MiMeDB: Showing metabocard for 1,2-Dioctanoyl-sn-glycero-3-phosphate (MMDBc0057171)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-11-09 19:22:49 UTC

Update Date

2025-10-07 16:09:54 UTC

Metabolite ID

MMDBc0057171

Metabolite Identification

Common Name

1,2-Dioctanoyl-sn-glycero-3-phosphate

Description

1,2-Dioctanoyl-sn-glycero-3-phosphate is a phospholipid belonging to the class of glycerophospholipids, characterized by its two octanoyl fatty acid chains esterified to the glycerol backbone at the sn-1 and sn-2 positions, with a phosphate group at the sn-3 position. This unique structure contributes to its role in various cellular processes, including membrane dynamics and signaling pathways. It has been implicated in the regulation of the mTOR pathway, where it acts as an activator, influencing cell viability and phosphorylation states. Specifically, studies have shown that the mTOR activator 1,2-dioctanoyl-sn-glycero-3-phosphate (C8-PA) enhances cell viability and counteracts the effects of mTOR inhibitors like rapamycin, which reduces cell viability in certain cancer cell lines (PMID:26287365 ). This highlights its potential involvement in lipid-mediated signaling mechanisms and cellular responses to stress or treatment, underscoring its relevance in metabolic and oncological research.

Structure

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

PA(8:0/8:0)
  Mrv1652309161705492D          

 29 28  0  0  1  0            999 V2000
   -0.1691    0.3607    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8792    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5896    0.3607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2414   -0.3494    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5796   -0.3494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5412    0.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2514    0.3607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0098    0.3436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2620    0.6480    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.9002    0.0209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2620    1.3958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2996    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2996    1.5409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0137    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7279    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4420    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1561    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8702    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5844    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2985    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3235   -0.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3235   -1.5406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0377   -0.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7518   -0.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4659   -0.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1801   -0.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8942   -0.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6083   -0.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3224   -0.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  1  4  1  1  0  0  0
  2  3  1  0  0  0  0
  3 12  1  0  0  0  0
  6  1  1  0  0  0  0
  7  6  1  0  0  0  0
  9  8  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  9  7  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21  5  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END

HMDB0114771
     RDKit          3D
PA(8:0/8:0)
 65 64  0  0  0  0  0  0  0  0999 V2000
    6.0688    4.4902   -1.5117 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5239    3.0896   -1.8622 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8238    2.0762   -0.9730 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3409    2.1158   -1.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6679    1.1240   -0.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1421   -0.2614   -0.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4976   -1.2446    0.4031 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0303   -1.1911    0.2521 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3543   -0.2660    0.7572 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3981   -2.1795   -0.4548 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0240   -2.2439   -0.6604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7198   -2.3600    0.6580 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1014   -3.3785    1.5553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3380   -4.6380    1.0365 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3301   -5.8628    1.9923 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.5208   -5.9827    3.2365 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9193   -5.5214    2.4187 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2316   -7.3016    1.0698 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0981   -2.4636    0.4816 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9366   -1.4337    0.8650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5319   -0.3622    1.3804 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4020   -1.6516    0.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7265   -1.2401   -0.7603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4054    0.2000   -0.9982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2166    1.0696   -0.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8556    2.5314   -0.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6504    3.4122    0.5523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3057    4.8595    0.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9400    5.1772   -1.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3080    4.9009   -2.1787 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6536    4.4530   -0.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3958    2.8334   -2.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6075    3.0295   -1.6132 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1250    2.2257    0.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2527    1.0827   -1.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0009    1.8866   -2.1622 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9611    3.1258   -0.8456 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7945    1.3757    0.8554 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5708    1.1894   -0.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8300   -0.5645   -1.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2436   -0.3924   -0.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7819   -1.0328    1.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8205   -2.2965    0.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3704   -1.3748   -1.2335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1954   -3.1526   -1.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5465   -1.3623    1.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9882   -3.2013    1.5880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4467   -3.2823    2.6157 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9776   -5.4675    3.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1464   -7.5997    0.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6060   -2.7343    0.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9387   -1.1029    1.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1728   -1.8688   -1.5178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8216   -1.3778   -0.9413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6218    0.4267   -2.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3035    0.3692   -0.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9445    0.8548    0.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3019    0.9094   -0.2179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1425    2.7551   -1.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7783    2.6781   -0.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7372    3.2641    0.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3848    3.1944    1.6040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2102    5.0312    0.2590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6853    5.1655   -0.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7340    5.4961    1.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 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
 15 17  1  0
 15 18  1  0
 12 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  0
  7 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  1
 13 47  1  0
 13 48  1  0
 17 49  1  0
 18 50  1  0
 22 51  1  0
 22 52  1  0
 23 53  1  0
 23 54  1  0
 24 55  1  0
 24 56  1  0
 25 57  1  0
 25 58  1  0
 26 59  1  0
 26 60  1  0
 27 61  1  0
 27 62  1  0
 28 63  1  0
 28 64  1  0
 28 65  1  0
M  END

PA(8:0/8:0)
  Mrv1652309161705492D          

 29 28  0  0  1  0            999 V2000
   -0.1691    0.3607    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8792    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5896    0.3607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2414   -0.3494    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5796   -0.3494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5412    0.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2514    0.3607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0098    0.3436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2620    0.6480    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.9002    0.0209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2620    1.3958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2996    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2996    1.5409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0137    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7279    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4420    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1561    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8702    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5844    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2985    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3235   -0.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3235   -1.5406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0377   -0.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7518   -0.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4659   -0.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1801   -0.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8942   -0.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6083   -0.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3224   -0.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  1  4  1  1  0  0  0
  2  3  1  0  0  0  0
  3 12  1  0  0  0  0
  6  1  1  0  0  0  0
  7  6  1  0  0  0  0
  9  8  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  9  7  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21  5  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0057171

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@](COC(=O)CCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C19H37O8P/c1-3-5-7-9-11-13-18(20)25-15-17(16-26-28(22,23)24)27-19(21)14-12-10-8-6-4-2/h17H,3-16H2,1-2H3,(H2,22,23,24)/t17-/m1/s1

> <INCHI_KEY>
XYSBQYUENLDGMI-QGZVFWFLSA-N

> <FORMULA>
C19H37O8P

> <MOLECULAR_WEIGHT>
424.471

> <EXACT_MASS>
424.222605149

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
46.5990807425399

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2R)-2,3-bis(octanoyloxy)propoxy]phosphonic acid

> <ALOGPS_LOGP>
3.37

> <JCHEM_LOGP>
4.766429110666664

> <ALOGPS_LOGS>
-4.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.343234649149876

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.3174060830586427

> <JCHEM_PKA_STRONGEST_BASIC>
-6.744159310865084

> <JCHEM_POLAR_SURFACE_AREA>
119.35999999999999

> <JCHEM_REFRACTIVITY>
104.95579999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.33e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2,3-bis(octanoyloxy)propoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0114771
     RDKit          3D
PA(8:0/8:0)
 65 64  0  0  0  0  0  0  0  0999 V2000
    6.0688    4.4902   -1.5117 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5239    3.0896   -1.8622 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8238    2.0762   -0.9730 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3409    2.1158   -1.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6679    1.1240   -0.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1421   -0.2614   -0.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4976   -1.2446    0.4031 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0303   -1.1911    0.2521 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3543   -0.2660    0.7572 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3981   -2.1795   -0.4548 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0240   -2.2439   -0.6604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7198   -2.3600    0.6580 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1014   -3.3785    1.5553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3380   -4.6380    1.0365 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3301   -5.8628    1.9923 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.5208   -5.9827    3.2365 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9193   -5.5214    2.4187 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2316   -7.3016    1.0698 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0981   -2.4636    0.4816 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9366   -1.4337    0.8650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5319   -0.3622    1.3804 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4020   -1.6516    0.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7265   -1.2401   -0.7603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4054    0.2000   -0.9982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2166    1.0696   -0.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8556    2.5314   -0.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6504    3.4122    0.5523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3057    4.8595    0.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9400    5.1772   -1.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3080    4.9009   -2.1787 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6536    4.4530   -0.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3958    2.8334   -2.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6075    3.0295   -1.6132 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1250    2.2257    0.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2527    1.0827   -1.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0009    1.8866   -2.1622 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9611    3.1258   -0.8456 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7945    1.3757    0.8554 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5708    1.1894   -0.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8300   -0.5645   -1.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2436   -0.3924   -0.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7819   -1.0328    1.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8205   -2.2965    0.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3704   -1.3748   -1.2335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1954   -3.1526   -1.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5465   -1.3623    1.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9882   -3.2013    1.5880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4467   -3.2823    2.6157 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9776   -5.4675    3.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1464   -7.5997    0.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6060   -2.7343    0.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9387   -1.1029    1.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1728   -1.8688   -1.5178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8216   -1.3778   -0.9413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6218    0.4267   -2.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3035    0.3692   -0.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9445    0.8548    0.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3019    0.9094   -0.2179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1425    2.7551   -1.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7783    2.6781   -0.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7372    3.2641    0.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3848    3.1944    1.6040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2102    5.0312    0.2590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6853    5.1655   -0.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7340    5.4961    1.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 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
 15 17  1  0
 15 18  1  0
 12 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  0
  7 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  1
 13 47  1  0
 13 48  1  0
 17 49  1  0
 18 50  1  0
 22 51  1  0
 22 52  1  0
 23 53  1  0
 23 54  1  0
 24 55  1  0
 24 56  1  0
 25 57  1  0
 25 58  1  0
 26 59  1  0
 26 60  1  0
 27 61  1  0
 27 62  1  0
 28 63  1  0
 28 64  1  0
 28 65  1  0
M  END

HEADER    PROTEIN                                 16-SEP-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: PA(8:0/8:0)                                       
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-SEP-17         0                                  
HETATM    1  C   UNK     0      -0.316   0.673   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.641   1.436   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.967   0.673   0.000  0.00  0.00           O+0
HETATM    4  H   UNK     0       0.451  -0.652   0.000  0.00  0.00           H+0
HETATM    5  O   UNK     0      -1.082  -0.652   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.010   1.439   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.336   0.673   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       5.618   0.641   0.000  0.00  0.00           O+0
HETATM    9  P   UNK     0       4.222   1.210   0.000  0.00  0.00           P+0
HETATM   10  O   UNK     0       3.547   0.039   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       4.222   2.606   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.293   1.436   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.293   2.876   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -5.626   0.665   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.959   1.436   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.292   0.665   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -9.625   1.436   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -10.958   0.665   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -12.291   1.436   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -13.624   0.665   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.471  -1.436   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.471  -2.876   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -3.804  -0.665   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.137  -1.436   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.470  -0.665   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -7.803  -1.436   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -9.136  -0.665   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -10.469  -1.436   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -11.802  -0.665   0.000  0.00  0.00           C+0
CONECT    1    2    5    4    6                                             
CONECT    2    1    3                                                       
CONECT    3    2   12                                                       
CONECT    4    1                                                            
CONECT    5    1   21                                                       
CONECT    6    1    7                                                       
CONECT    7    6    9                                                       
CONECT    8    9                                                            
CONECT    9    8   10   11    7                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    3   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21    5   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   56    0
END

COMPND    HMDB0114771
HETATM    1  C1  UNL     1       6.069   4.490  -1.512  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.524   3.090  -1.862  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.824   2.076  -0.973  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.341   2.116  -1.127  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.668   1.124  -0.207  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.142  -0.261  -0.540  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.498  -1.245   0.403  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.030  -1.191   0.252  1.00  0.00           C  
HETATM    9  O1  UNL     1       1.354  -0.266   0.757  1.00  0.00           O  
HETATM   10  O2  UNL     1       1.398  -2.179  -0.455  1.00  0.00           O  
HETATM   11  C9  UNL     1       0.024  -2.244  -0.660  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.720  -2.360   0.658  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.101  -3.379   1.555  1.00  0.00           C  
HETATM   14  O3  UNL     1      -0.338  -4.638   1.037  1.00  0.00           O  
HETATM   15  P1  UNL     1       0.330  -5.863   1.992  1.00  0.00           P  
HETATM   16  O4  UNL     1      -0.521  -5.983   3.236  1.00  0.00           O  
HETATM   17  O5  UNL     1       1.919  -5.521   2.419  1.00  0.00           O  
HETATM   18  O6  UNL     1       0.232  -7.302   1.070  1.00  0.00           O  
HETATM   19  O7  UNL     1      -2.098  -2.464   0.482  1.00  0.00           O  
HETATM   20  C12 UNL     1      -2.937  -1.434   0.865  1.00  0.00           C  
HETATM   21  O8  UNL     1      -2.532  -0.362   1.380  1.00  0.00           O  
HETATM   22  C13 UNL     1      -4.402  -1.652   0.633  1.00  0.00           C  
HETATM   23  C14 UNL     1      -4.727  -1.240  -0.760  1.00  0.00           C  
HETATM   24  C15 UNL     1      -4.405   0.200  -0.998  1.00  0.00           C  
HETATM   25  C16 UNL     1      -5.217   1.070  -0.067  1.00  0.00           C  
HETATM   26  C17 UNL     1      -4.856   2.531  -0.367  1.00  0.00           C  
HETATM   27  C18 UNL     1      -5.650   3.412   0.552  1.00  0.00           C  
HETATM   28  C19 UNL     1      -5.306   4.860   0.256  1.00  0.00           C  
HETATM   29  H1  UNL     1       6.940   5.177  -1.479  1.00  0.00           H  
HETATM   30  H2  UNL     1       5.308   4.901  -2.179  1.00  0.00           H  
HETATM   31  H3  UNL     1       5.654   4.453  -0.482  1.00  0.00           H  
HETATM   32  H4  UNL     1       6.396   2.833  -2.916  1.00  0.00           H  
HETATM   33  H5  UNL     1       7.607   3.030  -1.613  1.00  0.00           H  
HETATM   34  H6  UNL     1       6.125   2.226   0.069  1.00  0.00           H  
HETATM   35  H7  UNL     1       6.253   1.083  -1.294  1.00  0.00           H  
HETATM   36  H8  UNL     1       4.001   1.887  -2.162  1.00  0.00           H  
HETATM   37  H9  UNL     1       3.961   3.126  -0.846  1.00  0.00           H  
HETATM   38  H10 UNL     1       3.795   1.376   0.855  1.00  0.00           H  
HETATM   39  H11 UNL     1       2.571   1.189  -0.460  1.00  0.00           H  
HETATM   40  H12 UNL     1       3.830  -0.564  -1.579  1.00  0.00           H  
HETATM   41  H13 UNL     1       5.244  -0.392  -0.487  1.00  0.00           H  
HETATM   42  H14 UNL     1       3.782  -1.033   1.463  1.00  0.00           H  
HETATM   43  H15 UNL     1       3.821  -2.297   0.145  1.00  0.00           H  
HETATM   44  H16 UNL     1      -0.370  -1.375  -1.234  1.00  0.00           H  
HETATM   45  H17 UNL     1      -0.195  -3.153  -1.296  1.00  0.00           H  
HETATM   46  H18 UNL     1      -0.547  -1.362   1.162  1.00  0.00           H  
HETATM   47  H19 UNL     1       0.988  -3.201   1.588  1.00  0.00           H  
HETATM   48  H20 UNL     1      -0.447  -3.282   2.616  1.00  0.00           H  
HETATM   49  H21 UNL     1       1.978  -5.468   3.396  1.00  0.00           H  
HETATM   50  H22 UNL     1       1.146  -7.600   0.869  1.00  0.00           H  
HETATM   51  H23 UNL     1      -4.606  -2.734   0.815  1.00  0.00           H  
HETATM   52  H24 UNL     1      -4.939  -1.103   1.410  1.00  0.00           H  
HETATM   53  H25 UNL     1      -4.173  -1.869  -1.518  1.00  0.00           H  
HETATM   54  H26 UNL     1      -5.822  -1.378  -0.941  1.00  0.00           H  
HETATM   55  H27 UNL     1      -4.622   0.427  -2.067  1.00  0.00           H  
HETATM   56  H28 UNL     1      -3.303   0.369  -0.838  1.00  0.00           H  
HETATM   57  H29 UNL     1      -4.944   0.855   0.979  1.00  0.00           H  
HETATM   58  H30 UNL     1      -6.302   0.909  -0.218  1.00  0.00           H  
HETATM   59  H31 UNL     1      -5.143   2.755  -1.430  1.00  0.00           H  
HETATM   60  H32 UNL     1      -3.778   2.678  -0.228  1.00  0.00           H  
HETATM   61  H33 UNL     1      -6.737   3.264   0.418  1.00  0.00           H  
HETATM   62  H34 UNL     1      -5.385   3.194   1.604  1.00  0.00           H  
HETATM   63  H35 UNL     1      -4.210   5.031   0.259  1.00  0.00           H  
HETATM   64  H36 UNL     1      -5.685   5.165  -0.749  1.00  0.00           H  
HETATM   65  H37 UNL     1      -5.734   5.496   1.054  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3   32   33
CONECT    3    4   34   35
CONECT    4    5   36   37
CONECT    5    6   38   39
CONECT    6    7   40   41
CONECT    7    8   42   43
CONECT    8    9    9   10
CONECT   10   11
CONECT   11   12   44   45
CONECT   12   13   19   46
CONECT   13   14   47   48
CONECT   14   15
CONECT   15   16   16   17   18
CONECT   17   49
CONECT   18   50
CONECT   19   20
CONECT   20   21   21   22
CONECT   22   23   51   52
CONECT   23   24   53   54
CONECT   24   25   55   56
CONECT   25   26   57   58
CONECT   26   27   59   60
CONECT   27   28   61   62
CONECT   28   63   64   65
END

HMDB0114771
     RDKit          3D
PA(8:0/8:0)
 65 64  0  0  0  0  0  0  0  0999 V2000
    6.0688    4.4902   -1.5117 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5239    3.0896   -1.8622 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8238    2.0762   -0.9730 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3409    2.1158   -1.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6679    1.1240   -0.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1421   -0.2614   -0.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4976   -1.2446    0.4031 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0303   -1.1911    0.2521 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3543   -0.2660    0.7572 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3981   -2.1795   -0.4548 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0240   -2.2439   -0.6604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7198   -2.3600    0.6580 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1014   -3.3785    1.5553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3380   -4.6380    1.0365 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3301   -5.8628    1.9923 P   0  0  0  0  0  5  0  0  0  0  0  0
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    0.2316   -7.3016    1.0698 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9366   -1.4337    0.8650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5319   -0.3622    1.3804 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4020   -1.6516    0.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7265   -1.2401   -0.7603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4054    0.2000   -0.9982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2166    1.0696   -0.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8556    2.5314   -0.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6504    3.4122    0.5523 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.9400    5.1772   -1.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3080    4.9009   -2.1787 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6536    4.4530   -0.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3958    2.8334   -2.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6075    3.0295   -1.6132 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1250    2.2257    0.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2527    1.0827   -1.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0009    1.8866   -2.1622 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9611    3.1258   -0.8456 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7945    1.3757    0.8554 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5708    1.1894   -0.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8300   -0.5645   -1.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2436   -0.3924   -0.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7819   -1.0328    1.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8205   -2.2965    0.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3704   -1.3748   -1.2335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1954   -3.1526   -1.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5465   -1.3623    1.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9882   -3.2013    1.5880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4467   -3.2823    2.6157 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9776   -5.4675    3.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1464   -7.5997    0.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6060   -2.7343    0.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9387   -1.1029    1.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1728   -1.8688   -1.5178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8216   -1.3778   -0.9413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6218    0.4267   -2.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3035    0.3692   -0.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9445    0.8548    0.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3019    0.9094   -0.2179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1425    2.7551   -1.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7783    2.6781   -0.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7372    3.2641    0.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3848    3.1944    1.6040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2102    5.0312    0.2590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6853    5.1655   -0.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7340    5.4961    1.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
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  7  8  1  0
  8  9  2  0
  8 10  1  0
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  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  0
  7 43  1  0
 11 44  1  0
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 22 52  1  0
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 28 63  1  0
 28 64  1  0
 28 65  1  0
M  END

Synonyms

Value	Source
(2R)-2,3-Bis(octanoyloxy)propyl hydrogen phosphate	ChEBI
1,2-Dicapryloyl-sn-glycero-3-phosphate	ChEBI
1,2-Dioctanoyl-sn-glycero-3-phosphatidic acid	ChEBI
Dioctanoylphosphatidic acid	ChEBI
PA(16:0)	ChEBI
(2R)-2,3-Bis(octanoyloxy)propyl hydrogen phosphoric acid	Generator
1,2-Dicapryloyl-sn-glycero-3-phosphoric acid	Generator
1,2-Dioctanoyl-sn-glycero-3-phosphatidate	Generator
Dioctanoylphosphatidate	Generator
1-Capryloyl-2-capryloyl-sn-glycero-3-phosphate	HMDB
1-Capryloyl-2-capryloyl-sn-phosphatidic acid	HMDB
Phosphatidic acid(8:0/8:0)	HMDB
Phosphatidic acid(16:0)	HMDB
Phosphatidate(8:0/8:0)	HMDB
Phosphatidate(16:0)	HMDB
DiC8pa	HMDB
1-capryloyl-2-capryloyl-sn-glycero-3-phosphate	SMPDB, HMDB
1-capryloyl-2-capryloyl-sn-phosphatidic acid	SMPDB, HMDB
PA(16:0)	SMPDB, ChEBI
Phosphatidic acid(8:0/8:0)	SMPDB, HMDB
Phosphatidic acid(16:0)	SMPDB, HMDB
Phosphatidate(8:0/8:0)	SMPDB, HMDB
PA(8:0/8:0)	SMPDB

Molecular Formula

C₁₉H₃₇O₈P

Average Mass

424.471

Monoisotopic Mass

424.222605149

IUPAC Name

[(2R)-2,3-bis(octanoyloxy)propoxy]phosphonic acid

Traditional Name

(2R)-2,3-bis(octanoyloxy)propoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](COC(=O)CCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCC

InChI Identifier

InChI=1S/C19H37O8P/c1-3-5-7-9-11-13-18(20)25-15-17(16-26-28(22,23)24)27-19(21)14-12-10-8-6-4-2/h17H,3-16H2,1-2H3,(H2,22,23,24)/t17-/m1/s1

InChI Key

XYSBQYUENLDGMI-QGZVFWFLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,2-diacylglycerol-3-phosphates. These are glycerol-3-phosphates in which the glycerol moiety is bonded to two aliphatic chains through ester linkages.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphates

Direct Parent

1,2-diacylglycerol-3-phosphates

Alternative Parents

Substituents

1,2-diacylglycerol-3-phosphate
Fatty acid ester
Monoalkyl phosphate
Dicarboxylic acid or derivatives
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Carboxylic acid ester
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

octanoate ester (CHEBI:79075 )
1,2-diacyl-sn-glycerol 3-phosphate (CHEBI:79075 )
Diacylglycerophosphates (LMGP10010021 )

Functional Ontology

Not Available

Physical Properties

State

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.023 g/L	ALOGPS
logP	3.37	ALOGPS
logP	4.77	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	1.32	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	104.96 m³·mol⁻¹	ChemAxon
Polarizability	46.6 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-2982600000-8363a82a0fcf968daefb	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-003b-6952000000-04275a2d089ef16b6a0c	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f9l-7941000000-7897b3d3861f3263467f	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-4940300000-51d28b235cf2acb9b0fd	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9400000000-0cea4b834e9e6527db16	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-ae2d1a392d4c601b89cb	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0000900000-83861f4bdc4573966bb8	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0009900000-70ff72750740766f2ff8	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f6t-0009400000-c5af336c881f6f839538	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a6r-0000900000-8a1ad3af29b2312f7e8e	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0005900000-f6b7fe6dc78dbc38af25	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0059-0069300000-6f5b25f4f7f707867c84	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0000900000-b67b347553223a7556c8	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00fu-1770900000-e9fc6fbc349046b80854	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-1920100000-bd84110b6ee6a0b98554	2021-09-24	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)	2025-10-24	251.9
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	59.1
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-24	613.0
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	757.5
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	745.9
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-24	215.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	2595.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	263.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	277.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	491.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	272.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	170.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	202.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	94.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	281.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	416.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	402.3
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	1438.4
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	1348.9

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	1,2-Dioctanoyl-sn-glycero-3-phosphate_TMS_1	CCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCC	standard non polar	2025-10-24	1739.9
Gas Chromatography	1,2-Dioctanoyl-sn-glycero-3-phosphate_TMS_2	CCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCC	standard non polar	2025-10-24	1488.72
Gas Chromatography	1,2-Dioctanoyl-sn-glycero-3-phosphate_TMS_1	CCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCC	standard polar	2025-10-24	2667.34
Gas Chromatography	1,2-Dioctanoyl-sn-glycero-3-phosphate_TMS_2	CCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCC	standard polar	2025-10-24	2562.74

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

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

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
MMDBr0038992	1,2-Dioctanoyl-sn-glycero-3-phosphate	1-Dioctanoyl-sn-glycero-3-phosphate	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880

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

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

External Links

HMDB ID

HMDB0114771

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

113635

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

128167

PDB ID

Not Available

ChEBI ID

79075

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

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 1,2-Dioctanoyl-sn-glycero-3-phosphate (MMDBc0057171)

MOL for #<Metabolite:0x00007f2e50503180>

3D MOL for #<Metabolite:0x00007f2e50503180>

3D SDF for #<Metabolite:0x00007f2e50503180>

3D-SDF for #<Metabolite:0x00007f2e50503180>

PDB for #<Metabolite:0x00007f2e50503180>

3D PDB for #<Metabolite:0x00007f2e50503180>

SMILES for #<Metabolite:0x00007f2e50503180>

INCHI for #<Metabolite:0x00007f2e50503180>

Structure for #<Metabolite:0x00007f2e50503180>

3D Structure for #<Metabolite:0x00007f2e50503180>