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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2008-09-12 01:12:54 UTC

Update Date

2022-03-07 02:49:35 UTC

HMDB ID

HMDB0007004

Secondary Accession Numbers

HMDB07004

Metabolite Identification

Common Name

CPA(18:0/0:0)

Description

cPA(18:0/0:0) 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  -12.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5320  -12.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2465  -12.1517    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  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  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

HMDB0007004
     RDKit          3D
CPA(18:0/0:0)
 69 69  0  0  0  0  0  0  0  0999 V2000
  -10.2386    1.4555   -1.7813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8297    0.1428   -1.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3188    0.2019   -0.9404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8309   -1.0471   -0.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3235   -0.9859   -0.1498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9181    0.1725    0.6821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3938    0.2271    0.7634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8949   -1.0322    1.3957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3906   -0.9812    1.5290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7619   -0.8616    0.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2513   -0.8189    0.2294 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2880    0.3260    1.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8451    0.2091    0.8940 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4810    1.3162    1.6406 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9470    1.3692    1.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8284    0.2986    2.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8061   -1.0467    1.4021 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0914   -0.9473   -0.0588 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2308   -1.2276   -0.9325 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3355   -0.5338   -0.4972 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6592   -0.4267   -1.8624 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0747    0.0955   -2.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9779   -0.8175   -1.2727 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2171   -0.2205   -1.1510 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7982    1.4064   -0.9988 P   0  0  0  0  0  5  0  0  0  0  0  0
    9.9497    1.9180    0.4145 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6820    2.3735   -2.0982 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1805    1.3779   -1.4777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4359    1.7225   -2.5128 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1912    1.3013   -2.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3444    2.2268   -1.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3494   -0.0378   -0.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0324   -0.7005   -1.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1039    1.1088   -0.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8867    0.3574   -1.9430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0712   -1.9643   -0.8497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2342   -1.1457    0.7463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8200   -0.9447   -1.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0332   -1.9518    0.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2366   -0.0105    1.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2710    1.1556    0.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9782    0.3992   -0.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1553    1.1305    1.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3927   -1.2618    2.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1207   -1.9151    0.7413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1726   -0.1364    2.2156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0791   -1.9210    2.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1045    0.0357   -0.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0536   -1.7428   -0.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1219   -0.7212   -0.8103 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1813   -1.7619    0.6340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0476    1.3203    0.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1152    0.1977    2.1224 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0137   -0.7863    1.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0754    0.2590   -0.1664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1378    1.3458    2.7230 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1036    2.2908    1.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1543    1.5326    0.4051 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2961    2.3902    1.9417 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9003    0.6859    1.8205 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8510    0.2341    3.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9811   -1.7096    1.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7030   -1.6159    1.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5962   -1.3760   -2.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9784    0.3047   -2.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3051    0.0693   -3.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5723   -0.9927   -0.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0971   -1.7472   -1.8646 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5947    2.4318   -1.7044 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  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
  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
 21 64  1  0
 21 65  1  0
 22 66  1  0
 23 67  1  0
 23 68  1  0
 27 69  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  -12.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5320  -12.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2465  -12.1517    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  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  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>
HMDB0007004

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCCCCCCCCCCC(=O)OCC1COP(O)(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C21H41O6P/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/h20H,2-19H2,1H3,(H,23,24)

> <INCHI_KEY>
BAAJXXGEGGUMMX-UHFFFAOYSA-N

> <FORMULA>
C21H41O6P

> <MOLECULAR_WEIGHT>
420.5204

> <EXACT_MASS>
420.264075556

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
49.53049316577692

> <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 octadecanoate

> <ALOGPS_LOGP>
5.87

> <JCHEM_LOGP>
6.744148969666667

> <ALOGPS_LOGS>
-5.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8399068895320578

> <JCHEM_PKA_STRONGEST_BASIC>
-7.038668785414214

> <JCHEM_POLAR_SURFACE_AREA>
82.06

> <JCHEM_REFRACTIVITY>
110.40339999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.33e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-hydroxy-2-oxo-1,3,2λ⁵-dioxaphospholan-4-yl)methyl octadecanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0007004
     RDKit          3D
CPA(18:0/0:0)
 69 69  0  0  0  0  0  0  0  0999 V2000
  -10.2386    1.4555   -1.7813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8297    0.1428   -1.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3188    0.2019   -0.9404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8309   -1.0471   -0.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3235   -0.9859   -0.1498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9181    0.1725    0.6821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3938    0.2271    0.7634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8949   -1.0322    1.3957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3906   -0.9812    1.5290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7619   -0.8616    0.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2513   -0.8189    0.2294 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2880    0.3260    1.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8451    0.2091    0.8940 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4810    1.3162    1.6406 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9470    1.3692    1.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8284    0.2986    2.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8061   -1.0467    1.4021 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0914   -0.9473   -0.0588 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2308   -1.2276   -0.9325 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3355   -0.5338   -0.4972 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6592   -0.4267   -1.8624 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0747    0.0955   -2.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9779   -0.8175   -1.2727 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2171   -0.2205   -1.1510 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7982    1.4064   -0.9988 P   0  0  0  0  0  5  0  0  0  0  0  0
    9.9497    1.9180    0.4145 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6820    2.3735   -2.0982 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1805    1.3779   -1.4777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4359    1.7225   -2.5128 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1912    1.3013   -2.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3444    2.2268   -1.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3494   -0.0378   -0.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0324   -0.7005   -1.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1039    1.1088   -0.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8867    0.3574   -1.9430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0712   -1.9643   -0.8497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2342   -1.1457    0.7463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8200   -0.9447   -1.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0332   -1.9518    0.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2366   -0.0105    1.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2710    1.1556    0.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9782    0.3992   -0.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1553    1.1305    1.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3927   -1.2618    2.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1207   -1.9151    0.7413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1726   -0.1364    2.2156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0791   -1.9210    2.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1045    0.0357   -0.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0536   -1.7428   -0.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1219   -0.7212   -0.8103 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1813   -1.7619    0.6340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0476    1.3203    0.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1152    0.1977    2.1224 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0137   -0.7863    1.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0754    0.2590   -0.1664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1378    1.3458    2.7230 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1036    2.2908    1.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1543    1.5326    0.4051 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2961    2.3902    1.9417 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9003    0.6859    1.8205 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8510    0.2341    3.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9811   -1.7096    1.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7030   -1.6159    1.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5962   -1.3760   -2.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9784    0.3047   -2.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3051    0.0693   -3.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5723   -0.9927   -0.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0971   -1.7472   -1.8646 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5947    2.4318   -1.7044 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  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
  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
 21 64  1  0
 21 65  1  0
 22 66  1  0
 23 67  1  0
 23 68  1  0
 27 69  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 -22.683   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.793 -23.453   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      19.127 -22.683   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    HMDB0007004
HETATM    1  C1  UNL     1     -10.239   1.455  -1.781  1.00  0.00           C  
HETATM    2  C2  UNL     1      -9.830   0.143  -1.100  1.00  0.00           C  
HETATM    3  C3  UNL     1      -8.319   0.202  -0.940  1.00  0.00           C  
HETATM    4  C4  UNL     1      -7.831  -1.047  -0.280  1.00  0.00           C  
HETATM    5  C5  UNL     1      -6.323  -0.986  -0.150  1.00  0.00           C  
HETATM    6  C6  UNL     1      -5.918   0.172   0.682  1.00  0.00           C  
HETATM    7  C7  UNL     1      -4.394   0.227   0.763  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.895  -1.032   1.396  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.391  -0.981   1.529  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.762  -0.862   0.196  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.251  -0.819   0.229  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.288   0.326   1.015  1.00  0.00           C  
HETATM   13  C13 UNL     1       1.845   0.209   0.894  1.00  0.00           C  
HETATM   14  C14 UNL     1       2.481   1.316   1.641  1.00  0.00           C  
HETATM   15  C15 UNL     1       3.947   1.369   1.536  1.00  0.00           C  
HETATM   16  C16 UNL     1       4.828   0.299   2.000  1.00  0.00           C  
HETATM   17  C17 UNL     1       4.806  -1.047   1.402  1.00  0.00           C  
HETATM   18  C18 UNL     1       5.091  -0.947  -0.059  1.00  0.00           C  
HETATM   19  O1  UNL     1       4.231  -1.228  -0.932  1.00  0.00           O  
HETATM   20  O2  UNL     1       6.335  -0.534  -0.497  1.00  0.00           O  
HETATM   21  C19 UNL     1       6.659  -0.427  -1.862  1.00  0.00           C  
HETATM   22  C20 UNL     1       8.075   0.096  -2.051  1.00  0.00           C  
HETATM   23  C21 UNL     1       8.978  -0.817  -1.273  1.00  0.00           C  
HETATM   24  O3  UNL     1      10.217  -0.221  -1.151  1.00  0.00           O  
HETATM   25  P1  UNL     1       9.798   1.406  -0.999  1.00  0.00           P  
HETATM   26  O4  UNL     1       9.950   1.918   0.415  1.00  0.00           O  
HETATM   27  O5  UNL     1      10.682   2.373  -2.098  1.00  0.00           O  
HETATM   28  O6  UNL     1       8.180   1.378  -1.478  1.00  0.00           O  
HETATM   29  H1  UNL     1      -9.436   1.723  -2.513  1.00  0.00           H  
HETATM   30  H2  UNL     1     -11.191   1.301  -2.316  1.00  0.00           H  
HETATM   31  H3  UNL     1     -10.344   2.227  -1.019  1.00  0.00           H  
HETATM   32  H4  UNL     1     -10.349  -0.038  -0.163  1.00  0.00           H  
HETATM   33  H5  UNL     1     -10.032  -0.701  -1.779  1.00  0.00           H  
HETATM   34  H6  UNL     1      -8.104   1.109  -0.350  1.00  0.00           H  
HETATM   35  H7  UNL     1      -7.887   0.357  -1.943  1.00  0.00           H  
HETATM   36  H8  UNL     1      -8.071  -1.964  -0.850  1.00  0.00           H  
HETATM   37  H9  UNL     1      -8.234  -1.146   0.746  1.00  0.00           H  
HETATM   38  H10 UNL     1      -5.820  -0.945  -1.119  1.00  0.00           H  
HETATM   39  H11 UNL     1      -6.033  -1.952   0.366  1.00  0.00           H  
HETATM   40  H12 UNL     1      -6.237  -0.010   1.750  1.00  0.00           H  
HETATM   41  H13 UNL     1      -6.271   1.156   0.373  1.00  0.00           H  
HETATM   42  H14 UNL     1      -3.978   0.399  -0.252  1.00  0.00           H  
HETATM   43  H15 UNL     1      -4.155   1.130   1.360  1.00  0.00           H  
HETATM   44  H16 UNL     1      -4.393  -1.262   2.359  1.00  0.00           H  
HETATM   45  H17 UNL     1      -4.121  -1.915   0.741  1.00  0.00           H  
HETATM   46  H18 UNL     1      -2.173  -0.136   2.216  1.00  0.00           H  
HETATM   47  H19 UNL     1      -2.079  -1.921   2.065  1.00  0.00           H  
HETATM   48  H20 UNL     1      -2.104   0.036  -0.389  1.00  0.00           H  
HETATM   49  H21 UNL     1      -2.054  -1.743  -0.412  1.00  0.00           H  
HETATM   50  H22 UNL     1       0.122  -0.721  -0.810  1.00  0.00           H  
HETATM   51  H23 UNL     1       0.181  -1.762   0.634  1.00  0.00           H  
HETATM   52  H24 UNL     1       0.048   1.320   0.646  1.00  0.00           H  
HETATM   53  H25 UNL     1       0.115   0.198   2.122  1.00  0.00           H  
HETATM   54  H26 UNL     1       2.014  -0.786   1.362  1.00  0.00           H  
HETATM   55  H27 UNL     1       2.075   0.259  -0.166  1.00  0.00           H  
HETATM   56  H28 UNL     1       2.138   1.346   2.723  1.00  0.00           H  
HETATM   57  H29 UNL     1       2.104   2.291   1.165  1.00  0.00           H  
HETATM   58  H30 UNL     1       4.154   1.533   0.405  1.00  0.00           H  
HETATM   59  H31 UNL     1       4.296   2.390   1.942  1.00  0.00           H  
HETATM   60  H32 UNL     1       5.900   0.686   1.820  1.00  0.00           H  
HETATM   61  H33 UNL     1       4.851   0.234   3.148  1.00  0.00           H  
HETATM   62  H34 UNL     1       3.981  -1.710   1.562  1.00  0.00           H  
HETATM   63  H35 UNL     1       5.703  -1.616   1.830  1.00  0.00           H  
HETATM   64  H36 UNL     1       6.596  -1.376  -2.418  1.00  0.00           H  
HETATM   65  H37 UNL     1       5.978   0.305  -2.344  1.00  0.00           H  
HETATM   66  H38 UNL     1       8.305   0.069  -3.117  1.00  0.00           H  
HETATM   67  H39 UNL     1       8.572  -0.993  -0.255  1.00  0.00           H  
HETATM   68  H40 UNL     1       9.097  -1.747  -1.865  1.00  0.00           H  
HETATM   69  H41 UNL     1      11.595   2.432  -1.704  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   19   20
CONECT   20   21
CONECT   21   22   64   65
CONECT   22   23   28   66
CONECT   23   24   67   68
CONECT   24   25
CONECT   25   26   26   27   28
CONECT   27   69
END

HMDB0007004
     RDKit          3D
CPA(18:0/0:0)
 69 69  0  0  0  0  0  0  0  0999 V2000
  -10.2386    1.4555   -1.7813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8297    0.1428   -1.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3188    0.2019   -0.9404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8309   -1.0471   -0.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3235   -0.9859   -0.1498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9181    0.1725    0.6821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3938    0.2271    0.7634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8949   -1.0322    1.3957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3906   -0.9812    1.5290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7619   -0.8616    0.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2513   -0.8189    0.2294 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2880    0.3260    1.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8451    0.2091    0.8940 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4810    1.3162    1.6406 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9470    1.3692    1.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8284    0.2986    2.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8061   -1.0467    1.4021 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0914   -0.9473   -0.0588 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2308   -1.2276   -0.9325 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3355   -0.5338   -0.4972 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6592   -0.4267   -1.8624 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0747    0.0955   -2.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9779   -0.8175   -1.2727 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2171   -0.2205   -1.1510 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7982    1.4064   -0.9988 P   0  0  0  0  0  5  0  0  0  0  0  0
    9.9497    1.9180    0.4145 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6820    2.3735   -2.0982 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1805    1.3779   -1.4777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4359    1.7225   -2.5128 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1912    1.3013   -2.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3444    2.2268   -1.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3494   -0.0378   -0.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0324   -0.7005   -1.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1039    1.1088   -0.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8867    0.3574   -1.9430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0712   -1.9643   -0.8497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2342   -1.1457    0.7463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8200   -0.9447   -1.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0332   -1.9518    0.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2366   -0.0105    1.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2710    1.1556    0.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9782    0.3992   -0.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1553    1.1305    1.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3927   -1.2618    2.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1207   -1.9151    0.7413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1726   -0.1364    2.2156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0791   -1.9210    2.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1045    0.0357   -0.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0536   -1.7428   -0.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1219   -0.7212   -0.8103 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1813   -1.7619    0.6340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0476    1.3203    0.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1152    0.1977    2.1224 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0137   -0.7863    1.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0754    0.2590   -0.1664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1378    1.3458    2.7230 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1036    2.2908    1.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1543    1.5326    0.4051 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2961    2.3902    1.9417 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9003    0.6859    1.8205 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8510    0.2341    3.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9811   -1.7096    1.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7030   -1.6159    1.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5962   -1.3760   -2.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9784    0.3047   -2.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3051    0.0693   -3.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5723   -0.9927   -0.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0971   -1.7472   -1.8646 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5947    2.4318   -1.7044 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  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
  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
 21 64  1  0
 21 65  1  0
 22 66  1  0
 23 67  1  0
 23 68  1  0
 27 69  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Octadecanoyl-cyclophosphatidic acid	HMDB
1-Stearoyl-glycero-3-cyclophosphate	HMDB
CPA(18:0)	HMDB
Cyclic phosphatidic acid(18:0)	HMDB
Cyclic phosphatidic acid(18:0/0:0)	HMDB
(2-Hydroxy-2-oxo-1,3,2λ⁵-dioxaphospholan-4-yl)methyl octadecanoic acid	Generator

Chemical Formula

C₂₁H₄₁O₆P

Average Molecular Weight

420.5204

Monoisotopic Molecular Weight

420.264075556

IUPAC Name

(2-hydroxy-2-oxo-1,3,2λ⁵-dioxaphospholan-4-yl)methyl octadecanoate

Traditional Name

(2-hydroxy-2-oxo-1,3,2λ⁵-dioxaphospholan-4-yl)methyl octadecanoate

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCCC(=O)OCC1COP(O)(=O)O1

InChI Identifier

InChI=1S/C21H41O6P/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/h20H,2-19H2,1H3,(H,23,24)

InChI Key

BAAJXXGEGGUMMX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-acyl-sn-glycerol-2,3-cyclic-phosphates. These are monoacylglycerophosphates consisting of a sn-glycerol 2,3-cyclic phosphate that carries an acyl group at the 1-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphates

Direct Parent

1-acyl-sn-glycerol-2,3-cyclic-phosphates

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Touch

Smooth (HMDB: HMDB0007004)

Disposition

Biological location

Cell membrane (HMDB: HMDB0007004)
Intracellular membrane (HMDB: HMDB0007004)

Biofluid or Excreta

Blood (HMDB: HMDB0007004)

Tissue substructure

All tissues (HMDB: HMDB0007004)

Tissue

All Tissues (HMDB: HMDB0007004)

Cellular substructure

Membrane (HMDB: HMDB0007004)
Extracellular (HMDB: HMDB0007004)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0007004)

Source

Endogenous

Endogenous (HMDB: HMDB0007004)

Animal

Animal (HMDB: HMDB0007004)

Exogenous

Food

Food (HMDB: HMDB0007004)

Animal origin

Poultry

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
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)

Equine

Horse (FooDB: FOOD00378)

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)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0007004)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0007004)

Cellular process

Cell signaling (HMDB: HMDB0007004)

Biochemical pathway

Glycerophospholipid metabolism (HMDB: HMDB0007004)

Role

Biological role

Energy source (HMDB: HMDB0007004)

Industrial application

Food and nutrition

Food additive

Nutritional supplement

Nutritional supplement (HMDB: HMDB0007004)

Food additive (HMDB: HMDB0007004)

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0007004)

Emulsifier (HMDB: HMDB0007004)

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	0.0013 g/L	ALOGPS
logP	5.87	ALOGPS
logP	6.74	ChemAxon
logS	-5.5	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	19	ChemAxon
Refractivity	110.4 m³·mol⁻¹	ChemAxon
Polarizability	49.53 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]+	207.055	31661259
DarkChem	[M-H]-	204.179	31661259
DeepCCS	[M+H]+	189.574	30932474
DeepCCS	[M-H]-	186.121	30932474
DeepCCS	[M-2H]-	221.927	30932474
DeepCCS	[M+Na]+	198.219	30932474
AllCCS	[M+H]+	211.1	32859911
AllCCS	[M+H-H2O]+	209.1	32859911
AllCCS	[M+NH4]+	213.0	32859911
AllCCS	[M+Na]+	213.6	32859911
AllCCS	[M-H]-	204.8	32859911
AllCCS	[M+Na-2H]-	206.8	32859911
AllCCS	[M+HCOO]-	209.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
CPA(18:0/0:0)	CCCCCCCCCCCCCCCCCC(=O)OCC1COP(O)(=O)O1	3307.7	Standard polar	33892256
CPA(18:0/0:0)	CCCCCCCCCCCCCCCCCC(=O)OCC1COP(O)(=O)O1	2946.8	Standard non polar	33892256
CPA(18:0/0:0)	CCCCCCCCCCCCCCCCCC(=O)OCC1COP(O)(=O)O1	3129.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
CPA(18:0/0:0),1TMS,isomer #1	CCCCCCCCCCCCCCCCCC(=O)OCC1COP(=O)(O[Si](C)(C)C)O1	3129.0	Semi standard non polar	33892256
CPA(18:0/0:0),1TMS,isomer #1	CCCCCCCCCCCCCCCCCC(=O)OCC1COP(=O)(O[Si](C)(C)C)O1	3084.6	Standard non polar	33892256
CPA(18:0/0:0),1TMS,isomer #1	CCCCCCCCCCCCCCCCCC(=O)OCC1COP(=O)(O[Si](C)(C)C)O1	4009.6	Standard polar	33892256
CPA(18:0/0:0),1TBDMS,isomer #1	CCCCCCCCCCCCCCCCCC(=O)OCC1COP(=O)(O[Si](C)(C)C(C)(C)C)O1	3382.5	Semi standard non polar	33892256
CPA(18:0/0:0),1TBDMS,isomer #1	CCCCCCCCCCCCCCCCCC(=O)OCC1COP(=O)(O[Si](C)(C)C(C)(C)C)O1	3270.5	Standard non polar	33892256
CPA(18:0/0:0),1TBDMS,isomer #1	CCCCCCCCCCCCCCCCCC(=O)OCC1COP(=O)(O[Si](C)(C)C(C)(C)C)O1	4093.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - CPA(18:0/0:0) GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dr-2962000000-080c27238137c4fd88e7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - CPA(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 - CPA(18:0/0:0) 10V, Positive-QTOF	splash10-00y3-6860900000-aead5a658b6b9df3a229	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CPA(18:0/0:0) 20V, Positive-QTOF	splash10-000i-7981200000-125f7a030ba3d6ccb11b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CPA(18:0/0:0) 40V, Positive-QTOF	splash10-000l-8980000000-eae1a15d5077995f96c3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CPA(18:0/0:0) 10V, Negative-QTOF	splash10-0159-0190500000-768b8bee8dbec5a31a71	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CPA(18:0/0:0) 20V, Negative-QTOF	splash10-00lr-2390000000-94775e414eb2c3d89e95	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CPA(18:0/0:0) 40V, Negative-QTOF	splash10-004i-9020000000-3ae270aa714aadc44677	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CPA(18:0/0:0) 10V, Positive-QTOF	splash10-00di-3700900000-69d2ec81eace8f22cd7e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CPA(18:0/0:0) 20V, Positive-QTOF	splash10-052r-6900100000-ad2ff302a0c275b9f515	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CPA(18:0/0:0) 40V, Positive-QTOF	splash10-052f-9300000000-b2fc7b2c08917581b50a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CPA(18:0/0:0) 10V, Negative-QTOF	splash10-0159-0610900000-30d83a307029a94212ac	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CPA(18:0/0:0) 20V, Negative-QTOF	splash10-001i-4590000000-048c40aacbdb7dc84504	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CPA(18:0/0:0) 40V, Negative-QTOF	splash10-0059-9330000000-d9aa2b30226e57e4e68a	2021-09-23	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

FDB024198

KNApSAcK ID

Not Available

Chemspider ID

24766507

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

51040919

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

Not Available

Showing metabocard for CPA(18:0/0:0) (HMDB0007004)

MOL for HMDB0007004 (CPA(18:0/0:0))

3D MOL for HMDB0007004 (CPA(18:0/0:0))

3D SDF for HMDB0007004 (CPA(18:0/0:0))

3D-SDF for HMDB0007004 (CPA(18:0/0:0))

PDB for HMDB0007004 (CPA(18:0/0:0))

3D PDB for HMDB0007004 (CPA(18:0/0:0))

SMILES for HMDB0007004 (CPA(18:0/0:0))

INCHI for HMDB0007004 (CPA(18:0/0:0))

Structure for HMDB0007004 (CPA(18:0/0:0))

3D Structure for HMDB0007004 (CPA(18:0/0:0))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra