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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (32) Show 32 proteins XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2008-10-29 14:20:21 UTC

Update Date

2022-11-30 19:03:55 UTC

HMDB ID

HMDB0011144

Secondary Accession Numbers

HMDB11144

Metabolite Identification

Common Name

LysoPA(O-18:0/0:0)

Description

LysoPA(O-18:0/0:0) 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.LysoPA(O-18:0/0:0), in particular, consists of one octadecyl chain. 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.

Structure

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

LPA(18:0e/0:0)
  Mrv1652304052008232D          

 28 27  0  0  1  0            999 V2000
    9.1943   -4.4806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0108   -3.6472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0277   -5.2971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8442   -4.4637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0193   -4.4722    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.3810   -4.0225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6710   -4.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9522   -4.0378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2421   -4.4579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6798   -5.2676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5233   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8092   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0951   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3810   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6669   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9528   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2386   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5245   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1896   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9037   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6178   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3319   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0460   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7601   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4743   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1884   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9025   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6166   -4.4662    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
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 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  1  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
M  END

HMDB0011144
     RDKit          3D
LysoPA(O-18:0/0:0)
 73 72  0  0  0  0  0  0  0  0999 V2000
   10.7766    0.3326    0.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4255   -1.1153    0.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1419   -1.4178   -0.5250 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8935   -0.8411    0.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7696    0.6294    0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4080    1.0663    0.6865 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2656    0.5967   -0.1832 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0033    1.0957    0.4474 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7398    0.7147   -0.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5957   -0.7639   -0.4543 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4611   -1.3186   -1.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0667   -1.1346   -0.8177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5077    0.2224   -0.7810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0419    0.0439   -0.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5562    1.4191   -0.3845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9549    1.7372   -0.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6755    1.3978    1.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8262   -0.0440    1.3614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4820   -0.7679    0.4510 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7734   -0.7443    0.2028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5405    0.4372   -0.2534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1185    0.9895   -1.4461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9985   -0.0424   -0.5226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4297   -0.5985    0.6702 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0074   -1.1721    0.5462 P   0  0  0  0  0  5  0  0  0  0  0  0
  -11.7826   -1.0217    1.8249 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9697   -2.7906    0.0600 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8141   -0.2515   -0.6369 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7547    0.8131    1.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2154    0.8903   -0.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8600    0.4497   -0.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2191   -1.6834   -0.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4219   -1.4668    1.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2943   -1.0809   -1.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9924   -2.5506   -0.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9869   -1.3206   -0.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8381   -1.2290    1.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4903    1.0654    0.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8542    1.1316   -0.8505 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3449    0.6900    1.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3804    2.1599    0.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3850    0.9210   -1.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1993   -0.5327   -0.1623 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0334    2.1918    0.5835 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8646    0.6552    1.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9419    1.2472    0.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7961    1.1947   -1.3579 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7853   -1.2762    0.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5267   -1.0941   -1.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6282   -2.4616   -1.2654 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6410   -1.0449   -2.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5514   -1.7063   -1.5996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2106   -1.7344    0.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1876    0.9035    0.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5533    0.6437   -1.8028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9393   -0.3763    0.6280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5012   -0.6759   -1.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2128    1.8928   -1.3727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8985    2.0024    0.3517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5428    1.3741   -1.0589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0676    2.8747   -0.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1421    1.8202    2.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6724    1.9010    1.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4508   -0.0664    2.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8545   -0.5266    1.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0070   -1.5607   -0.5732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3334   -1.1578    1.1231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6816    1.2165    0.5139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2447    1.9663   -1.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9376   -0.7926   -1.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6243    0.7908   -0.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1421   -3.0229   -0.4029 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7669   -0.0932   -0.3836 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  1  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  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 25 28  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  0
  7 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
  9 47  1  0
 10 48  1  0
 10 49  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  0
 12 53  1  0
 13 54  1  0
 13 55  1  0
 14 56  1  0
 14 57  1  0
 15 58  1  0
 15 59  1  0
 16 60  1  0
 16 61  1  0
 17 62  1  0
 17 63  1  0
 18 64  1  0
 18 65  1  0
 20 66  1  0
 20 67  1  0
 21 68  1  0
 22 69  1  0
 23 70  1  0
 23 71  1  0
 27 72  1  0
 28 73  1  0
M  END

LPA(18:0e/0:0)
  Mrv1652304052008232D          

 28 27  0  0  1  0            999 V2000
    9.1943   -4.4806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0108   -3.6472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0277   -5.2971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8442   -4.4637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0193   -4.4722    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.3810   -4.0225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6710   -4.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9522   -4.0378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2421   -4.4579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6798   -5.2676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5233   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8092   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0951   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3810   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6669   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9528   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2386   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5245   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1896   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9037   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6178   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3319   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0460   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7601   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4743   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1884   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9025   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6166   -4.4662    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
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 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  1  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
M  END
> <DATABASE_ID>
HMDB0011144

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCCCCCCCCCCCOCC(O)COP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H45O6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-26-19-21(22)20-27-28(23,24)25/h21-22H,2-20H2,1H3,(H2,23,24,25)

> <INCHI_KEY>
HUUYDUFSUADEJQ-UHFFFAOYSA-N

> <FORMULA>
C21H45O6P

> <MOLECULAR_WEIGHT>
424.559

> <EXACT_MASS>
424.295376167

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
51.92622487145914

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[2-hydroxy-3-(octadecyloxy)propoxy]phosphonic acid

> <ALOGPS_LOGP>
5.43

> <JCHEM_LOGP>
6.228406774333335

> <ALOGPS_LOGS>
-5.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.532823087649438

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5070267056744795

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3931742588163853

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
114.42779999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.41e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-3-(octadecyloxy)propoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0011144
     RDKit          3D
LysoPA(O-18:0/0:0)
 73 72  0  0  0  0  0  0  0  0999 V2000
   10.7766    0.3326    0.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4255   -1.1153    0.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1419   -1.4178   -0.5250 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8935   -0.8411    0.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7696    0.6294    0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4080    1.0663    0.6865 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2656    0.5967   -0.1832 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0033    1.0957    0.4474 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7398    0.7147   -0.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5957   -0.7639   -0.4543 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4611   -1.3186   -1.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0667   -1.1346   -0.8177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5077    0.2224   -0.7810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0419    0.0439   -0.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5562    1.4191   -0.3845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9549    1.7372   -0.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6755    1.3978    1.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8262   -0.0440    1.3614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4820   -0.7679    0.4510 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7734   -0.7443    0.2028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5405    0.4372   -0.2534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1185    0.9895   -1.4461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9985   -0.0424   -0.5226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4297   -0.5985    0.6702 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0074   -1.1721    0.5462 P   0  0  0  0  0  5  0  0  0  0  0  0
  -11.7826   -1.0217    1.8249 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9697   -2.7906    0.0600 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8141   -0.2515   -0.6369 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7547    0.8131    1.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2154    0.8903   -0.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8600    0.4497   -0.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2191   -1.6834   -0.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4219   -1.4668    1.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2943   -1.0809   -1.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9924   -2.5506   -0.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9869   -1.3206   -0.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8381   -1.2290    1.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4903    1.0654    0.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8542    1.1316   -0.8505 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3449    0.6900    1.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3804    2.1599    0.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3850    0.9210   -1.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1993   -0.5327   -0.1623 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0334    2.1918    0.5835 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8646    0.6552    1.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9419    1.2472    0.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7961    1.1947   -1.3579 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7853   -1.2762    0.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5267   -1.0941   -1.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6282   -2.4616   -1.2654 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6410   -1.0449   -2.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5514   -1.7063   -1.5996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2106   -1.7344    0.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1876    0.9035    0.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5533    0.6437   -1.8028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9393   -0.3763    0.6280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5012   -0.6759   -1.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2128    1.8928   -1.3727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8985    2.0024    0.3517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5428    1.3741   -1.0589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0676    2.8747   -0.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1421    1.8202    2.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6724    1.9010    1.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4508   -0.0664    2.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8545   -0.5266    1.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0070   -1.5607   -0.5732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3334   -1.1578    1.1231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6816    1.2165    0.5139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2447    1.9663   -1.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9376   -0.7926   -1.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6243    0.7908   -0.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1421   -3.0229   -0.4029 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7669   -0.0932   -0.3836 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  1  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  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 25 28  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  0
  7 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
  9 47  1  0
 10 48  1  0
 10 49  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  0
 12 53  1  0
 13 54  1  0
 13 55  1  0
 14 56  1  0
 14 57  1  0
 15 58  1  0
 15 59  1  0
 16 60  1  0
 16 61  1  0
 17 62  1  0
 17 63  1  0
 18 64  1  0
 18 65  1  0
 20 66  1  0
 20 67  1  0
 21 68  1  0
 22 69  1  0
 23 70  1  0
 23 71  1  0
 27 72  1  0
 28 73  1  0
M  END

HEADER    PROTEIN                                 05-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: LPA(18:0e/0:0)                                    
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      18.718  -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      14.319  -8.293   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.977  -7.537   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      11.652  -8.321   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      10.310  -7.566   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.977  -8.337   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.644  -7.566   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.311  -8.337   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.978  -7.566   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.645  -8.337   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.312  -7.566   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.979  -8.337   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.354  -7.566   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.687  -8.337   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.020  -7.566   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.353  -8.337   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.686  -7.566   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -7.019  -8.337   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -8.352  -7.566   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -9.685  -8.337   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -11.018  -7.566   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -12.351  -8.337   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   11                                                       
CONECT   10    7                                                            
CONECT   11    9   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                                                       
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                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   54    0
END

COMPND    HMDB0011144
HETATM    1  C1  UNL     1      10.777   0.333   0.124  1.00  0.00           C  
HETATM    2  C2  UNL     1      10.426  -1.115   0.160  1.00  0.00           C  
HETATM    3  C3  UNL     1       9.142  -1.418  -0.525  1.00  0.00           C  
HETATM    4  C4  UNL     1       7.894  -0.841   0.039  1.00  0.00           C  
HETATM    5  C5  UNL     1       7.770   0.629   0.127  1.00  0.00           C  
HETATM    6  C6  UNL     1       6.408   1.066   0.686  1.00  0.00           C  
HETATM    7  C7  UNL     1       5.266   0.597  -0.183  1.00  0.00           C  
HETATM    8  C8  UNL     1       4.003   1.096   0.447  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.740   0.715  -0.341  1.00  0.00           C  
HETATM   10  C10 UNL     1       2.596  -0.764  -0.454  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.461  -1.319  -1.192  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.067  -1.135  -0.818  1.00  0.00           C  
HETATM   13  C13 UNL     1      -0.508   0.222  -0.781  1.00  0.00           C  
HETATM   14  C14 UNL     1      -2.042   0.044  -0.406  1.00  0.00           C  
HETATM   15  C15 UNL     1      -2.556   1.419  -0.385  1.00  0.00           C  
HETATM   16  C16 UNL     1      -3.955   1.737  -0.145  1.00  0.00           C  
HETATM   17  C17 UNL     1      -4.676   1.398   1.080  1.00  0.00           C  
HETATM   18  C18 UNL     1      -4.826  -0.044   1.361  1.00  0.00           C  
HETATM   19  O1  UNL     1      -5.482  -0.768   0.451  1.00  0.00           O  
HETATM   20  C19 UNL     1      -6.773  -0.744   0.203  1.00  0.00           C  
HETATM   21  C20 UNL     1      -7.540   0.437  -0.253  1.00  0.00           C  
HETATM   22  O2  UNL     1      -7.119   0.990  -1.446  1.00  0.00           O  
HETATM   23  C21 UNL     1      -8.998  -0.042  -0.523  1.00  0.00           C  
HETATM   24  O3  UNL     1      -9.430  -0.598   0.670  1.00  0.00           O  
HETATM   25  P1  UNL     1     -11.007  -1.172   0.546  1.00  0.00           P  
HETATM   26  O4  UNL     1     -11.783  -1.022   1.825  1.00  0.00           O  
HETATM   27  O5  UNL     1     -10.970  -2.791   0.060  1.00  0.00           O  
HETATM   28  O6  UNL     1     -11.814  -0.252  -0.637  1.00  0.00           O  
HETATM   29  H1  UNL     1      10.755   0.813   1.125  1.00  0.00           H  
HETATM   30  H2  UNL     1      10.215   0.890  -0.637  1.00  0.00           H  
HETATM   31  H3  UNL     1      11.860   0.450  -0.220  1.00  0.00           H  
HETATM   32  H4  UNL     1      11.219  -1.683  -0.393  1.00  0.00           H  
HETATM   33  H5  UNL     1      10.422  -1.467   1.225  1.00  0.00           H  
HETATM   34  H6  UNL     1       9.294  -1.081  -1.610  1.00  0.00           H  
HETATM   35  H7  UNL     1       8.992  -2.551  -0.594  1.00  0.00           H  
HETATM   36  H8  UNL     1       6.987  -1.321  -0.420  1.00  0.00           H  
HETATM   37  H9  UNL     1       7.838  -1.229   1.114  1.00  0.00           H  
HETATM   38  H10 UNL     1       8.490   1.065   0.881  1.00  0.00           H  
HETATM   39  H11 UNL     1       7.854   1.132  -0.850  1.00  0.00           H  
HETATM   40  H12 UNL     1       6.345   0.690   1.714  1.00  0.00           H  
HETATM   41  H13 UNL     1       6.380   2.160   0.718  1.00  0.00           H  
HETATM   42  H14 UNL     1       5.385   0.921  -1.213  1.00  0.00           H  
HETATM   43  H15 UNL     1       5.199  -0.533  -0.162  1.00  0.00           H  
HETATM   44  H16 UNL     1       4.033   2.192   0.583  1.00  0.00           H  
HETATM   45  H17 UNL     1       3.865   0.655   1.449  1.00  0.00           H  
HETATM   46  H18 UNL     1       1.942   1.247   0.196  1.00  0.00           H  
HETATM   47  H19 UNL     1       2.796   1.195  -1.358  1.00  0.00           H  
HETATM   48  H20 UNL     1       2.785  -1.276   0.533  1.00  0.00           H  
HETATM   49  H21 UNL     1       3.527  -1.094  -1.043  1.00  0.00           H  
HETATM   50  H22 UNL     1       1.628  -2.462  -1.265  1.00  0.00           H  
HETATM   51  H23 UNL     1       1.641  -1.045  -2.301  1.00  0.00           H  
HETATM   52  H24 UNL     1      -0.551  -1.706  -1.600  1.00  0.00           H  
HETATM   53  H25 UNL     1      -0.211  -1.734   0.120  1.00  0.00           H  
HETATM   54  H26 UNL     1      -0.188   0.904   0.002  1.00  0.00           H  
HETATM   55  H27 UNL     1      -0.553   0.644  -1.803  1.00  0.00           H  
HETATM   56  H28 UNL     1      -1.939  -0.376   0.628  1.00  0.00           H  
HETATM   57  H29 UNL     1      -2.501  -0.676  -1.070  1.00  0.00           H  
HETATM   58  H30 UNL     1      -2.213   1.893  -1.373  1.00  0.00           H  
HETATM   59  H31 UNL     1      -1.898   2.002   0.352  1.00  0.00           H  
HETATM   60  H32 UNL     1      -4.543   1.374  -1.059  1.00  0.00           H  
HETATM   61  H33 UNL     1      -4.068   2.875  -0.285  1.00  0.00           H  
HETATM   62  H34 UNL     1      -4.142   1.820   2.008  1.00  0.00           H  
HETATM   63  H35 UNL     1      -5.672   1.901   1.132  1.00  0.00           H  
HETATM   64  H36 UNL     1      -5.451  -0.066   2.365  1.00  0.00           H  
HETATM   65  H37 UNL     1      -3.854  -0.527   1.649  1.00  0.00           H  
HETATM   66  H38 UNL     1      -7.007  -1.561  -0.573  1.00  0.00           H  
HETATM   67  H39 UNL     1      -7.333  -1.158   1.123  1.00  0.00           H  
HETATM   68  H40 UNL     1      -7.682   1.217   0.514  1.00  0.00           H  
HETATM   69  H41 UNL     1      -7.245   1.966  -1.441  1.00  0.00           H  
HETATM   70  H42 UNL     1      -8.938  -0.793  -1.325  1.00  0.00           H  
HETATM   71  H43 UNL     1      -9.624   0.791  -0.855  1.00  0.00           H  
HETATM   72  H44 UNL     1     -10.142  -3.023  -0.403  1.00  0.00           H  
HETATM   73  H45 UNL     1     -12.767  -0.093  -0.384  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3   32   33
CONECT    3    4   34   35
CONECT    4    5   36   37
CONECT    5    6   38   39
CONECT    6    7   40   41
CONECT    7    8   42   43
CONECT    8    9   44   45
CONECT    9   10   46   47
CONECT   10   11   48   49
CONECT   11   12   50   51
CONECT   12   13   52   53
CONECT   13   14   54   55
CONECT   14   15   56   57
CONECT   15   16   58   59
CONECT   16   17   60   61
CONECT   17   18   62   63
CONECT   18   19   64   65
CONECT   19   20
CONECT   20   21   66   67
CONECT   21   22   23   68
CONECT   22   69
CONECT   23   24   70   71
CONECT   24   25
CONECT   25   26   26   27   28
CONECT   27   72
CONECT   28   73
END

HMDB0011144
     RDKit          3D
LysoPA(O-18:0/0:0)
 73 72  0  0  0  0  0  0  0  0999 V2000
   10.7766    0.3326    0.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4255   -1.1153    0.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1419   -1.4178   -0.5250 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8935   -0.8411    0.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7696    0.6294    0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4080    1.0663    0.6865 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2656    0.5967   -0.1832 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0033    1.0957    0.4474 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7398    0.7147   -0.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5957   -0.7639   -0.4543 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4611   -1.3186   -1.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0667   -1.1346   -0.8177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5077    0.2224   -0.7810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0419    0.0439   -0.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5562    1.4191   -0.3845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9549    1.7372   -0.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6755    1.3978    1.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8262   -0.0440    1.3614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4820   -0.7679    0.4510 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7734   -0.7443    0.2028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5405    0.4372   -0.2534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1185    0.9895   -1.4461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9985   -0.0424   -0.5226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4297   -0.5985    0.6702 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0074   -1.1721    0.5462 P   0  0  0  0  0  5  0  0  0  0  0  0
  -11.7826   -1.0217    1.8249 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9697   -2.7906    0.0600 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8141   -0.2515   -0.6369 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7547    0.8131    1.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2154    0.8903   -0.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8600    0.4497   -0.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2191   -1.6834   -0.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4219   -1.4668    1.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2943   -1.0809   -1.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9924   -2.5506   -0.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9869   -1.3206   -0.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8381   -1.2290    1.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4903    1.0654    0.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8542    1.1316   -0.8505 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3449    0.6900    1.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3804    2.1599    0.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3850    0.9210   -1.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1993   -0.5327   -0.1623 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0334    2.1918    0.5835 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8646    0.6552    1.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9419    1.2472    0.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7961    1.1947   -1.3579 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7853   -1.2762    0.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5267   -1.0941   -1.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6282   -2.4616   -1.2654 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6410   -1.0449   -2.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5514   -1.7063   -1.5996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2106   -1.7344    0.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1876    0.9035    0.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5533    0.6437   -1.8028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9393   -0.3763    0.6280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5012   -0.6759   -1.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2128    1.8928   -1.3727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8985    2.0024    0.3517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5428    1.3741   -1.0589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0676    2.8747   -0.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1421    1.8202    2.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6724    1.9010    1.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4508   -0.0664    2.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8545   -0.5266    1.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0070   -1.5607   -0.5732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3334   -1.1578    1.1231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6816    1.2165    0.5139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2447    1.9663   -1.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9376   -0.7926   -1.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6243    0.7908   -0.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1421   -3.0229   -0.4029 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7669   -0.0932   -0.3836 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  1  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  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 25 28  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  0
  7 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
  9 47  1  0
 10 48  1  0
 10 49  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  0
 12 53  1  0
 13 54  1  0
 13 55  1  0
 14 56  1  0
 14 57  1  0
 15 58  1  0
 15 59  1  0
 16 60  1  0
 16 61  1  0
 17 62  1  0
 17 63  1  0
 18 64  1  0
 18 65  1  0
 20 66  1  0
 20 67  1  0
 21 68  1  0
 22 69  1  0
 23 70  1  0
 23 71  1  0
 27 72  1  0
 28 73  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Octadecyl-sn-glycero-3-phosphate	HMDB
LysoPA(18:0E)	HMDB
LysoPA(O-18:0)	HMDB
PA(O-18:0/0:0)	HMDB
[(2R)-2-Hydroxy-3-octadecoxy-propyl] dihydrogen phosphate	HMDB
LPA(18:0E/0:0)	HMDB

Chemical Formula

C₂₁H₄₅O₆P

Average Molecular Weight

424.559

Monoisotopic Molecular Weight

424.295376167

IUPAC Name

[2-hydroxy-3-(octadecyloxy)propoxy]phosphonic acid

Traditional Name

2-hydroxy-3-(octadecyloxy)propoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCCCOCC(O)COP(O)(O)=O

InChI Identifier

InChI=1S/C21H45O6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-26-19-21(22)20-27-28(23,24)25/h21-22H,2-20H2,1H3,(H2,23,24,25)

InChI Key

HUUYDUFSUADEJQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monoalkylglycerophosphates. Monoalkylglycerophosphates are compounds containing glycerophosphate moiety attached to an fatty acyl chain through an ether bond.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphates

Direct Parent

Monoalkylglycerophosphates

Alternative Parents

Substituents

Monoalkylglycerophosphate
Monoalkyl phosphate
Glycerol ether
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Secondary alcohol
Ether
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Feces (PMID: 26848182)

Cellular substructure

Extracellular (HMDB: HMDB0011144)
Membrane (HMDB: HMDB0011144)

Source

Exogenous

Exogenous (HMDB: HMDB0011144)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0011144)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Plasmalogen Synthesis (PathBank: SMP0087517)

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	0.0024 g/L	ALOGPS
logP	5.43	ALOGPS
logP	6.23	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	1.51	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	114.43 m³·mol⁻¹	ChemAxon
Polarizability	51.93 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]+	194.554	30932474
DeepCCS	[M-H]-	191.102	30932474
DeepCCS	[M-2H]-	225.672	30932474
DeepCCS	[M+Na]+	202.301	30932474
AllCCS	[M+H]+	213.5	32859911
AllCCS	[M+H-H2O]+	211.5	32859911
AllCCS	[M+NH4]+	215.3	32859911
AllCCS	[M+Na]+	215.8	32859911
AllCCS	[M-H]-	206.8	32859911
AllCCS	[M+Na-2H]-	209.0	32859911
AllCCS	[M+HCOO]-	211.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	11.09 minutes	32390414
Predicted by Siyang on May 30, 2022	15.3934 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.7 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	60.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2789.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	224.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	215.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	166.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	526.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	748.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	766.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	415.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1562.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	605.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1425.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	623.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	435.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	381.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	295.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	16.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
LysoPA(O-18:0/0:0)	CCCCCCCCCCCCCCCCCCOCC(O)COP(O)(O)=O	3431.6	Standard polar	33892256
LysoPA(O-18:0/0:0)	CCCCCCCCCCCCCCCCCCOCC(O)COP(O)(O)=O	2829.5	Standard non polar	33892256
LysoPA(O-18:0/0:0)	CCCCCCCCCCCCCCCCCCOCC(O)COP(O)(O)=O	3197.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
LysoPA(O-18:0/0:0),1TMS,isomer #1	CCCCCCCCCCCCCCCCCCOCC(COP(=O)(O)O)O[Si](C)(C)C	3250.7	Semi standard non polar	33892256
LysoPA(O-18:0/0:0),1TMS,isomer #2	CCCCCCCCCCCCCCCCCCOCC(O)COP(=O)(O)O[Si](C)(C)C	3214.7	Semi standard non polar	33892256
LysoPA(O-18:0/0:0),2TMS,isomer #1	CCCCCCCCCCCCCCCCCCOCC(COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C	3202.0	Semi standard non polar	33892256
LysoPA(O-18:0/0:0),2TMS,isomer #1	CCCCCCCCCCCCCCCCCCOCC(COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C	3067.7	Standard non polar	33892256
LysoPA(O-18:0/0:0),2TMS,isomer #1	CCCCCCCCCCCCCCCCCCOCC(COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C	3733.5	Standard polar	33892256
LysoPA(O-18:0/0:0),2TMS,isomer #2	CCCCCCCCCCCCCCCCCCOCC(O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3215.6	Semi standard non polar	33892256
LysoPA(O-18:0/0:0),2TMS,isomer #2	CCCCCCCCCCCCCCCCCCOCC(O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3099.4	Standard non polar	33892256
LysoPA(O-18:0/0:0),2TMS,isomer #2	CCCCCCCCCCCCCCCCCCOCC(O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3442.2	Standard polar	33892256
LysoPA(O-18:0/0:0),3TMS,isomer #1	CCCCCCCCCCCCCCCCCCOCC(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3216.8	Semi standard non polar	33892256
LysoPA(O-18:0/0:0),3TMS,isomer #1	CCCCCCCCCCCCCCCCCCOCC(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3107.2	Standard non polar	33892256
LysoPA(O-18:0/0:0),3TMS,isomer #1	CCCCCCCCCCCCCCCCCCOCC(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3260.0	Standard polar	33892256
LysoPA(O-18:0/0:0),1TBDMS,isomer #1	CCCCCCCCCCCCCCCCCCOCC(COP(=O)(O)O)O[Si](C)(C)C(C)(C)C	3520.8	Semi standard non polar	33892256
LysoPA(O-18:0/0:0),1TBDMS,isomer #2	CCCCCCCCCCCCCCCCCCOCC(O)COP(=O)(O)O[Si](C)(C)C(C)(C)C	3458.7	Semi standard non polar	33892256
LysoPA(O-18:0/0:0),2TBDMS,isomer #1	CCCCCCCCCCCCCCCCCCOCC(COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3685.0	Semi standard non polar	33892256
LysoPA(O-18:0/0:0),2TBDMS,isomer #1	CCCCCCCCCCCCCCCCCCOCC(COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3341.9	Standard non polar	33892256
LysoPA(O-18:0/0:0),2TBDMS,isomer #1	CCCCCCCCCCCCCCCCCCOCC(COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3811.3	Standard polar	33892256
LysoPA(O-18:0/0:0),2TBDMS,isomer #2	CCCCCCCCCCCCCCCCCCOCC(O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3671.0	Semi standard non polar	33892256
LysoPA(O-18:0/0:0),2TBDMS,isomer #2	CCCCCCCCCCCCCCCCCCOCC(O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3328.1	Standard non polar	33892256
LysoPA(O-18:0/0:0),2TBDMS,isomer #2	CCCCCCCCCCCCCCCCCCOCC(O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3594.5	Standard polar	33892256
LysoPA(O-18:0/0:0),3TBDMS,isomer #1	CCCCCCCCCCCCCCCCCCOCC(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3910.9	Semi standard non polar	33892256
LysoPA(O-18:0/0:0),3TBDMS,isomer #1	CCCCCCCCCCCCCCCCCCOCC(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3482.5	Standard non polar	33892256
LysoPA(O-18:0/0:0),3TBDMS,isomer #1	CCCCCCCCCCCCCCCCCCOCC(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3469.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - LysoPA(O-18:0/0:0) GC-MS (1 TMS) - 70eV, Positive	splash10-03di-9470000000-767f506dcd3b43c89de4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - LysoPA(O-18:0/0:0) 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(O-18:0/0:0) 10V, Positive-QTOF	splash10-004i-2135900000-7c0ef85e3ad7588d5753	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPA(O-18:0/0:0) 20V, Positive-QTOF	splash10-0zi1-9476200000-0b62a2b23bd2c2bd072f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPA(O-18:0/0:0) 40V, Positive-QTOF	splash10-0udi-8891000000-f8c957954f4425e7e3c4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPA(O-18:0/0:0) 10V, Negative-QTOF	splash10-00fr-6110900000-8f719fedcd8fb1e4993c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPA(O-18:0/0:0) 20V, Negative-QTOF	splash10-004i-9000000000-0ea6133aa158799eba68	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPA(O-18:0/0:0) 40V, Negative-QTOF	splash10-004i-9000000000-8f8d66131a6962c70022	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPA(O-18:0/0:0) 10V, Negative-QTOF	splash10-00di-0000900000-ff350a6e4e4ad403170c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPA(O-18:0/0:0) 20V, Negative-QTOF	splash10-004i-9000100000-2f4e56c32a15bea85646	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPA(O-18:0/0:0) 40V, Negative-QTOF	splash10-004i-9000000000-a5e502a2627af2048a1f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPA(O-18:0/0:0) 10V, Positive-QTOF	splash10-004i-4105900000-6c1e7cdab36e3a134666	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPA(O-18:0/0:0) 20V, Positive-QTOF	splash10-004i-9414200000-cd77a5ab324c3617b32a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPA(O-18:0/0:0) 40V, Positive-QTOF	splash10-052e-9100000000-586af9b8586d3135a523	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Plasmalogen Synthesis		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Crohns disease	26848182	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Iron deficiency	26848182	details

Associated Disorders and Diseases

Disease References

Crohn's disease
Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
Iron deficiency
Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]

Associated OMIM IDs

266600 (Crohn's disease)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB098854

KNApSAcK ID

Not Available

Chemspider ID

16017852

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12051354

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

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 ]
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.

Only showing the first 10 proteins. There are 32 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. 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

2. 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

3. 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

4. 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

Enzyme Details

5. Acyl-CoA:lysophosphatidylglycerol acyltransferase 1

General function:: Involved in acyltransferase activity
Specific function:: Lysophoshatidylglycerol (LPG) specific acyltransferase that recognizes various acyl-CoAs and LPGs as substrates but demonstrates a clear preference for long chain saturated fatty acyl-CoAs and oleoyl-CoA as acyl donors. Prefers oleoyl-LPG over palmitoyl-LPG as an acyl receptor and oleoyl-CoA over lauroyl-CoA as an acyl donor
Gene Name:: LPGAT1
Uniprot ID:: Q92604
Molecular weight:: 43089.1

Enzyme Details

6. Focal adhesion kinase 1

General function:: Involved in binding
Specific function:: Non-receptor protein-tyrosine kinase implicated in signaling pathways involved in cell motility, proliferation and apoptosis. Activated by tyrosine-phosphorylation in response to either integrin clustering induced by cell adhesion or antibody cross-linking, or via G-protein coupled receptor (GPCR) occupancy by ligands such as bombesin or lysophosphatidic acid, or via LDL receptor occupancy. Plays a potential role in oncogenic transformations resulting in increased kinase activity
Gene Name:: PTK2
Uniprot ID:: Q05397
Molecular weight:: 119232.0

Enzyme Details

7. Protein-tyrosine kinase 2-beta

General function:: Involved in binding
Specific function:: Involved in calcium induced regulation of ion channel and activation of the map kinase signaling pathway. May represent an important signaling intermediate between neuropeptide activated receptors or neurotransmitters that increase calcium flux and the downstream signals that regulate neuronal activity. Interacts with the SH2 domain of Grb2. May phosphorylate the voltage-gated potassium channel protein Kv1.2. Its activation is highly correlated with the stimulation of c-Jun N-terminal kinase activity. Involved in osmotic stress-dependent SNCA 'Tyr-125' phosphorylation
Gene Name:: PTK2B
Uniprot ID:: Q14289
Molecular weight:: 115873.6

Enzyme Details

8. 1-acyl-sn-glycerol-3-phosphate acyltransferase gamma

General function:: Involved in acyltransferase activity
Specific function:: Converts lysophosphatidic acid (LPA) into phosphatidic acid by incorporating an acyl moiety at the sn-2 position of the glycerol backbone. Acts on LPA containing saturated or unsaturated fatty acids C16:0-C20:4 at the sn-1 position using C18:1, C20:4 or C18:2-CoA as the acyl donor. Also acts on lysophosphatidylcholine, lysophosphatidylinositol and lysophosphatidylserine using C18:1 or C20:4-CoA.
Gene Name:: AGPAT3
Uniprot ID:: Q9NRZ7
Molecular weight:: 43380.605

Enzyme Details

9. 1-acyl-sn-glycerol-3-phosphate acyltransferase beta

General function:: Lipid transport and metabolism
Specific function:: Converts lysophosphatidic acid (LPA) into phosphatidic acid by incorporating an acyl moiety at the sn-2 position of the glycerol backbone.
Gene Name:: AGPAT2
Uniprot ID:: O15120
Molecular weight:: 27278.915

Enzyme Details

10. 1-acyl-sn-glycerol-3-phosphate acyltransferase alpha

General function:: Involved in acyltransferase activity
Specific function:: Converts lysophosphatidic acid (LPA) into phosphatidic acid by incorporating an acyl moiety at the sn-2 position of the glycerol backbone.
Gene Name:: AGPAT1
Uniprot ID:: Q99943
Molecular weight:: 31716.27

Only showing the first 10 proteins. There are 32 proteins in total.

Show all enzymes and transporters

Showing metabocard for LysoPA(O-18:0/0:0) (HMDB0011144)

MOL for HMDB0011144 (LysoPA(O-18:0/0:0))

3D MOL for HMDB0011144 (LysoPA(O-18:0/0:0))

3D SDF for HMDB0011144 (LysoPA(O-18:0/0:0))

3D-SDF for HMDB0011144 (LysoPA(O-18:0/0:0))

PDB for HMDB0011144 (LysoPA(O-18:0/0:0))

3D PDB for HMDB0011144 (LysoPA(O-18:0/0:0))

SMILES for HMDB0011144 (LysoPA(O-18:0/0:0))

INCHI for HMDB0011144 (LysoPA(O-18:0/0:0))

Structure for HMDB0011144 (LysoPA(O-18:0/0:0))

3D Structure for HMDB0011144 (LysoPA(O-18:0/0:0))

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes