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Record Information

Version

5.0

Status

Predicted

Creation Date

2021-09-12 01:51:03 UTC

Update Date

2022-11-30 19:53:44 UTC

HMDB ID

HMDB0260477

Secondary Accession Numbers

None

Metabolite Identification

Common Name

MG(6 keto-PGF1alpha/0:0/0:0)

Description

MG(6 keto-PGF1alpha/0:0/0:0) is an oxidized monoacyglycerol (MG). Oxidized monoacyglycerols are glycerolipids in which the fatty acyl chain has undergone oxidation. As all oxidized lipids, oxidized monoacyglycerols 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 other lipids, monoacyglycerols can be substituted by different fatty acids, with varying lengths, saturation and degrees of oxidation attached at the C-1, C-2 and C-3 positions. Lipids 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 lipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized lipids is continually in flux, owing to lipid degradation and the continuous lipid remodeling that occurs while these molecules are in membranes. Oxidized MGs can be synthesized via three different routes. In one route, the oxidized MG is synthetized de novo following the same mechanisms as for MGs but incorporating an oxidized acyl chain (PMID: 33329396 ). An alternative is the transacylation 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 MG backbone, mainly through the action of LOX (PMID: 33329396 ).

Structure

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


  Mrv1652309122103512D          

 31 31  0  0  1  0            999 V2000
    6.0409   -0.6271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3264   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3264   -1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6119   -0.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8974   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1830   -0.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4685   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7540   -0.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7540    0.1979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0396   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0396   -1.8646    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7070   -2.3495    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4916   -2.0945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4521   -3.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6271   -3.1341    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1421   -3.8015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3721   -2.3495    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4125   -2.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5840   -1.2876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3686   -1.0326    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9817   -1.5847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5402   -0.2257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3248    0.0293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4963    0.8362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2809    1.0912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4525    1.8982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7553   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4698   -0.6271    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.1843   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8987   -0.6271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4698    0.1979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 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
  1 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
 28 31  1  1  0  0  0
M  END

HMDB0260477
     RDKit          3D
MG(6 keto-PGF1alpha/0:0/0:0)
 71 71  0  0  0  0  0  0  0  0999 V2000
   10.1423   -0.4538    1.8632 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1376   -0.5343    0.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7182   -0.8191   -0.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8524    0.2985    0.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4173    0.2747   -0.1226 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6913   -0.9110    0.3769 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2503   -2.0741   -0.1246 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2516   -0.8792   -0.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4945    0.1169    0.3482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0765    0.3419    0.0704 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9992    1.6871   -0.6519 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6553    2.7258    0.1883 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0264    1.5030   -1.7870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1159    0.0363   -2.0514 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1000   -0.4948   -2.8027 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3465   -0.6497   -0.7261 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0728   -1.0616   -0.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9070    0.0030    0.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6998    0.8203    1.0727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1749    0.1549   -0.5688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3825    0.1324    0.3384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6666    0.2959   -0.4202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8703    0.2450    0.4972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0950    0.4158   -0.3315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0090    0.5960   -1.5806 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3572    0.3827    0.2400 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4817    0.5505   -0.5922 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7496    0.4765    0.2278 C   0  0  1  0  0  0  0  0  0  0  0  0
  -11.8825    0.6373   -0.5495 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7840   -0.8557    0.9408 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9155   -0.9365    1.7755 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1964   -0.6265    2.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8857    0.5683    2.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5315   -1.2250    2.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4123    0.4655   -0.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8649   -1.2700   -0.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4252   -1.8291    0.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7795   -0.7881   -1.2696 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8749    0.4155    1.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3257    1.2773   -0.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9787    1.2438    0.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3628    0.3018   -1.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7643   -0.9422    1.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8396   -2.8961    0.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8272   -1.6555   -0.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9684    0.9145    0.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5801    0.5334    1.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9810    1.9496   -1.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3743    3.4304    0.2384 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3715    2.0420   -2.7102 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0378    1.8922   -1.5678 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0649   -0.1127   -2.6505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4051   -1.2140   -3.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8779   -1.5951   -0.9752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3970   -1.9359   -0.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2990   -1.5141    0.9606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2612   -0.5598   -1.4059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1812    1.1818   -1.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4250   -0.8629    0.8574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2818    0.8921    1.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7574   -0.5154   -1.1543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6581    1.2805   -0.9780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9486   -0.7448    1.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8455    1.0450    1.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3865    1.5948   -1.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4720   -0.1653   -1.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7068    1.2852    0.9809 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6676    0.3931   -0.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8512   -1.0167    1.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8400   -1.6891    0.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7212   -1.5732    2.5101 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
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 16 10  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  5 42  1  0
  6 43  1  1
  7 44  1  0
  8 45  1  0
  9 46  1  0
 10 47  1  1
 11 48  1  6
 12 49  1  0
 13 50  1  0
 13 51  1  0
 14 52  1  6
 15 53  1  0
 16 54  1  6
 17 55  1  0
 17 56  1  0
 20 57  1  0
 20 58  1  0
 21 59  1  0
 21 60  1  0
 22 61  1  0
 22 62  1  0
 23 63  1  0
 23 64  1  0
 27 65  1  0
 27 66  1  0
 28 67  1  1
 29 68  1  0
 30 69  1  0
 30 70  1  0
 31 71  1  0
M  END


  Mrv1652309122103512D          

 31 31  0  0  1  0            999 V2000
    6.0409   -0.6271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3264   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3264   -1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6119   -0.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8974   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1830   -0.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4685   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7540   -0.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7540    0.1979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0396   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0396   -1.8646    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7070   -2.3495    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4916   -2.0945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4521   -3.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6271   -3.1341    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1421   -3.8015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3721   -2.3495    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4125   -2.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5840   -1.2876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3686   -1.0326    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9817   -1.5847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5402   -0.2257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3248    0.0293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4963    0.8362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2809    1.0912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4525    1.8982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7553   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4698   -0.6271    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.1843   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8987   -0.6271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4698    0.1979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 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
  1 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
 28 31  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0260477

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC(=O)CCCCC(=O)OC[C@@H](O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C23H40O8/c1-2-3-4-7-16(25)10-11-19-20(22(29)13-21(19)28)12-17(26)8-5-6-9-23(30)31-15-18(27)14-24/h10-11,16,18-22,24-25,27-29H,2-9,12-15H2,1H3/b11-10+/t16-,18-,19+,20+,21+,22-/m0/s1

> <INCHI_KEY>
MPSATYYKSWVJNQ-DCBGHZSBSA-N

> <FORMULA>
C23H40O8

> <MOLECULAR_WEIGHT>
444.565

> <EXACT_MASS>
444.272318248

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
50.06235782926309

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2,3-dihydroxypropyl 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]-6-oxoheptanoate

> <ALOGPS_LOGP>
0.93

> <JCHEM_LOGP>
0.6192154506666656

> <ALOGPS_LOGS>
-3.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.514665297154714

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.566559403391707

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6263123618974902

> <JCHEM_POLAR_SURFACE_AREA>
144.52

> <JCHEM_REFRACTIVITY>
117.01939999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.00e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2,3-dihydroxypropyl 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]-6-oxoheptanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0260477
     RDKit          3D
MG(6 keto-PGF1alpha/0:0/0:0)
 71 71  0  0  0  0  0  0  0  0999 V2000
   10.1423   -0.4538    1.8632 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1376   -0.5343    0.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7182   -0.8191   -0.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8524    0.2985    0.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4173    0.2747   -0.1226 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6913   -0.9110    0.3769 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2503   -2.0741   -0.1246 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2516   -0.8792   -0.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4945    0.1169    0.3482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0765    0.3419    0.0704 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9992    1.6871   -0.6519 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6553    2.7258    0.1883 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0264    1.5030   -1.7870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1159    0.0363   -2.0514 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1000   -0.4948   -2.8027 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3465   -0.6497   -0.7261 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0728   -1.0616   -0.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9070    0.0030    0.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6998    0.8203    1.0727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1749    0.1549   -0.5688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3825    0.1324    0.3384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6666    0.2959   -0.4202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8703    0.2450    0.4972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0950    0.4158   -0.3315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0090    0.5960   -1.5806 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3572    0.3827    0.2400 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4817    0.5505   -0.5922 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7496    0.4765    0.2278 C   0  0  1  0  0  0  0  0  0  0  0  0
  -11.8825    0.6373   -0.5495 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7840   -0.8557    0.9408 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9155   -0.9365    1.7755 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1964   -0.6265    2.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8857    0.5683    2.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5315   -1.2250    2.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4123    0.4655   -0.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8649   -1.2700   -0.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4252   -1.8291    0.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7795   -0.7881   -1.2696 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8749    0.4155    1.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3257    1.2773   -0.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9787    1.2438    0.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3628    0.3018   -1.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7643   -0.9422    1.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8396   -2.8961    0.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8272   -1.6555   -0.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9684    0.9145    0.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5801    0.5334    1.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9810    1.9496   -1.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3743    3.4304    0.2384 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3715    2.0420   -2.7102 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0378    1.8922   -1.5678 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0649   -0.1127   -2.6505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4051   -1.2140   -3.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8779   -1.5951   -0.9752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3970   -1.9359   -0.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2990   -1.5141    0.9606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2612   -0.5598   -1.4059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1812    1.1818   -1.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4250   -0.8629    0.8574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2818    0.8921    1.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7574   -0.5154   -1.1543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6581    1.2805   -0.9780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9486   -0.7448    1.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8455    1.0450    1.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3865    1.5948   -1.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4720   -0.1653   -1.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7068    1.2852    0.9809 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6676    0.3931   -0.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8512   -1.0167    1.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8400   -1.6891    0.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7212   -1.5732    2.5101 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
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 16 10  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  5 42  1  0
  6 43  1  1
  7 44  1  0
  8 45  1  0
  9 46  1  0
 10 47  1  1
 11 48  1  6
 12 49  1  0
 13 50  1  0
 13 51  1  0
 14 52  1  6
 15 53  1  0
 16 54  1  6
 17 55  1  0
 17 56  1  0
 20 57  1  0
 20 58  1  0
 21 59  1  0
 21 60  1  0
 22 61  1  0
 22 62  1  0
 23 63  1  0
 23 64  1  0
 27 65  1  0
 27 66  1  0
 28 67  1  1
 29 68  1  0
 30 69  1  0
 30 70  1  0
 31 71  1  0
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      11.276  -1.171   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       9.943  -1.941   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       9.943  -3.481   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       8.609  -1.171   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.275  -1.941   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.942  -1.171   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.608  -1.941   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.274  -1.171   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.274   0.369   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.941  -1.941   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.941  -3.481   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.186  -4.386   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.651  -3.910   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.711  -5.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.171  -5.850   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.265  -7.096   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.695  -4.386   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.770  -3.910   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.090  -2.403   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.555  -1.928   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.699  -2.958   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.875  -0.421   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.340   0.055   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.660   1.561   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.124   2.037   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.445   3.543   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.610  -1.941   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.944  -1.171   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      15.277  -1.941   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      16.611  -1.171   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      13.944   0.369   0.000  0.00  0.00           O+0
CONECT    1    2   27                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   11   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27    1   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   62    0
END

COMPND    HMDB0260477
HETATM    1  C1  UNL     1      10.142  -0.454   1.863  1.00  0.00           C  
HETATM    2  C2  UNL     1      10.138  -0.534   0.359  1.00  0.00           C  
HETATM    3  C3  UNL     1       8.718  -0.819  -0.167  1.00  0.00           C  
HETATM    4  C4  UNL     1       7.852   0.299   0.285  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.417   0.275  -0.123  1.00  0.00           C  
HETATM    6  C6  UNL     1       5.691  -0.911   0.377  1.00  0.00           C  
HETATM    7  O1  UNL     1       6.250  -2.074  -0.125  1.00  0.00           O  
HETATM    8  C7  UNL     1       4.252  -0.879  -0.023  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.494   0.117   0.348  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.077   0.342   0.070  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.999   1.687  -0.652  1.00  0.00           C  
HETATM   12  O2  UNL     1       1.655   2.726   0.188  1.00  0.00           O  
HETATM   13  C11 UNL     1       1.026   1.503  -1.787  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.116   0.036  -2.051  1.00  0.00           C  
HETATM   15  O3  UNL     1       0.100  -0.495  -2.803  1.00  0.00           O  
HETATM   16  C13 UNL     1       1.347  -0.650  -0.726  1.00  0.00           C  
HETATM   17  C14 UNL     1       0.073  -1.062  -0.053  1.00  0.00           C  
HETATM   18  C15 UNL     1      -0.907   0.003   0.196  1.00  0.00           C  
HETATM   19  O4  UNL     1      -0.700   0.820   1.073  1.00  0.00           O  
HETATM   20  C16 UNL     1      -2.175   0.155  -0.569  1.00  0.00           C  
HETATM   21  C17 UNL     1      -3.383   0.132   0.338  1.00  0.00           C  
HETATM   22  C18 UNL     1      -4.667   0.296  -0.420  1.00  0.00           C  
HETATM   23  C19 UNL     1      -5.870   0.245   0.497  1.00  0.00           C  
HETATM   24  C20 UNL     1      -7.095   0.416  -0.331  1.00  0.00           C  
HETATM   25  O5  UNL     1      -7.009   0.596  -1.581  1.00  0.00           O  
HETATM   26  O6  UNL     1      -8.357   0.383   0.240  1.00  0.00           O  
HETATM   27  C21 UNL     1      -9.482   0.551  -0.592  1.00  0.00           C  
HETATM   28  C22 UNL     1     -10.750   0.477   0.228  1.00  0.00           C  
HETATM   29  O7  UNL     1     -11.882   0.637  -0.550  1.00  0.00           O  
HETATM   30  C23 UNL     1     -10.784  -0.856   0.941  1.00  0.00           C  
HETATM   31  O8  UNL     1     -11.916  -0.936   1.775  1.00  0.00           O  
HETATM   32  H1  UNL     1      11.196  -0.626   2.199  1.00  0.00           H  
HETATM   33  H2  UNL     1       9.886   0.568   2.222  1.00  0.00           H  
HETATM   34  H3  UNL     1       9.531  -1.225   2.346  1.00  0.00           H  
HETATM   35  H4  UNL     1      10.412   0.466  -0.035  1.00  0.00           H  
HETATM   36  H5  UNL     1      10.865  -1.270  -0.028  1.00  0.00           H  
HETATM   37  H6  UNL     1       8.425  -1.829   0.133  1.00  0.00           H  
HETATM   38  H7  UNL     1       8.779  -0.788  -1.270  1.00  0.00           H  
HETATM   39  H8  UNL     1       7.875   0.416   1.418  1.00  0.00           H  
HETATM   40  H9  UNL     1       8.326   1.277  -0.050  1.00  0.00           H  
HETATM   41  H10 UNL     1       5.979   1.244   0.219  1.00  0.00           H  
HETATM   42  H11 UNL     1       6.363   0.302  -1.254  1.00  0.00           H  
HETATM   43  H12 UNL     1       5.764  -0.942   1.495  1.00  0.00           H  
HETATM   44  H13 UNL     1       5.840  -2.896   0.240  1.00  0.00           H  
HETATM   45  H14 UNL     1       3.827  -1.656  -0.608  1.00  0.00           H  
HETATM   46  H15 UNL     1       3.968   0.915   0.958  1.00  0.00           H  
HETATM   47  H16 UNL     1       1.580   0.533   1.069  1.00  0.00           H  
HETATM   48  H17 UNL     1       2.981   1.950  -1.123  1.00  0.00           H  
HETATM   49  H18 UNL     1       2.374   3.430   0.238  1.00  0.00           H  
HETATM   50  H19 UNL     1       1.371   2.042  -2.710  1.00  0.00           H  
HETATM   51  H20 UNL     1       0.038   1.892  -1.568  1.00  0.00           H  
HETATM   52  H21 UNL     1       2.065  -0.113  -2.650  1.00  0.00           H  
HETATM   53  H22 UNL     1       0.405  -1.214  -3.424  1.00  0.00           H  
HETATM   54  H23 UNL     1       1.878  -1.595  -0.975  1.00  0.00           H  
HETATM   55  H24 UNL     1      -0.397  -1.936  -0.600  1.00  0.00           H  
HETATM   56  H25 UNL     1       0.299  -1.514   0.961  1.00  0.00           H  
HETATM   57  H26 UNL     1      -2.261  -0.560  -1.406  1.00  0.00           H  
HETATM   58  H27 UNL     1      -2.181   1.182  -1.046  1.00  0.00           H  
HETATM   59  H28 UNL     1      -3.425  -0.863   0.857  1.00  0.00           H  
HETATM   60  H29 UNL     1      -3.282   0.892   1.136  1.00  0.00           H  
HETATM   61  H30 UNL     1      -4.757  -0.515  -1.154  1.00  0.00           H  
HETATM   62  H31 UNL     1      -4.658   1.280  -0.978  1.00  0.00           H  
HETATM   63  H32 UNL     1      -5.949  -0.745   1.006  1.00  0.00           H  
HETATM   64  H33 UNL     1      -5.845   1.045   1.268  1.00  0.00           H  
HETATM   65  H34 UNL     1      -9.387   1.595  -1.009  1.00  0.00           H  
HETATM   66  H35 UNL     1      -9.472  -0.165  -1.435  1.00  0.00           H  
HETATM   67  H36 UNL     1     -10.707   1.285   0.981  1.00  0.00           H  
HETATM   68  H37 UNL     1     -12.668   0.393  -0.003  1.00  0.00           H  
HETATM   69  H38 UNL     1      -9.851  -1.017   1.518  1.00  0.00           H  
HETATM   70  H39 UNL     1     -10.840  -1.689   0.192  1.00  0.00           H  
HETATM   71  H40 UNL     1     -11.721  -1.573   2.510  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3   35   36
CONECT    3    4   37   38
CONECT    4    5   39   40
CONECT    5    6   41   42
CONECT    6    7    8   43
CONECT    7   44
CONECT    8    9    9   45
CONECT    9   10   46
CONECT   10   11   16   47
CONECT   11   12   13   48
CONECT   12   49
CONECT   13   14   50   51
CONECT   14   15   16   52
CONECT   15   53
CONECT   16   17   54
CONECT   17   18   55   56
CONECT   18   19   19   20
CONECT   20   21   57   58
CONECT   21   22   59   60
CONECT   22   23   61   62
CONECT   23   24   63   64
CONECT   24   25   25   26
CONECT   26   27
CONECT   27   28   65   66
CONECT   28   29   30   67
CONECT   29   68
CONECT   30   31   69   70
CONECT   31   71
END

HMDB0260477
     RDKit          3D
MG(6 keto-PGF1alpha/0:0/0:0)
 71 71  0  0  0  0  0  0  0  0999 V2000
   10.1423   -0.4538    1.8632 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1376   -0.5343    0.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7182   -0.8191   -0.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8524    0.2985    0.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4173    0.2747   -0.1226 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6913   -0.9110    0.3769 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2503   -2.0741   -0.1246 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2516   -0.8792   -0.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4945    0.1169    0.3482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0765    0.3419    0.0704 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9992    1.6871   -0.6519 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6553    2.7258    0.1883 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0264    1.5030   -1.7870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1159    0.0363   -2.0514 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1000   -0.4948   -2.8027 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3465   -0.6497   -0.7261 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0728   -1.0616   -0.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9070    0.0030    0.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6998    0.8203    1.0727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1749    0.1549   -0.5688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3825    0.1324    0.3384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6666    0.2959   -0.4202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8703    0.2450    0.4972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0950    0.4158   -0.3315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0090    0.5960   -1.5806 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3572    0.3827    0.2400 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4817    0.5505   -0.5922 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7496    0.4765    0.2278 C   0  0  1  0  0  0  0  0  0  0  0  0
  -11.8825    0.6373   -0.5495 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7840   -0.8557    0.9408 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9155   -0.9365    1.7755 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1964   -0.6265    2.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8857    0.5683    2.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5315   -1.2250    2.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4123    0.4655   -0.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8649   -1.2700   -0.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4252   -1.8291    0.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7795   -0.7881   -1.2696 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8749    0.4155    1.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3257    1.2773   -0.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9787    1.2438    0.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3628    0.3018   -1.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7643   -0.9422    1.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8396   -2.8961    0.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8272   -1.6555   -0.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9684    0.9145    0.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5801    0.5334    1.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9810    1.9496   -1.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3743    3.4304    0.2384 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3715    2.0420   -2.7102 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0378    1.8922   -1.5678 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0649   -0.1127   -2.6505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4051   -1.2140   -3.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8779   -1.5951   -0.9752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3970   -1.9359   -0.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2990   -1.5141    0.9606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2612   -0.5598   -1.4059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1812    1.1818   -1.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4250   -0.8629    0.8574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2818    0.8921    1.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7574   -0.5154   -1.1543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6581    1.2805   -0.9780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9486   -0.7448    1.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8455    1.0450    1.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3865    1.5948   -1.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4720   -0.1653   -1.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7068    1.2852    0.9809 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6676    0.3931   -0.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8512   -1.0167    1.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8400   -1.6891    0.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7212   -1.5732    2.5101 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
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 16 10  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  5 42  1  0
  6 43  1  1
  7 44  1  0
  8 45  1  0
  9 46  1  0
 10 47  1  1
 11 48  1  6
 12 49  1  0
 13 50  1  0
 13 51  1  0
 14 52  1  6
 15 53  1  0
 16 54  1  6
 17 55  1  0
 17 56  1  0
 20 57  1  0
 20 58  1  0
 21 59  1  0
 21 60  1  0
 22 61  1  0
 22 62  1  0
 23 63  1  0
 23 64  1  0
 27 65  1  0
 27 66  1  0
 28 67  1  1
 29 68  1  0
 30 69  1  0
 30 70  1  0
 31 71  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2S)-2,3-Dihydroxypropyl 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]-6-oxoheptanoic acid	Generator

Chemical Formula

C₂₃H₄₀O₈

Average Molecular Weight

444.565

Monoisotopic Molecular Weight

444.272318248

IUPAC Name

(2S)-2,3-dihydroxypropyl 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]-6-oxoheptanoate

Traditional Name

(2S)-2,3-dihydroxypropyl 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]-6-oxoheptanoate

CAS Registry Number

Not Available

SMILES

CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC(=O)CCCCC(=O)OC[C@@H](O)CO

InChI Identifier

InChI=1S/C23H40O8/c1-2-3-4-7-16(25)10-11-19-20(22(29)13-21(19)28)12-17(26)8-5-6-9-23(30)31-15-18(27)14-24/h10-11,16,18-22,24-25,27-29H,2-9,12-15H2,1H3/b11-10+/t16-,18-,19+,20+,21+,22-/m0/s1

InChI Key

MPSATYYKSWVJNQ-DCBGHZSBSA-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
Fatty alcohol
Monoradylglycerol
Monoacylglycerol
1-acyl-sn-glycerol
Glycerolipid
Fatty acid ester
Cyclopentanol
Cyclic alcohol
Secondary alcohol
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

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	0.93	ALOGPS
logP	0.62	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	13.57	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	117.02 m³·mol⁻¹	ChemAxon
Polarizability	50.06 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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]+	214.241	32859911
AllCCS	[M+H-H2O]+	212.308	32859911
AllCCS	[M+Na]+	216.514	32859911
AllCCS	[M+NH4]+	216.01	32859911
AllCCS	[M-H]-	209.407	32859911
AllCCS	[M+Na-2H]-	211.274	32859911
AllCCS	[M+HCOO]-	213.489	32859911
DeepCCS	[M+H]+	203.672	30932474
DeepCCS	[M-H]-	201.276	30932474
DeepCCS	[M-2H]-	234.409	30932474
DeepCCS	[M+Na]+	209.539	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
MG(6 keto-PGF1alpha/0:0/0:0)	CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC(=O)CCCCC(=O)OC[C@@H](O)CO	4765.2	Standard polar	33892256
MG(6 keto-PGF1alpha/0:0/0:0)	CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC(=O)CCCCC(=O)OC[C@@H](O)CO	3265.7	Standard non polar	33892256
MG(6 keto-PGF1alpha/0:0/0:0)	CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC(=O)CCCCC(=O)OC[C@@H](O)CO	3602.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
MG(6 keto-PGF1alpha/0:0/0:0),6TMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C)C[C@H](O[Si](C)(C)C)[C@@H]1CC(=CCCCC(=O)OC[C@H](CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3385.9	Semi standard non polar	33892256
MG(6 keto-PGF1alpha/0:0/0:0),6TMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C)C[C@H](O[Si](C)(C)C)[C@@H]1CC(=CCCCC(=O)OC[C@H](CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3094.5	Standard non polar	33892256
MG(6 keto-PGF1alpha/0:0/0:0),6TMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C)C[C@H](O[Si](C)(C)C)[C@@H]1CC(=CCCCC(=O)OC[C@H](CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3541.7	Standard polar	33892256
MG(6 keto-PGF1alpha/0:0/0:0),6TMS,isomer #2	CCCCC[C@@H](/C=C/[C@@H]1[C@@H](C=C(CCCCC(=O)OC[C@H](CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C)O[Si](C)(C)C	3391.1	Semi standard non polar	33892256
MG(6 keto-PGF1alpha/0:0/0:0),6TMS,isomer #2	CCCCC[C@@H](/C=C/[C@@H]1[C@@H](C=C(CCCCC(=O)OC[C@H](CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C)O[Si](C)(C)C	3048.6	Standard non polar	33892256
MG(6 keto-PGF1alpha/0:0/0:0),6TMS,isomer #2	CCCCC[C@@H](/C=C/[C@@H]1[C@@H](C=C(CCCCC(=O)OC[C@H](CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C)O[Si](C)(C)C	3559.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - MG(6 keto-PGF1alpha/0:0/0:0) GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-9324600000-668e054193f4144b5835	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - MG(6 keto-PGF1alpha/0:0/0:0) GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - MG(6 keto-PGF1alpha/0:0/0:0) GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - MG(6 keto-PGF1alpha/0:0/0:0) GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - MG(6 keto-PGF1alpha/0:0/0:0) GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - MG(6 keto-PGF1alpha/0:0/0:0) GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - MG(6 keto-PGF1alpha/0:0/0:0) GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - MG(6 keto-PGF1alpha/0:0/0:0) GC-MS (TMS_1_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - MG(6 keto-PGF1alpha/0:0/0:0) GC-MS (TMS_1_7) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - MG(6 keto-PGF1alpha/0:0/0:0) GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - MG(6 keto-PGF1alpha/0:0/0:0) GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - MG(6 keto-PGF1alpha/0:0/0:0) GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - MG(6 keto-PGF1alpha/0:0/0:0) GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - MG(6 keto-PGF1alpha/0:0/0:0) GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - MG(6 keto-PGF1alpha/0:0/0:0) GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - MG(6 keto-PGF1alpha/0:0/0:0) GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - MG(6 keto-PGF1alpha/0:0/0:0) GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - MG(6 keto-PGF1alpha/0:0/0:0) GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - MG(6 keto-PGF1alpha/0:0/0:0) GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - MG(6 keto-PGF1alpha/0:0/0:0) GC-MS (TMS_2_11) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - MG(6 keto-PGF1alpha/0:0/0:0) GC-MS (TMS_2_12) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - MG(6 keto-PGF1alpha/0:0/0:0) GC-MS (TMS_2_13) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - MG(6 keto-PGF1alpha/0:0/0:0) GC-MS (TMS_2_14) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - MG(6 keto-PGF1alpha/0:0/0:0) GC-MS (TMS_2_15) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - MG(6 keto-PGF1alpha/0:0/0:0) GC-MS (TMS_2_16) - 70eV, Positive	Not Available	2021-11-05	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 ]

Showing metabocard for MG(6 keto-PGF1alpha/0:0/0:0) (HMDB0260477)

MOL for HMDB0260477 (MG(6 keto-PGF1alpha/0:0/0:0))

3D MOL for HMDB0260477 (MG(6 keto-PGF1alpha/0:0/0:0))

3D SDF for HMDB0260477 (MG(6 keto-PGF1alpha/0:0/0:0))

3D-SDF for HMDB0260477 (MG(6 keto-PGF1alpha/0:0/0:0))

PDB for HMDB0260477 (MG(6 keto-PGF1alpha/0:0/0:0))

3D PDB for HMDB0260477 (MG(6 keto-PGF1alpha/0:0/0:0))

SMILES for HMDB0260477 (MG(6 keto-PGF1alpha/0:0/0:0))

INCHI for HMDB0260477 (MG(6 keto-PGF1alpha/0:0/0:0))

Structure for HMDB0260477 (MG(6 keto-PGF1alpha/0:0/0:0))

3D Structure for HMDB0260477 (MG(6 keto-PGF1alpha/0:0/0:0))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra