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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (46) Show 46 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2008-09-12 01:27:10 UTC

Update Date

2022-11-30 19:03:05 UTC

HMDB ID

HMDB0007851

Secondary Accession Numbers

HMDB07851

Metabolite Identification

Common Name

LysoPA(0:0/18:1(9Z))

Description

LysoPA(0:0/18:1(9Z)) 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. 1-Palmitoyl lysophosphatidic acid is the major component of lysophosphatidic acid (LPA) in plasma, and is in a reduced ratio in individuals with gynecological cancers (PMID 11585410 ). 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

LPA(0:0/18:1(9Z))
  Mrv1652304052008222D          

 29 28  0  0  1  0            999 V2000
    9.1946   -4.4808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0111   -3.6473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0281   -5.2973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8446   -4.4638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0196   -4.4723    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.3813   -4.0227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6712   -4.4428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9524   -4.0379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2423   -4.4581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6800   -5.2678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9700   -5.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9700   -6.4593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2558   -5.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5417   -5.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8276   -5.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1135   -5.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3993   -5.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6852   -5.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9710   -5.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2569   -5.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4318   -5.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2823   -5.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9964   -5.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7105   -5.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4247   -5.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1388   -5.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8530   -5.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5671   -5.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2813   -5.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  5  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 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
 20 21  2  0  0  0  0
 21 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
 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

HMDB0007851
     RDKit          3D
LysoPA(0:0/18:1(9Z))
 70 69  0  0  0  0  0  0  0  0999 V2000
  -10.7353   -0.3087   -1.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2486   -0.5447   -1.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6796   -0.1030   -0.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1846   -0.3226   -0.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6271    0.1231    1.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1476   -0.0635    1.2756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7194   -1.5130    1.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1839   -1.5689    1.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8202   -1.0529    2.5261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0748   -0.0030    2.6662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4920    0.8174    1.5977 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0361    0.7721    1.7677 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6679    1.6148    0.6705 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1479    1.6529    0.7422 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8624    0.3657    0.6444 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6832   -0.4503   -0.5703 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0803    0.1532   -1.8682 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4980    0.5569   -1.9447 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7569    1.7881   -1.9908 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5716   -0.3352   -1.9685 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8897    0.1933   -2.0545 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7124   -0.5089   -3.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8458   -1.8618   -2.8076 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5402   -0.0554   -0.6822 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8420    0.4540   -0.7144 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6675    0.2687    0.7299 P   0  0  0  0  0  5  0  0  0  0  0  0
   10.0181   -1.1603    1.0098 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6600    0.8220    1.9753 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0489    1.2472    0.6520 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2782   -0.8471   -2.2898 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1491   -0.5498   -0.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9017    0.7771   -1.6995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8308    0.0631   -2.3430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0080   -1.6124   -1.7078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8472    0.9876   -0.1150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1726   -0.6710    0.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7496    0.2771   -0.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9979   -1.3797   -0.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8414    1.1978    1.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1715   -0.4150    2.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8103    0.3222    2.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6736    0.5818    0.5114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0785   -1.9330    0.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0962   -2.1017    1.9593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9014   -2.6510    1.1389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7158   -1.0922    0.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2267   -1.6190    3.3936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8495    0.3141    3.6934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8160    1.9081    1.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7130    0.5336    0.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3182   -0.2706    1.5823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3162    1.1819    2.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2814    2.6625    0.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2452    1.3054   -0.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5550    2.4284    0.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4028    2.0752    1.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9667    0.5978    0.7242 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6627   -0.2802    1.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3423   -1.3635   -0.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6609   -0.8886   -0.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3994    0.9683   -2.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9501   -0.6472   -2.6560 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8799    1.3055   -2.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7154   -0.0527   -3.1157 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2746   -0.3438   -4.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4136   -2.4428   -3.4855 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5991   -1.1321   -0.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9635    0.4835    0.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9216    1.7641    2.1789 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3450    1.2539   -0.3027 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  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 26 29  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 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
 12 52  1  0
 13 53  1  0
 13 54  1  0
 14 55  1  0
 14 56  1  0
 15 57  1  0
 15 58  1  0
 16 59  1  0
 16 60  1  0
 17 61  1  0
 17 62  1  0
 21 63  1  0
 22 64  1  0
 22 65  1  0
 23 66  1  0
 24 67  1  0
 24 68  1  0
 28 69  1  0
 29 70  1  0
M  END

LPA(0:0/18:1(9Z))
  Mrv1652304052008222D          

 29 28  0  0  1  0            999 V2000
    9.1946   -4.4808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0111   -3.6473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0281   -5.2973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8446   -4.4638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0196   -4.4723    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.3813   -4.0227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6712   -4.4428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9524   -4.0379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2423   -4.4581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6800   -5.2678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9700   -5.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9700   -6.4593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2558   -5.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5417   -5.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8276   -5.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1135   -5.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3993   -5.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6852   -5.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9710   -5.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2569   -5.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4318   -5.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2823   -5.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9964   -5.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7105   -5.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4247   -5.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1388   -5.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8530   -5.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5671   -5.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2813   -5.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  5  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 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
 20 21  2  0  0  0  0
 21 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
 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>
HMDB0007851

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCC\C=C/CCCCCCCC(=O)OC(CO)COP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H41O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)28-20(18-22)19-27-29(24,25)26/h9-10,20,22H,2-8,11-19H2,1H3,(H2,24,25,26)/b10-9-

> <INCHI_KEY>
ZOOLJLSXNRZLDH-KTKRTIGZSA-N

> <FORMULA>
C21H41O7P

> <MOLECULAR_WEIGHT>
436.526

> <EXACT_MASS>
436.258990658

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
49.59874152548529

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{3-hydroxy-2-[(9Z)-octadec-9-enoyloxy]propoxy}phosphonic acid

> <ALOGPS_LOGP>
4.70

> <JCHEM_LOGP>
5.485689521666666

> <ALOGPS_LOGS>
-5.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.345670795497995

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.3198427043855556

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9837580757427844

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
115.29899999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
21

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.74e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-2-[(9Z)-octadec-9-enoyloxy]propoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0007851
     RDKit          3D
LysoPA(0:0/18:1(9Z))
 70 69  0  0  0  0  0  0  0  0999 V2000
  -10.7353   -0.3087   -1.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2486   -0.5447   -1.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6796   -0.1030   -0.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1846   -0.3226   -0.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6271    0.1231    1.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1476   -0.0635    1.2756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7194   -1.5130    1.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1839   -1.5689    1.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8202   -1.0529    2.5261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0748   -0.0030    2.6662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4920    0.8174    1.5977 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0361    0.7721    1.7677 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6679    1.6148    0.6705 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1479    1.6529    0.7422 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8624    0.3657    0.6444 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6832   -0.4503   -0.5703 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0803    0.1532   -1.8682 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4980    0.5569   -1.9447 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7569    1.7881   -1.9908 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5716   -0.3352   -1.9685 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8897    0.1933   -2.0545 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7124   -0.5089   -3.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8458   -1.8618   -2.8076 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5402   -0.0554   -0.6822 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8420    0.4540   -0.7144 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6675    0.2687    0.7299 P   0  0  0  0  0  5  0  0  0  0  0  0
   10.0181   -1.1603    1.0098 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6600    0.8220    1.9753 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0489    1.2472    0.6520 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2782   -0.8471   -2.2898 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1491   -0.5498   -0.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9017    0.7771   -1.6995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8308    0.0631   -2.3430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0080   -1.6124   -1.7078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8472    0.9876   -0.1150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1726   -0.6710    0.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7496    0.2771   -0.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9979   -1.3797   -0.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8414    1.1978    1.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1715   -0.4150    2.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8103    0.3222    2.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6736    0.5818    0.5114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0785   -1.9330    0.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0962   -2.1017    1.9593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9014   -2.6510    1.1389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7158   -1.0922    0.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2267   -1.6190    3.3936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8495    0.3141    3.6934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8160    1.9081    1.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7130    0.5336    0.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3182   -0.2706    1.5823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3162    1.1819    2.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2814    2.6625    0.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2452    1.3054   -0.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5550    2.4284    0.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4028    2.0752    1.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9667    0.5978    0.7242 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6627   -0.2802    1.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3423   -1.3635   -0.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6609   -0.8886   -0.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3994    0.9683   -2.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9501   -0.6472   -2.6560 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8799    1.3055   -2.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7154   -0.0527   -3.1157 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2746   -0.3438   -4.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4136   -2.4428   -3.4855 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5991   -1.1321   -0.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9635    0.4835    0.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9216    1.7641    2.1789 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3450    1.2539   -0.3027 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  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 26 29  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 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
 12 52  1  0
 13 53  1  0
 13 54  1  0
 14 55  1  0
 14 56  1  0
 15 57  1  0
 15 58  1  0
 16 59  1  0
 16 60  1  0
 17 61  1  0
 17 62  1  0
 21 63  1  0
 22 64  1  0
 22 65  1  0
 23 66  1  0
 24 67  1  0
 24 68  1  0
 28 69  1  0
 29 70  1  0
M  END

HEADER    PROTEIN                                 05-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: LPA(0:0/18:1(9Z))                                 
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-APR-20         0                                  
HETATM    1  O   UNK     0      17.163  -8.364   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      18.687  -6.808   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      18.719  -9.888   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      20.243  -8.332   0.000  0.00  0.00           O+0
HETATM    5  P   UNK     0      18.703  -8.348   0.000  0.00  0.00           P+0
HETATM    6  C   UNK     0      15.645  -7.509   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.320  -8.293   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.978  -7.537   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      11.652  -8.322   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      14.336  -9.833   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      13.011 -10.617   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      13.011 -12.057   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      11.677  -9.846   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.345 -10.617   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.012  -9.846   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.679 -10.617   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.345  -9.846   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.012 -10.617   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.679  -9.846   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.346 -10.617   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.806 -10.617   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.527  -9.846   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.860 -10.617   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.193  -9.846   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.526 -10.617   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.859  -9.846   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -7.192 -10.617   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -8.525  -9.846   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -9.858 -10.617   0.000  0.00  0.00           C+0
CONECT    1    6    5                                                       
CONECT    2    5                                                            
CONECT    3    5                                                            
CONECT    4    5                                                            
CONECT    5    1    2    3    4                                             
CONECT    6    1    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   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                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   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    HMDB0007851
HETATM    1  C1  UNL     1     -10.735  -0.309  -1.507  1.00  0.00           C  
HETATM    2  C2  UNL     1      -9.249  -0.545  -1.510  1.00  0.00           C  
HETATM    3  C3  UNL     1      -8.680  -0.103  -0.170  1.00  0.00           C  
HETATM    4  C4  UNL     1      -7.185  -0.323  -0.144  1.00  0.00           C  
HETATM    5  C5  UNL     1      -6.627   0.123   1.195  1.00  0.00           C  
HETATM    6  C6  UNL     1      -5.148  -0.063   1.276  1.00  0.00           C  
HETATM    7  C7  UNL     1      -4.719  -1.513   1.102  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.184  -1.569   1.191  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.820  -1.053   2.526  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.075  -0.003   2.666  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.492   0.817   1.598  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.036   0.772   1.768  1.00  0.00           C  
HETATM   13  C13 UNL     1       0.668   1.615   0.670  1.00  0.00           C  
HETATM   14  C14 UNL     1       2.148   1.653   0.742  1.00  0.00           C  
HETATM   15  C15 UNL     1       2.862   0.366   0.644  1.00  0.00           C  
HETATM   16  C16 UNL     1       2.683  -0.450  -0.570  1.00  0.00           C  
HETATM   17  C17 UNL     1       3.080   0.153  -1.868  1.00  0.00           C  
HETATM   18  C18 UNL     1       4.498   0.557  -1.945  1.00  0.00           C  
HETATM   19  O1  UNL     1       4.757   1.788  -1.991  1.00  0.00           O  
HETATM   20  O2  UNL     1       5.572  -0.335  -1.969  1.00  0.00           O  
HETATM   21  C19 UNL     1       6.890   0.193  -2.055  1.00  0.00           C  
HETATM   22  C20 UNL     1       7.712  -0.509  -3.086  1.00  0.00           C  
HETATM   23  O3  UNL     1       7.846  -1.862  -2.808  1.00  0.00           O  
HETATM   24  C21 UNL     1       7.540  -0.055  -0.682  1.00  0.00           C  
HETATM   25  O4  UNL     1       8.842   0.454  -0.714  1.00  0.00           O  
HETATM   26  P1  UNL     1       9.667   0.269   0.730  1.00  0.00           P  
HETATM   27  O5  UNL     1      10.018  -1.160   1.010  1.00  0.00           O  
HETATM   28  O6  UNL     1       8.660   0.822   1.975  1.00  0.00           O  
HETATM   29  O7  UNL     1      11.049   1.247   0.652  1.00  0.00           O  
HETATM   30  H1  UNL     1     -11.278  -0.847  -2.290  1.00  0.00           H  
HETATM   31  H2  UNL     1     -11.149  -0.550  -0.522  1.00  0.00           H  
HETATM   32  H3  UNL     1     -10.902   0.777  -1.700  1.00  0.00           H  
HETATM   33  H4  UNL     1      -8.831   0.063  -2.343  1.00  0.00           H  
HETATM   34  H5  UNL     1      -9.008  -1.612  -1.708  1.00  0.00           H  
HETATM   35  H6  UNL     1      -8.847   0.988  -0.115  1.00  0.00           H  
HETATM   36  H7  UNL     1      -9.173  -0.671   0.624  1.00  0.00           H  
HETATM   37  H8  UNL     1      -6.750   0.277  -0.969  1.00  0.00           H  
HETATM   38  H9  UNL     1      -6.998  -1.380  -0.345  1.00  0.00           H  
HETATM   39  H10 UNL     1      -6.841   1.198   1.326  1.00  0.00           H  
HETATM   40  H11 UNL     1      -7.171  -0.415   2.003  1.00  0.00           H  
HETATM   41  H12 UNL     1      -4.810   0.322   2.258  1.00  0.00           H  
HETATM   42  H13 UNL     1      -4.674   0.582   0.511  1.00  0.00           H  
HETATM   43  H14 UNL     1      -5.078  -1.933   0.165  1.00  0.00           H  
HETATM   44  H15 UNL     1      -5.096  -2.102   1.959  1.00  0.00           H  
HETATM   45  H16 UNL     1      -2.901  -2.651   1.139  1.00  0.00           H  
HETATM   46  H17 UNL     1      -2.716  -1.092   0.345  1.00  0.00           H  
HETATM   47  H18 UNL     1      -3.227  -1.619   3.394  1.00  0.00           H  
HETATM   48  H19 UNL     1      -1.850   0.314   3.693  1.00  0.00           H  
HETATM   49  H20 UNL     1      -1.816   1.908   1.706  1.00  0.00           H  
HETATM   50  H21 UNL     1      -1.713   0.534   0.577  1.00  0.00           H  
HETATM   51  H22 UNL     1       0.318  -0.271   1.582  1.00  0.00           H  
HETATM   52  H23 UNL     1       0.316   1.182   2.736  1.00  0.00           H  
HETATM   53  H24 UNL     1       0.281   2.662   0.852  1.00  0.00           H  
HETATM   54  H25 UNL     1       0.245   1.305  -0.286  1.00  0.00           H  
HETATM   55  H26 UNL     1       2.555   2.428   0.047  1.00  0.00           H  
HETATM   56  H27 UNL     1       2.403   2.075   1.764  1.00  0.00           H  
HETATM   57  H28 UNL     1       3.967   0.598   0.724  1.00  0.00           H  
HETATM   58  H29 UNL     1       2.663  -0.280   1.526  1.00  0.00           H  
HETATM   59  H30 UNL     1       3.342  -1.364  -0.440  1.00  0.00           H  
HETATM   60  H31 UNL     1       1.661  -0.889  -0.675  1.00  0.00           H  
HETATM   61  H32 UNL     1       2.399   0.968  -2.207  1.00  0.00           H  
HETATM   62  H33 UNL     1       2.950  -0.647  -2.656  1.00  0.00           H  
HETATM   63  H34 UNL     1       6.880   1.306  -2.145  1.00  0.00           H  
HETATM   64  H35 UNL     1       8.715  -0.053  -3.116  1.00  0.00           H  
HETATM   65  H36 UNL     1       7.275  -0.344  -4.104  1.00  0.00           H  
HETATM   66  H37 UNL     1       7.414  -2.443  -3.485  1.00  0.00           H  
HETATM   67  H38 UNL     1       7.599  -1.132  -0.521  1.00  0.00           H  
HETATM   68  H39 UNL     1       6.964   0.484   0.090  1.00  0.00           H  
HETATM   69  H40 UNL     1       8.922   1.764   2.179  1.00  0.00           H  
HETATM   70  H41 UNL     1      11.345   1.254  -0.303  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3   33   34
CONECT    3    4   35   36
CONECT    4    5   37   38
CONECT    5    6   39   40
CONECT    6    7   41   42
CONECT    7    8   43   44
CONECT    8    9   45   46
CONECT    9   10   10   47
CONECT   10   11   48
CONECT   11   12   49   50
CONECT   12   13   51   52
CONECT   13   14   53   54
CONECT   14   15   55   56
CONECT   15   16   57   58
CONECT   16   17   59   60
CONECT   17   18   61   62
CONECT   18   19   19   20
CONECT   20   21
CONECT   21   22   24   63
CONECT   22   23   64   65
CONECT   23   66
CONECT   24   25   67   68
CONECT   25   26
CONECT   26   27   27   28   29
CONECT   28   69
CONECT   29   70
END

HMDB0007851
     RDKit          3D
LysoPA(0:0/18:1(9Z))
 70 69  0  0  0  0  0  0  0  0999 V2000
  -10.7353   -0.3087   -1.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2486   -0.5447   -1.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6796   -0.1030   -0.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1846   -0.3226   -0.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6271    0.1231    1.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1476   -0.0635    1.2756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7194   -1.5130    1.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1839   -1.5689    1.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8202   -1.0529    2.5261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0748   -0.0030    2.6662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4920    0.8174    1.5977 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0361    0.7721    1.7677 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6679    1.6148    0.6705 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1479    1.6529    0.7422 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8624    0.3657    0.6444 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6832   -0.4503   -0.5703 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0803    0.1532   -1.8682 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4980    0.5569   -1.9447 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7569    1.7881   -1.9908 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5716   -0.3352   -1.9685 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8897    0.1933   -2.0545 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7124   -0.5089   -3.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8458   -1.8618   -2.8076 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5402   -0.0554   -0.6822 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8420    0.4540   -0.7144 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6675    0.2687    0.7299 P   0  0  0  0  0  5  0  0  0  0  0  0
   10.0181   -1.1603    1.0098 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6600    0.8220    1.9753 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0489    1.2472    0.6520 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2782   -0.8471   -2.2898 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1491   -0.5498   -0.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9017    0.7771   -1.6995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8308    0.0631   -2.3430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0080   -1.6124   -1.7078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8472    0.9876   -0.1150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1726   -0.6710    0.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7496    0.2771   -0.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9979   -1.3797   -0.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8414    1.1978    1.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1715   -0.4150    2.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8103    0.3222    2.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6736    0.5818    0.5114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0785   -1.9330    0.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0962   -2.1017    1.9593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9014   -2.6510    1.1389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7158   -1.0922    0.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2267   -1.6190    3.3936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8495    0.3141    3.6934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8160    1.9081    1.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7130    0.5336    0.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3182   -0.2706    1.5823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3162    1.1819    2.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2814    2.6625    0.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2452    1.3054   -0.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5550    2.4284    0.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4028    2.0752    1.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9667    0.5978    0.7242 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6627   -0.2802    1.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3423   -1.3635   -0.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6609   -0.8886   -0.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3994    0.9683   -2.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9501   -0.6472   -2.6560 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8799    1.3055   -2.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7154   -0.0527   -3.1157 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2746   -0.3438   -4.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4136   -2.4428   -3.4855 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5991   -1.1321   -0.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9635    0.4835    0.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9216    1.7641    2.1789 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3450    1.2539   -0.3027 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  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 26 29  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 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
 12 52  1  0
 13 53  1  0
 13 54  1  0
 14 55  1  0
 14 56  1  0
 15 57  1  0
 15 58  1  0
 16 59  1  0
 16 60  1  0
 17 61  1  0
 17 62  1  0
 21 63  1  0
 22 64  1  0
 22 65  1  0
 23 66  1  0
 24 67  1  0
 24 68  1  0
 28 69  1  0
 29 70  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Lysophosphatidic acid(18:1)	HMDB
LPA(0:0/18:1(9Z))	HMDB
LPA(0:0/18:1)	HMDB
Lysophosphatidic acid(0:0/18:1)	HMDB
2-Oleoyl-glycero-3-phosphate	HMDB
2-(9Z-Octadecenoyl)-phosphatidic acid	HMDB
2-(9Z-Octadecenoyl)-glycero-3-phosphate	HMDB
LPA(18:1)	HMDB
{3-hydroxy-2-[(9Z)-octadec-9-enoyloxy]propoxy}phosphonate	HMDB

Chemical Formula

C₂₁H₄₁O₇P

Average Molecular Weight

436.526

Monoisotopic Molecular Weight

436.258990658

IUPAC Name

{3-hydroxy-2-[(9Z)-octadec-9-enoyloxy]propoxy}phosphonic acid

Traditional Name

3-hydroxy-2-[(9Z)-octadec-9-enoyloxy]propoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCC\C=C/CCCCCCCC(=O)OC(CO)COP(O)(O)=O

InChI Identifier

InChI=1S/C21H41O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)28-20(18-22)19-27-29(24,25)26/h9-10,20,22H,2-8,11-19H2,1H3,(H2,24,25,26)/b10-9-

InChI Key

ZOOLJLSXNRZLDH-KTKRTIGZSA-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

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	0.0017 g/L	ALOGPS
logP	4.7	ALOGPS
logP	5.49	ChemAxon
logS	-5.4	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	21	ChemAxon
Refractivity	115.3 m³·mol⁻¹	ChemAxon
Polarizability	49.6 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]+	208.99	30932474
DeepCCS	[M-H]-	206.44	30932474
DeepCCS	[M-2H]-	239.827	30932474
DeepCCS	[M+Na]+	216.455	30932474
AllCCS	[M+H]+	212.3	32859911
AllCCS	[M+H-H2O]+	210.3	32859911
AllCCS	[M+NH4]+	214.1	32859911
AllCCS	[M+Na]+	214.6	32859911
AllCCS	[M-H]-	206.5	32859911
AllCCS	[M+Na-2H]-	209.1	32859911
AllCCS	[M+HCOO]-	212.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
LysoPA(0:0/18:1(9Z))	CCCCCCCC\C=C/CCCCCCCC(=O)OC(CO)COP(O)(O)=O	3305.8	Standard polar	33892256
LysoPA(0:0/18:1(9Z))	CCCCCCCC\C=C/CCCCCCCC(=O)OC(CO)COP(O)(O)=O	2840.5	Standard non polar	33892256
LysoPA(0:0/18:1(9Z))	CCCCCCCC\C=C/CCCCCCCC(=O)OC(CO)COP(O)(O)=O	3196.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
LysoPA(0:0/18:1(9Z)),1TMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(O)O	3283.1	Semi standard non polar	33892256
LysoPA(0:0/18:1(9Z)),1TMS,isomer #2	CCCCCCCC/C=C\CCCCCCCC(=O)OC(CO)COP(=O)(O)O[Si](C)(C)C	3261.4	Semi standard non polar	33892256
LysoPA(0:0/18:1(9Z)),2TMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(O)O[Si](C)(C)C	3244.6	Semi standard non polar	33892256
LysoPA(0:0/18:1(9Z)),2TMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(O)O[Si](C)(C)C	3007.0	Standard non polar	33892256
LysoPA(0:0/18:1(9Z)),2TMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(O)O[Si](C)(C)C	3831.6	Standard polar	33892256
LysoPA(0:0/18:1(9Z)),2TMS,isomer #2	CCCCCCCC/C=C\CCCCCCCC(=O)OC(CO)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3223.6	Semi standard non polar	33892256
LysoPA(0:0/18:1(9Z)),2TMS,isomer #2	CCCCCCCC/C=C\CCCCCCCC(=O)OC(CO)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3028.7	Standard non polar	33892256
LysoPA(0:0/18:1(9Z)),2TMS,isomer #2	CCCCCCCC/C=C\CCCCCCCC(=O)OC(CO)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3577.9	Standard polar	33892256
LysoPA(0:0/18:1(9Z)),3TMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3200.4	Semi standard non polar	33892256
LysoPA(0:0/18:1(9Z)),3TMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3038.8	Standard non polar	33892256
LysoPA(0:0/18:1(9Z)),3TMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3312.5	Standard polar	33892256
LysoPA(0:0/18:1(9Z)),1TBDMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=O)OC(CO[Si](C)(C)C(C)(C)C)COP(=O)(O)O	3542.3	Semi standard non polar	33892256
LysoPA(0:0/18:1(9Z)),1TBDMS,isomer #2	CCCCCCCC/C=C\CCCCCCCC(=O)OC(CO)COP(=O)(O)O[Si](C)(C)C(C)(C)C	3488.9	Semi standard non polar	33892256
LysoPA(0:0/18:1(9Z)),2TBDMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=O)OC(CO[Si](C)(C)C(C)(C)C)COP(=O)(O)O[Si](C)(C)C(C)(C)C	3718.2	Semi standard non polar	33892256
LysoPA(0:0/18:1(9Z)),2TBDMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=O)OC(CO[Si](C)(C)C(C)(C)C)COP(=O)(O)O[Si](C)(C)C(C)(C)C	3312.6	Standard non polar	33892256
LysoPA(0:0/18:1(9Z)),2TBDMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=O)OC(CO[Si](C)(C)C(C)(C)C)COP(=O)(O)O[Si](C)(C)C(C)(C)C	3889.5	Standard polar	33892256
LysoPA(0:0/18:1(9Z)),2TBDMS,isomer #2	CCCCCCCC/C=C\CCCCCCCC(=O)OC(CO)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3688.6	Semi standard non polar	33892256
LysoPA(0:0/18:1(9Z)),2TBDMS,isomer #2	CCCCCCCC/C=C\CCCCCCCC(=O)OC(CO)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3291.6	Standard non polar	33892256
LysoPA(0:0/18:1(9Z)),2TBDMS,isomer #2	CCCCCCCC/C=C\CCCCCCCC(=O)OC(CO)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3705.9	Standard polar	33892256
LysoPA(0:0/18:1(9Z)),3TBDMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=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	3913.6	Semi standard non polar	33892256
LysoPA(0:0/18:1(9Z)),3TBDMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=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	3437.7	Standard non polar	33892256
LysoPA(0:0/18:1(9Z)),3TBDMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=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	3505.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - LysoPA(0:0/18:1(9Z)) GC-MS (1 TMS) - 70eV, Positive	splash10-0002-9440100000-ab03835ae710fd43beb6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - LysoPA(0:0/18:1(9Z)) GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - LysoPA(0:0/18:1(9Z)) 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 - LysoPA(0:0/18:1(9Z)) 10V, Positive-QTOF	splash10-000i-0129600000-5ca2a4097210a07fde89	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPA(0:0/18:1(9Z)) 20V, Positive-QTOF	splash10-00kr-2596000000-0230da3bf40a3c82a409	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPA(0:0/18:1(9Z)) 40V, Positive-QTOF	splash10-0005-9200000000-12275d7160c2db8764aa	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPA(0:0/18:1(9Z)) 10V, Negative-QTOF	splash10-000i-4000900000-3a15ded6fecbf39f71f3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPA(0:0/18:1(9Z)) 20V, Negative-QTOF	splash10-004j-9100000000-ab65385a900f3ce6c54d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPA(0:0/18:1(9Z)) 40V, Negative-QTOF	splash10-004i-9000000000-27f25c6ffe2d7e505bb9	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

All Tissues

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

Not Available

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

56947016

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Shen Z, Wu M, Elson P, Kennedy AW, Belinson J, Casey G, Xu Y: Fatty acid composition of lysophosphatidic acid and lysophosphatidylinositol in plasma from patients with ovarian cancer and other gynecological diseases. Gynecol Oncol. 2001 Oct;83(1):25-30. [PubMed:11585410 ]
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 ]

Only showing the first 10 proteins. There are 46 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Phospholipase D2

General function:: Involved in protein binding
Specific function:: May have a role in signal-induced cytoskeletal regulation and/or endocytosis (By similarity).
Gene Name:: PLD2
Uniprot ID:: O14939
Molecular weight:: 104656.485

Enzyme Details

2. Ectonucleotide pyrophosphatase/phosphodiesterase family member 2

General function:: Involved in catalytic activity
Specific function:: Hydrolyzes lysophospholipids to produce lysophosphatidic acid (LPA) in extracellular fluids. Major substrate is lysophosphatidylcholine. Also can act on sphingosylphosphphorylcholine producing sphingosine-1-phosphate, a modulator of cell motility. Can hydrolyze, in vitro, bis-pNPP, to some extent pNP-TMP, and barely ATP. Involved in several motility-related processes such as angiogenesis and neurite outgrowth. Acts as an angiogenic factor by stimulating migration of smooth muscle cells and microtubule formation. Stimulates migration of melanoma cells, probably via a pertussis toxin-sensitive G protein. May have a role in induction of parturition. Possible involvement in cell proliferation and adipose tissue development. Tumor cell motility-stimulating factor.
Gene Name:: ENPP2
Uniprot ID:: Q13822
Molecular weight:: 98992.78

Enzyme Details

3. Diacylglycerol kinase theta

General function:: Involved in diacylglycerol kinase activity
Specific function:: Phosphorylates diacylglycerol (DAG) to generate phosphatidic acid (PA). May regulate the activity of protein kinase C by controlling the balance between these two signaling lipids. Activated in the nucleus in response to alpha-thrombin and nerve growth factor. May be involved in cAMP- induced activation of NR5A1 and subsequent steroidogenic gene transcription by delivering PA as ligand for NR5A1. Acts synergistically with NR5A1 on CYP17 transcriptional activity
Gene Name:: DGKQ
Uniprot ID:: P52824
Molecular weight:: 101154.0

Enzyme Details

4. Lipid phosphate phosphohydrolase 2

General function:: Involved in catalytic activity
Specific function:: Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). In addition it hydrolyzes lysophosphatidic acid (LPA), ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is PA > C-1-P > LPA > S-1-P.
Gene Name:: PPAP2C
Uniprot ID:: O43688
Molecular weight:: 32573.435

Enzyme Details

5. Diacylglycerol kinase alpha

General function:: Involved in diacylglycerol kinase activity
Specific function:: Upon cell stimulation converts the second messenger diacylglycerol into phosphatidate, initiating the resynthesis of phosphatidylinositols and attenuating protein kinase C activity
Gene Name:: DGKA
Uniprot ID:: P23743
Molecular weight:: 82629.5

Enzyme Details

6. Diacylglycerol kinase delta

General function:: Involved in diacylglycerol kinase activity
Specific function:: Isoform 2 may be involved in cell growth and tumorigenesis. Involved in clathrin-dependent endocytosis
Gene Name:: DGKD
Uniprot ID:: Q16760
Molecular weight:: 134524.2

Enzyme Details

7. Lipid phosphate phosphohydrolase 1

General function:: Involved in catalytic activity
Specific function:: Broad-specificity phosphohydrolase that dephosphorylates exogenous bioactive glycerolipids and sphingolipids. Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). Pivotal regulator of lysophosphatidic acid (LPA) signaling in the cardiovascular system. Major enzyme responsible of dephosphorylating LPA in platelets, which terminates signaling actions of LPA. May control circulating, and possibly also regulate localized, LPA levels resulting from platelet activation. It has little activity towards ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is LPA > PA > S-1-P > C-1-P. It's down-regulation may contribute to the development of colon adenocarcinoma.
Gene Name:: PPAP2A
Uniprot ID:: O14494
Molecular weight:: 32155.715

Enzyme Details

8. Diacylglycerol kinase beta

General function:: Involved in diacylglycerol kinase activity
Specific function:: Exhibits high phosphorylation activity for long-chain diacylglycerols
Gene Name:: DGKB
Uniprot ID:: Q9Y6T7
Molecular weight:: 90594.7

Enzyme Details

9. Diacylglycerol kinase iota

General function:: Involved in diacylglycerol kinase activity
Specific function:: ATP + 1,2-diacylglycerol = ADP + 1,2-diacyl- sn-glycerol 3-phosphate
Gene Name:: DGKI
Uniprot ID:: O75912
Molecular weight:: 116996.2

Enzyme Details

10. Lipid phosphate phosphohydrolase 3

General function:: Involved in catalytic activity
Specific function:: Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). In addition it hydrolyzes lysophosphatidic acid (LPA), ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is LPA = PA > C-1-P > S-1-P. May be involved in cell adhesion and in cell-cell interactions.
Gene Name:: PPAP2B
Uniprot ID:: O14495
Molecular weight:: 35115.61

Only showing the first 10 proteins. There are 46 proteins in total.

Show all enzymes and transporters

Showing metabocard for LysoPA(0:0/18:1(9Z)) (HMDB0007851)

MOL for HMDB0007851 (LysoPA(0:0/18:1(9Z)))

3D MOL for HMDB0007851 (LysoPA(0:0/18:1(9Z)))

3D SDF for HMDB0007851 (LysoPA(0:0/18:1(9Z)))

3D-SDF for HMDB0007851 (LysoPA(0:0/18:1(9Z)))

PDB for HMDB0007851 (LysoPA(0:0/18:1(9Z)))

3D PDB for HMDB0007851 (LysoPA(0:0/18:1(9Z)))

SMILES for HMDB0007851 (LysoPA(0:0/18:1(9Z)))

INCHI for HMDB0007851 (LysoPA(0:0/18:1(9Z)))

Structure for HMDB0007851 (LysoPA(0:0/18:1(9Z)))

3D Structure for HMDB0007851 (LysoPA(0:0/18:1(9Z)))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes