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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2008-09-12 01:12:57 UTC

Update Date

2022-03-07 02:49:35 UTC

HMDB ID

HMDB0007007

Secondary Accession Numbers

HMDB07007

Metabolite Identification

Common Name

CPA(18:2(9Z,12Z)/0:0)

Description

cPA(18:2(9Z,12Z)/0:0) is a cyclic phosphatidic acid or cyclic lysophosphatidic acid. It is a glycerophospholipid in which a cyclic phosphate moiety occupies two glycerol substitution sites. Lysophosphatidic acids can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1). Fatty acids containing 16 and 18 carbons are the most common. Cyclic phosphatidic acids have been detected in a wide range of organisms including humans, especially in the brain but also in serum (at a concentration of 10-7M). cPA's have a cyclic phosphate at the sn-2 and sn-3 positions of the glycerol carbons, and this structure is absolutely necessary for their activities. In particular, it is found in tissues subject to injury, and while it may have some similar signalling functions to lysophosphatidic acid per se, it also has some quite distinct biological activities. For example, cyclic phosphatidic acid is known to be a specific inhibitor of DNA polymerase alpha. It has an appreciable effect on the inhibition of cancer cell invasion and metastasis.

Structure

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

  Mrv0541 02231221002D          

 28 28  0  0  0  0            999 V2000
   19.2636  -10.7119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7097  -11.4089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8543  -11.4089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1159  -11.0032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3912  -12.1518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2595  -12.1011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1377  -11.9098    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   21.0237  -11.8210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2910  -12.7854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5307  -12.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2451  -12.5643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9596  -12.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6741  -12.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3885  -12.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1031  -12.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8175  -12.5643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5320  -12.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2465  -12.5643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9609  -12.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6754  -12.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3899  -12.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1044  -12.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8189  -12.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5333  -12.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2478  -12.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9623  -12.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6767  -12.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6767  -13.3893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  3  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  4  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  2  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  2  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 25 24  1  0  0  0  0
 26 25  1  0  0  0  0
 27 26  1  0  0  0  0
 28 27  2  0  0  0  0
  5 27  1  0  0  0  0
M  END

HMDB0007007
     RDKit          3D
CPA(18:2(9Z,12Z)/0:0)
 65 65  0  0  0  0  0  0  0  0999 V2000
   11.2425    0.7677   -0.1919 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0375    0.0150   -0.6839 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9752   -0.0919    0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7813   -0.8528   -0.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6979   -0.9843    0.9408 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2054    0.3039    1.4051 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9596    0.6656    1.2886 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8476   -0.1130    0.6927 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2439    0.6131   -0.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9949    0.9660   -0.4733 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0496    0.7027    0.6068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1181   -0.1768    0.1191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8242    0.5431   -0.9822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9726   -0.2530   -1.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9781   -0.5246   -0.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5246    0.7386    0.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5190    0.4367    1.2311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7109   -0.2703    0.6791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7965   -0.3782   -0.5592 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6820   -0.7871    1.4772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8183   -1.4269    1.0919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8720   -0.5787    0.5005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5507    0.2599   -0.6590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7475    0.9469   -0.9914 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9115   -0.2321   -0.7008 P   0  0  0  0  0  5  0  0  0  0  0  0
  -11.5173   -0.7710   -1.9725 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0937    0.3354    0.3641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9894   -1.3846    0.1083 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4870    0.5191    0.8576 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1126    0.4480   -0.8225 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1326    1.8599   -0.3534 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3481   -0.9725   -1.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5752    0.5453   -1.5469 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4231   -0.7000    1.2258 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7171    0.8870    0.8122 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0517   -1.8812   -0.4234 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3985   -0.3263   -1.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1292   -1.5855    1.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9111   -1.6002    0.5098 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8775    1.0421    1.8840 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6408    1.6682    1.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1635   -1.0945    0.2909 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1509   -0.3445    1.5124 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292    0.8242   -1.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6665    1.5052   -1.3881 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5178    1.7035    0.7969 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4206    0.4145    1.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2432   -1.1419   -0.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7545   -0.3428    1.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1381    0.7233   -1.8582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1949    1.5463   -0.6846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5110    0.2754   -2.3261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6267   -1.2527   -1.8800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5081   -1.1119    0.3990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7754   -1.1539   -0.8158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7237    1.3572    0.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0303    1.3234   -0.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0227   -0.2573    1.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8323    1.3358    1.8004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2839   -2.0032    1.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5727   -2.3077    0.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2997    0.1075    1.2933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8810    1.1004   -0.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2468   -0.2233   -1.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9033    0.6439   -0.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  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
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 25 28  1  0
 28 22  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
  7 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 14 52  1  0
 14 53  1  0
 15 54  1  0
 15 55  1  0
 16 56  1  0
 16 57  1  0
 17 58  1  0
 17 59  1  0
 21 60  1  0
 21 61  1  0
 22 62  1  0
 23 63  1  0
 23 64  1  0
 27 65  1  0
M  END

  Mrv0541 02231221002D          

 28 28  0  0  0  0            999 V2000
   19.2636  -10.7119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7097  -11.4089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8543  -11.4089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1159  -11.0032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3912  -12.1518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2595  -12.1011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1377  -11.9098    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   21.0237  -11.8210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2910  -12.7854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5307  -12.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2451  -12.5643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9596  -12.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6741  -12.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3885  -12.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1031  -12.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8175  -12.5643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5320  -12.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2465  -12.5643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9609  -12.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6754  -12.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3899  -12.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1044  -12.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8189  -12.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5333  -12.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2478  -12.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9623  -12.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6767  -12.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6767  -13.3893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  3  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  4  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  2  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  2  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 25 24  1  0  0  0  0
 26 25  1  0  0  0  0
 27 26  1  0  0  0  0
 28 27  2  0  0  0  0
  5 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0007007

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC1COP(O)(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C21H37O6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(22)25-18-20-19-26-28(23,24)27-20/h6-7,9-10,20H,2-5,8,11-19H2,1H3,(H,23,24)/b7-6-,10-9-

> <INCHI_KEY>
AZRMIMGGEACCGU-HZJYTTRNSA-N

> <FORMULA>
C21H37O6P

> <MOLECULAR_WEIGHT>
416.4886

> <EXACT_MASS>
416.232775428

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
46.5665370435898

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-hydroxy-2-oxo-1,3,2λ⁵-dioxaphospholan-4-yl)methyl (9Z,12Z)-octadeca-9,12-dienoate

> <ALOGPS_LOGP>
5.47

> <JCHEM_LOGP>
6.020305656333333

> <ALOGPS_LOGS>
-5.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8399068895320578

> <JCHEM_PKA_STRONGEST_BASIC>
-7.038668785414281

> <JCHEM_POLAR_SURFACE_AREA>
82.06

> <JCHEM_REFRACTIVITY>
112.63659999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.96e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-hydroxy-2-oxo-1,3,2λ⁵-dioxaphospholan-4-yl)methyl (9Z,12Z)-octadeca-9,12-dienoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0007007
     RDKit          3D
CPA(18:2(9Z,12Z)/0:0)
 65 65  0  0  0  0  0  0  0  0999 V2000
   11.2425    0.7677   -0.1919 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0375    0.0150   -0.6839 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9752   -0.0919    0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7813   -0.8528   -0.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6979   -0.9843    0.9408 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2054    0.3039    1.4051 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9596    0.6656    1.2886 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8476   -0.1130    0.6927 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2439    0.6131   -0.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9949    0.9660   -0.4733 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0496    0.7027    0.6068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1181   -0.1768    0.1191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8242    0.5431   -0.9822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9726   -0.2530   -1.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9781   -0.5246   -0.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5246    0.7386    0.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5190    0.4367    1.2311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7109   -0.2703    0.6791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7965   -0.3782   -0.5592 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6820   -0.7871    1.4772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8183   -1.4269    1.0919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8720   -0.5787    0.5005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5507    0.2599   -0.6590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7475    0.9469   -0.9914 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9115   -0.2321   -0.7008 P   0  0  0  0  0  5  0  0  0  0  0  0
  -11.5173   -0.7710   -1.9725 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0937    0.3354    0.3641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9894   -1.3846    0.1083 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4870    0.5191    0.8576 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1126    0.4480   -0.8225 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1326    1.8599   -0.3534 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3481   -0.9725   -1.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5752    0.5453   -1.5469 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4231   -0.7000    1.2258 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7171    0.8870    0.8122 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0517   -1.8812   -0.4234 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3985   -0.3263   -1.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1292   -1.5855    1.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9111   -1.6002    0.5098 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8775    1.0421    1.8840 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6408    1.6682    1.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1635   -1.0945    0.2909 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1509   -0.3445    1.5124 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292    0.8242   -1.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6665    1.5052   -1.3881 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5178    1.7035    0.7969 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4206    0.4145    1.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2432   -1.1419   -0.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7545   -0.3428    1.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1381    0.7233   -1.8582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1949    1.5463   -0.6846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5110    0.2754   -2.3261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6267   -1.2527   -1.8800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5081   -1.1119    0.3990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7754   -1.1539   -0.8158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7237    1.3572    0.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0303    1.3234   -0.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0227   -0.2573    1.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8323    1.3358    1.8004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2839   -2.0032    1.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5727   -2.3077    0.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2997    0.1075    1.2933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8810    1.1004   -0.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2468   -0.2233   -1.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9033    0.6439   -0.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  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
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 25 28  1  0
 28 22  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
  7 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 14 52  1  0
 14 53  1  0
 15 54  1  0
 15 55  1  0
 16 56  1  0
 16 57  1  0
 17 58  1  0
 17 59  1  0
 21 60  1  0
 21 61  1  0
 22 62  1  0
 23 63  1  0
 23 64  1  0
 27 65  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      35.959 -19.996   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      34.925 -21.297   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      33.328 -21.297   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      37.550 -20.539   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      32.464 -22.683   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      35.951 -22.589   0.000  0.00  0.00           O+0
HETATM    7  P   UNK     0      37.590 -22.232   0.000  0.00  0.00           P+0
HETATM    8  O   UNK     0      39.244 -22.066   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      37.877 -23.866   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.457 -22.683   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.791 -23.453   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.125 -22.683   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.458 -23.453   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.792 -22.683   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.126 -23.453   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.459 -23.453   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.793 -22.683   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      19.127 -23.453   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      20.460 -23.453   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      21.794 -22.683   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      23.128 -23.453   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      24.462 -22.683   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      25.795 -23.453   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      27.129 -22.683   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      28.463 -23.453   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      29.796 -22.683   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      31.130 -23.453   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      31.130 -24.993   0.000  0.00  0.00           O+0
CONECT    1    2    4                                                       
CONECT    2    1    3    6                                                  
CONECT    3    2    5                                                       
CONECT    4    1    7                                                       
CONECT    5    3   27                                                       
CONECT    6    2    7                                                       
CONECT    7    6    4    8    9                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10   11                                                            
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
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    5                                                  
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   56    0
END

COMPND    HMDB0007007
HETATM    1  C1  UNL     1      11.242   0.768  -0.192  1.00  0.00           C  
HETATM    2  C2  UNL     1      10.037   0.015  -0.684  1.00  0.00           C  
HETATM    3  C3  UNL     1       8.975  -0.092   0.413  1.00  0.00           C  
HETATM    4  C4  UNL     1       7.781  -0.853  -0.118  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.698  -0.984   0.941  1.00  0.00           C  
HETATM    6  C6  UNL     1       6.205   0.304   1.405  1.00  0.00           C  
HETATM    7  C7  UNL     1       4.960   0.666   1.289  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.848  -0.113   0.693  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.244   0.613  -0.457  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.995   0.966  -0.473  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.050   0.703   0.607  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.118  -0.177   0.119  1.00  0.00           C  
HETATM   13  C13 UNL     1      -0.824   0.543  -0.982  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.973  -0.253  -1.524  1.00  0.00           C  
HETATM   15  C15 UNL     1      -2.978  -0.525  -0.426  1.00  0.00           C  
HETATM   16  C16 UNL     1      -3.525   0.739   0.162  1.00  0.00           C  
HETATM   17  C17 UNL     1      -4.519   0.437   1.231  1.00  0.00           C  
HETATM   18  C18 UNL     1      -5.711  -0.270   0.679  1.00  0.00           C  
HETATM   19  O1  UNL     1      -5.796  -0.378  -0.559  1.00  0.00           O  
HETATM   20  O2  UNL     1      -6.682  -0.787   1.477  1.00  0.00           O  
HETATM   21  C19 UNL     1      -7.818  -1.427   1.092  1.00  0.00           C  
HETATM   22  C20 UNL     1      -8.872  -0.579   0.501  1.00  0.00           C  
HETATM   23  C21 UNL     1      -8.551   0.260  -0.659  1.00  0.00           C  
HETATM   24  O3  UNL     1      -9.747   0.947  -0.991  1.00  0.00           O  
HETATM   25  P1  UNL     1     -10.911  -0.232  -0.701  1.00  0.00           P  
HETATM   26  O4  UNL     1     -11.517  -0.771  -1.972  1.00  0.00           O  
HETATM   27  O5  UNL     1     -12.094   0.335   0.364  1.00  0.00           O  
HETATM   28  O6  UNL     1      -9.989  -1.385   0.108  1.00  0.00           O  
HETATM   29  H1  UNL     1      11.487   0.519   0.858  1.00  0.00           H  
HETATM   30  H2  UNL     1      12.113   0.448  -0.823  1.00  0.00           H  
HETATM   31  H3  UNL     1      11.133   1.860  -0.353  1.00  0.00           H  
HETATM   32  H4  UNL     1      10.348  -0.972  -1.039  1.00  0.00           H  
HETATM   33  H5  UNL     1       9.575   0.545  -1.547  1.00  0.00           H  
HETATM   34  H6  UNL     1       9.423  -0.700   1.226  1.00  0.00           H  
HETATM   35  H7  UNL     1       8.717   0.887   0.812  1.00  0.00           H  
HETATM   36  H8  UNL     1       8.052  -1.881  -0.423  1.00  0.00           H  
HETATM   37  H9  UNL     1       7.399  -0.326  -1.007  1.00  0.00           H  
HETATM   38  H10 UNL     1       7.129  -1.585   1.787  1.00  0.00           H  
HETATM   39  H11 UNL     1       5.911  -1.600   0.510  1.00  0.00           H  
HETATM   40  H12 UNL     1       6.878   1.042   1.884  1.00  0.00           H  
HETATM   41  H13 UNL     1       4.641   1.668   1.665  1.00  0.00           H  
HETATM   42  H14 UNL     1       4.164  -1.094   0.291  1.00  0.00           H  
HETATM   43  H15 UNL     1       3.151  -0.345   1.512  1.00  0.00           H  
HETATM   44  H16 UNL     1       3.929   0.824  -1.279  1.00  0.00           H  
HETATM   45  H17 UNL     1       1.666   1.505  -1.388  1.00  0.00           H  
HETATM   46  H18 UNL     1       0.518   1.703   0.797  1.00  0.00           H  
HETATM   47  H19 UNL     1       1.421   0.414   1.573  1.00  0.00           H  
HETATM   48  H20 UNL     1       0.243  -1.142  -0.259  1.00  0.00           H  
HETATM   49  H21 UNL     1      -0.755  -0.343   1.000  1.00  0.00           H  
HETATM   50  H22 UNL     1      -0.138   0.723  -1.858  1.00  0.00           H  
HETATM   51  H23 UNL     1      -1.195   1.546  -0.685  1.00  0.00           H  
HETATM   52  H24 UNL     1      -2.511   0.275  -2.326  1.00  0.00           H  
HETATM   53  H25 UNL     1      -1.627  -1.253  -1.880  1.00  0.00           H  
HETATM   54  H26 UNL     1      -2.508  -1.112   0.399  1.00  0.00           H  
HETATM   55  H27 UNL     1      -3.775  -1.154  -0.816  1.00  0.00           H  
HETATM   56  H28 UNL     1      -2.724   1.357   0.639  1.00  0.00           H  
HETATM   57  H29 UNL     1      -4.030   1.323  -0.655  1.00  0.00           H  
HETATM   58  H30 UNL     1      -4.023  -0.257   1.968  1.00  0.00           H  
HETATM   59  H31 UNL     1      -4.832   1.336   1.800  1.00  0.00           H  
HETATM   60  H32 UNL     1      -8.284  -2.003   1.972  1.00  0.00           H  
HETATM   61  H33 UNL     1      -7.573  -2.308   0.397  1.00  0.00           H  
HETATM   62  H34 UNL     1      -9.300   0.107   1.293  1.00  0.00           H  
HETATM   63  H35 UNL     1      -7.881   1.100  -0.342  1.00  0.00           H  
HETATM   64  H36 UNL     1      -8.247  -0.223  -1.584  1.00  0.00           H  
HETATM   65  H37 UNL     1     -12.903   0.644  -0.096  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    7   40
CONECT    7    8   41
CONECT    8    9   42   43
CONECT    9   10   10   44
CONECT   10   11   45
CONECT   11   12   46   47
CONECT   12   13   48   49
CONECT   13   14   50   51
CONECT   14   15   52   53
CONECT   15   16   54   55
CONECT   16   17   56   57
CONECT   17   18   58   59
CONECT   18   19   19   20
CONECT   20   21
CONECT   21   22   60   61
CONECT   22   23   28   62
CONECT   23   24   63   64
CONECT   24   25
CONECT   25   26   26   27   28
CONECT   27   65
END

HMDB0007007
     RDKit          3D
CPA(18:2(9Z,12Z)/0:0)
 65 65  0  0  0  0  0  0  0  0999 V2000
   11.2425    0.7677   -0.1919 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0375    0.0150   -0.6839 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9752   -0.0919    0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7813   -0.8528   -0.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6979   -0.9843    0.9408 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2054    0.3039    1.4051 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9596    0.6656    1.2886 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8476   -0.1130    0.6927 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2439    0.6131   -0.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9949    0.9660   -0.4733 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0496    0.7027    0.6068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1181   -0.1768    0.1191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8242    0.5431   -0.9822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9726   -0.2530   -1.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9781   -0.5246   -0.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5246    0.7386    0.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5190    0.4367    1.2311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7109   -0.2703    0.6791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7965   -0.3782   -0.5592 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6820   -0.7871    1.4772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8183   -1.4269    1.0919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8720   -0.5787    0.5005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5507    0.2599   -0.6590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7475    0.9469   -0.9914 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9115   -0.2321   -0.7008 P   0  0  0  0  0  5  0  0  0  0  0  0
  -11.5173   -0.7710   -1.9725 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0937    0.3354    0.3641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9894   -1.3846    0.1083 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4870    0.5191    0.8576 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1126    0.4480   -0.8225 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1326    1.8599   -0.3534 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3481   -0.9725   -1.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5752    0.5453   -1.5469 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4231   -0.7000    1.2258 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7171    0.8870    0.8122 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0517   -1.8812   -0.4234 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3985   -0.3263   -1.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1292   -1.5855    1.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9111   -1.6002    0.5098 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8775    1.0421    1.8840 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6408    1.6682    1.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1635   -1.0945    0.2909 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1509   -0.3445    1.5124 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292    0.8242   -1.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6665    1.5052   -1.3881 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5178    1.7035    0.7969 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4206    0.4145    1.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2432   -1.1419   -0.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7545   -0.3428    1.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1381    0.7233   -1.8582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1949    1.5463   -0.6846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5110    0.2754   -2.3261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6267   -1.2527   -1.8800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5081   -1.1119    0.3990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7754   -1.1539   -0.8158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7237    1.3572    0.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0303    1.3234   -0.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0227   -0.2573    1.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8323    1.3358    1.8004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2839   -2.0032    1.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5727   -2.3077    0.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2997    0.1075    1.2933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8810    1.1004   -0.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2468   -0.2233   -1.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9033    0.6439   -0.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  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
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 25 28  1  0
 28 22  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
  7 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 14 52  1  0
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 15 54  1  0
 15 55  1  0
 16 56  1  0
 16 57  1  0
 17 58  1  0
 17 59  1  0
 21 60  1  0
 21 61  1  0
 22 62  1  0
 23 63  1  0
 23 64  1  0
 27 65  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(9Z,12Z-Octadecadienoyl)-cyclophosphatidic acid	HMDB
1-Linoleoyl-glycero-3-cyclophosphate	HMDB
CPA(18:2)	HMDB
CPA(18:2/0:0)	HMDB
CPA(18:2n6/0:0)	HMDB
CPA(18:2W6/0:0)	HMDB
Cyclic phosphatidic acid(18:2)	HMDB
Cyclic phosphatidic acid(18:2/0:0)	HMDB
Cyclic phosphatidic acid(18:2n6/0:0)	HMDB
Cyclic phosphatidic acid(18:2W6/0:0)	HMDB
(2-Hydroxy-2-oxo-1,3,2λ⁵-dioxaphospholan-4-yl)methyl (9Z,12Z)-octadeca-9,12-dienoic acid	Generator

Chemical Formula

C₂₁H₃₇O₆P

Average Molecular Weight

416.4886

Monoisotopic Molecular Weight

416.232775428

IUPAC Name

(2-hydroxy-2-oxo-1,3,2λ⁵-dioxaphospholan-4-yl)methyl (9Z,12Z)-octadeca-9,12-dienoate

Traditional Name

(2-hydroxy-2-oxo-1,3,2λ⁵-dioxaphospholan-4-yl)methyl (9Z,12Z)-octadeca-9,12-dienoate

CAS Registry Number

Not Available

SMILES

CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC1COP(O)(=O)O1

InChI Identifier

InChI=1S/C21H37O6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(22)25-18-20-19-26-28(23,24)27-20/h6-7,9-10,20H,2-5,8,11-19H2,1H3,(H,23,24)/b7-6-,10-9-

InChI Key

AZRMIMGGEACCGU-HZJYTTRNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic acids and derivatives

Alternative Parents

Substituents

Octadecanoid
Monoacylglycerophosphate
1-acyl-sn-glycerol-2,3-cyclic-phosphate
Fatty acid ester
Organic phosphoric acid derivative
1,3_dioxaphospholane
Carboxylic acid ester
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

All Tissues (HMDB: HMDB0007007)

Cellular substructure

Membrane (HMDB: HMDB0007007)
Extracellular (HMDB: HMDB0007007)

Source

Exogenous

Exogenous (HMDB: HMDB0007007)

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: HMDB0007007)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.003 g/L	ALOGPS
logP	5.47	ALOGPS
logP	6.02	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	1.84	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	112.64 m³·mol⁻¹	ChemAxon
Polarizability	46.57 Å³	ChemAxon
Number of Rings	1	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
DarkChem	[M+H]+	209.591	31661259
DarkChem	[M-H]-	207.071	31661259
DeepCCS	[M+H]+	194.632	30932474
DeepCCS	[M-H]-	191.497	30932474
DeepCCS	[M-2H]-	227.134	30932474
DeepCCS	[M+Na]+	203.424	30932474
AllCCS	[M+H]+	205.8	32859911
AllCCS	[M+H-H2O]+	203.6	32859911
AllCCS	[M+NH4]+	207.8	32859911
AllCCS	[M+Na]+	208.4	32859911
AllCCS	[M-H]-	202.6	32859911
AllCCS	[M+Na-2H]-	205.0	32859911
AllCCS	[M+HCOO]-	207.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
CPA(18:2(9Z,12Z)/0:0)	CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC1COP(O)(=O)O1	3472.6	Standard polar	33892256
CPA(18:2(9Z,12Z)/0:0)	CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC1COP(O)(=O)O1	2881.6	Standard non polar	33892256
CPA(18:2(9Z,12Z)/0:0)	CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC1COP(O)(=O)O1	3069.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
CPA(18:2(9Z,12Z)/0:0),1TMS,isomer #1	CCCCC/C=C\C/C=C\CCCCCCCC(=O)OCC1COP(=O)(O[Si](C)(C)C)O1	3143.1	Semi standard non polar	33892256
CPA(18:2(9Z,12Z)/0:0),1TMS,isomer #1	CCCCC/C=C\C/C=C\CCCCCCCC(=O)OCC1COP(=O)(O[Si](C)(C)C)O1	3027.9	Standard non polar	33892256
CPA(18:2(9Z,12Z)/0:0),1TMS,isomer #1	CCCCC/C=C\C/C=C\CCCCCCCC(=O)OCC1COP(=O)(O[Si](C)(C)C)O1	3831.2	Standard polar	33892256
CPA(18:2(9Z,12Z)/0:0),1TBDMS,isomer #1	CCCCC/C=C\C/C=C\CCCCCCCC(=O)OCC1COP(=O)(O[Si](C)(C)C(C)(C)C)O1	3355.9	Semi standard non polar	33892256
CPA(18:2(9Z,12Z)/0:0),1TBDMS,isomer #1	CCCCC/C=C\C/C=C\CCCCCCCC(=O)OCC1COP(=O)(O[Si](C)(C)C(C)(C)C)O1	3194.3	Standard non polar	33892256
CPA(18:2(9Z,12Z)/0:0),1TBDMS,isomer #1	CCCCC/C=C\C/C=C\CCCCCCCC(=O)OCC1COP(=O)(O[Si](C)(C)C(C)(C)C)O1	3906.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - CPA(18:2(9Z,12Z)/0:0) GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dr-2952000000-c0519122e2b544b85a14	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - CPA(18:2(9Z,12Z)/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 - CPA(18:2(9Z,12Z)/0:0) 10V, Positive-QTOF	splash10-02tl-6962700000-fd6a067d9b2506028479	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CPA(18:2(9Z,12Z)/0:0) 20V, Positive-QTOF	splash10-000l-7982000000-3362e04a0657ecc99d23	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CPA(18:2(9Z,12Z)/0:0) 40V, Positive-QTOF	splash10-000l-8980000000-234150ca739b2a147582	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CPA(18:2(9Z,12Z)/0:0) 10V, Negative-QTOF	splash10-02di-0190400000-a2bcebde9d73d9cf1899	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CPA(18:2(9Z,12Z)/0:0) 20V, Negative-QTOF	splash10-01t9-2390000000-5f7e7ca43b69afd0ebe3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CPA(18:2(9Z,12Z)/0:0) 40V, Negative-QTOF	splash10-01t9-9020000000-ddf47d71ce6180b3d578	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CPA(18:2(9Z,12Z)/0:0) 10V, Positive-QTOF	splash10-014i-3912800000-70ba0af05975baf60338	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CPA(18:2(9Z,12Z)/0:0) 20V, Positive-QTOF	splash10-052r-8900000000-b0adf8157e99287ca2c4	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CPA(18:2(9Z,12Z)/0:0) 40V, Positive-QTOF	splash10-0ar0-9200000000-29b86fd8d43ea6f6bb72	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CPA(18:2(9Z,12Z)/0:0) 10V, Negative-QTOF	splash10-0159-0610900000-391f2cefc4d87610f3f8	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CPA(18:2(9Z,12Z)/0:0) 20V, Negative-QTOF	splash10-004i-5590000000-6bc1ad5dd6ae7845aead	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CPA(18:2(9Z,12Z)/0:0) 40V, Negative-QTOF	splash10-004i-9430000000-5be340c9713dd4f72ad2	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

FDB024201

KNApSAcK ID

Not Available

Chemspider ID

24766509

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53477947

PDB ID

Not Available

ChEBI ID

137248

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

Not Available

Showing metabocard for CPA(18:2(9Z,12Z)/0:0) (HMDB0007007)

MOL for HMDB0007007 (CPA(18:2(9Z,12Z)/0:0))

3D MOL for HMDB0007007 (CPA(18:2(9Z,12Z)/0:0))

3D SDF for HMDB0007007 (CPA(18:2(9Z,12Z)/0:0))

3D-SDF for HMDB0007007 (CPA(18:2(9Z,12Z)/0:0))

PDB for HMDB0007007 (CPA(18:2(9Z,12Z)/0:0))

3D PDB for HMDB0007007 (CPA(18:2(9Z,12Z)/0:0))

SMILES for HMDB0007007 (CPA(18:2(9Z,12Z)/0:0))

INCHI for HMDB0007007 (CPA(18:2(9Z,12Z)/0:0))

Structure for HMDB0007007 (CPA(18:2(9Z,12Z)/0:0))

3D Structure for HMDB0007007 (CPA(18:2(9Z,12Z)/0:0))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra