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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-08-31 15:10:17 UTC

Update Date

2021-09-26 22:48:58 UTC

HMDB ID

HMDB0242470

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate

Description

(2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate, also known as 1-oleoyl-lysophosphatidic acid or monooleylphosphatidate, belongs to the class of organic compounds known as 1-acylglycerol-3-phosphates. These are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-1 position. Based on a literature review very few articles have been published on (2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate. This compound has been identified in human blood as reported by (PMID: 31557052 ). (2-hydroxy-3-phosphonooxypropyl) octadec-9-enoate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

Structure #1
  Mrv0541 02241206032D          

 29 28  0  0  0  0            999 V2000
    1.3776    9.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776    8.2204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921    7.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921    6.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066    6.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066    5.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211    5.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211    4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8092    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    4.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9526    3.6829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6506    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8256    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5237    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2381    3.2704    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  4  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 21  1  0  0  0  0
 18 20  1  0  0  0  0
 18 27  1  0  0  0  0
 19 20  1  0  0  0  0
 19 28  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  2  0  0  0  0
 21 27  1  0  0  0  0
 24 29  1  0  0  0  0
 25 29  1  0  0  0  0
 26 29  2  0  0  0  0
 28 29  1  0  0  0  0
M  END

HMDB0242470
     RDKit          3D
(2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate
 70 69  0  0  0  0  0  0  0  0999 V2000
    9.8175    2.3923    0.4509 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4582    1.1837   -0.3644 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9376    1.0737   -0.5297 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3734    0.9606    0.8478 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8598    0.8433    0.8781 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3990   -0.3739    0.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9170   -0.5113    0.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1814    0.6430   -0.4527 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7185    0.3895   -0.3756 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0103    0.3306   -1.4736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4590    0.0817   -1.4977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7881   -1.1755   -2.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1268   -2.3674   -1.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5581   -2.5914   -0.2462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0570   -2.8083   -0.2303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4799   -3.0430    1.2019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9632   -3.2756    1.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6362   -2.0418    0.6765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8859   -1.9799   -0.5563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9829   -0.9910    1.4674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6076    0.1997    1.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9853    0.0537    0.5913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0483   -0.6898   -0.5463 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7286    1.3660    0.4831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2511    2.1802   -0.5155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1980    3.6000   -0.4908 P   0  0  0  0  0  5  0  0  0  0  0  0
   -8.4532    3.9336    0.9619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3963    4.8159   -1.3057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7171    3.2638   -1.1840 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7430    2.8836    0.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9753    2.1375    1.5153 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9601    3.1208    0.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9539    1.1733   -1.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7683    0.2491    0.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7642    0.1217   -1.0766 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5955    1.9609   -1.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6621    1.8515    1.4277 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7792    0.0418    1.3189 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5726    0.7219    1.9424 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3810    1.7685    0.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8468   -1.2562    0.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8031   -0.3929   -0.9148 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6677   -1.4565   -0.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6083   -0.6695    1.2187 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4328    1.5615    0.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4917    0.7936   -1.4971 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2769    0.2593    0.5999 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5043    0.4689   -2.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8661   -0.0173   -0.4936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9652    0.9210   -2.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4470   -1.0628   -3.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8783   -1.3435   -2.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3559   -3.2475   -2.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9804   -2.2954   -1.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1182   -3.5279    0.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3017   -1.7489    0.4041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3129   -3.6976   -0.8140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5966   -1.8766   -0.5471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2520   -2.1430    1.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9104   -3.8710    1.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3284   -3.3469    2.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2695   -4.1392    0.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5510    0.9144    1.9745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9494    0.6927    0.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5633   -0.5269    1.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8703   -1.2354   -0.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6720    1.9129    1.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8095    1.1087    0.3357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0686    5.3468   -1.8041 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0308    2.3823   -0.8570 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  3
 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
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 26 29  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  0
 12 52  1  0
 13 53  1  0
 13 54  1  0
 14 55  1  0
 14 56  1  0
 15 57  1  0
 15 58  1  0
 16 59  1  0
 16 60  1  0
 17 61  1  0
 17 62  1  0
 21 63  1  0
 21 64  1  0
 22 65  1  0
 23 66  1  0
 24 67  1  0
 24 68  1  0
 28 69  1  0
 29 70  1  0
M  END

Structure #1
  Mrv0541 02241206032D          

 29 28  0  0  0  0            999 V2000
    1.3776    9.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776    8.2204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921    7.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921    6.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066    6.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066    5.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211    5.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211    4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8092    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    4.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9526    3.6829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6506    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8256    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5237    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2381    3.2704    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  4  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 21  1  0  0  0  0
 18 20  1  0  0  0  0
 18 27  1  0  0  0  0
 19 20  1  0  0  0  0
 19 28  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  2  0  0  0  0
 21 27  1  0  0  0  0
 24 29  1  0  0  0  0
 25 29  1  0  0  0  0
 26 29  2  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0242470

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCC=CCCCCCCCC(=O)OCC(O)COP(O)(O)=O

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

> <INCHI_KEY>
WRGQSWVCFNIUNZ-UHFFFAOYSA-N

> <FORMULA>
C21H41O7P

> <MOLECULAR_WEIGHT>
436.5198

> <EXACT_MASS>
436.258990178

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
50.13039993180073

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.69

> <JCHEM_LOGP>
5.485689521666666

> <ALOGPS_LOGS>
-5.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.531115837556444

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.505317785248875

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4039997949880556

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
115.29899999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
21

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.64e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
LPA

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0242470
     RDKit          3D
(2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate
 70 69  0  0  0  0  0  0  0  0999 V2000
    9.8175    2.3923    0.4509 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4582    1.1837   -0.3644 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9376    1.0737   -0.5297 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3734    0.9606    0.8478 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8598    0.8433    0.8781 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3990   -0.3739    0.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9170   -0.5113    0.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1814    0.6430   -0.4527 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7185    0.3895   -0.3756 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0103    0.3306   -1.4736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4590    0.0817   -1.4977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7881   -1.1755   -2.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1268   -2.3674   -1.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5581   -2.5914   -0.2462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0570   -2.8083   -0.2303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4799   -3.0430    1.2019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9632   -3.2756    1.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6362   -2.0418    0.6765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8859   -1.9799   -0.5563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9829   -0.9910    1.4674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6076    0.1997    1.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9853    0.0537    0.5913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0483   -0.6898   -0.5463 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7286    1.3660    0.4831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2511    2.1802   -0.5155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1980    3.6000   -0.4908 P   0  0  0  0  0  5  0  0  0  0  0  0
   -8.4532    3.9336    0.9619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3963    4.8159   -1.3057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7171    3.2638   -1.1840 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7430    2.8836    0.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9753    2.1375    1.5153 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9601    3.1208    0.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9539    1.1733   -1.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7683    0.2491    0.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7642    0.1217   -1.0766 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5955    1.9609   -1.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6621    1.8515    1.4277 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7792    0.0418    1.3189 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5726    0.7219    1.9424 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3810    1.7685    0.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8468   -1.2562    0.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8031   -0.3929   -0.9148 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6677   -1.4565   -0.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6083   -0.6695    1.2187 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4328    1.5615    0.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4917    0.7936   -1.4971 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2769    0.2593    0.5999 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5043    0.4689   -2.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8661   -0.0173   -0.4936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9652    0.9210   -2.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4470   -1.0628   -3.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8783   -1.3435   -2.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3559   -3.2475   -2.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9804   -2.2954   -1.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1182   -3.5279    0.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3017   -1.7489    0.4041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3129   -3.6976   -0.8140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5966   -1.8766   -0.5471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2520   -2.1430    1.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9104   -3.8710    1.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3284   -3.3469    2.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2695   -4.1392    0.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5510    0.9144    1.9745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9494    0.6927    0.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5633   -0.5269    1.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8703   -1.2354   -0.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6720    1.9129    1.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8095    1.1087    0.3357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0686    5.3468   -1.8041 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0308    2.3823   -0.8570 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  3
 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
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 26 29  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  0
 12 52  1  0
 13 53  1  0
 13 54  1  0
 14 55  1  0
 14 56  1  0
 15 57  1  0
 15 58  1  0
 16 59  1  0
 16 60  1  0
 17 61  1  0
 17 62  1  0
 21 63  1  0
 21 64  1  0
 22 65  1  0
 23 66  1  0
 24 67  1  0
 24 68  1  0
 28 69  1  0
 29 70  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       2.572  16.885   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.572  15.345   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.905  14.575   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.905  13.035   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.239  12.265   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.239  10.725   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.573   9.955   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.573   8.415   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.906   7.645   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.906   6.105   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.240   5.335   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.574   6.105   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.907   5.335   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.241   6.105   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.575   5.335   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.908   6.105   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.242   5.335   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      21.243   6.105   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      23.911   6.105   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      22.577   5.335   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      18.576   6.105   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      22.577   3.795   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      18.576   7.645   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      27.912   6.875   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      27.348   4.771   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      25.808   7.438   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      19.909   5.335   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      25.244   5.335   0.000  0.00  0.00           O+0
HETATM   29  P   UNK     0      26.578   6.105   0.000  0.00  0.00           P+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   21                                                       
CONECT   18   20   27                                                       
CONECT   19   20   28                                                       
CONECT   20   18   19   22                                                  
CONECT   21   17   23   27                                                  
CONECT   22   20                                                            
CONECT   23   21                                                            
CONECT   24   29                                                            
CONECT   25   29                                                            
CONECT   26   29                                                            
CONECT   27   18   21                                                       
CONECT   28   19   29                                                       
CONECT   29   24   25   26   28                                             
MASTER        0    0    0    0    0    0    0    0   29    0   56    0
END

COMPND    HMDB0242470
HETATM    1  C1  UNL     1       9.817   2.392   0.451  1.00  0.00           C  
HETATM    2  C2  UNL     1       9.458   1.184  -0.364  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.938   1.074  -0.530  1.00  0.00           C  
HETATM    4  C4  UNL     1       7.373   0.961   0.848  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.860   0.843   0.878  1.00  0.00           C  
HETATM    6  C6  UNL     1       5.399  -0.374   0.128  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.917  -0.511   0.160  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.181   0.643  -0.453  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.718   0.389  -0.376  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.010   0.331  -1.474  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.459   0.082  -1.498  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.788  -1.175  -2.281  1.00  0.00           C  
HETATM   13  C13 UNL     1      -0.127  -2.367  -1.671  1.00  0.00           C  
HETATM   14  C14 UNL     1      -0.558  -2.591  -0.246  1.00  0.00           C  
HETATM   15  C15 UNL     1      -2.057  -2.808  -0.230  1.00  0.00           C  
HETATM   16  C16 UNL     1      -2.480  -3.043   1.202  1.00  0.00           C  
HETATM   17  C17 UNL     1      -3.963  -3.276   1.234  1.00  0.00           C  
HETATM   18  C18 UNL     1      -4.636  -2.042   0.677  1.00  0.00           C  
HETATM   19  O1  UNL     1      -4.886  -1.980  -0.556  1.00  0.00           O  
HETATM   20  O2  UNL     1      -4.983  -0.991   1.467  1.00  0.00           O  
HETATM   21  C19 UNL     1      -5.608   0.200   1.117  1.00  0.00           C  
HETATM   22  C20 UNL     1      -6.985   0.054   0.591  1.00  0.00           C  
HETATM   23  O3  UNL     1      -7.048  -0.690  -0.546  1.00  0.00           O  
HETATM   24  C21 UNL     1      -7.729   1.366   0.483  1.00  0.00           C  
HETATM   25  O4  UNL     1      -7.251   2.180  -0.515  1.00  0.00           O  
HETATM   26  P1  UNL     1      -8.198   3.600  -0.491  1.00  0.00           P  
HETATM   27  O5  UNL     1      -8.453   3.934   0.962  1.00  0.00           O  
HETATM   28  O6  UNL     1      -7.396   4.816  -1.306  1.00  0.00           O  
HETATM   29  O7  UNL     1      -9.717   3.264  -1.184  1.00  0.00           O  
HETATM   30  H1  UNL     1      10.743   2.884   0.057  1.00  0.00           H  
HETATM   31  H2  UNL     1       9.975   2.137   1.515  1.00  0.00           H  
HETATM   32  H3  UNL     1       8.960   3.121   0.435  1.00  0.00           H  
HETATM   33  H4  UNL     1       9.954   1.173  -1.356  1.00  0.00           H  
HETATM   34  H5  UNL     1       9.768   0.249   0.171  1.00  0.00           H  
HETATM   35  H6  UNL     1       7.764   0.122  -1.077  1.00  0.00           H  
HETATM   36  H7  UNL     1       7.595   1.961  -1.082  1.00  0.00           H  
HETATM   37  H8  UNL     1       7.662   1.852   1.428  1.00  0.00           H  
HETATM   38  H9  UNL     1       7.779   0.042   1.319  1.00  0.00           H  
HETATM   39  H10 UNL     1       5.573   0.722   1.942  1.00  0.00           H  
HETATM   40  H11 UNL     1       5.381   1.768   0.490  1.00  0.00           H  
HETATM   41  H12 UNL     1       5.847  -1.256   0.640  1.00  0.00           H  
HETATM   42  H13 UNL     1       5.803  -0.393  -0.915  1.00  0.00           H  
HETATM   43  H14 UNL     1       3.668  -1.456  -0.401  1.00  0.00           H  
HETATM   44  H15 UNL     1       3.608  -0.670   1.219  1.00  0.00           H  
HETATM   45  H16 UNL     1       3.433   1.561   0.133  1.00  0.00           H  
HETATM   46  H17 UNL     1       3.492   0.794  -1.497  1.00  0.00           H  
HETATM   47  H18 UNL     1       1.277   0.259   0.600  1.00  0.00           H  
HETATM   48  H19 UNL     1       1.504   0.469  -2.434  1.00  0.00           H  
HETATM   49  H20 UNL     1      -0.866  -0.017  -0.494  1.00  0.00           H  
HETATM   50  H21 UNL     1      -0.965   0.921  -2.052  1.00  0.00           H  
HETATM   51  H22 UNL     1      -0.447  -1.063  -3.354  1.00  0.00           H  
HETATM   52  H23 UNL     1      -1.878  -1.343  -2.344  1.00  0.00           H  
HETATM   53  H24 UNL     1      -0.356  -3.247  -2.316  1.00  0.00           H  
HETATM   54  H25 UNL     1       0.980  -2.295  -1.661  1.00  0.00           H  
HETATM   55  H26 UNL     1      -0.118  -3.528   0.175  1.00  0.00           H  
HETATM   56  H27 UNL     1      -0.302  -1.749   0.404  1.00  0.00           H  
HETATM   57  H28 UNL     1      -2.313  -3.698  -0.814  1.00  0.00           H  
HETATM   58  H29 UNL     1      -2.597  -1.877  -0.547  1.00  0.00           H  
HETATM   59  H30 UNL     1      -2.252  -2.143   1.820  1.00  0.00           H  
HETATM   60  H31 UNL     1      -1.910  -3.871   1.666  1.00  0.00           H  
HETATM   61  H32 UNL     1      -4.328  -3.347   2.294  1.00  0.00           H  
HETATM   62  H33 UNL     1      -4.270  -4.139   0.633  1.00  0.00           H  
HETATM   63  H34 UNL     1      -5.551   0.914   1.974  1.00  0.00           H  
HETATM   64  H35 UNL     1      -4.949   0.693   0.334  1.00  0.00           H  
HETATM   65  H36 UNL     1      -7.563  -0.527   1.377  1.00  0.00           H  
HETATM   66  H37 UNL     1      -7.870  -1.235  -0.636  1.00  0.00           H  
HETATM   67  H38 UNL     1      -7.672   1.913   1.442  1.00  0.00           H  
HETATM   68  H39 UNL     1      -8.810   1.109   0.336  1.00  0.00           H  
HETATM   69  H40 UNL     1      -8.069   5.347  -1.804  1.00  0.00           H  
HETATM   70  H41 UNL     1     -10.031   2.382  -0.857  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3   33   34
CONECT    3    4   35   36
CONECT    4    5   37   38
CONECT    5    6   39   40
CONECT    6    7   41   42
CONECT    7    8   43   44
CONECT    8    9   45   46
CONECT    9   10   10   47
CONECT   10   11   48
CONECT   11   12   49   50
CONECT   12   13   51   52
CONECT   13   14   53   54
CONECT   14   15   55   56
CONECT   15   16   57   58
CONECT   16   17   59   60
CONECT   17   18   61   62
CONECT   18   19   19   20
CONECT   20   21
CONECT   21   22   63   64
CONECT   22   23   24   65
CONECT   23   66
CONECT   24   25   67   68
CONECT   25   26
CONECT   26   27   27   28   29
CONECT   28   69
CONECT   29   70
END

HMDB0242470
     RDKit          3D
(2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate
 70 69  0  0  0  0  0  0  0  0999 V2000
    9.8175    2.3923    0.4509 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4582    1.1837   -0.3644 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9376    1.0737   -0.5297 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3734    0.9606    0.8478 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8598    0.8433    0.8781 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3990   -0.3739    0.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9170   -0.5113    0.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1814    0.6430   -0.4527 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7185    0.3895   -0.3756 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0103    0.3306   -1.4736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4590    0.0817   -1.4977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7881   -1.1755   -2.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1268   -2.3674   -1.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5581   -2.5914   -0.2462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0570   -2.8083   -0.2303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4799   -3.0430    1.2019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9632   -3.2756    1.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6362   -2.0418    0.6765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8859   -1.9799   -0.5563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9829   -0.9910    1.4674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6076    0.1997    1.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9853    0.0537    0.5913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0483   -0.6898   -0.5463 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7286    1.3660    0.4831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2511    2.1802   -0.5155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1980    3.6000   -0.4908 P   0  0  0  0  0  5  0  0  0  0  0  0
   -8.4532    3.9336    0.9619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3963    4.8159   -1.3057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7171    3.2638   -1.1840 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7430    2.8836    0.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9753    2.1375    1.5153 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9601    3.1208    0.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9539    1.1733   -1.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7683    0.2491    0.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7642    0.1217   -1.0766 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5955    1.9609   -1.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6621    1.8515    1.4277 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7792    0.0418    1.3189 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5726    0.7219    1.9424 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3810    1.7685    0.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8468   -1.2562    0.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8031   -0.3929   -0.9148 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6677   -1.4565   -0.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6083   -0.6695    1.2187 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4328    1.5615    0.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4917    0.7936   -1.4971 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2769    0.2593    0.5999 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5043    0.4689   -2.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8661   -0.0173   -0.4936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9652    0.9210   -2.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4470   -1.0628   -3.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8783   -1.3435   -2.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3559   -3.2475   -2.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9804   -2.2954   -1.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1182   -3.5279    0.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3017   -1.7489    0.4041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3129   -3.6976   -0.8140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5966   -1.8766   -0.5471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2520   -2.1430    1.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9104   -3.8710    1.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3284   -3.3469    2.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2695   -4.1392    0.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5510    0.9144    1.9745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9494    0.6927    0.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5633   -0.5269    1.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8703   -1.2354   -0.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6720    1.9129    1.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8095    1.1087    0.3357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0686    5.3468   -1.8041 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0308    2.3823   -0.8570 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  3
 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
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 26 29  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  0
 12 52  1  0
 13 53  1  0
 13 54  1  0
 14 55  1  0
 14 56  1  0
 15 57  1  0
 15 58  1  0
 16 59  1  0
 16 60  1  0
 17 61  1  0
 17 62  1  0
 21 63  1  0
 21 64  1  0
 22 65  1  0
 23 66  1  0
 24 67  1  0
 24 68  1  0
 28 69  1  0
 29 70  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoic acid	Generator
1-Octadec-9-enoylglycero-3-phosphoric acid	HMDB
1-Oleoyl-lysophosphatidic acid	HMDB
LPA (lysophosphatidic acid)	HMDB
Monooleylphosphatidic acid, sodium salt, (R)-isomer	HMDB
MOPA	HMDB
1-O-Oleyllysophosphatidic acid	HMDB
Monooleylphosphatidic acid	HMDB
Monooleylphosphatidic acid, (R)-isomer	HMDB
Monooleylphosphatidate	HMDB
Lysophosphatidate	HMDB
1-Oleoyl-lyso-phosphatidic acid	HMDB
9-Octadecenoic acid (9Z)-, 2-hydroxy-3-(phosphonooxy)propyl ester	HMDB

Chemical Formula

C₂₁H₄₁O₇P

Average Molecular Weight

436.5198

Monoisotopic Molecular Weight

436.258990178

IUPAC Name

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

Traditional Name

LPA

CAS Registry Number

Not Available

SMILES

CCCCCCCCC=CCCCCCCCC(=O)OCC(O)COP(O)(O)=O

InChI Identifier

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

InChI Key

WRGQSWVCFNIUNZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-acylglycerol-3-phosphates. These are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-1 position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphates

Direct Parent

1-acylglycerol-3-phosphates

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-lysophosphatidic acid (CHEBI:52288 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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
logP	4.69	ALOGPS
logP	5.49	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	1.51	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	115.3 m³·mol⁻¹	ChemAxon
Polarizability	50.13 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	201.692	30932474
DeepCCS	[M-H]-	199.142	30932474
DeepCCS	[M-2H]-	232.671	30932474
DeepCCS	[M+Na]+	209.299	30932474
AllCCS	[M+H]+	211.9	32859911
AllCCS	[M+H-H2O]+	210.0	32859911
AllCCS	[M+NH4]+	213.7	32859911
AllCCS	[M+Na]+	214.3	32859911
AllCCS	[M-H]-	206.4	32859911
AllCCS	[M+Na-2H]-	209.1	32859911
AllCCS	[M+HCOO]-	212.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate	CCCCCCCCC=CCCCCCCCC(=O)OCC(O)COP(O)(O)=O	3496.9	Standard polar	33892256
(2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate	CCCCCCCCC=CCCCCCCCC(=O)OCC(O)COP(O)(O)=O	2826.6	Standard non polar	33892256
(2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate	CCCCCCCCC=CCCCCCCCC(=O)OCC(O)COP(O)(O)=O	3230.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate,2TMS,isomer #1	CCCCCCCCC=CCCCCCCCC(=O)OCC(COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C	3290.6	Semi standard non polar	33892256
(2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate,2TMS,isomer #1	CCCCCCCCC=CCCCCCCCC(=O)OCC(COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C	3051.8	Standard non polar	33892256
(2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate,2TMS,isomer #1	CCCCCCCCC=CCCCCCCCC(=O)OCC(COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C	3869.3	Standard polar	33892256
(2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate,2TMS,isomer #2	CCCCCCCCC=CCCCCCCCC(=O)OCC(O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3259.9	Semi standard non polar	33892256
(2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate,2TMS,isomer #2	CCCCCCCCC=CCCCCCCCC(=O)OCC(O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3058.6	Standard non polar	33892256
(2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate,2TMS,isomer #2	CCCCCCCCC=CCCCCCCCC(=O)OCC(O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3586.1	Standard polar	33892256
(2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate,3TMS,isomer #1	CCCCCCCCC=CCCCCCCCC(=O)OCC(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3246.9	Semi standard non polar	33892256
(2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate,3TMS,isomer #1	CCCCCCCCC=CCCCCCCCC(=O)OCC(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3082.3	Standard non polar	33892256
(2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate,3TMS,isomer #1	CCCCCCCCC=CCCCCCCCC(=O)OCC(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3343.3	Standard polar	33892256
(2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate,2TBDMS,isomer #1	CCCCCCCCC=CCCCCCCCC(=O)OCC(COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3751.5	Semi standard non polar	33892256
(2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate,2TBDMS,isomer #1	CCCCCCCCC=CCCCCCCCC(=O)OCC(COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3334.9	Standard non polar	33892256
(2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate,2TBDMS,isomer #1	CCCCCCCCC=CCCCCCCCC(=O)OCC(COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3910.9	Standard polar	33892256
(2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate,2TBDMS,isomer #2	CCCCCCCCC=CCCCCCCCC(=O)OCC(O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3717.0	Semi standard non polar	33892256
(2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate,2TBDMS,isomer #2	CCCCCCCCC=CCCCCCCCC(=O)OCC(O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3311.7	Standard non polar	33892256
(2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate,2TBDMS,isomer #2	CCCCCCCCC=CCCCCCCCC(=O)OCC(O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3713.9	Standard polar	33892256
(2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate,3TBDMS,isomer #1	CCCCCCCCC=CCCCCCCCC(=O)OCC(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3942.7	Semi standard non polar	33892256
(2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate,3TBDMS,isomer #1	CCCCCCCCC=CCCCCCCCC(=O)OCC(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3459.9	Standard non polar	33892256
(2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate,3TBDMS,isomer #1	CCCCCCCCC=CCCCCCCCC(=O)OCC(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3525.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ot-9860000000-034768140b699bb1a3d8	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	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 - (2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate 10V, Positive-QTOF	splash10-05n0-1664900000-bb79121315c57148ba9d	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate 20V, Positive-QTOF	splash10-0ap0-3953100000-045b38adbf2db451a314	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate 40V, Positive-QTOF	splash10-0avr-8790000000-c38761e8c2b5b8c14b27	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate 10V, Negative-QTOF	splash10-01s9-4190400000-6eb0fb76d4152dc445c1	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate 20V, Negative-QTOF	splash10-004i-9050000000-59ba3ab3aaa16aad0dab	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate 40V, Negative-QTOF	splash10-004i-9000000000-1ed06123f93f668d7936	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate 10V, Positive-QTOF	splash10-000i-0000900000-7e12cb76d12b3f802c50	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate 20V, Positive-QTOF	splash10-000i-0000900000-7e12cb76d12b3f802c50	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate 40V, Positive-QTOF	splash10-01b9-0950700000-73c60165df02c9a64da0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate 10V, Negative-QTOF	splash10-000i-0000900000-d085ce376977617b0999	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate 20V, Negative-QTOF	splash10-000i-0000900000-d085ce376977617b0999	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate 40V, Negative-QTOF	splash10-0uei-2950600000-58d696695f1cde07ed4d	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3850

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3988

PDB ID

Not Available

ChEBI ID

52288

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for (2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate (HMDB0242470)

MOL for HMDB0242470 ((2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate)

3D MOL for HMDB0242470 ((2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate)

3D SDF for HMDB0242470 ((2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate)

3D-SDF for HMDB0242470 ((2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate)

PDB for HMDB0242470 ((2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate)

3D PDB for HMDB0242470 ((2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate)

SMILES for HMDB0242470 ((2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate)

INCHI for HMDB0242470 ((2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate)

Structure for HMDB0242470 ((2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate)

3D Structure for HMDB0242470 ((2-Hydroxy-3-phosphonooxypropyl) octadec-9-enoate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra