin_TMS_13	C[Si](C)(C)O[C@@H]([C@H](O)CO)[C@@H](CN1C2=NC(=O)[NH]C(=O)C2=NC2=CC=CC=C21)O[Si](C)(C)C	standard non polar	2025-10-24	1323.94
Gas Chromatography	Reduced riboflavin_TMS_14	C[Si](C)(C)O[C@@H]([C@H](O)CO)[C@H](O)CN1C2=NC(=O)N([Si](C)(C)C)C(=O)C2=NC2=CC=CC=C21	standard non polar	2025-10-24	2255.17
Gas Chromatography	Reduced riboflavin_TMS_15	C[Si](C)(C)O[C@H](CN1C2=NC(=O)N([Si](C)(C)C)C(=O)C2=NC2=CC=CC=C21)[C@@H](O)[C@H](O)CO	standard non polar	2025-10-24	1970.84
Gas Chromatography	Reduced riboflavin_TMS_16	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)CN1C2=NC(=O)[NH]C(=O)C2=NC2=CC=CC=C21	standard non polar	2025-10-24	1122.51
Gas Chromatography	Reduced riboflavin_TMS_17	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](CN1C2=NC(=O)[NH]C(=O)C2=NC2=CC=CC=C21)O[Si](C)(C)C	standard non polar	2025-10-24	2239.47
Gas Chromatography	Reduced riboflavin_TMS_18	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O)[C@H](O)CN1C2=NC(=O)N([Si](C)(C)C)C(=O)C2=NC2=CC=CC=C21	standard non polar	2025-10-24	1112.79
Gas Chromatography	Reduced riboflavin_TMS_19	C[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](CN1C2=NC(=O)[NH]C(=O)C2=NC2=CC=CC=C21)O[Si](C)(C)C	standard non polar	2025-10-24	1338.36
Gas Chromatography	Reduced riboflavin_TMS_20	C[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C)[C@H](O)CN1C2=NC(=O)N([Si](C)(C)C)C(=O)C2=NC2=CC=CC=C21	standard non polar	2025-10-24	1552.53
Gas Chromatography	Reduced riboflavin_TMS_21	C[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](CN1C2=NC(=O)N([Si](C)(C)C)C(=O)C2=NC2=CC=CC=C21)O[Si](C)(C)C	standard non polar	2025-10-24	1196.52
Gas Chromatography	Reduced riboflavin_TMS_22	C[Si](C)(C)O[C@H](CO)[C@H](O[Si](C)(C)C)[C@@H](CN1C2=NC(=O)[NH]C(=O)C2=NC2=CC=CC=C21)O[Si](C)(C)C	standard non polar	2025-10-24	2331.35
Gas Chromatography	Reduced riboflavin_TMS_23	C[Si](C)(C)O[C@H](CO)[C@H](O[Si](C)(C)C)[C@H](O)CN1C2=NC(=O)N([Si](C)(C)C)C(=O)C2=NC2=CC=CC=C21	standard non polar	2025-10-24	2111.88
Gas Chromatography	Reduced riboflavin_TMS_24	C[Si](C)(C)O[C@H](CO)[C@H](O)[C@@H](CN1C2=NC(=O)N([Si](C)(C)C)C(=O)C2=NC2=CC=CC=C21)O[Si](C)(C)C	standard non polar	2025-10-24	1754.51
Gas Chromatography	Reduced riboflavin_TMS_25	C[Si](C)(C)O[C@@H]([C@H](O)CO)[C@@H](CN1C2=NC(=O)N([Si](C)(C)C)C(=O)C2=NC2=CC=CC=C21)O[Si](C)(C)C	standard non polar	2025-10-24	2178.93
Gas Chromatography	Reduced riboflavin_TMS_26	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](CN1C2=NC(=O)[NH]C(=O)C2=NC2=CC=CC=C21)O[Si](C)(C)C	standard non polar	2025-10-24	1380.07
Gas Chromatography	Reduced riboflavin_TMS_27	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)CN1C2=NC(=O)N([Si](C)(C)C)C(=O)C2=NC2=CC=CC=C21	standard non polar	2025-10-24	1940.96
Gas Chromatography	Reduced riboflavin_TMS_28	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](CN1C2=NC(=O)N([Si](C)(C)C)C(=O)C2=NC2=CC=CC=C21)O[Si](C)(C)C	standard non polar	2025-10-24	1474.69
Gas Chromatography	Reduced riboflavin_TMS_29	C[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](CN1C2=NC(=O)N([Si](C)(C)C)C(=O)C2=NC2=CC=CC=C21)O[Si](C)(C)C	standard non polar	2025-10-24	986.223
Gas Chromatography	Reduced riboflavin_TMS_30	C[Si](C)(C)O[C@H](CO)[C@H](O[Si](C)(C)C)[C@@H](CN1C2=NC(=O)N([Si](C)(C)C)C(=O)C2=NC2=CC=CC=C21)O[Si](C)(C)C	standard non polar	2025-10-24	2151.0
Gas Chromatography	Reduced riboflavin_TMS_31	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](CN1C2=NC(=O)N([Si](C)(C)C)C(=O)C2=NC2=CC=CC=C21)O[Si](C)(C)C	standard non polar	2025-10-24	2148.93
Gas Chromatography	Reduced riboflavin_TMS_1	C[Si](C)(C)OC[C@@H](O)[C@H](O)[C@H](O)CN1C2=NC(=O)[NH]C(=O)C2=NC2=CC=CC=C21	standard polar	2025-10-24	1989.43
Gas Chromatography	Reduced riboflavin_TMS_2	C[Si](C)(C)O[C@H](CO)[C@H](O)[C@H](O)CN1C2=NC(=O)[NH]C(=O)C2=NC2=CC=CC=C21	standard polar	2025-10-24	2142.7
Gas Chromatography	Reduced riboflavin_TMS_3	C[Si](C)(C)O[C@@H]([C@H](O)CO)[C@H](O)CN1C2=NC(=O)[NH]C(=O)C2=NC2=CC=CC=C21	standard polar	2025-10-24	1599.31
Gas Chromatography	Reduced riboflavin_TMS_4	C[Si](C)(C)O[C@H](CN1C2=NC(=O)[NH]C(=O)C2=NC2=CC=CC=C21)[C@@H](O)[C@H](O)CO	standard polar	2025-10-24	2277.46
Gas Chromatography	Reduced riboflavin_TMS_5	C[Si](C)(C)N1C(=O)N=C2C(=NC3=CC=CC=C3N2C[C@@H](O)[C@@H](O)[C@H](O)CO)C1=O	standard polar	2025-10-24	2078.77
Gas Chromatography	Reduced riboflavin_TMS_6	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O)[C@H](O)CN1C2=NC(=O)[NH]C(=O)C2=NC2=CC=CC=C21	standard polar	2025-10-24	1619.58
Gas Chromatography	Reduced riboflavin_TMS_7	C[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C)[C@H](O)CN1C2=NC(=O)[NH]C(=O)C2=NC2=CC=CC=C21	standard polar	2025-10-24	1983.89
Gas Chromatography	Reduced riboflavin_TMS_8	C[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](CN1C2=NC(=O)[NH]C(=O)C2=NC2=CC=CC=C21)O[Si](C)(C)C	standard polar	2025-10-24	1658.84
Gas Chromatography	Reduced riboflavin_TMS_9	C[Si](C)(C)OC[C@@H](O)[C@H](O)[C@H](O)CN1C2=NC(=O)N([Si](C)(C)C)C(=O)C2=NC2=CC=CC=C21	standard polar	2025-10-24	2761.44
Gas Chromatography	Reduced riboflavin_TMS_10	C[Si](C)(C)O[C@H](CO)[C@H](O[Si](C)(C)C)[C@H](O)CN1C2=NC(=O)[NH]C(=O)C2=NC2=CC=CC=C21	standard polar	2025-10-24	2617.47
Gas Chromatography	Reduced riboflavin_TMS_11	C[Si](C)(C)O[C@H](CO)[C@H](O)[C@@H](CN1C2=NC(=O)[NH]C(=O)C2=NC2=CC=CC=C21)O[Si](C)(C)C	standard polar	2025-10-24	3051.04
Gas Chromatography	Reduced riboflavin_TMS_12	C[Si](C)(C)O[C@H](CO)[C@H](O)[C@H](O)CN1C2=NC(=O)N([Si](C)(C)C)C(=O)C2=NC2=CC=CC=C21	standard polar	2025-10-24	2075.93
Gas Chromatography	Reduced riboflavin_TMS_13	C[Si](C)(C)O[C@@H]([C@H](O)CO)[C@@H](CN1C2=NC(=O)[NH]C(=O)C2=NC2=CC=CC=C21)O[Si](C)(C)C	standard polar	2025-10-24	2912.0
Gas Chromatography	Reduced riboflavin_TMS_14	C[Si](C)(C)O[C@@H]([C@H](O)CO)[C@H](O)CN1C2=NC(=O)N([Si](C)(C)C)C(=O)C2=NC2=CC=CC=C21	standard polar	2025-10-24	2113.72
Gas Chromatography	Reduced riboflavin_TMS_15	C[Si](C)(C)O[C@H](CN1C2=NC(=O)N([Si](C)(C)C)C(=O)C2=NC2=CC=CC=C21)[C@@H](O)[C@H](O)CO	standard polar	2025-10-24	2462.78
Gas Chromatography	Reduced riboflavin_TMS_16	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)CN1C2=NC(=O)[NH]C(=O)C2=NC2=CC=CC=C21	standard polar	2025-10-24	2560.95
Gas Chromatography	Reduced riboflavin_TMS_17	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](CN1C2=NC(=O)[NH]C(=O)C2=NC2=CC=CC=C21)O[Si](C)(C)C	standard polar	2025-10-24	1471.04
Gas Chromatography	Reduced riboflavin_TMS_18	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O)[C@H](O)CN1C2=NC(=O)N([Si](C)(C)C)C(=O)C2=NC2=CC=CC=C21	standard polar	2025-10-24	2157.23
Gas Chromatography	Reduced riboflavin_TMS_19	C[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](CN1C2=NC(=O)[NH]C(=O)C2=NC2=CC=CC=C21)O[Si](C)(C)C	standard polar	2025-10-24	3287.28
Gas Chromatography	Reduced riboflavin_TMS_20	C[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C)[C@H](O)CN1C2=NC(=O)N([Si](C)(C)C)C(=O)C2=NC2=CC=CC=C21	standard polar	2025-10-24	2637.94
Gas Chromatography	Reduced riboflavin_TMS_21	C[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](CN1C2=NC(=O)N([Si](C)(C)C)C(=O)C2=NC2=CC=CC=C21)O[Si](C)(C)C	standard polar	2025-10-24	1178.82
Gas Chromatography	Reduced riboflavin_TMS_22	C[Si](C)(C)O[C@H](CO)[C@H](O[Si](C)(C)C)[C@@H](CN1C2=NC(=O)[NH]C(=O)C2=NC2=CC=CC=C21)O[Si](C)(C)C	standard polar	2025-10-24	2268.0
Gas Chromatography	Reduced riboflavin_TMS_23	C[Si](C)(C)O[C@H](CO)[C@H](O[Si](C)(C)C)[C@H](O)CN1C2=NC(=O)N([Si](C)(C)C)C(=O)C2=NC2=CC=CC=C21	standard polar	2025-10-24	1719.84
Gas Chromatography	Reduced riboflavin_TMS_24	C[Si](C)(C)O[C@H](CO)[C@H](O)[C@@H](CN1C2=NC(=O)N([Si](C)(C)C)C(=O)C2=NC2=CC=CC=C21)O[Si](C)(C)C	standard polar	2025-10-24	1558.0
Gas Chromatography	Reduced riboflavin_TMS_25	C[Si](C)(C)O[C@@H]([C@H](O)CO)[C@@H](CN1C2=NC(=O)N([Si](C)(C)C)C(=O)C2=NC2=CC=CC=C21)O[Si](C)(C)C	standard polar	2025-10-24	1717.76
Gas Chromatography	Reduced riboflavin_TMS_26	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](CN1C2=NC(=O)[NH]C(=O)C2=NC2=CC=CC=C21)O[Si](C)(C)C	standard polar	2025-10-24	2947.62
Gas Chromatography	Reduced riboflavin_TMS_27	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)CN1C2=NC(=O)N([Si](C)(C)C)C(=O)C2=NC2=CC=CC=C21	standard polar	2025-10-24	1996.4
Gas Chromatography	Reduced riboflavin_TMS_28	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](CN1C2=NC(=O)N([Si](C)(C)C)C(=O)C2=NC2=CC=CC=C21)O[Si](C)(C)C	standard polar	2025-10-24	1012.18
Gas Chromatography	Reduced riboflavin_TMS_29	C[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](CN1C2=NC(=O)N([Si](C)(C)C)C(=O)C2=NC2=CC=CC=C21)O[Si](C)(C)C	standard polar	2025-10-24	1062.57
Gas Chromatography	Reduced riboflavin_TMS_30	C[Si](C)(C)O[C@H](CO)[C@H](O[Si](C)(C)C)[C@@H](CN1C2=NC(=O)N([Si](C)(C)C)C(=O)C2=NC2=CC=CC=C21)O[Si](C)(C)C	standard polar	2025-10-24	2536.46
Gas Chromatography	Reduced riboflavin_TMS_31	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](CN1C2=NC(=O)N([Si](C)(C)C)C(=O)C2=NC2=CC=CC=C21)O[Si](C)(C)C	standard polar	2025-10-24	1999.36

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192340	Flavin reductase (NADPH)	Unknown	P30043	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
MMDBr0019183	Riboflavin	Reduced riboflavin	NAD(P)H-flavin reductase	Reduction	PathBank	31602464

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Proteobacteria	123	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human sputum; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab	Unknown; Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	229	Pig ; Human feces; Human ; Human subgingival plaque; Cattle	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	81	Human feces; Human pleural fluid plaque; Human dental plaque; Human sputum; Human ; Human nasopharyngeal swab; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	62	Human feces; Human appendix biopsy; Human ; Human gastric fluid; Human saliva; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria/Eubacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	4	Human feces; Human	Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	2		Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Tenericutes	2	Human feces	Metabolic reconstruction
Bacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human sputum; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab	Unknown; Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

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

External Links

HMDB ID

HMDB0001557

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB112174

KNApSAcK ID

Not Available

Chemspider ID

17216138

KEGG Compound ID

C01007

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6322

PubChem Compound

22833571

PDB ID

Not Available

ChEBI ID

169293

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]
Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]
Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for Reduced riboflavin (MMDBc0030337)

MOL for #<Metabolite:0x00007f9adb0745b8>

3D MOL for #<Metabolite:0x00007f9adb0745b8>

3D SDF for #<Metabolite:0x00007f9adb0745b8>

3D-SDF for #<Metabolite:0x00007f9adb0745b8>

PDB for #<Metabolite:0x00007f9adb0745b8>

3D PDB for #<Metabolite:0x00007f9adb0745b8>

SMILES for #<Metabolite:0x00007f9adb0745b8>

INCHI for #<Metabolite:0x00007f9adb0745b8>

Structure for #<Metabolite:0x00007f9adb0745b8>

3D Structure for #<Metabolite:0x00007f9adb0745b8>