NP-MRD: Showing NP-Card for 1-oleoyl lysophosphatidic acid (NP0306195)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Show more...Show more...

Record Information

Version

2.0

Created at

2022-09-10 22:31:09 UTC

Updated at

2022-09-10 22:31:09 UTC

NP-MRD ID

NP0306195

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-oleoyl lysophosphatidic acid

Description

PA(18:1(9Z)/0:0)Is a phosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PA(18:1(9Z)/0:0), In particular, consists of two 9Z-octadecenoyl chain at positions C-1 and C2. The oleic acid moiety is derived from vegetable oils, especially olive and canola oil, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. 1-oleoyl lysophosphatidic acid is found in Amaranthus blitum. 1-oleoyl lysophosphatidic acid was first documented in 2000 (PMID: 10779388). Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids (PMID: 16651401) (PMID: 17887800) (PMID: 18006645) (PMID: 20005724).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv0541 02231221472D          

 30 29  0  0  1  0            999 V2000
    9.2142   -8.2346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8892   -8.6244    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.5644   -8.2346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5390   -8.6244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2395   -8.6244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4161   -9.4040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3015   -9.4337    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1345   -8.6244    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.8417   -9.7048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1345   -7.5244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1229   -9.0271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1001   -8.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3856   -8.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6711   -8.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9567   -8.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2422   -8.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5277   -8.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8132   -8.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0987   -8.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3843   -8.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6698   -8.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9553   -8.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2409   -8.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5263   -8.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8119   -8.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0974   -8.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3829   -8.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6685   -8.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9540   -8.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9540   -7.3869    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  1  0  0  0
  2  7  1  6  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  8 11  1  0  0  0  0
  8  4  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  2  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  1  0  0  0  0
 29 28  1  0  0  0  0
 30 29  2  0  0  0  0
  5 29  1  0  0  0  0
M  END

     RDKit          3D

 70 69  0  0  0  0  0  0  0  0999 V2000
  -10.5030   -1.2334   -0.4507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7358   -0.0099   -0.9338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0400    0.6892    0.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0583   -0.2243    0.9024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0207   -0.6692   -0.0941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9919   -1.5857    0.5311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2410   -0.9391    1.6622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4844    0.3008    1.2250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5062   -0.0256    0.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2170    0.1773    0.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5644    0.7422    1.5394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8184    2.0042    1.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2431    1.7925    0.2359 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2367    0.7809    0.6792 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3402    0.5860   -0.3706 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0905    1.8462   -0.6389 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1563    1.6234   -1.6610 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1712    0.6457   -1.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0811    0.2722    0.0367 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1661    0.1889   -1.9645 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1567   -0.6950   -1.6000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0994   -0.1390   -0.5850 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4781    0.1844    0.5766 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2428   -1.1093   -0.2943 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1237   -0.4707    0.5656 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4269   -1.4932    0.9340 P   0  0  0  0  0  5  0  0  0  0  0  0
   12.2003   -0.9319    2.1137 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5110   -1.5640   -0.3826 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9283   -3.0470    1.3268 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6108   -1.1359    0.6547 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5162   -1.2500   -0.8702 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0076   -2.1775   -0.7261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0158   -0.2531   -1.7216 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4671    0.7463   -1.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5462    1.5835   -0.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7742    1.0866    0.9497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6281    0.2374    1.7999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6246   -1.1259    1.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5577   -1.3274   -0.8404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5960    0.1611   -0.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3352   -1.9686   -0.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5404   -2.4480    0.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4795   -1.6707    2.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8994   -0.7152    2.5086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1985    1.0482    0.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1227    0.7935    2.1288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8818   -0.4628   -0.7683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5996   -0.1221   -0.5333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8086   -0.0270    1.8867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2339    0.8278    2.4323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3889    2.3439    2.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4698    2.8260    0.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2931    1.4653   -0.6983 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7089    2.8017    0.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7410   -0.2235    0.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6834    0.9897    1.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8236    0.2875   -1.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9362   -0.2472   -0.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4077    2.6530   -1.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5568    2.2620    0.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6659    2.5894   -1.8832 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7360    1.1938   -2.5916 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7472   -1.0060   -2.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7091   -1.6669   -1.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5811    0.7547   -1.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8012    1.0460    0.9329 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7174   -1.4549   -1.2271 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7750   -1.9750    0.2449 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3147   -0.7858   -0.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2192   -3.3500    0.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 28  1  0
 26 27  2  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  6
 23 66  1  0
 24 67  1  0
 24 68  1  0
 28 69  1  0
 29 70  1  0
M  END

  Mrv0541 02231221472D          

 30 29  0  0  1  0            999 V2000
    9.2142   -8.2346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8892   -8.6244    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.5644   -8.2346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5390   -8.6244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2395   -8.6244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4161   -9.4040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3015   -9.4337    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1345   -8.6244    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.8417   -9.7048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1345   -7.5244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1229   -9.0271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1001   -8.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3856   -8.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6711   -8.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9567   -8.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2422   -8.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5277   -8.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8132   -8.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0987   -8.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3843   -8.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6698   -8.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9553   -8.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2409   -8.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5263   -8.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8119   -8.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0974   -8.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3829   -8.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6685   -8.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9540   -8.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9540   -7.3869    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  1  0  0  0
  2  7  1  6  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  8 11  1  0  0  0  0
  8  4  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  2  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  1  0  0  0  0
 29 28  1  0  0  0  0
 30 29  2  0  0  0  0
  5 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0306195

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@](O)([H])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)/b10-9-/t20-/m1/s1

> <INCHI_KEY>
WRGQSWVCFNIUNZ-GDCKJWNLSA-N

> <FORMULA>
C21H41O7P

> <MOLECULAR_WEIGHT>
436.5198

> <EXACT_MASS>
436.258990178

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
49.155153434673906

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2R)-2-hydroxy-3-[(9Z)-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>
6.531115837556447

> <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>
1-oleoyl lysophosphatidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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      17.200 -15.371   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.460 -16.099   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.720 -15.371   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      15.939 -16.099   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      20.980 -16.099   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      19.443 -17.554   0.000  0.00  0.00           O+0
HETATM    7  H   UNK     0      17.363 -17.610   0.000  0.00  0.00           H+0
HETATM    8  P   UNK     0      13.318 -16.099   0.000  0.00  0.00           P+0
HETATM    9  O   UNK     0      14.638 -18.116   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      13.318 -14.046   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      11.429 -16.851   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      44.987 -15.329   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      43.653 -16.099   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      42.319 -15.329   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      40.986 -16.099   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      39.652 -15.329   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      38.318 -16.099   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      36.985 -15.329   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      35.651 -16.099   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      34.317 -15.329   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      32.984 -15.329   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      31.650 -16.099   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      30.316 -15.329   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      28.982 -16.099   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      27.649 -15.329   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      26.315 -16.099   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      24.981 -15.329   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      23.648 -16.099   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      22.314 -15.329   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      22.314 -13.789   0.000  0.00  0.00           O+0
CONECT    1    2    4                                                       
CONECT    2    1    3    6    7                                             
CONECT    3    2    5                                                       
CONECT    4    1    8                                                       
CONECT    5    3   29                                                       
CONECT    6    2                                                            
CONECT    7    2                                                            
CONECT    8    9   10   11    4                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8                                                            
CONECT   12   13                                                            
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30    5                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   58    0
END

View in JSmol

Synonyms

Value	Source
1-(9Z-Octadecenoyl)-sn-glycero-3-phosphate	ChEBI
1-O-Oleoyl-sn-glycerol 3-phosphate	ChEBI
1-O-Oleyl-sn-glycerol 3-phosphate	ChEBI
1-Oleoyl lysophosphatidic acid	ChEBI
1-Oleoyl-2-lyso-sn-glycerol 3-phosphatidic acid	ChEBI
1-Oleoyl-sn-glycero-3-phosphate	ChEBI
1-Oleoylglycerol 3-phosphate	ChEBI
1-Oleyl-2-lyso-sn-glycerol 3-phosphatidic acid	ChEBI
1-Oleyl-sn-glycerol 3-phosphate	ChEBI
1-Oleylglycerol 3-phosphate	ChEBI
1-Oleyllysophosphatidic acid	ChEBI
18:1 LPA	ChEBI
LPA 18:1	ChEBI
LPA(18:1(9Z)/0:0)	ChEBI
LPA(18:1)	ChEBI
LPA(18:1/0:0)	ChEBI
LPA(18:1n9/0:0)	ChEBI
LPA(18:1W9/0:0)	ChEBI
LysoPA(18:1(9Z)/0:0)	ChEBI
LysoPA(18:1)	ChEBI
LysoPA(18:1W9/0:0)	ChEBI
Lysophosphatidic acid(18:1)	ChEBI
Lysophosphatidic acid(18:1/0:0)	ChEBI
Lysophosphatidic acid(18:1n9/0:0)	ChEBI
Lysophosphatidic acid(18:1W9/0:0)	ChEBI
Monooleylphosphatidic acid	ChEBI
PA(18:1/0:0)	ChEBI
1-(9Z-Octadecenoyl)-sn-glycero-3-phosphoric acid	Generator
1-O-Oleoyl-sn-glycerol 3-phosphoric acid	Generator
1-O-Oleyl-sn-glycerol 3-phosphoric acid	Generator
1-Oleoyl lysophosphatidate	Generator
1-Oleoyl-2-lyso-sn-glycerol 3-phosphatidate	Generator
1-Oleoyl-sn-glycero-3-phosphoric acid	Generator
1-Oleoylglycerol 3-phosphoric acid	Generator
1-Oleyl-2-lyso-sn-glycerol 3-phosphatidate	Generator
1-Oleyl-sn-glycerol 3-phosphoric acid	Generator
1-Oleylglycerol 3-phosphoric acid	Generator
1-Oleyllysophosphatidate	Generator
Lysophosphatidate(18:1)	Generator
Lysophosphatidate(18:1/0:0)	Generator
Lysophosphatidate(18:1n9/0:0)	Generator
Lysophosphatidate(18:1W9/0:0)	Generator
Monooleylphosphatidate	Generator
1-O-Oleyllysophosphatidic acid	MeSH
9-Octadecenoic acid (9Z)-, 2-hydroxy-3-(phosphonooxy)propyl ester	MeSH
1-Oleoyl-lyso-phosphatidic acid	MeSH
Monooleylphosphatidic acid, sodium salt, (R)-isomer	MeSH
1-Oleoyl-lysophosphatidic acid	MeSH
LPA (lysophosphatidic acid)	MeSH
Lysophosphatidic acid	MeSH
Monooleylphosphatidic acid, (R)-isomer	MeSH
MOPA	MeSH

Chemical Formula

C₂₁H₄₁O₇P

Average Mass

436.5198 Da

Monoisotopic Mass

436.25899 Da

IUPAC Name

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

Traditional Name

1-oleoyl lysophosphatidic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@](O)([H])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)/b10-9-/t20-/m1/s1

InChI Key

WRGQSWVCFNIUNZ-GDCKJWNLSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Amaranthus blitum	LOTUS Database	35616633

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

1-acyl-sn-glycerol 3-phosphate (CHEBI:62837 )
Monoacylglycerophosphates (LMGP10050008 )

Physical Properties

State

Not Available

Experimental 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

Predicted 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	49.16 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5311263

PDB ID

Not Available

ChEBI ID

62837

Good Scents ID

Not Available

References

General References

Casas-Gonzalez P, Vazquez-Prado J, Garcia-Sainz JA: Lysophosphatidic acid modulates alpha(1b)-adrenoceptor phosphorylation and function: roles of Gi and phosphoinositide 3-kinase. Mol Pharmacol. 2000 May;57(5):1027-33. [PubMed:10779388 ]
Kotarsky K, Boketoft A, Bristulf J, Nilsson NE, Norberg A, Hansson S, Owman C, Sillard R, Leeb-Lundberg LM, Olde B: Lysophosphatidic acid binds to and activates GPR92, a G protein-coupled receptor highly expressed in gastrointestinal lymphocytes. J Pharmacol Exp Ther. 2006 Aug;318(2):619-28. doi: 10.1124/jpet.105.098848. Epub 2006 May 1. [PubMed:16651401 ]
Liu XW, Sok DE, Yook HS, Sohn CB, Chung YJ, Kim MR: Inhibition of lysophospholipase D activity by unsaturated lysophosphatidic acids or seed extracts containing 1-linoleoyl and 1-oleoyl lysophosphatidic acid. J Agric Food Chem. 2007 Oct 17;55(21):8717-22. doi: 10.1021/jf071080u. Epub 2007 Sep 24. [PubMed:17887800 ]
Zhao C, Fernandes MJ, Prestwich GD, Turgeon M, Di Battista J, Clair T, Poubelle PE, Bourgoin SG: Regulation of lysophosphatidic acid receptor expression and function in human synoviocytes: implications for rheumatoid arthritis? Mol Pharmacol. 2008 Feb;73(2):587-600. doi: 10.1124/mol.107.038216. Epub 2007 Nov 15. [PubMed:18006645 ]
Hoeglund AB, Howard AL, Wanjala IW, Pham TC, Parrill AL, Baker DL: Characterization of non-lipid autotaxin inhibitors. Bioorg Med Chem. 2010 Jan 15;18(2):769-76. doi: 10.1016/j.bmc.2009.11.056. Epub 2009 Nov 27. [PubMed:20005724 ]
LOTUS database [Link]

Showing NP-Card for 1-oleoyl lysophosphatidic acid (NP0306195)

MOL for NP0306195 (1-oleoyl lysophosphatidic acid)

3D MOL for NP0306195 (1-oleoyl lysophosphatidic acid)

3D SDF for NP0306195 (1-oleoyl lysophosphatidic acid)

3D-SDF for NP0306195 (1-oleoyl lysophosphatidic acid)

PDB for NP0306195 (1-oleoyl lysophosphatidic acid)

3D PDB for NP0306195 (1-oleoyl lysophosphatidic acid)

SMILES for NP0306195 (1-oleoyl lysophosphatidic acid)

INCHI for NP0306195 (1-oleoyl lysophosphatidic acid)

Structure for NP0306195 (1-oleoyl lysophosphatidic acid)

3D Structure for NP0306195 (1-oleoyl lysophosphatidic acid)