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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 08:57:37 UTC

Update Date

2022-11-30 19:55:38 UTC

HMDB ID

HMDB0264960

Secondary Accession Numbers

None

Metabolite Identification

Common Name

PA(PGJ2/20:3(5Z,8Z,11Z))

Description

PA(PGJ2/20:3(5Z,8Z,11Z)) 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(PGJ2/20:3(5Z,8Z,11Z)), in particular, consists of one chain of one Prostaglandin J2 at the C-1 position and one chain of 5Z,8Z,11Z-eicosatrienoyl 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


  Mrv1652309122110572D          

 54 54  0  0  1  0            999 V2000
    5.0293   -5.7373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0293   -4.9123    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.2043   -4.9123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8543   -4.9123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0293   -4.0873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3148   -3.6748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3148   -2.8498    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6004   -2.4373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8859   -2.8498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1714   -2.4373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1714   -1.6123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4569   -2.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7425   -2.4373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0280   -2.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0280   -3.6748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7425   -4.0873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4569   -3.6748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1714   -4.0873    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9251   -3.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4771   -4.3648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0646   -5.0793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4002   -5.8330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2576   -4.9078    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6446   -5.4598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8599   -5.2049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2468   -5.7569    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4184   -6.5639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5378   -5.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1509   -6.0540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9355   -5.7990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5486   -6.3511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3332   -6.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0293   -2.4373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7438   -2.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7438   -3.6748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4582   -2.4373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1727   -2.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8872   -2.4373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6016   -2.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3161   -2.4373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3161   -1.6123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0306   -1.1998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0306   -0.3748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3161    0.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3161    0.8627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6016    1.2752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8872    0.8627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1727    1.2752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4582    0.8627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4582    0.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7438   -0.3748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7438   -1.1998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0293   -1.6123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3148   -1.1998    0.0000 C   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
  2  4  2  0  0  0  0
  2  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
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 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  2  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
  7 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 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  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
M  END

HMDB0264960
     RDKit          3D
PA(PGJ2/20:3(5Z,8Z,11Z))
123123  0  0  0  0  0  0  0  0999 V2000
   14.2541   -2.4492   -0.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0008   -1.3180   -1.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4726    0.0633   -0.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1418    0.3119   -1.4676 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9735   -0.3932   -0.8918 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7855   -0.0101    0.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5254    1.4779    0.6312 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3156    1.9360    2.0736 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1931    1.3159    2.7426 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1380    1.9249    3.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9485    3.3425    3.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8299    3.9737    2.5042 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8886    3.4011    1.8257 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7341    1.9619    1.5943 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4324    1.4703    2.1799 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5085    0.8764    1.4615 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6106    0.6064    0.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5121   -0.8860   -0.2699 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2219   -1.5125    0.1136 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0687   -0.9955   -0.6656 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.1786   -1.6393 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7458   -1.3244   -0.4389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2914   -0.7599   -1.2760 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1918    0.0944   -0.4244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1612    0.8165   -1.0210 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2900    0.5525   -1.7142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6102   -0.6385   -1.8977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1527    1.6416   -2.2625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2767    1.2271   -3.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3195    0.3303   -2.4923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9621    0.9039   -1.3101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9516    0.3296   -0.1327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3226   -0.9560    0.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3562   -1.9469    0.7480 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.6757   -3.2452    1.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0867   -3.6854    2.2693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0585   -2.7512    2.7980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8569   -2.9293    3.7278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9611   -1.4627    2.0187 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.2578   -0.7973    1.9224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9517   -0.5750    0.8361 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2954    0.1363    0.9099 C   0  0  1  0  0  0  0  0  0  0  0  0
  -11.4917    0.6703    2.1833 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2734    1.2589   -0.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4200    2.1458   -0.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.7345    1.6761   -0.6366 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.4887    0.6774    0.1620 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.8436    0.5069   -0.5958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9506   -1.8711   -2.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5793   -2.8037   -1.2344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2622   -3.9931   -2.2300 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.7939   -5.3279   -1.6677 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9377   -3.8850   -2.2780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6827   -3.8427   -3.8133 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6024   -2.2705    0.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6751   -3.0170   -1.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.9941   -3.2416   -0.0634 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.2068   -1.5200   -2.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.0299   -1.3063   -0.5326 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.1715    0.8274   -1.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.4821    0.3115    0.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9437    1.4212   -1.4568 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2613    0.0344   -2.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9293   -1.4786   -1.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0511    0.0519   -1.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6696   -0.2980    1.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8909   -0.5859    0.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3891    2.0744    0.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6702    1.7079   -0.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4100    3.0130    2.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2625    1.5674    2.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2080    0.2185    2.8501 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3593    1.3152    3.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0249    3.7948    4.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8820    3.8283    2.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7766    5.1206    2.5656 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1168    4.1000    1.3753 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5379    1.2864    1.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5861    1.9176    0.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2512    1.6149    3.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5959    0.5650    2.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6736    1.0586   -0.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4209    1.0732   -0.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6342   -1.0615   -1.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3446   -1.4461    0.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3031   -2.6030   -0.1446 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0293   -1.5070    1.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2110   -0.1145   -2.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4944    0.8389    0.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5746   -0.5289    0.4561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5116    2.3484   -2.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5418    2.2898   -1.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7829    2.1309   -3.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8455    0.7233   -4.0228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9866   -0.6831   -2.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1425    0.2851   -3.2808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4797    1.8769   -1.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4785    0.8907    0.6877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8589   -1.4220   -0.6291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5541   -0.7684    1.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0590   -2.1423   -0.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9578   -3.7197    0.4711 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309122110572D          

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    5.0293   -1.6123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3148   -1.1998    0.0000 C   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
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 18 23  1  0  0  0  0
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  7 33  1  1  0  0  0
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 53 54  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0264960

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCC\C=C/C\C=C/C\C=C/CCCC(=O)O[C@H](COC(=O)CCC\C=C/C[C@H]1C=CC(=O)[C@@H]1\C=C\[C@@H](O)CCCCC)COP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C43H69O10P/c1-3-5-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26-30-43(47)53-39(36-52-54(48,49)50)35-51-42(46)29-25-22-21-24-27-37-31-34-41(45)40(37)33-32-38(44)28-23-6-4-2/h12-13,15-16,18-19,21,24,31-34,37-40,44H,3-11,14,17,20,22-23,25-30,35-36H2,1-2H3,(H2,48,49,50)/b13-12-,16-15-,19-18-,24-21-,33-32+/t37-,38-,39+,40+/m0/s1

> <INCHI_KEY>
PUGSHPDTAYCMPW-KESJWDQISA-N

> <FORMULA>
C43H69O10P

> <MOLECULAR_WEIGHT>
776.989

> <EXACT_MASS>
776.46283542

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
123

> <JCHEM_AVERAGE_POLARIZABILITY>
89.71633003984773

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R)-3-{[(5Z)-7-[(1S,5R)-5-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-4-oxocyclopent-2-en-1-yl]hept-5-enoyl]oxy}-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]propoxy]phosphonic acid

> <ALOGPS_LOGP>
7.33

> <JCHEM_LOGP>
10.691405626666668

> <ALOGPS_LOGS>
-6.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.343234650586371

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.3179343438779263

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5977836657948066

> <JCHEM_POLAR_SURFACE_AREA>
156.65999999999997

> <JCHEM_REFRACTIVITY>
222.33190000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
35

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.19e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-3-{[(5Z)-7-[(1S,5R)-5-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-4-oxocyclopent-2-en-1-yl]hept-5-enoyl]oxy}-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]propoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0264960
     RDKit          3D
PA(PGJ2/20:3(5Z,8Z,11Z))
123123  0  0  0  0  0  0  0  0999 V2000
   14.2541   -2.4492   -0.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0008   -1.3180   -1.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4726    0.0633   -0.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1418    0.3119   -1.4676 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9735   -0.3932   -0.8918 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7855   -0.0101    0.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5254    1.4779    0.6312 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3156    1.9360    2.0736 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1931    1.3159    2.7426 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1380    1.9249    3.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9485    3.3425    3.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8299    3.9737    2.5042 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8886    3.4011    1.8257 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7341    1.9619    1.5943 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4324    1.4703    2.1799 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5085    0.8764    1.4615 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6106    0.6064    0.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5121   -0.8860   -0.2699 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2219   -1.5125    0.1136 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0687   -0.9955   -0.6656 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7458   -1.3244   -0.4389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2914   -0.7599   -1.2760 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1918    0.0944   -0.4244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1612    0.8165   -1.0210 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6102   -0.6385   -1.8977 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.2767    1.2271   -3.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3195    0.3303   -2.4923 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.3226   -0.9560    0.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3562   -1.9469    0.7480 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.6757   -3.2452    1.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0867   -3.6854    2.2693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0585   -2.7512    2.7980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8569   -2.9293    3.7278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9611   -1.4627    2.0187 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.2578   -0.7973    1.9224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9517   -0.5750    0.8361 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2954    0.1363    0.9099 C   0  0  1  0  0  0  0  0  0  0  0  0
  -11.4917    0.6703    2.1833 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2734    1.2589   -0.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4200    2.1458   -0.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.7345    1.6761   -0.6366 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.4887    0.6774    0.1620 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.8436    0.5069   -0.5958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9506   -1.8711   -2.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5793   -2.8037   -1.2344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2622   -3.9931   -2.2300 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.7939   -5.3279   -1.6677 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9377   -3.8850   -2.2780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6827   -3.8427   -3.8133 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6024   -2.2705    0.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6751   -3.0170   -1.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.9941   -3.2416   -0.0634 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.2068   -1.5200   -2.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.0299   -1.3063   -0.5326 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.1715    0.8274   -1.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.4821    0.3115    0.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9437    1.4212   -1.4568 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2613    0.0344   -2.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9293   -1.4786   -1.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0511    0.0519   -1.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6696   -0.2980    1.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8909   -0.5859    0.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3891    2.0744    0.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6702    1.7079   -0.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4100    3.0130    2.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2625    1.5674    2.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2080    0.2185    2.8501 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3593    1.3152    3.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0249    3.7948    4.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8820    3.8283    2.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7766    5.1206    2.5656 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1168    4.1000    1.3753 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5379    1.2864    1.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5861    1.9176    0.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2512    1.6149    3.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5959    0.5650    2.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6736    1.0586   -0.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4209    1.0732   -0.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6342   -1.0615   -1.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3446   -1.4461    0.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3031   -2.6030   -0.1446 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0293   -1.5070    1.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2110   -0.1145   -2.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4944    0.8389    0.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5746   -0.5289    0.4561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5116    2.3484   -2.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5418    2.2898   -1.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7829    2.1309   -3.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8455    0.7233   -4.0228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9866   -0.6831   -2.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1425    0.2851   -3.2808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4797    1.8769   -1.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4785    0.8907    0.6877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8589   -1.4220   -0.6291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5541   -0.7684    1.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0590   -2.1423   -0.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9578   -3.7197    0.4711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7480   -4.6147    2.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2029   -0.8362    2.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7154   -0.4399    2.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5928   -0.8819   -0.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0164   -0.6609    0.6980 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8955    1.4569    2.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9410    0.8952   -1.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3806    1.9053    0.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1253    2.9777   -0.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4972    2.7568    0.7697 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.6365    1.2293   -1.6901 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.4476    2.5594   -0.7846 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.7160    1.0671    1.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0825   -0.3502    0.1539 H   0  0  0  0  0  0  0  0  0  0  0  0
  -16.5212   -0.0149    0.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
  -16.1735    1.5358   -0.8149 H   0  0  0  0  0  0  0  0  0  0  0  0
  -15.6244   -0.1044   -1.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0451   -2.4762   -2.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4904   -1.6228   -2.9293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3216   -3.3488   -1.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2210   -4.6965   -4.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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M  END

HEADER    PROTEIN                                 12-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-21         0                                  
HETATM    1  O   UNK     0       9.388 -10.710   0.000  0.00  0.00           O+0
HETATM    2  P   UNK     0       9.388  -9.170   0.000  0.00  0.00           P+0
HETATM    3  O   UNK     0       7.848  -9.170   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      10.928  -9.170   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       9.388  -7.630   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.054  -6.860   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.054  -5.320   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.721  -4.550   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.387  -5.320   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.053  -4.550   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.053  -3.010   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.720  -5.320   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.386  -4.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.052  -5.320   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.052  -6.860   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.386  -7.630   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.720  -6.860   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.053  -7.630   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.460  -7.003   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.491  -8.148   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.721  -9.481   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.347 -10.888   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.214  -9.161   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.070 -10.192   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.605  -9.716   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.461 -10.746   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.781 -12.253   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.004 -10.270   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.148 -11.301   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -3.613 -10.825   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -4.757 -11.855   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -6.222 -11.379   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       9.388  -4.550   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      10.722  -5.320   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      10.722  -6.860   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      12.055  -4.550   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      13.389  -5.320   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      14.723  -4.550   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      16.056  -5.320   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      17.390  -4.550   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      17.390  -3.010   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      18.724  -2.240   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      18.724  -0.700   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      17.390   0.070   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      17.390   1.610   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      16.056   2.380   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      14.723   1.610   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      13.389   2.380   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      12.055   1.610   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      12.055   0.070   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      10.722  -0.700   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      10.722  -2.240   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       9.388  -3.010   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       8.054  -2.240   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   33                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   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   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   18   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33    7   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  108    0
END

COMPND    HMDB0264960
HETATM    1  C1  UNL     1      14.254  -2.449  -0.450  1.00  0.00           C  
HETATM    2  C2  UNL     1      15.001  -1.318  -1.023  1.00  0.00           C  
HETATM    3  C3  UNL     1      14.473   0.063  -0.868  1.00  0.00           C  
HETATM    4  C4  UNL     1      13.142   0.312  -1.468  1.00  0.00           C  
HETATM    5  C5  UNL     1      11.973  -0.393  -0.892  1.00  0.00           C  
HETATM    6  C6  UNL     1      11.785  -0.010   0.556  1.00  0.00           C  
HETATM    7  C7  UNL     1      11.525   1.478   0.631  1.00  0.00           C  
HETATM    8  C8  UNL     1      11.316   1.936   2.074  1.00  0.00           C  
HETATM    9  C9  UNL     1      10.193   1.316   2.743  1.00  0.00           C  
HETATM   10  C10 UNL     1       9.138   1.925   3.246  1.00  0.00           C  
HETATM   11  C11 UNL     1       8.948   3.343   3.197  1.00  0.00           C  
HETATM   12  C12 UNL     1       7.830   3.974   2.504  1.00  0.00           C  
HETATM   13  C13 UNL     1       6.889   3.401   1.826  1.00  0.00           C  
HETATM   14  C14 UNL     1       6.734   1.962   1.594  1.00  0.00           C  
HETATM   15  C15 UNL     1       5.432   1.470   2.180  1.00  0.00           C  
HETATM   16  C16 UNL     1       4.508   0.876   1.462  1.00  0.00           C  
HETATM   17  C17 UNL     1       4.611   0.606   0.010  1.00  0.00           C  
HETATM   18  C18 UNL     1       4.512  -0.886  -0.270  1.00  0.00           C  
HETATM   19  C19 UNL     1       3.222  -1.513   0.114  1.00  0.00           C  
HETATM   20  C20 UNL     1       2.069  -0.996  -0.666  1.00  0.00           C  
HETATM   21  O1  UNL     1       2.254  -0.179  -1.639  1.00  0.00           O  
HETATM   22  O2  UNL     1       0.746  -1.324  -0.439  1.00  0.00           O  
HETATM   23  C21 UNL     1      -0.291  -0.760  -1.276  1.00  0.00           C  
HETATM   24  C22 UNL     1      -1.192   0.094  -0.424  1.00  0.00           C  
HETATM   25  O3  UNL     1      -2.161   0.816  -1.021  1.00  0.00           O  
HETATM   26  C23 UNL     1      -3.290   0.553  -1.714  1.00  0.00           C  
HETATM   27  O4  UNL     1      -3.610  -0.638  -1.898  1.00  0.00           O  
HETATM   28  C24 UNL     1      -4.153   1.642  -2.263  1.00  0.00           C  
HETATM   29  C25 UNL     1      -5.277   1.227  -3.103  1.00  0.00           C  
HETATM   30  C26 UNL     1      -6.320   0.330  -2.492  1.00  0.00           C  
HETATM   31  C27 UNL     1      -6.962   0.904  -1.310  1.00  0.00           C  
HETATM   32  C28 UNL     1      -6.952   0.330  -0.133  1.00  0.00           C  
HETATM   33  C29 UNL     1      -6.323  -0.956   0.231  1.00  0.00           C  
HETATM   34  C30 UNL     1      -7.356  -1.947   0.748  1.00  0.00           C  
HETATM   35  C31 UNL     1      -6.676  -3.245   1.104  1.00  0.00           C  
HETATM   36  C32 UNL     1      -7.087  -3.685   2.269  1.00  0.00           C  
HETATM   37  C33 UNL     1      -8.058  -2.751   2.798  1.00  0.00           C  
HETATM   38  O5  UNL     1      -8.857  -2.929   3.728  1.00  0.00           O  
HETATM   39  C34 UNL     1      -7.961  -1.463   2.019  1.00  0.00           C  
HETATM   40  C35 UNL     1      -9.258  -0.797   1.922  1.00  0.00           C  
HETATM   41  C36 UNL     1      -9.952  -0.575   0.836  1.00  0.00           C  
HETATM   42  C37 UNL     1     -11.295   0.136   0.910  1.00  0.00           C  
HETATM   43  O6  UNL     1     -11.492   0.670   2.183  1.00  0.00           O  
HETATM   44  C38 UNL     1     -11.273   1.259  -0.072  1.00  0.00           C  
HETATM   45  C39 UNL     1     -12.420   2.146  -0.205  1.00  0.00           C  
HETATM   46  C40 UNL     1     -13.735   1.676  -0.637  1.00  0.00           C  
HETATM   47  C41 UNL     1     -14.489   0.677   0.162  1.00  0.00           C  
HETATM   48  C42 UNL     1     -15.844   0.507  -0.596  1.00  0.00           C  
HETATM   49  C43 UNL     1      -0.951  -1.871  -2.027  1.00  0.00           C  
HETATM   50  O7  UNL     1      -1.579  -2.804  -1.234  1.00  0.00           O  
HETATM   51  P1  UNL     1      -2.262  -3.993  -2.230  1.00  0.00           P  
HETATM   52  O8  UNL     1      -1.794  -5.328  -1.668  1.00  0.00           O  
HETATM   53  O9  UNL     1      -3.938  -3.885  -2.278  1.00  0.00           O  
HETATM   54  O10 UNL     1      -1.683  -3.843  -3.813  1.00  0.00           O  
HETATM   55  H1  UNL     1      13.602  -2.270   0.401  1.00  0.00           H  
HETATM   56  H2  UNL     1      13.675  -3.017  -1.238  1.00  0.00           H  
HETATM   57  H3  UNL     1      14.994  -3.242  -0.063  1.00  0.00           H  
HETATM   58  H4  UNL     1      15.207  -1.520  -2.117  1.00  0.00           H  
HETATM   59  H5  UNL     1      16.030  -1.306  -0.533  1.00  0.00           H  
HETATM   60  H6  UNL     1      15.171   0.827  -1.303  1.00  0.00           H  
HETATM   61  H7  UNL     1      14.482   0.311   0.240  1.00  0.00           H  
HETATM   62  H8  UNL     1      12.944   1.421  -1.457  1.00  0.00           H  
HETATM   63  H9  UNL     1      13.261   0.034  -2.575  1.00  0.00           H  
HETATM   64  H10 UNL     1      11.929  -1.479  -1.027  1.00  0.00           H  
HETATM   65  H11 UNL     1      11.051   0.052  -1.411  1.00  0.00           H  
HETATM   66  H12 UNL     1      12.670  -0.298   1.145  1.00  0.00           H  
HETATM   67  H13 UNL     1      10.891  -0.586   0.920  1.00  0.00           H  
HETATM   68  H14 UNL     1      12.389   2.074   0.277  1.00  0.00           H  
HETATM   69  H15 UNL     1      10.670   1.708  -0.021  1.00  0.00           H  
HETATM   70  H16 UNL     1      11.410   3.013   2.061  1.00  0.00           H  
HETATM   71  H17 UNL     1      12.262   1.567   2.598  1.00  0.00           H  
HETATM   72  H18 UNL     1      10.208   0.219   2.850  1.00  0.00           H  
HETATM   73  H19 UNL     1       8.359   1.315   3.781  1.00  0.00           H  
HETATM   74  H20 UNL     1       9.025   3.795   4.267  1.00  0.00           H  
HETATM   75  H21 UNL     1       9.882   3.828   2.745  1.00  0.00           H  
HETATM   76  H22 UNL     1       7.777   5.121   2.566  1.00  0.00           H  
HETATM   77  H23 UNL     1       6.117   4.100   1.375  1.00  0.00           H  
HETATM   78  H24 UNL     1       7.538   1.286   1.745  1.00  0.00           H  
HETATM   79  H25 UNL     1       6.586   1.918   0.441  1.00  0.00           H  
HETATM   80  H26 UNL     1       5.251   1.615   3.250  1.00  0.00           H  
HETATM   81  H27 UNL     1       3.596   0.565   2.005  1.00  0.00           H  
HETATM   82  H28 UNL     1       3.674   1.059  -0.463  1.00  0.00           H  
HETATM   83  H29 UNL     1       5.421   1.073  -0.539  1.00  0.00           H  
HETATM   84  H30 UNL     1       4.634  -1.061  -1.382  1.00  0.00           H  
HETATM   85  H31 UNL     1       5.345  -1.446   0.196  1.00  0.00           H  
HETATM   86  H32 UNL     1       3.303  -2.603  -0.145  1.00  0.00           H  
HETATM   87  H33 UNL     1       3.029  -1.507   1.208  1.00  0.00           H  
HETATM   88  H34 UNL     1       0.211  -0.115  -2.004  1.00  0.00           H  
HETATM   89  H35 UNL     1      -0.494   0.839   0.108  1.00  0.00           H  
HETATM   90  H36 UNL     1      -1.575  -0.529   0.456  1.00  0.00           H  
HETATM   91  H37 UNL     1      -3.512   2.348  -2.865  1.00  0.00           H  
HETATM   92  H38 UNL     1      -4.542   2.290  -1.431  1.00  0.00           H  
HETATM   93  H39 UNL     1      -5.783   2.131  -3.511  1.00  0.00           H  
HETATM   94  H40 UNL     1      -4.846   0.723  -4.023  1.00  0.00           H  
HETATM   95  H41 UNL     1      -5.987  -0.683  -2.326  1.00  0.00           H  
HETATM   96  H42 UNL     1      -7.142   0.285  -3.281  1.00  0.00           H  
HETATM   97  H43 UNL     1      -7.480   1.877  -1.437  1.00  0.00           H  
HETATM   98  H44 UNL     1      -7.478   0.891   0.688  1.00  0.00           H  
HETATM   99  H45 UNL     1      -5.859  -1.422  -0.629  1.00  0.00           H  
HETATM  100  H46 UNL     1      -5.554  -0.768   1.042  1.00  0.00           H  
HETATM  101  H47 UNL     1      -8.059  -2.142  -0.074  1.00  0.00           H  
HETATM  102  H48 UNL     1      -5.958  -3.720   0.471  1.00  0.00           H  
HETATM  103  H49 UNL     1      -6.748  -4.615   2.757  1.00  0.00           H  
HETATM  104  H50 UNL     1      -7.203  -0.836   2.573  1.00  0.00           H  
HETATM  105  H51 UNL     1      -9.715  -0.440   2.862  1.00  0.00           H  
HETATM  106  H52 UNL     1      -9.593  -0.882  -0.117  1.00  0.00           H  
HETATM  107  H53 UNL     1     -12.016  -0.661   0.698  1.00  0.00           H  
HETATM  108  H54 UNL     1     -10.895   1.457   2.274  1.00  0.00           H  
HETATM  109  H55 UNL     1     -10.941   0.895  -1.094  1.00  0.00           H  
HETATM  110  H56 UNL     1     -10.381   1.905   0.235  1.00  0.00           H  
HETATM  111  H57 UNL     1     -12.125   2.978  -0.938  1.00  0.00           H  
HETATM  112  H58 UNL     1     -12.497   2.757   0.770  1.00  0.00           H  
HETATM  113  H59 UNL     1     -13.637   1.229  -1.690  1.00  0.00           H  
HETATM  114  H60 UNL     1     -14.448   2.559  -0.785  1.00  0.00           H  
HETATM  115  H61 UNL     1     -14.716   1.067   1.173  1.00  0.00           H  
HETATM  116  H62 UNL     1     -14.083  -0.350   0.154  1.00  0.00           H  
HETATM  117  H63 UNL     1     -16.521  -0.015   0.091  1.00  0.00           H  
HETATM  118  H64 UNL     1     -16.174   1.536  -0.815  1.00  0.00           H  
HETATM  119  H65 UNL     1     -15.624  -0.104  -1.481  1.00  0.00           H  
HETATM  120  H66 UNL     1      -0.045  -2.476  -2.449  1.00  0.00           H  
HETATM  121  H67 UNL     1      -1.490  -1.623  -2.929  1.00  0.00           H  
HETATM  122  H68 UNL     1      -4.322  -3.349  -1.539  1.00  0.00           H  
HETATM  123  H69 UNL     1      -1.221  -4.696  -4.090  1.00  0.00           H  
CONECT    1    2   55   56   57
CONECT    2    3   58   59
CONECT    3    4   60   61
CONECT    4    5   62   63
CONECT    5    6   64   65
CONECT    6    7   66   67
CONECT    7    8   68   69
CONECT    8    9   70   71
CONECT    9   10   10   72
CONECT   10   11   73
CONECT   11   12   74   75
CONECT   12   13   13   76
CONECT   13   14   77
CONECT   14   15   78   79
CONECT   15   16   16   80
CONECT   16   17   81
CONECT   17   18   82   83
CONECT   18   19   84   85
CONECT   19   20   86   87
CONECT   20   21   21   22
CONECT   22   23
CONECT   23   24   49   88
CONECT   24   25   89   90
CONECT   25   26
CONECT   26   27   27   28
CONECT   28   29   91   92
CONECT   29   30   93   94
CONECT   30   31   95   96
CONECT   31   32   32   97
CONECT   32   33   98
CONECT   33   34   99  100
CONECT   34   35   39  101
CONECT   35   36   36  102
CONECT   36   37  103
CONECT   37   38   38   39
CONECT   39   40  104
CONECT   40   41   41  105
CONECT   41   42  106
CONECT   42   43   44  107
CONECT   43  108
CONECT   44   45  109  110
CONECT   45   46  111  112
CONECT   46   47  113  114
CONECT   47   48  115  116
CONECT   48  117  118  119
CONECT   49   50  120  121
CONECT   50   51
CONECT   51   52   52   53   54
CONECT   53  122
CONECT   54  123
END

HMDB0264960
     RDKit          3D
PA(PGJ2/20:3(5Z,8Z,11Z))
123123  0  0  0  0  0  0  0  0999 V2000
   14.2541   -2.4492   -0.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0008   -1.3180   -1.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4726    0.0633   -0.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1418    0.3119   -1.4676 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9735   -0.3932   -0.8918 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7855   -0.0101    0.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5254    1.4779    0.6312 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3156    1.9360    2.0736 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1931    1.3159    2.7426 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1380    1.9249    3.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9485    3.3425    3.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8299    3.9737    2.5042 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8886    3.4011    1.8257 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7341    1.9619    1.5943 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4324    1.4703    2.1799 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5085    0.8764    1.4615 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6106    0.6064    0.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5121   -0.8860   -0.2699 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2219   -1.5125    0.1136 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0687   -0.9955   -0.6656 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.1786   -1.6393 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7458   -1.3244   -0.4389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2914   -0.7599   -1.2760 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1918    0.0944   -0.4244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1612    0.8165   -1.0210 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2900    0.5525   -1.7142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6102   -0.6385   -1.8977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1527    1.6416   -2.2625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2767    1.2271   -3.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3195    0.3303   -2.4923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9621    0.9039   -1.3101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9516    0.3296   -0.1327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3226   -0.9560    0.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3562   -1.9469    0.7480 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.6757   -3.2452    1.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0867   -3.6854    2.2693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0585   -2.7512    2.7980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8569   -2.9293    3.7278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9611   -1.4627    2.0187 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.2578   -0.7973    1.9224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9517   -0.5750    0.8361 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2954    0.1363    0.9099 C   0  0  1  0  0  0  0  0  0  0  0  0
  -11.4917    0.6703    2.1833 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2734    1.2589   -0.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4200    2.1458   -0.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.7345    1.6761   -0.6366 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.4887    0.6774    0.1620 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.8436    0.5069   -0.5958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9506   -1.8711   -2.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5793   -2.8037   -1.2344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2622   -3.9931   -2.2300 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.7939   -5.3279   -1.6677 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9377   -3.8850   -2.2780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6827   -3.8427   -3.8133 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6024   -2.2705    0.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6751   -3.0170   -1.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.9941   -3.2416   -0.0634 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.2068   -1.5200   -2.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.0299   -1.3063   -0.5326 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.1715    0.8274   -1.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.4821    0.3115    0.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9437    1.4212   -1.4568 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2613    0.0344   -2.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9293   -1.4786   -1.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0511    0.0519   -1.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6696   -0.2980    1.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8909   -0.5859    0.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3891    2.0744    0.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6702    1.7079   -0.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4100    3.0130    2.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2625    1.5674    2.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2080    0.2185    2.8501 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3593    1.3152    3.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0249    3.7948    4.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8820    3.8283    2.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7766    5.1206    2.5656 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1168    4.1000    1.3753 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5379    1.2864    1.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5861    1.9176    0.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2512    1.6149    3.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5959    0.5650    2.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6736    1.0586   -0.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4209    1.0732   -0.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6342   -1.0615   -1.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3446   -1.4461    0.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3031   -2.6030   -0.1446 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0293   -1.5070    1.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2110   -0.1145   -2.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4944    0.8389    0.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5746   -0.5289    0.4561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5116    2.3484   -2.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5418    2.2898   -1.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7829    2.1309   -3.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8455    0.7233   -4.0228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9866   -0.6831   -2.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1425    0.2851   -3.2808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4797    1.8769   -1.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4785    0.8907    0.6877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8589   -1.4220   -0.6291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5541   -0.7684    1.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0590   -2.1423   -0.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9578   -3.7197    0.4711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7480   -4.6147    2.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2029   -0.8362    2.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7154   -0.4399    2.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5928   -0.8819   -0.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0164   -0.6609    0.6980 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8955    1.4569    2.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9410    0.8952   -1.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3806    1.9053    0.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1253    2.9777   -0.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4972    2.7568    0.7697 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.6365    1.2293   -1.6901 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.4476    2.5594   -0.7846 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.7160    1.0671    1.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0825   -0.3502    0.1539 H   0  0  0  0  0  0  0  0  0  0  0  0
  -16.5212   -0.0149    0.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
  -16.1735    1.5358   -0.8149 H   0  0  0  0  0  0  0  0  0  0  0  0
  -15.6244   -0.1044   -1.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0451   -2.4762   -2.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4904   -1.6228   -2.9293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3216   -3.3488   -1.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2210   -4.6965   -4.0901 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
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 48119  1  0
 49120  1  0
 49121  1  0
 53122  1  0
 54123  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
[(2R)-3-{[(5Z)-7-[(1S,5R)-5-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-4-oxocyclopent-2-en-1-yl]hept-5-enoyl]oxy}-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]propoxy]phosphonate	HMDB

Chemical Formula

C₄₃H₆₉O₁₀P

Average Molecular Weight

776.989

Monoisotopic Molecular Weight

776.46283542

IUPAC Name

[(2R)-3-{[(5Z)-7-[(1S,5R)-5-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-4-oxocyclopent-2-en-1-yl]hept-5-enoyl]oxy}-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]propoxy]phosphonic acid

Traditional Name

(2R)-3-{[(5Z)-7-[(1S,5R)-5-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-4-oxocyclopent-2-en-1-yl]hept-5-enoyl]oxy}-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]propoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCC\C=C/C\C=C/C\C=C/CCCC(=O)O[C@H](COC(=O)CCC\C=C/C[C@H]1C=CC(=O)[C@@H]1\C=C\[C@@H](O)CCCCC)COP(O)(O)=O

InChI Identifier

InChI=1S/C43H69O10P/c1-3-5-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26-30-43(47)53-39(36-52-54(48,49)50)35-51-42(46)29-25-22-21-24-27-37-31-34-41(45)40(37)33-32-38(44)28-23-6-4-2/h12-13,15-16,18-19,21,24,31-34,37-40,44H,3-11,14,17,20,22-23,25-30,35-36H2,1-2H3,(H2,48,49,50)/b13-12-,16-15-,19-18-,24-21-,33-32+/t37-,38-,39+,40+/m0/s1

InChI Key

PUGSHPDTAYCMPW-KESJWDQISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Prostaglandins and related compounds

Alternative Parents

Substituents

Prostaglandin skeleton
1,2-diacylglycerol-3-phosphate
Glycerophospholipid
Sn-glycerol-3-phosphate
Monoalkyl phosphate
Fatty acid ester
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Dicarboxylic acid or derivatives
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Endogenous (HMDB: HMDB0264960)

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	7.33	ALOGPS
logP	10.69	ChemAxon
logS	-6.8	ALOGPS
pKa (Strongest Acidic)	1.32	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	156.66 Å²	ChemAxon
Rotatable Bond Count	35	ChemAxon
Refractivity	222.33 m³·mol⁻¹	ChemAxon
Polarizability	89.72 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]+	280.443	32859911
AllCCS	[M+H-H2O]+	280.356	32859911
AllCCS	[M+Na]+	280.493	32859911
AllCCS	[M+NH4]+	280.487	32859911
AllCCS	[M-H]-	271.825	32859911
AllCCS	[M+Na-2H]-	278.661	32859911
AllCCS	[M+HCOO]-	286.185	32859911
DeepCCS	[M+H]+	280.466	30932474
DeepCCS	[M-H]-	278.641	30932474
DeepCCS	[M-2H]-	312.438	30932474
DeepCCS	[M+Na]+	286.214	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	8.58 minutes	32390414
Predicted by Siyang on May 30, 2022	27.2377 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.01 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	4970.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	224.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	308.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	209.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	880.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1519.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	900.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	288.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	3009.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	1064.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2457.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	1040.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	667.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	233.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	500.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	10.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
PA(PGJ2/20:3(5Z,8Z,11Z))	CCCCCCCC\C=C/C\C=C/C\C=C/CCCC(=O)O[C@H](COC(=O)CCC\C=C/C[C@H]1C=CC(=O)[C@@H]1\C=C\[C@@H](O)CCCCC)COP(O)(O)=O	5864.7	Standard polar	33892256
PA(PGJ2/20:3(5Z,8Z,11Z))	CCCCCCCC\C=C/C\C=C/C\C=C/CCCC(=O)O[C@H](COC(=O)CCC\C=C/C[C@H]1C=CC(=O)[C@@H]1\C=C\[C@@H](O)CCCCC)COP(O)(O)=O	4688.0	Standard non polar	33892256
PA(PGJ2/20:3(5Z,8Z,11Z))	CCCCCCCC\C=C/C\C=C/C\C=C/CCCC(=O)O[C@H](COC(=O)CCC\C=C/C[C@H]1C=CC(=O)[C@@H]1\C=C\[C@@H](O)CCCCC)COP(O)(O)=O	5656.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - PA(PGJ2/20:3(5Z,8Z,11Z)) GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PA(PGJ2/20:3(5Z,8Z,11Z)) GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PA(PGJ2/20:3(5Z,8Z,11Z)) GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PA(PGJ2/20:3(5Z,8Z,11Z)) GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PA(PGJ2/20:3(5Z,8Z,11Z)) GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PA(PGJ2/20:3(5Z,8Z,11Z)) GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	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 - PA(PGJ2/20:3(5Z,8Z,11Z)) 10V, Positive-QTOF	splash10-0a6r-0000000900-10d76f9b8fa69e1b65e9	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PA(PGJ2/20:3(5Z,8Z,11Z)) 20V, Positive-QTOF	splash10-004i-0000005900-2c30ccee18d27333aaa0	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PA(PGJ2/20:3(5Z,8Z,11Z)) 40V, Positive-QTOF	splash10-00bc-0000906200-82104cbb4b12c0a26827	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PA(PGJ2/20:3(5Z,8Z,11Z)) 10V, Positive-QTOF	splash10-0002-0000000900-89dac90664ae901c8431	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PA(PGJ2/20:3(5Z,8Z,11Z)) 20V, Positive-QTOF	splash10-0udk-0000000900-c33dab7fe21b9273f57a	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PA(PGJ2/20:3(5Z,8Z,11Z)) 40V, Positive-QTOF	splash10-0hgn-0000920600-2c375f9a85c0bc9d1425	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PA(PGJ2/20:3(5Z,8Z,11Z)) 10V, Negative-QTOF	splash10-004i-0000000900-27171473b664437a63d0	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PA(PGJ2/20:3(5Z,8Z,11Z)) 20V, Negative-QTOF	splash10-05ru-0006900400-25b6daecc4de1a936952	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PA(PGJ2/20:3(5Z,8Z,11Z)) 40V, Negative-QTOF	splash10-053r-0009300000-24e877790185b09e7908	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

156968312

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.

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Showing metabocard for PA(PGJ2/20:3(5Z,8Z,11Z)) (HMDB0264960)

MOL for HMDB0264960 (PA(PGJ2/20:3(5Z,8Z,11Z)))

3D MOL for HMDB0264960 (PA(PGJ2/20:3(5Z,8Z,11Z)))

3D SDF for HMDB0264960 (PA(PGJ2/20:3(5Z,8Z,11Z)))

3D-SDF for HMDB0264960 (PA(PGJ2/20:3(5Z,8Z,11Z)))

PDB for HMDB0264960 (PA(PGJ2/20:3(5Z,8Z,11Z)))

3D PDB for HMDB0264960 (PA(PGJ2/20:3(5Z,8Z,11Z)))

SMILES for HMDB0264960 (PA(PGJ2/20:3(5Z,8Z,11Z)))

INCHI for HMDB0264960 (PA(PGJ2/20:3(5Z,8Z,11Z)))

Structure for HMDB0264960 (PA(PGJ2/20:3(5Z,8Z,11Z)))

3D Structure for HMDB0264960 (PA(PGJ2/20:3(5Z,8Z,11Z)))

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes