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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (61) Show 61 proteins XML

Record Information

Version

5.0

Status

Predicted

Creation Date

2021-09-12 11:37:52 UTC

Update Date

2022-11-30 19:56:23 UTC

HMDB ID

HMDB0266645

Secondary Accession Numbers

None

Metabolite Identification

Common Name

PA(8:0/18:1(9Z)-O(12,13))

Description

PA(8:0/18:1(9Z)-O(12,13)) is an oxidized phosphatidic acid (PA). Oxidized phosphatidic acids are glycerophospholipids in which a phosphate moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidic acids belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396 ). As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PA(8:0/18:1(9Z)-O(12,13)), in particular, consists of one chain of one octanoyl at the C-1 position and one chain of 12,13-epoxy-octadecenoyl at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PAs can be synthesized via three different routes. In one route, the oxidized PA is synthetized de novo following the same mechanisms as for PAs but incorporating oxidized acyl chains (PMID: 33329396 ). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396 ). The third pathway results from the oxidation of the acyl chain while still attached to the PA backbone, mainly through the action of LOX (PMID: 33329396 ).

Structure

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

PA(8:0/18:1(9Z)-O(12,13))
  Mrv1652309122113382D          

 40 40  0  0  1  0            999 V2000
   -3.8021    0.3607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9591    0.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2447    0.7720    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6571    1.4866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1679    0.0575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    1.1846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0970    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3824    0.3590    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6679    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9699   -0.3554    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7950   -0.3554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5121    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5121    1.5410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2262    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9404    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6545    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3686    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0827    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7968    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5109    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5096   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5096   -1.5394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2237   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9378   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6519   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3660   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0801   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7942   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5083   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2225   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0475   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7616   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4757   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4757   -1.5394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1898   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9040   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.6181   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.3322   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.0463   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.7604   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  2  9  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  3  1  0  0  0  0
  7  1  1  0  0  0  0
  8  7  1  0  0  0  0
  8 10  1  1  0  0  0
  8 11  1  0  0  0  0
  9  8  1  0  0  0  0
 11 21  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
M  END

HMDB0266645
     RDKit          3D
PA(8:0/18:1(9Z)-O(12,13))
 92 92  0  0  0  0  0  0  0  0999 V2000
  -11.8148   -0.4674   -0.7135 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4131   -0.5768   -0.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3025   -0.0377    1.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8067   -0.1905    1.6353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7045    0.3389    2.9996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4293    0.3641    3.7355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3536    1.1634    3.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9065    0.5063    1.8286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0850   -0.7239    1.7490 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3341    1.1533    0.7967 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8847    0.6641   -0.3835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7602   -0.2999   -0.4356 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0604   -1.7410   -0.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2378   -2.0766   -0.8311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6753   -3.6722   -0.6190 P   0  0  0  0  0  5  0  0  0  0  0  0
   -7.0694   -3.8450   -1.2289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8323   -4.0245    1.0263 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6111   -4.7398   -1.3817 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5748    0.1755    0.1716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4172    0.5141   -0.4772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4196    0.3846   -1.7343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1983    1.0118    0.2165 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7283   -0.1524    0.4832 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2032   -0.8765   -0.7086 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9282   -0.1854   -1.7754 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006    0.4817   -1.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1732    1.6439   -0.5677 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6012    2.2314   -0.3969 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0397    2.6290   -1.7279 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0875    2.1625   -2.3440 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9729    1.1515   -1.7485 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4021    1.6623   -1.6022 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0566    2.0381   -2.7684 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5262    0.8509   -2.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8847    0.9048   -1.5366 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7956    0.4140   -0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3047   -1.0098   -0.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2410   -1.4256    1.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7534   -2.8529    1.5624 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2592   -1.4742   -0.8207 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4764    0.1481   -0.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8291    0.0243   -1.7219 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0399   -1.6254   -0.2113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7443    0.0358   -0.8570 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5868    1.0272    1.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9099   -0.6089    1.8934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6122   -1.2955    1.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2819    0.3819    0.8468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4622   -0.2173    3.6321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1214    1.4086    2.9561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0596   -0.7120    3.8659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5932    0.6941    4.8038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7630    2.1817    2.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4966    1.3022    3.7925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6879    0.2399   -1.0526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5398    1.5664   -1.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4618   -0.3009   -1.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2257   -2.3149   -0.7081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9855   -2.0743    0.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3711   -3.3777    1.5966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8661   -4.1853   -1.7589 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3084    1.8010   -0.3366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4502    1.4384    1.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0059   -0.9314    1.0063 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4590   -0.0081    1.2718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8756   -1.7068   -0.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3372   -1.4783   -1.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2370    0.5297   -2.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1432   -0.9729   -2.5833 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6815    0.8726   -2.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9623   -0.2914   -1.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5866    2.4939   -1.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7780    1.4668    0.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1642    1.4916    0.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4080    3.1552    0.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4176    3.3896   -2.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2834    2.5705   -3.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0563    0.3352   -2.5373 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6154    0.6385   -0.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6183    2.2943   -0.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2290   -0.0611   -2.7649 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3350    1.9160   -1.5758 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5645    0.2198   -2.0781 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0813    1.0400    0.4910 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8163    0.4600    0.3111 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9386   -1.6963   -0.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2758   -1.1175   -0.4312 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2438   -1.2846    1.8715 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5209   -0.7655    1.9528 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3533   -3.5322    0.9322 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6872   -2.8754    1.2385 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8325   -3.1080    2.6441 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  2  0
  8 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  2  0
 15 17  1  0
 15 18  1  0
 12 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 34 32  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  2 43  1  0
  2 44  1  0
  3 45  1  0
  3 46  1  0
  4 47  1  0
  4 48  1  0
  5 49  1  0
  5 50  1  0
  6 51  1  0
  6 52  1  0
  7 53  1  0
  7 54  1  0
 11 55  1  0
 11 56  1  0
 12 57  1  6
 13 58  1  0
 13 59  1  0
 17 60  1  0
 18 61  1  0
 22 62  1  0
 22 63  1  0
 23 64  1  0
 23 65  1  0
 24 66  1  0
 24 67  1  0
 25 68  1  0
 25 69  1  0
 26 70  1  0
 26 71  1  0
 27 72  1  0
 27 73  1  0
 28 74  1  0
 28 75  1  0
 29 76  1  0
 30 77  1  0
 31 78  1  0
 31 79  1  0
 32 80  1  0
 34 81  1  0
 35 82  1  0
 35 83  1  0
 36 84  1  0
 36 85  1  0
 37 86  1  0
 37 87  1  0
 38 88  1  0
 38 89  1  0
 39 90  1  0
 39 91  1  0
 39 92  1  0
M  END

PA(8:0/18:1(9Z)-O(12,13))
  Mrv1652309122113382D          

 40 40  0  0  1  0            999 V2000
   -3.8021    0.3607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9591    0.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2447    0.7720    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6571    1.4866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1679    0.0575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    1.1846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0970    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3824    0.3590    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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  -15.7604   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  2  9  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  3  1  0  0  0  0
  7  1  1  0  0  0  0
  8  7  1  0  0  0  0
  8 10  1  1  0  0  0
  8 11  1  0  0  0  0
  9  8  1  0  0  0  0
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 21 22  2  0  0  0  0
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 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
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 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
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 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0266645

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@](COC(=O)CCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/CC1OC1CCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C29H53O9P/c1-3-5-7-12-17-21-28(30)35-23-25(24-36-39(32,33)34)37-29(31)22-18-14-11-9-8-10-13-16-20-27-26(38-27)19-15-6-4-2/h13,16,25-27H,3-12,14-15,17-24H2,1-2H3,(H2,32,33,34)/b16-13-/t25-,26?,27?/m1/s1

> <INCHI_KEY>
BAOKIHSKOOWGLQ-NWUHCHHHSA-N

> <FORMULA>
C29H53O9P

> <MOLECULAR_WEIGHT>
576.708

> <EXACT_MASS>
576.342720285

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
92

> <JCHEM_AVERAGE_POLARIZABILITY>
66.41541075847644

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R)-3-(octanoyloxy)-2-{[(9Z)-11-(3-pentyloxiran-2-yl)undec-9-enoyl]oxy}propoxy]phosphonic acid

> <ALOGPS_LOGP>
5.79

> <JCHEM_LOGP>
7.550275542333333

> <ALOGPS_LOGS>
-6.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.34323464916217

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.3174073878699715

> <JCHEM_PKA_STRONGEST_BASIC>
-4.203574435518867

> <JCHEM_POLAR_SURFACE_AREA>
131.89000000000001

> <JCHEM_REFRACTIVITY>
151.6033

> <JCHEM_ROTATABLE_BOND_COUNT>
28

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.67e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-3-(octanoyloxy)-2-{[(9Z)-11-(3-pentyloxiran-2-yl)undec-9-enoyl]oxy}propoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0266645
     RDKit          3D
PA(8:0/18:1(9Z)-O(12,13))
 92 92  0  0  0  0  0  0  0  0999 V2000
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 39 91  1  0
 39 92  1  0
M  END

HEADER    PROTEIN                                 12-SEP-21   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: PA(8:0/18:1(9Z)-O(12,13))                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-21         0                                  
HETATM    1  O   UNK     0      -7.097   0.673   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      -1.790   0.671   0.000  0.00  0.00           O+0
HETATM    3  P   UNK     0      -0.457   1.441   0.000  0.00  0.00           P+0
HETATM    4  O   UNK     0      -1.227   2.775   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       0.313   0.107   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       0.877   2.211   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -5.781   1.440   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.447   0.670   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.113   1.440   0.000  0.00  0.00           C+0
HETATM   10  H   UNK     0      -3.677  -0.663   0.000  0.00  0.00           H+0
HETATM   11  O   UNK     0      -5.217  -0.663   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -8.423   1.436   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -8.423   2.876   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -9.756   0.665   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -11.089   1.436   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -12.422   0.665   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -13.755   1.436   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -15.088   0.665   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -16.421   1.436   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -17.754   0.665   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.551  -1.433   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -6.551  -2.873   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -7.884  -0.662   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -9.217  -1.433   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -10.550  -0.662   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -11.883  -1.433   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -13.216  -0.662   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -14.549  -1.433   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -15.882  -0.662   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -17.215  -1.433   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -18.755  -1.433   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -20.088  -0.662   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -21.421  -1.433   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0     -21.421  -2.873   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0     -22.754  -0.662   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -24.087  -1.433   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0     -25.420  -0.662   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0     -26.753  -1.433   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0     -28.086  -0.662   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0     -29.419  -1.433   0.000  0.00  0.00           C+0
CONECT    1   12    7                                                       
CONECT    2    9    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3                                                            
CONECT    7    1    8                                                       
CONECT    8    7   10   11    9                                             
CONECT    9    2    8                                                       
CONECT   10    8                                                            
CONECT   11    8   21                                                       
CONECT   12    1   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   11   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   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                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33   35                                                       
CONECT   35   33   34   36                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   80    0
END

COMPND    HMDB0266645
HETATM    1  C1  UNL     1     -11.815  -0.467  -0.714  1.00  0.00           C  
HETATM    2  C2  UNL     1     -10.413  -0.577  -0.212  1.00  0.00           C  
HETATM    3  C3  UNL     1     -10.303  -0.038   1.193  1.00  0.00           C  
HETATM    4  C4  UNL     1      -8.807  -0.190   1.635  1.00  0.00           C  
HETATM    5  C5  UNL     1      -8.704   0.339   3.000  1.00  0.00           C  
HETATM    6  C6  UNL     1      -7.429   0.364   3.735  1.00  0.00           C  
HETATM    7  C7  UNL     1      -6.354   1.163   3.088  1.00  0.00           C  
HETATM    8  C8  UNL     1      -5.906   0.506   1.829  1.00  0.00           C  
HETATM    9  O1  UNL     1      -6.085  -0.724   1.749  1.00  0.00           O  
HETATM   10  O2  UNL     1      -5.334   1.153   0.797  1.00  0.00           O  
HETATM   11  C9  UNL     1      -4.885   0.664  -0.383  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.760  -0.300  -0.436  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.060  -1.741  -0.178  1.00  0.00           C  
HETATM   14  O3  UNL     1      -5.238  -2.077  -0.831  1.00  0.00           O  
HETATM   15  P1  UNL     1      -5.675  -3.672  -0.619  1.00  0.00           P  
HETATM   16  O4  UNL     1      -7.069  -3.845  -1.229  1.00  0.00           O  
HETATM   17  O5  UNL     1      -5.832  -4.025   1.026  1.00  0.00           O  
HETATM   18  O6  UNL     1      -4.611  -4.740  -1.382  1.00  0.00           O  
HETATM   19  O7  UNL     1      -2.575   0.175   0.172  1.00  0.00           O  
HETATM   20  C12 UNL     1      -1.417   0.514  -0.477  1.00  0.00           C  
HETATM   21  O8  UNL     1      -1.420   0.385  -1.734  1.00  0.00           O  
HETATM   22  C13 UNL     1      -0.198   1.012   0.216  1.00  0.00           C  
HETATM   23  C14 UNL     1       0.728  -0.152   0.483  1.00  0.00           C  
HETATM   24  C15 UNL     1       1.203  -0.876  -0.709  1.00  0.00           C  
HETATM   25  C16 UNL     1       1.928  -0.185  -1.775  1.00  0.00           C  
HETATM   26  C17 UNL     1       3.201   0.482  -1.487  1.00  0.00           C  
HETATM   27  C18 UNL     1       3.173   1.644  -0.568  1.00  0.00           C  
HETATM   28  C19 UNL     1       4.601   2.231  -0.397  1.00  0.00           C  
HETATM   29  C20 UNL     1       5.040   2.629  -1.728  1.00  0.00           C  
HETATM   30  C21 UNL     1       6.088   2.162  -2.344  1.00  0.00           C  
HETATM   31  C22 UNL     1       6.973   1.151  -1.749  1.00  0.00           C  
HETATM   32  C23 UNL     1       8.402   1.662  -1.602  1.00  0.00           C  
HETATM   33  O9  UNL     1       9.057   2.038  -2.768  1.00  0.00           O  
HETATM   34  C24 UNL     1       9.526   0.851  -2.207  1.00  0.00           C  
HETATM   35  C25 UNL     1      10.885   0.905  -1.537  1.00  0.00           C  
HETATM   36  C26 UNL     1      10.796   0.414  -0.101  1.00  0.00           C  
HETATM   37  C27 UNL     1      10.305  -1.010  -0.041  1.00  0.00           C  
HETATM   38  C28 UNL     1      10.241  -1.426   1.423  1.00  0.00           C  
HETATM   39  C29 UNL     1       9.753  -2.853   1.562  1.00  0.00           C  
HETATM   40  H1  UNL     1     -12.259  -1.474  -0.821  1.00  0.00           H  
HETATM   41  H2  UNL     1     -12.476   0.148  -0.055  1.00  0.00           H  
HETATM   42  H3  UNL     1     -11.829   0.024  -1.722  1.00  0.00           H  
HETATM   43  H4  UNL     1     -10.040  -1.625  -0.211  1.00  0.00           H  
HETATM   44  H5  UNL     1      -9.744   0.036  -0.857  1.00  0.00           H  
HETATM   45  H6  UNL     1     -10.587   1.027   1.197  1.00  0.00           H  
HETATM   46  H7  UNL     1     -10.910  -0.609   1.893  1.00  0.00           H  
HETATM   47  H8  UNL     1      -8.612  -1.296   1.543  1.00  0.00           H  
HETATM   48  H9  UNL     1      -8.282   0.382   0.847  1.00  0.00           H  
HETATM   49  H10 UNL     1      -9.462  -0.217   3.632  1.00  0.00           H  
HETATM   50  H11 UNL     1      -9.121   1.409   2.956  1.00  0.00           H  
HETATM   51  H12 UNL     1      -7.060  -0.712   3.866  1.00  0.00           H  
HETATM   52  H13 UNL     1      -7.593   0.694   4.804  1.00  0.00           H  
HETATM   53  H14 UNL     1      -6.763   2.182   2.879  1.00  0.00           H  
HETATM   54  H15 UNL     1      -5.497   1.302   3.792  1.00  0.00           H  
HETATM   55  H16 UNL     1      -5.688   0.240  -1.053  1.00  0.00           H  
HETATM   56  H17 UNL     1      -4.540   1.566  -1.001  1.00  0.00           H  
HETATM   57  H18 UNL     1      -3.462  -0.301  -1.559  1.00  0.00           H  
HETATM   58  H19 UNL     1      -3.226  -2.315  -0.708  1.00  0.00           H  
HETATM   59  H20 UNL     1      -3.985  -2.074   0.861  1.00  0.00           H  
HETATM   60  H21 UNL     1      -5.371  -3.378   1.597  1.00  0.00           H  
HETATM   61  H22 UNL     1      -3.866  -4.185  -1.759  1.00  0.00           H  
HETATM   62  H23 UNL     1       0.308   1.801  -0.337  1.00  0.00           H  
HETATM   63  H24 UNL     1      -0.450   1.438   1.219  1.00  0.00           H  
HETATM   64  H25 UNL     1       0.006  -0.931   1.006  1.00  0.00           H  
HETATM   65  H26 UNL     1       1.459  -0.008   1.272  1.00  0.00           H  
HETATM   66  H27 UNL     1       1.876  -1.707  -0.326  1.00  0.00           H  
HETATM   67  H28 UNL     1       0.337  -1.478  -1.141  1.00  0.00           H  
HETATM   68  H29 UNL     1       1.237   0.530  -2.349  1.00  0.00           H  
HETATM   69  H30 UNL     1       2.143  -0.973  -2.583  1.00  0.00           H  
HETATM   70  H31 UNL     1       3.681   0.873  -2.451  1.00  0.00           H  
HETATM   71  H32 UNL     1       3.962  -0.291  -1.160  1.00  0.00           H  
HETATM   72  H33 UNL     1       2.587   2.494  -1.032  1.00  0.00           H  
HETATM   73  H34 UNL     1       2.778   1.467   0.418  1.00  0.00           H  
HETATM   74  H35 UNL     1       5.164   1.492   0.143  1.00  0.00           H  
HETATM   75  H36 UNL     1       4.408   3.155   0.229  1.00  0.00           H  
HETATM   76  H37 UNL     1       4.418   3.390  -2.237  1.00  0.00           H  
HETATM   77  H38 UNL     1       6.283   2.571  -3.357  1.00  0.00           H  
HETATM   78  H39 UNL     1       7.056   0.335  -2.537  1.00  0.00           H  
HETATM   79  H40 UNL     1       6.615   0.639  -0.866  1.00  0.00           H  
HETATM   80  H41 UNL     1       8.618   2.294  -0.707  1.00  0.00           H  
HETATM   81  H42 UNL     1       9.229  -0.061  -2.765  1.00  0.00           H  
HETATM   82  H43 UNL     1      11.335   1.916  -1.576  1.00  0.00           H  
HETATM   83  H44 UNL     1      11.564   0.220  -2.078  1.00  0.00           H  
HETATM   84  H45 UNL     1      10.081   1.040   0.491  1.00  0.00           H  
HETATM   85  H46 UNL     1      11.816   0.460   0.311  1.00  0.00           H  
HETATM   86  H47 UNL     1      10.939  -1.696  -0.620  1.00  0.00           H  
HETATM   87  H48 UNL     1       9.276  -1.117  -0.431  1.00  0.00           H  
HETATM   88  H49 UNL     1      11.244  -1.285   1.872  1.00  0.00           H  
HETATM   89  H50 UNL     1       9.521  -0.765   1.953  1.00  0.00           H  
HETATM   90  H51 UNL     1      10.353  -3.532   0.932  1.00  0.00           H  
HETATM   91  H52 UNL     1       8.687  -2.875   1.239  1.00  0.00           H  
HETATM   92  H53 UNL     1       9.832  -3.108   2.644  1.00  0.00           H  
CONECT    1    2   40   41   42
CONECT    2    3   43   44
CONECT    3    4   45   46
CONECT    4    5   47   48
CONECT    5    6   49   50
CONECT    6    7   51   52
CONECT    7    8   53   54
CONECT    8    9    9   10
CONECT   10   11
CONECT   11   12   55   56
CONECT   12   13   19   57
CONECT   13   14   58   59
CONECT   14   15
CONECT   15   16   16   17   18
CONECT   17   60
CONECT   18   61
CONECT   19   20
CONECT   20   21   21   22
CONECT   22   23   62   63
CONECT   23   24   64   65
CONECT   24   25   66   67
CONECT   25   26   68   69
CONECT   26   27   70   71
CONECT   27   28   72   73
CONECT   28   29   74   75
CONECT   29   30   30   76
CONECT   30   31   77
CONECT   31   32   78   79
CONECT   32   33   34   80
CONECT   33   34
CONECT   34   35   81
CONECT   35   36   82   83
CONECT   36   37   84   85
CONECT   37   38   86   87
CONECT   38   39   88   89
CONECT   39   90   91   92
END

HMDB0266645
     RDKit          3D
PA(8:0/18:1(9Z)-O(12,13))
 92 92  0  0  0  0  0  0  0  0999 V2000
  -11.8148   -0.4674   -0.7135 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4131   -0.5768   -0.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3025   -0.0377    1.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8067   -0.1905    1.6353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7045    0.3389    2.9996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4293    0.3641    3.7355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3536    1.1634    3.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9065    0.5063    1.8286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0850   -0.7239    1.7490 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3341    1.1533    0.7967 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8847    0.6641   -0.3835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7602   -0.2999   -0.4356 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0604   -1.7410   -0.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2378   -2.0766   -0.8311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6753   -3.6722   -0.6190 P   0  0  0  0  0  5  0  0  0  0  0  0
   -7.0694   -3.8450   -1.2289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8323   -4.0245    1.0263 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6111   -4.7398   -1.3817 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5748    0.1755    0.1716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4172    0.5141   -0.4772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4196    0.3846   -1.7343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1983    1.0118    0.2165 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7283   -0.1524    0.4832 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2032   -0.8765   -0.7086 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9282   -0.1854   -1.7754 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006    0.4817   -1.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1732    1.6439   -0.5677 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6012    2.2314   -0.3969 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0397    2.6290   -1.7279 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0875    2.1625   -2.3440 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9729    1.1515   -1.7485 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4021    1.6623   -1.6022 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0566    2.0381   -2.7684 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5262    0.8509   -2.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8847    0.9048   -1.5366 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7956    0.4140   -0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3047   -1.0098   -0.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2410   -1.4256    1.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7534   -2.8529    1.5624 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2592   -1.4742   -0.8207 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4764    0.1481   -0.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8291    0.0243   -1.7219 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0399   -1.6254   -0.2113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7443    0.0358   -0.8570 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5868    1.0272    1.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9099   -0.6089    1.8934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6122   -1.2955    1.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2819    0.3819    0.8468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4622   -0.2173    3.6321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1214    1.4086    2.9561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0596   -0.7120    3.8659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5932    0.6941    4.8038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7630    2.1817    2.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4966    1.3022    3.7925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6879    0.2399   -1.0526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5398    1.5664   -1.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4618   -0.3009   -1.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2257   -2.3149   -0.7081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9855   -2.0743    0.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3711   -3.3777    1.5966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8661   -4.1853   -1.7589 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3084    1.8010   -0.3366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4502    1.4384    1.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0059   -0.9314    1.0063 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4590   -0.0081    1.2718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8756   -1.7068   -0.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3372   -1.4783   -1.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2370    0.5297   -2.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1432   -0.9729   -2.5833 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6815    0.8726   -2.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9623   -0.2914   -1.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5866    2.4939   -1.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7780    1.4668    0.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1642    1.4916    0.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4080    3.1552    0.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4176    3.3896   -2.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2834    2.5705   -3.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0563    0.3352   -2.5373 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6154    0.6385   -0.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6183    2.2943   -0.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2290   -0.0611   -2.7649 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3350    1.9160   -1.5758 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5645    0.2198   -2.0781 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0813    1.0400    0.4910 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8163    0.4600    0.3111 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9386   -1.6963   -0.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2758   -1.1175   -0.4312 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2438   -1.2846    1.8715 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5209   -0.7655    1.9528 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3533   -3.5322    0.9322 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6872   -2.8754    1.2385 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8325   -3.1080    2.6441 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  2  0
  8 10  1  0
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 15 16  2  0
 15 17  1  0
 15 18  1  0
 12 19  1  0
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  4 47  1  0
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 39 92  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
[(2R)-3-(Octanoyloxy)-2-{[(9Z)-11-(3-pentyloxiran-2-yl)undec-9-enoyl]oxy}propoxy]phosphonate	Generator

Chemical Formula

C₂₉H₅₃O₉P

Average Molecular Weight

576.708

Monoisotopic Molecular Weight

576.342720285

IUPAC Name

[(2R)-3-(octanoyloxy)-2-{[(9Z)-11-(3-pentyloxiran-2-yl)undec-9-enoyl]oxy}propoxy]phosphonic acid

Traditional Name

(2R)-3-(octanoyloxy)-2-{[(9Z)-11-(3-pentyloxiran-2-yl)undec-9-enoyl]oxy}propoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](COC(=O)CCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/CC1OC1CCCCC

InChI Identifier

InChI=1S/C29H53O9P/c1-3-5-7-12-17-21-28(30)35-23-25(24-36-39(32,33)34)37-29(31)22-18-14-11-9-8-10-13-16-20-27-26(38-27)19-15-6-4-2/h13,16,25-27H,3-12,14-15,17-24H2,1-2H3,(H2,32,33,34)/b16-13-/t25-,26?,27?/m1/s1

InChI Key

BAOKIHSKOOWGLQ-NWUHCHHHSA-N

Chemical Taxonomy

Classification

Not classified

Ontology

Not Available

Not Available

Not Available

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	5.79	ALOGPS
logP	7.55	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	1.32	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	131.89 Å²	ChemAxon
Rotatable Bond Count	28	ChemAxon
Refractivity	151.6 m³·mol⁻¹	ChemAxon
Polarizability	66.42 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
AllCCS	[M+H]+	244.04	32859911
AllCCS	[M+H-H2O]+	243.094	32859911
AllCCS	[M+Na]+	245.122	32859911
AllCCS	[M+NH4]+	244.885	32859911
AllCCS	[M-H]-	233.32	32859911
AllCCS	[M+Na-2H]-	237.624	32859911
AllCCS	[M+HCOO]-	242.479	32859911
DeepCCS	[M+H]+	227.969	30932474
DeepCCS	[M-H]-	225.611	30932474
DeepCCS	[M-2H]-	258.495	30932474
DeepCCS	[M+Na]+	234.062	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
PA(8:0/18:1(9Z)-O(12,13))	[H][C@@](COC(=O)CCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/CC1OC1CCCCC	4039.4	Standard polar	33892256
PA(8:0/18:1(9Z)-O(12,13))	[H][C@@](COC(=O)CCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/CC1OC1CCCCC	3470.7	Standard non polar	33892256
PA(8:0/18:1(9Z)-O(12,13))	[H][C@@](COC(=O)CCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/CC1OC1CCCCC	4002.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
PA(8:0/18:1(9Z)-O(12,13)),1TMS,isomer #1	CCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CC1OC1CCCCC	4015.6	Semi standard non polar	33892256
PA(8:0/18:1(9Z)-O(12,13)),1TMS,isomer #1	CCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CC1OC1CCCCC	3676.0	Standard non polar	33892256
PA(8:0/18:1(9Z)-O(12,13)),1TMS,isomer #1	CCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CC1OC1CCCCC	5115.2	Standard polar	33892256
PA(8:0/18:1(9Z)-O(12,13)),2TMS,isomer #1	CCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CC1OC1CCCCC	4012.7	Semi standard non polar	33892256
PA(8:0/18:1(9Z)-O(12,13)),2TMS,isomer #1	CCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CC1OC1CCCCC	3689.5	Standard non polar	33892256
PA(8:0/18:1(9Z)-O(12,13)),2TMS,isomer #1	CCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CC1OC1CCCCC	4410.0	Standard polar	33892256
PA(8:0/18:1(9Z)-O(12,13)),1TBDMS,isomer #1	CCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCC/C=C\CC1OC1CCCCC	4256.6	Semi standard non polar	33892256
PA(8:0/18:1(9Z)-O(12,13)),1TBDMS,isomer #1	CCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCC/C=C\CC1OC1CCCCC	3814.5	Standard non polar	33892256
PA(8:0/18:1(9Z)-O(12,13)),1TBDMS,isomer #1	CCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCC/C=C\CC1OC1CCCCC	5123.6	Standard polar	33892256
PA(8:0/18:1(9Z)-O(12,13)),2TBDMS,isomer #1	CCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCC/C=C\CC1OC1CCCCC	4479.3	Semi standard non polar	33892256
PA(8:0/18:1(9Z)-O(12,13)),2TBDMS,isomer #1	CCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCC/C=C\CC1OC1CCCCC	3939.4	Standard non polar	33892256
PA(8:0/18:1(9Z)-O(12,13)),2TBDMS,isomer #1	CCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCC/C=C\CC1OC1CCCCC	4487.9	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PA(8:0/18:1(9Z)-O(12,13)) 10V, Positive-QTOF	splash10-0a6r-0000090000-7a46b8417074eeee5329	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PA(8:0/18:1(9Z)-O(12,13)) 20V, Positive-QTOF	splash10-004i-0000590000-dec1379bf86fe2341446	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PA(8:0/18:1(9Z)-O(12,13)) 40V, Positive-QTOF	splash10-003r-0030910000-ad93ee0ef5b86e3d5727	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PA(8:0/18:1(9Z)-O(12,13)) 10V, Negative-QTOF	splash10-004i-0000090000-548c11cea898bc47828e	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PA(8:0/18:1(9Z)-O(12,13)) 20V, Negative-QTOF	splash10-004i-0490440000-b116d4a2a6a55c07fa43	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PA(8:0/18:1(9Z)-O(12,13)) 40V, Negative-QTOF	splash10-002e-1970210000-42ea7f13edf83d2ee249	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PA(8:0/18:1(9Z)-O(12,13)) 10V, Positive-QTOF	splash10-0002-0000090000-0b2bf2564ce9e2ae5a7a	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PA(8:0/18:1(9Z)-O(12,13)) 20V, Positive-QTOF	splash10-0udk-0000090000-fcb9aaba29b06a77c015	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PA(8:0/18:1(9Z)-O(12,13)) 40V, Positive-QTOF	splash10-0zmj-0007890000-d9c11da1c8e6fbc9febd	2021-09-28	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

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

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

Not Available

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

Hajeyah AA, Griffiths WJ, Wang Y, Finch AJ, O'Donnell VB: The Biosynthesis of Enzymatically Oxidized Lipids. Front Endocrinol (Lausanne). 2020 Nov 19;11:591819. doi: 10.3389/fendo.2020.591819. eCollection 2020. [PubMed:33329396 ]

Only showing the first 10 proteins. There are 61 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Phospholipase D2

General function:: Involved in protein binding
Specific function:: May have a role in signal-induced cytoskeletal regulation and/or endocytosis (By similarity).
Gene Name:: PLD2
Uniprot ID:: O14939
Molecular weight:: 104656.485

Enzyme Details

2. Diacylglycerol kinase theta

General function:: Involved in diacylglycerol kinase activity
Specific function:: Phosphorylates diacylglycerol (DAG) to generate phosphatidic acid (PA). May regulate the activity of protein kinase C by controlling the balance between these two signaling lipids. Activated in the nucleus in response to alpha-thrombin and nerve growth factor. May be involved in cAMP- induced activation of NR5A1 and subsequent steroidogenic gene transcription by delivering PA as ligand for NR5A1. Acts synergistically with NR5A1 on CYP17 transcriptional activity
Gene Name:: DGKQ
Uniprot ID:: P52824
Molecular weight:: 101154.0

Enzyme Details

3. Diacylglycerol kinase gamma

General function:: Involved in diacylglycerol kinase activity
Specific function:: Reverses the normal flow of glycerolipid biosynthesis by phosphorylating diacylglycerol back to phosphatidic acid
Gene Name:: DGKG
Uniprot ID:: P49619
Molecular weight:: 89095.3

Enzyme Details

4. Lipid phosphate phosphohydrolase 2

General function:: Involved in catalytic activity
Specific function:: Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). In addition it hydrolyzes lysophosphatidic acid (LPA), ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is PA > C-1-P > LPA > S-1-P.
Gene Name:: PPAP2C
Uniprot ID:: O43688
Molecular weight:: 32573.435

Enzyme Details

5. Diacylglycerol kinase alpha

General function:: Involved in diacylglycerol kinase activity
Specific function:: Upon cell stimulation converts the second messenger diacylglycerol into phosphatidate, initiating the resynthesis of phosphatidylinositols and attenuating protein kinase C activity
Gene Name:: DGKA
Uniprot ID:: P23743
Molecular weight:: 82629.5

Enzyme Details

6. Diacylglycerol kinase delta

General function:: Involved in diacylglycerol kinase activity
Specific function:: Isoform 2 may be involved in cell growth and tumorigenesis. Involved in clathrin-dependent endocytosis
Gene Name:: DGKD
Uniprot ID:: Q16760
Molecular weight:: 134524.2

Enzyme Details

7. Lipid phosphate phosphohydrolase 1

General function:: Involved in catalytic activity
Specific function:: Broad-specificity phosphohydrolase that dephosphorylates exogenous bioactive glycerolipids and sphingolipids. Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). Pivotal regulator of lysophosphatidic acid (LPA) signaling in the cardiovascular system. Major enzyme responsible of dephosphorylating LPA in platelets, which terminates signaling actions of LPA. May control circulating, and possibly also regulate localized, LPA levels resulting from platelet activation. It has little activity towards ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is LPA > PA > S-1-P > C-1-P. It's down-regulation may contribute to the development of colon adenocarcinoma.
Gene Name:: PPAP2A
Uniprot ID:: O14494
Molecular weight:: 32155.715

Enzyme Details

8. Diacylglycerol kinase beta

General function:: Involved in diacylglycerol kinase activity
Specific function:: Exhibits high phosphorylation activity for long-chain diacylglycerols
Gene Name:: DGKB
Uniprot ID:: Q9Y6T7
Molecular weight:: 90594.7

Enzyme Details

9. Diacylglycerol kinase iota

General function:: Involved in diacylglycerol kinase activity
Specific function:: ATP + 1,2-diacylglycerol = ADP + 1,2-diacyl- sn-glycerol 3-phosphate
Gene Name:: DGKI
Uniprot ID:: O75912
Molecular weight:: 116996.2

Enzyme Details

10. Lipid phosphate phosphohydrolase 3

General function:: Involved in catalytic activity
Specific function:: Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). In addition it hydrolyzes lysophosphatidic acid (LPA), ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is LPA = PA > C-1-P > S-1-P. May be involved in cell adhesion and in cell-cell interactions.
Gene Name:: PPAP2B
Uniprot ID:: O14495
Molecular weight:: 35115.61

Only showing the first 10 proteins. There are 61 proteins in total.

Show all enzymes and transporters

Showing metabocard for PA(8:0/18:1(9Z)-O(12,13)) (HMDB0266645)

MOL for HMDB0266645 (PA(8:0/18:1(9Z)-O(12,13)))

3D MOL for HMDB0266645 (PA(8:0/18:1(9Z)-O(12,13)))

3D SDF for HMDB0266645 (PA(8:0/18:1(9Z)-O(12,13)))

3D-SDF for HMDB0266645 (PA(8:0/18:1(9Z)-O(12,13)))

PDB for HMDB0266645 (PA(8:0/18:1(9Z)-O(12,13)))

3D PDB for HMDB0266645 (PA(8:0/18:1(9Z)-O(12,13)))

SMILES for HMDB0266645 (PA(8:0/18:1(9Z)-O(12,13)))

INCHI for HMDB0266645 (PA(8:0/18:1(9Z)-O(12,13)))

Structure for HMDB0266645 (PA(8:0/18:1(9Z)-O(12,13)))

3D Structure for HMDB0266645 (PA(8:0/18:1(9Z)-O(12,13)))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

MS/MS Spectra

Enzymes