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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-07-25 00:01:42 UTC

Update Date

2022-03-07 02:51:26 UTC

HMDB ID

HMDB0012496

Secondary Accession Numbers

HMDB12496

Metabolite Identification

Common Name

1-Lyso-2-arachidonoyl-phosphatidate

Description

LPA(0:0/20:4n6) is a lysophosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. Lysophosphatidic acids can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) or C-2 (sn-2) position. Fatty acids containing 16 and 18 carbons are the most common. Lysophosphatidic acid is the simplest possible glycerophospholipid. It is the biosynthetic precursor of phosphatidic acid. Although it is present at very low levels only in animal tissues, it is extremely important biologically, influencing many biochemical processes. In particular, lysophosphatidic acid is an intercellular lipid mediator with growth factor-like activities, and is rapidly produced and released from activated platelets to influence target cells.LPA is a pluripotent lipid mediator controlling growth, motility, and differentiation, that has a strong influence on the chemotaxis and ultrastructure of human neutrophils (PMID 7416233 ). In serum and plasma, LPA is mainly converted from lysophospholipids, whereas in platelets and some cancer cells it is converted from phosphatidic acid. In each pathway, at least two phospholipase activities are required: phospholipase A1 (PLA1)/PLA2 plus lysophospholipase D (lysoPLD) activities are involved in the first pathway and phospholipase D (PLD) plus PLA1/PLA2 activities are involved in the second pathway. (PMID 15271293 ).

Structure

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


  Mrv1652305171802112D          

 31 30  0  0  0  0            999 V2000
   -3.0832   -5.7823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3533   -5.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8132   -4.3791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0832   -3.5995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5431   -2.9759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8132   -2.1963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2731   -1.5727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5431   -0.7931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0030   -0.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1929   -0.3254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6528    0.2982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9229    1.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3828    1.7014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6528    2.4810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1127    3.1046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6974    2.9487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0476    3.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5877    4.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3979    3.8842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6679    3.1046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9379    4.5078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7481    4.3519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0181    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4780    2.9487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2882    4.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0983    4.8196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6384    5.4433    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.1785    6.0669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2620    4.9032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0148    5.9834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  4  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  4  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  4  0  0  0
 15 16  2  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
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 30 28  1  0  0  0  0
 31 28  1  0  0  0  0
M  END

HMDB0012496
     RDKit          3D
1-Lyso-2-arachidonoyl-phosphatidate
 70 69  0  0  0  0  0  0  0  0999 V2000
   -7.7088    2.3395    0.2027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5972    1.8270    1.5994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3057    0.3718    1.7825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3096   -0.5979    1.2742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6113   -0.6582   -0.1567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5883   -1.0818   -1.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3657   -1.4995   -0.8987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4555   -1.8906   -2.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2312   -1.0759   -2.0517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9756   -0.1024   -1.1910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7371    0.7263   -1.2308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8420    0.3441   -2.3246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6223   -0.0821   -2.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0654   -0.2544   -0.8598 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4337   -1.6839   -0.7741 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6291   -2.1269   -0.6612 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8473   -1.3075   -0.5965 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7898   -1.6416   -1.7420 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0034   -0.8029   -1.6547 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7894   -1.0194   -0.4185 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5284   -1.8564    0.4736 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9454   -0.2493   -0.1606 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6902   -0.4623    1.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0905   -0.8542    0.5825 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8996   -1.0846    1.6736 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7395    0.8597    1.7575 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3729    1.7674    0.8848 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4952    3.3028    1.5993 P   0  0  0  0  0  5  0  0  0  0  0  0
    9.4574    3.1741    2.7613 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9493    3.7374    2.1249 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0838    4.3614    0.4171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2121    1.6425   -0.4859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7635    2.5226   -0.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1464    3.3391    0.1078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5478    2.0979    2.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8218    2.4638    2.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2779    0.1684    1.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1957    0.2487    2.9126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0589   -1.6186    1.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2643   -0.3606    1.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1400    0.2746   -0.4841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4746   -1.4250   -0.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8673   -1.0553   -2.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9755   -1.6002    0.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9928   -1.8891   -2.9970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1333   -2.9602   -1.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4741   -1.2487   -2.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6990    0.1054   -0.4187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2843    0.8220   -0.2561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1175    1.7699   -1.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2468    0.4298   -3.3551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0390   -0.3412   -3.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9010    0.4557   -0.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5990   -0.0449    0.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4124   -2.3832   -0.8139 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7852   -3.2237   -0.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6732   -0.2265   -0.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3050   -1.4780    0.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2762   -1.4276   -2.6988 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0650   -2.7165   -1.7157 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6742    0.2801   -1.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6876   -0.9185   -2.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2343   -1.2631    1.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4991   -0.0012   -0.0146 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0632   -1.7184   -0.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4431   -1.8913    1.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2754    0.7872    2.7260 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7161    1.2415    1.9249 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2470    3.4624    1.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4386    5.2008    0.8283 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  2  3
  7  8  1  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 11 12  1  0
 12 13  2  3
 13 14  1  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 17 18  1  0
 18 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
 23 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 28 31  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  5 42  1  0
  6 43  1  0
  7 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  0
 13 52  1  0
 14 53  1  0
 14 54  1  0
 15 55  1  0
 16 56  1  0
 17 57  1  0
 17 58  1  0
 18 59  1  0
 18 60  1  0
 19 61  1  0
 19 62  1  0
 23 63  1  0
 24 64  1  0
 24 65  1  0
 25 66  1  0
 26 67  1  0
 26 68  1  0
 30 69  1  0
 31 70  1  0
M  END


  Mrv1652305171802112D          

 31 30  0  0  0  0            999 V2000
   -3.0832   -5.7823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3533   -5.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8132   -4.3791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0832   -3.5995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5431   -2.9759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8132   -2.1963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2731   -1.5727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5431   -0.7931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0030   -0.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1929   -0.3254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6528    0.2982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9229    1.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3828    1.7014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6528    2.4810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1127    3.1046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6974    2.9487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0476    3.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5877    4.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3979    3.8842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6679    3.1046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9379    4.5078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7481    4.3519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0181    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4780    2.9487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2882    4.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0983    4.8196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6384    5.4433    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.1785    6.0669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2620    4.9032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0148    5.9834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  4  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  4  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  4  0  0  0
 15 16  2  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
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 30 28  1  0  0  0  0
 31 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012496

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO)COP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H39O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(25)30-22(20-24)21-29-31(26,27)28/h6-7,9-10,12-13,15-16,22,24H,2-5,8,11,14,17-21H2,1H3,(H2,26,27,28)

> <INCHI_KEY>
BDCFJMBXZCIVRH-UHFFFAOYSA-N

> <FORMULA>
C23H39O7P

> <MOLECULAR_WEIGHT>
458.532

> <EXACT_MASS>
458.243340594

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
49.14155179920617

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[3-hydroxy-2-(icosa-5,8,11,14-tetraenoyloxy)propoxy]phosphonic acid

> <ALOGPS_LOGP>
4.97

> <JCHEM_LOGP>
5.289061881666667

> <ALOGPS_LOGS>
-5.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.345670791975908

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.3198427008627798

> <JCHEM_PKA_STRONGEST_BASIC>
-2.983758076417394

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
127.85079999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.66e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-2-(icosa-5,8,11,14-tetraenoyloxy)propoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012496
     RDKit          3D
1-Lyso-2-arachidonoyl-phosphatidate
 70 69  0  0  0  0  0  0  0  0999 V2000
   -7.7088    2.3395    0.2027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5972    1.8270    1.5994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3057    0.3718    1.7825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3096   -0.5979    1.2742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6113   -0.6582   -0.1567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5883   -1.0818   -1.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3657   -1.4995   -0.8987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4555   -1.8906   -2.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2312   -1.0759   -2.0517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9756   -0.1024   -1.1910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7371    0.7263   -1.2308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8420    0.3441   -2.3246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6223   -0.0821   -2.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0654   -0.2544   -0.8598 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4337   -1.6839   -0.7741 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6291   -2.1269   -0.6612 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8473   -1.3075   -0.5965 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7898   -1.6416   -1.7420 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0034   -0.8029   -1.6547 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7894   -1.0194   -0.4185 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5284   -1.8564    0.4736 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9454   -0.2493   -0.1606 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6902   -0.4623    1.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0905   -0.8542    0.5825 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8996   -1.0846    1.6736 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7395    0.8597    1.7575 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3729    1.7674    0.8848 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4952    3.3028    1.5993 P   0  0  0  0  0  5  0  0  0  0  0  0
    9.4574    3.1741    2.7613 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9493    3.7374    2.1249 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0838    4.3614    0.4171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2121    1.6425   -0.4859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7635    2.5226   -0.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1464    3.3391    0.1078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5478    2.0979    2.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8218    2.4638    2.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2779    0.1684    1.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1957    0.2487    2.9126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0589   -1.6186    1.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2643   -0.3606    1.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1400    0.2746   -0.4841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4746   -1.4250   -0.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8673   -1.0553   -2.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9755   -1.6002    0.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9928   -1.8891   -2.9970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1333   -2.9602   -1.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4741   -1.2487   -2.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6990    0.1054   -0.4187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2843    0.8220   -0.2561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1175    1.7699   -1.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2468    0.4298   -3.3551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0390   -0.3412   -3.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9010    0.4557   -0.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5990   -0.0449    0.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4124   -2.3832   -0.8139 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7852   -3.2237   -0.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6732   -0.2265   -0.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3050   -1.4780    0.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2762   -1.4276   -2.6988 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0650   -2.7165   -1.7157 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6742    0.2801   -1.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6876   -0.9185   -2.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2343   -1.2631    1.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4991   -0.0012   -0.0146 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0632   -1.7184   -0.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4431   -1.8913    1.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2754    0.7872    2.7260 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7161    1.2415    1.9249 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2470    3.4624    1.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4386    5.2008    0.8283 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  2  3
  7  8  1  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 11 12  1  0
 12 13  2  3
 13 14  1  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 17 18  1  0
 18 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
 23 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 28 31  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  5 42  1  0
  6 43  1  0
  7 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  0
 13 52  1  0
 14 53  1  0
 14 54  1  0
 15 55  1  0
 16 56  1  0
 17 57  1  0
 17 58  1  0
 18 59  1  0
 18 60  1  0
 19 61  1  0
 19 62  1  0
 23 63  1  0
 24 64  1  0
 24 65  1  0
 25 66  1  0
 26 67  1  0
 26 68  1  0
 30 69  1  0
 31 70  1  0
M  END

HEADER    PROTEIN                                 17-MAY-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-MAY-18         0                                  
HETATM    1  C   UNK     0      -5.755 -10.794   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.259  -9.338   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.251  -8.174   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.755  -6.719   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.747  -5.555   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.251  -4.100   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.243  -2.936   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.747  -1.481   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.739  -0.316   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.227  -0.607   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.219   0.557   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.723   2.012   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.714   3.176   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.219   4.631   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.210   5.795   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.302   5.504   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.310   6.668   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.822   6.377   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.830   7.541   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.343   7.250   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.847   5.795   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       7.351   8.415   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.863   8.124   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.367   6.668   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.359   5.504   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       9.871   9.288   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      11.383   8.997   0.000  0.00  0.00           O+0
HETATM   28  P   UNK     0      12.392  10.161   0.000  0.00  0.00           P+0
HETATM   29  O   UNK     0      13.400  11.325   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      13.556   9.153   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      11.228  11.169   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   60    0
END

COMPND    HMDB0012496
HETATM    1  C1  UNL     1      -7.709   2.340   0.203  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.597   1.827   1.599  1.00  0.00           C  
HETATM    3  C3  UNL     1      -7.306   0.372   1.782  1.00  0.00           C  
HETATM    4  C4  UNL     1      -8.310  -0.598   1.274  1.00  0.00           C  
HETATM    5  C5  UNL     1      -8.611  -0.658  -0.157  1.00  0.00           C  
HETATM    6  C6  UNL     1      -7.588  -1.082  -1.104  1.00  0.00           C  
HETATM    7  C7  UNL     1      -6.366  -1.499  -0.899  1.00  0.00           C  
HETATM    8  C8  UNL     1      -5.456  -1.891  -2.008  1.00  0.00           C  
HETATM    9  C9  UNL     1      -4.231  -1.076  -2.052  1.00  0.00           C  
HETATM   10  C10 UNL     1      -3.976  -0.102  -1.191  1.00  0.00           C  
HETATM   11  C11 UNL     1      -2.737   0.726  -1.231  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.842   0.344  -2.325  1.00  0.00           C  
HETATM   13  C13 UNL     1      -0.622  -0.082  -2.162  1.00  0.00           C  
HETATM   14  C14 UNL     1       0.065  -0.254  -0.860  1.00  0.00           C  
HETATM   15  C15 UNL     1       0.434  -1.684  -0.774  1.00  0.00           C  
HETATM   16  C16 UNL     1       1.629  -2.127  -0.661  1.00  0.00           C  
HETATM   17  C17 UNL     1       2.847  -1.307  -0.597  1.00  0.00           C  
HETATM   18  C18 UNL     1       3.790  -1.642  -1.742  1.00  0.00           C  
HETATM   19  C19 UNL     1       5.003  -0.803  -1.655  1.00  0.00           C  
HETATM   20  C20 UNL     1       5.789  -1.019  -0.419  1.00  0.00           C  
HETATM   21  O1  UNL     1       5.528  -1.856   0.474  1.00  0.00           O  
HETATM   22  O2  UNL     1       6.945  -0.249  -0.161  1.00  0.00           O  
HETATM   23  C21 UNL     1       7.690  -0.462   1.021  1.00  0.00           C  
HETATM   24  C22 UNL     1       9.090  -0.854   0.582  1.00  0.00           C  
HETATM   25  O3  UNL     1       9.900  -1.085   1.674  1.00  0.00           O  
HETATM   26  C23 UNL     1       7.740   0.860   1.758  1.00  0.00           C  
HETATM   27  O4  UNL     1       8.373   1.767   0.885  1.00  0.00           O  
HETATM   28  P1  UNL     1       8.495   3.303   1.599  1.00  0.00           P  
HETATM   29  O5  UNL     1       9.457   3.174   2.761  1.00  0.00           O  
HETATM   30  O6  UNL     1       6.949   3.737   2.125  1.00  0.00           O  
HETATM   31  O7  UNL     1       9.084   4.361   0.417  1.00  0.00           O  
HETATM   32  H1  UNL     1      -7.212   1.642  -0.486  1.00  0.00           H  
HETATM   33  H2  UNL     1      -8.764   2.523  -0.115  1.00  0.00           H  
HETATM   34  H3  UNL     1      -7.146   3.339   0.108  1.00  0.00           H  
HETATM   35  H4  UNL     1      -8.548   2.098   2.174  1.00  0.00           H  
HETATM   36  H5  UNL     1      -6.822   2.464   2.127  1.00  0.00           H  
HETATM   37  H6  UNL     1      -6.278   0.168   1.400  1.00  0.00           H  
HETATM   38  H7  UNL     1      -7.196   0.249   2.913  1.00  0.00           H  
HETATM   39  H8  UNL     1      -8.059  -1.619   1.703  1.00  0.00           H  
HETATM   40  H9  UNL     1      -9.264  -0.361   1.876  1.00  0.00           H  
HETATM   41  H10 UNL     1      -9.140   0.275  -0.484  1.00  0.00           H  
HETATM   42  H11 UNL     1      -9.475  -1.425  -0.261  1.00  0.00           H  
HETATM   43  H12 UNL     1      -7.867  -1.055  -2.197  1.00  0.00           H  
HETATM   44  H13 UNL     1      -5.976  -1.600   0.092  1.00  0.00           H  
HETATM   45  H14 UNL     1      -5.993  -1.889  -2.997  1.00  0.00           H  
HETATM   46  H15 UNL     1      -5.133  -2.960  -1.866  1.00  0.00           H  
HETATM   47  H16 UNL     1      -3.474  -1.249  -2.811  1.00  0.00           H  
HETATM   48  H17 UNL     1      -4.699   0.105  -0.419  1.00  0.00           H  
HETATM   49  H18 UNL     1      -2.284   0.822  -0.256  1.00  0.00           H  
HETATM   50  H19 UNL     1      -3.118   1.770  -1.485  1.00  0.00           H  
HETATM   51  H20 UNL     1      -2.247   0.430  -3.355  1.00  0.00           H  
HETATM   52  H21 UNL     1      -0.039  -0.341  -3.065  1.00  0.00           H  
HETATM   53  H22 UNL     1       0.901   0.456  -0.756  1.00  0.00           H  
HETATM   54  H23 UNL     1      -0.599  -0.045   0.014  1.00  0.00           H  
HETATM   55  H24 UNL     1      -0.412  -2.383  -0.814  1.00  0.00           H  
HETATM   56  H25 UNL     1       1.785  -3.224  -0.605  1.00  0.00           H  
HETATM   57  H26 UNL     1       2.673  -0.226  -0.651  1.00  0.00           H  
HETATM   58  H27 UNL     1       3.305  -1.478   0.404  1.00  0.00           H  
HETATM   59  H28 UNL     1       3.276  -1.428  -2.699  1.00  0.00           H  
HETATM   60  H29 UNL     1       4.065  -2.717  -1.716  1.00  0.00           H  
HETATM   61  H30 UNL     1       4.674   0.280  -1.659  1.00  0.00           H  
HETATM   62  H31 UNL     1       5.688  -0.918  -2.528  1.00  0.00           H  
HETATM   63  H32 UNL     1       7.234  -1.263   1.640  1.00  0.00           H  
HETATM   64  H33 UNL     1       9.499  -0.001  -0.015  1.00  0.00           H  
HETATM   65  H34 UNL     1       9.063  -1.718  -0.107  1.00  0.00           H  
HETATM   66  H35 UNL     1      10.443  -1.891   1.483  1.00  0.00           H  
HETATM   67  H36 UNL     1       8.275   0.787   2.726  1.00  0.00           H  
HETATM   68  H37 UNL     1       6.716   1.241   1.925  1.00  0.00           H  
HETATM   69  H38 UNL     1       6.247   3.462   1.513  1.00  0.00           H  
HETATM   70  H39 UNL     1       9.439   5.201   0.828  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3   35   36
CONECT    3    4   37   38
CONECT    4    5   39   40
CONECT    5    6   41   42
CONECT    6    7    7   43
CONECT    7    8   44
CONECT    8    9   45   46
CONECT    9   10   10   47
CONECT   10   11   48
CONECT   11   12   49   50
CONECT   12   13   13   51
CONECT   13   14   52
CONECT   14   15   53   54
CONECT   15   16   16   55
CONECT   16   17   56
CONECT   17   18   57   58
CONECT   18   19   59   60
CONECT   19   20   61   62
CONECT   20   21   21   22
CONECT   22   23
CONECT   23   24   26   63
CONECT   24   25   64   65
CONECT   25   66
CONECT   26   27   67   68
CONECT   27   28
CONECT   28   29   29   30   31
CONECT   30   69
CONECT   31   70
END

HMDB0012496
     RDKit          3D
1-Lyso-2-arachidonoyl-phosphatidate
 70 69  0  0  0  0  0  0  0  0999 V2000
   -7.7088    2.3395    0.2027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5972    1.8270    1.5994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3057    0.3718    1.7825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3096   -0.5979    1.2742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6113   -0.6582   -0.1567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5883   -1.0818   -1.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3657   -1.4995   -0.8987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4555   -1.8906   -2.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2312   -1.0759   -2.0517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9756   -0.1024   -1.1910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7371    0.7263   -1.2308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8420    0.3441   -2.3246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6223   -0.0821   -2.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0654   -0.2544   -0.8598 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4337   -1.6839   -0.7741 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6291   -2.1269   -0.6612 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8473   -1.3075   -0.5965 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7898   -1.6416   -1.7420 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0034   -0.8029   -1.6547 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7894   -1.0194   -0.4185 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5284   -1.8564    0.4736 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9454   -0.2493   -0.1606 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6902   -0.4623    1.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0905   -0.8542    0.5825 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8996   -1.0846    1.6736 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7395    0.8597    1.7575 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3729    1.7674    0.8848 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4952    3.3028    1.5993 P   0  0  0  0  0  5  0  0  0  0  0  0
    9.4574    3.1741    2.7613 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9493    3.7374    2.1249 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0838    4.3614    0.4171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2121    1.6425   -0.4859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7635    2.5226   -0.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1464    3.3391    0.1078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5478    2.0979    2.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8218    2.4638    2.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2779    0.1684    1.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1957    0.2487    2.9126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0589   -1.6186    1.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2643   -0.3606    1.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1400    0.2746   -0.4841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4746   -1.4250   -0.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8673   -1.0553   -2.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9755   -1.6002    0.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9928   -1.8891   -2.9970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1333   -2.9602   -1.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4741   -1.2487   -2.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6990    0.1054   -0.4187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2843    0.8220   -0.2561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1175    1.7699   -1.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2468    0.4298   -3.3551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0390   -0.3412   -3.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9010    0.4557   -0.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5990   -0.0449    0.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4124   -2.3832   -0.8139 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7852   -3.2237   -0.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6732   -0.2265   -0.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3050   -1.4780    0.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2762   -1.4276   -2.6988 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0650   -2.7165   -1.7157 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6742    0.2801   -1.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6876   -0.9185   -2.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2343   -1.2631    1.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4991   -0.0012   -0.0146 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0632   -1.7184   -0.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4431   -1.8913    1.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2754    0.7872    2.7260 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7161    1.2415    1.9249 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2470    3.4624    1.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4386    5.2008    0.8283 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  2  3
  7  8  1  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 11 12  1  0
 12 13  2  3
 13 14  1  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 17 18  1  0
 18 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
 23 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 28 31  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  5 42  1  0
  6 43  1  0
  7 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  0
 13 52  1  0
 14 53  1  0
 14 54  1  0
 15 55  1  0
 16 56  1  0
 17 57  1  0
 17 58  1  0
 18 59  1  0
 18 60  1  0
 19 61  1  0
 19 62  1  0
 23 63  1  0
 24 64  1  0
 24 65  1  0
 25 66  1  0
 26 67  1  0
 26 68  1  0
 30 69  1  0
 31 70  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Lyso-2-arachidonoyl-phosphatidic acid	Generator
2-(5Z,8Z,11Z,14Z)-Eicosatetraenoyl-sn-glycero-3-phosphate	HMDB
2-(5Z,8Z,11Z,14Z)-Icosatetraenoyl-sn-glycero-3-phosphate(2-)	HMDB
2-(5Z,8Z,11Z,14Z)-Eicosatetraenoyl-sn-glycero-3-phosphoric acid	HMDB
2-(5Z,8Z,11Z,14Z)-Icosatetraenoyl-sn-glycero-3-phosphoric acid(2-)	HMDB
1-Lyso-2-all-cis-5,8,11,14-eicosatetraenoyl-sn-glycero-3-phosphatidic acid	HMDB
2-all-cis-5,8,11,14-Eicosatetraenoyl-lysophosphatidic acid	HMDB
2-Arachidonoyl-lysophosphatidic acid	HMDB
2-Arachidonoyl-sn-glycero-3-phosphate	HMDB
L-beta-Arachidonoyl-alpha-lysophosphatidic acid	HMDB
[3-Hydroxy-2-(icosa-5,8,11,14-tetraenoyloxy)propoxy]phosphonate	HMDB

Chemical Formula

C₂₃H₃₉O₇P

Average Molecular Weight

458.532

Monoisotopic Molecular Weight

458.243340594

IUPAC Name

[3-hydroxy-2-(icosa-5,8,11,14-tetraenoyloxy)propoxy]phosphonic acid

Traditional Name

3-hydroxy-2-(icosa-5,8,11,14-tetraenoyloxy)propoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO)COP(O)(O)=O

InChI Identifier

InChI=1S/C23H39O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(25)30-22(20-24)21-29-31(26,27)28/h6-7,9-10,12-13,15-16,22,24H,2-5,8,11,14,17-21H2,1H3,(H2,26,27,28)

InChI Key

BDCFJMBXZCIVRH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-acylglycerol-3-phosphates. These are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-2 position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphates

Direct Parent

2-acylglycerol-3-phosphates

Alternative Parents

Substituents

2-acylglycerol-3-phosphate
Fatty acid ester
Monoalkyl phosphate
Fatty acyl
Alkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Primary alcohol
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0012496)
Membrane (HMDB: HMDB0012496)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0034 g/L	ALOGPS
logP	4.97	ALOGPS
logP	5.29	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	1.32	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	127.85 m³·mol⁻¹	ChemAxon
Polarizability	49.14 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	204.878	30932474
DeepCCS	[M-H]-	202.328	30932474
DeepCCS	[M-2H]-	236.259	30932474
DeepCCS	[M+Na]+	212.548	30932474
AllCCS	[M+H]+	216.2	32859911
AllCCS	[M+H-H2O]+	214.2	32859911
AllCCS	[M+NH4]+	218.0	32859911
AllCCS	[M+Na]+	218.5	32859911
AllCCS	[M-H]-	211.3	32859911
AllCCS	[M+Na-2H]-	214.5	32859911
AllCCS	[M+HCOO]-	218.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-Lyso-2-arachidonoyl-phosphatidate	CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO)COP(O)(O)=O	3905.8	Standard polar	33892256
1-Lyso-2-arachidonoyl-phosphatidate	CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO)COP(O)(O)=O	2888.3	Standard non polar	33892256
1-Lyso-2-arachidonoyl-phosphatidate	CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO)COP(O)(O)=O	3395.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1-Lyso-2-arachidonoyl-phosphatidate,1TMS,isomer #1	CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(O)O	3498.4	Semi standard non polar	33892256
1-Lyso-2-arachidonoyl-phosphatidate,1TMS,isomer #2	CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO)COP(=O)(O)O[Si](C)(C)C	3441.3	Semi standard non polar	33892256
1-Lyso-2-arachidonoyl-phosphatidate,2TMS,isomer #1	CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(O)O[Si](C)(C)C	3473.7	Semi standard non polar	33892256
1-Lyso-2-arachidonoyl-phosphatidate,2TMS,isomer #1	CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(O)O[Si](C)(C)C	3162.0	Standard non polar	33892256
1-Lyso-2-arachidonoyl-phosphatidate,2TMS,isomer #1	CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(O)O[Si](C)(C)C	3865.7	Standard polar	33892256
1-Lyso-2-arachidonoyl-phosphatidate,2TMS,isomer #2	CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3429.1	Semi standard non polar	33892256
1-Lyso-2-arachidonoyl-phosphatidate,2TMS,isomer #2	CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3167.6	Standard non polar	33892256
1-Lyso-2-arachidonoyl-phosphatidate,2TMS,isomer #2	CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3663.7	Standard polar	33892256
1-Lyso-2-arachidonoyl-phosphatidate,3TMS,isomer #1	CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3457.2	Semi standard non polar	33892256
1-Lyso-2-arachidonoyl-phosphatidate,3TMS,isomer #1	CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3197.1	Standard non polar	33892256
1-Lyso-2-arachidonoyl-phosphatidate,3TMS,isomer #1	CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3320.8	Standard polar	33892256
1-Lyso-2-arachidonoyl-phosphatidate,1TBDMS,isomer #1	CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO[Si](C)(C)C(C)(C)C)COP(=O)(O)O	3735.7	Semi standard non polar	33892256
1-Lyso-2-arachidonoyl-phosphatidate,1TBDMS,isomer #2	CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO)COP(=O)(O)O[Si](C)(C)C(C)(C)C	3654.7	Semi standard non polar	33892256
1-Lyso-2-arachidonoyl-phosphatidate,2TBDMS,isomer #1	CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO[Si](C)(C)C(C)(C)C)COP(=O)(O)O[Si](C)(C)C(C)(C)C	3923.9	Semi standard non polar	33892256
1-Lyso-2-arachidonoyl-phosphatidate,2TBDMS,isomer #1	CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO[Si](C)(C)C(C)(C)C)COP(=O)(O)O[Si](C)(C)C(C)(C)C	3486.2	Standard non polar	33892256
1-Lyso-2-arachidonoyl-phosphatidate,2TBDMS,isomer #1	CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO[Si](C)(C)C(C)(C)C)COP(=O)(O)O[Si](C)(C)C(C)(C)C	3902.6	Standard polar	33892256
1-Lyso-2-arachidonoyl-phosphatidate,2TBDMS,isomer #2	CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3858.0	Semi standard non polar	33892256
1-Lyso-2-arachidonoyl-phosphatidate,2TBDMS,isomer #2	CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3455.0	Standard non polar	33892256
1-Lyso-2-arachidonoyl-phosphatidate,2TBDMS,isomer #2	CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3753.2	Standard polar	33892256
1-Lyso-2-arachidonoyl-phosphatidate,3TBDMS,isomer #1	CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO[Si](C)(C)C(C)(C)C)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4083.9	Semi standard non polar	33892256
1-Lyso-2-arachidonoyl-phosphatidate,3TBDMS,isomer #1	CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO[Si](C)(C)C(C)(C)C)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3585.3	Standard non polar	33892256
1-Lyso-2-arachidonoyl-phosphatidate,3TBDMS,isomer #1	CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO[Si](C)(C)C(C)(C)C)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3474.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Lyso-2-arachidonoyl-phosphatidate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Lyso-2-arachidonoyl-phosphatidate 10V, Negative-QTOF	splash10-0a4i-4000900000-819e2d5b9aaa86be40d0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Lyso-2-arachidonoyl-phosphatidate 20V, Negative-QTOF	splash10-004j-9100000000-6307eb82a131f0391d31	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Lyso-2-arachidonoyl-phosphatidate 40V, Negative-QTOF	splash10-004i-9000000000-7e1087b9c9e914081e89	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Lyso-2-arachidonoyl-phosphatidate 10V, Positive-QTOF	splash10-08fr-0229500000-aa32372cdeaa104ea519	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Lyso-2-arachidonoyl-phosphatidate 20V, Positive-QTOF	splash10-03dr-2398000000-0d4ebdc1c1453eec2997	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Lyso-2-arachidonoyl-phosphatidate 40V, Positive-QTOF	splash10-003v-9321000000-9e9c620862b97b08242c	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029101

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

76043735

PDB ID

Not Available

ChEBI ID

78209

Food Biomarker Ontology

Not Available

VMH ID

CE3481

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Gerrard JM, Clawson CC, White JG: Lysophosphatidic acids: III. Enhancement of neutrophil chemotaxis. Am J Pathol. 1980 Sep;100(3):609-18. [PubMed:7416233 ]
Aoki J: Mechanisms of lysophosphatidic acid production. Semin Cell Dev Biol. 2004 Oct;15(5):477-89. [PubMed:15271293 ]
Moritz A, De Graan PN, Gispen WH, Wirtz KW: Phosphatidic acid is a specific activator of phosphatidylinositol-4-phosphate kinase. J Biol Chem. 1992 Apr 15;267(11):7207-10. [PubMed:1313792 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
Moolenaar WH, Kruijer W, Tilly BC, Verlaan I, Bierman AJ, de Laat SW: Growth factor-like action of phosphatidic acid. Nature. 1986 Sep 11-17;323(6084):171-3. [PubMed:3748188 ]
Yang CY, Frohman MA: Mitochondria: signaling with phosphatidic acid. Int J Biochem Cell Biol. 2012 Aug;44(8):1346-50. doi: 10.1016/j.biocel.2012.05.006. Epub 2012 May 15. [PubMed:22609101 ]
Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 1-Lyso-2-arachidonoyl-phosphatidate (HMDB0012496)

MOL for HMDB0012496 (1-Lyso-2-arachidonoyl-phosphatidate)

3D MOL for HMDB0012496 (1-Lyso-2-arachidonoyl-phosphatidate)

3D SDF for HMDB0012496 (1-Lyso-2-arachidonoyl-phosphatidate)

3D-SDF for HMDB0012496 (1-Lyso-2-arachidonoyl-phosphatidate)

PDB for HMDB0012496 (1-Lyso-2-arachidonoyl-phosphatidate)

3D PDB for HMDB0012496 (1-Lyso-2-arachidonoyl-phosphatidate)

SMILES for HMDB0012496 (1-Lyso-2-arachidonoyl-phosphatidate)

INCHI for HMDB0012496 (1-Lyso-2-arachidonoyl-phosphatidate)

Structure for HMDB0012496 (1-Lyso-2-arachidonoyl-phosphatidate)

3D Structure for HMDB0012496 (1-Lyso-2-arachidonoyl-phosphatidate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra