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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2008-10-29 12:42:36 UTC

Update Date

2022-03-07 02:51:03 UTC

HMDB ID

HMDB0011137

Secondary Accession Numbers

HMDB11137

Metabolite Identification

Common Name

11-Epi-PGF2a

Description

11-epi-PGF2alpha is an intermediate in Arachidonic acid metabolism. 11-epi-PGF2alpha is converted from (5Z,13E)-(15S)-9alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoate via the enzyme prostaglandin-F synthase (EC 1.1.1.188).Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways.

Structure

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

HMDB0011137
     RDKit          3D
11-Epi-PGF2a
 59 59  0  0  0  0  0  0  0  0999 V2000
   -6.2807    1.8825   -1.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8207    2.6080    0.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2607    1.6297    1.1840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1033    0.8979    0.5660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0026    1.8440    0.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8313    1.0859   -0.4461 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3595    0.4209   -1.5745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2802    0.0920    0.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5931   -0.9866    0.1643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0430   -1.9764    1.0991 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4263   -2.1741    1.0120 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0789   -1.4263   -0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5224   -1.6186   -0.2042 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4709   -0.7141   -0.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2022    0.7056    0.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7571    1.5297   -1.0876 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4479    2.9877   -0.8149 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9764    3.8010   -1.9386 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8577    5.0518   -1.9729 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6396    3.2158   -3.0272 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6325   -3.6422    0.9820 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8947   -4.1669   -0.2686 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3030   -4.2625    1.4367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6759   -3.3227    0.7578 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5941   -3.5016   -0.6048 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0944    2.4860   -1.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4437    1.7899   -1.7353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7467    0.9292   -0.7555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0663    3.3678   -0.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7228    3.0670    0.6695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8779    2.1353    2.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0452    0.9076    1.4907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5265    0.3623   -0.3321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7330    0.0796    1.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7254    2.5185    0.9702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3952    2.4746   -0.6876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0667    1.7842   -0.8293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5405   -0.5180   -1.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4518    0.2611    1.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4287   -1.1437   -0.8956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3622   -1.7767    2.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8821   -1.7816    1.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6685   -1.7778   -1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8279   -0.3631   -0.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9003   -2.6583   -0.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5405   -0.9952   -0.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7857    1.0911    0.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1525    0.9900    0.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8626    1.4400   -1.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2841    1.2306   -2.0328 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9285    3.3252    0.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3283    3.1279   -0.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5388    3.6230   -3.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3903   -4.0077    1.7190 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3941   -4.9995   -0.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1636   -4.1206    2.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2106   -5.2992    1.1036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6949   -3.4163    1.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3009   -4.0935   -0.9580 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
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 11 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 24 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  6
  7 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  1
 11 42  1  0
 12 43  1  0
 12 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 17 52  1  0
 20 53  1  0
 21 54  1  0
 22 55  1  0
 23 56  1  0
 23 57  1  0
 24 58  1  1
 25 59  1  0
M  END

  Mrv0541 02241201202D          

 25 25  0  0  1  0            999 V2000
   21.8488   -8.3399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3337   -7.6724    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.3337   -9.0073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1184   -7.9274    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.1184   -8.7524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0788   -6.8878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7858   -7.4424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0238   -8.3399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6113   -9.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7863   -9.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3738   -8.3399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5488   -8.3399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1363   -7.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3113   -7.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8988   -6.9110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8988   -8.3399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6308   -6.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3759   -5.4901    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.9279   -4.8770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6730   -4.0923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2250   -3.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9701   -2.6946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5221   -2.0815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0788   -9.7920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5689   -5.3186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  5  1  0  0  0  0
  2  6  1  1  0  0  0
  4  7  1  1  0  0  0
  8  1  1  6  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 14  2  0  0  0  0
 17  6  2  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24  3  1  6  0  0  0
 18 25  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0011137

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC[C@H](O)\C=C\[C@H]1[C@@H](O)CC(O)C1C\C=C/CCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16?,17+,18?,19-/m0/s1

> <INCHI_KEY>
PXGPLTODNUVGFL-BTJIPTOOSA-N

> <FORMULA>
C20H34O5

> <MOLECULAR_WEIGHT>
354.481

> <EXACT_MASS>
354.240624198

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
40.87274478878586

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z)-7-[(2R,3S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid

> <ALOGPS_LOGP>
3.11

> <JCHEM_LOGP>
2.6110544173333317

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.513964334215405

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.355294048784039

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6263153076120291

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
100.47069999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.17e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5Z)-7-[(2R,3S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0011137
     RDKit          3D
11-Epi-PGF2a
 59 59  0  0  0  0  0  0  0  0999 V2000
   -6.2807    1.8825   -1.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8207    2.6080    0.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2607    1.6297    1.1840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1033    0.8979    0.5660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0026    1.8440    0.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8313    1.0859   -0.4461 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3595    0.4209   -1.5745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2802    0.0920    0.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5931   -0.9866    0.1643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0430   -1.9764    1.0991 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4263   -2.1741    1.0120 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0789   -1.4263   -0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5224   -1.6186   -0.2042 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4709   -0.7141   -0.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2022    0.7056    0.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7571    1.5297   -1.0876 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4479    2.9877   -0.8149 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9764    3.8010   -1.9386 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8577    5.0518   -1.9729 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6396    3.2158   -3.0272 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6325   -3.6422    0.9820 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8947   -4.1669   -0.2686 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3030   -4.2625    1.4367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6759   -3.3227    0.7578 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5941   -3.5016   -0.6048 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0944    2.4860   -1.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4437    1.7899   -1.7353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7467    0.9292   -0.7555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0663    3.3678   -0.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7228    3.0670    0.6695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8779    2.1353    2.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0452    0.9076    1.4907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5265    0.3623   -0.3321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7330    0.0796    1.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7254    2.5185    0.9702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3952    2.4746   -0.6876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0667    1.7842   -0.8293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5405   -0.5180   -1.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4518    0.2611    1.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4287   -1.1437   -0.8956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3622   -1.7767    2.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8821   -1.7816    1.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6685   -1.7778   -1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8279   -0.3631   -0.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9003   -2.6583   -0.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5405   -0.9952   -0.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7857    1.0911    0.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1525    0.9900    0.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8626    1.4400   -1.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2841    1.2306   -2.0328 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9285    3.3252    0.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3283    3.1279   -0.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5388    3.6230   -3.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3903   -4.0077    1.7190 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3941   -4.9995   -0.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1636   -4.1206    2.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2106   -5.2992    1.1036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6949   -3.4163    1.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3009   -4.0935   -0.9580 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
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 11 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 24 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  6
  7 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  1
 11 42  1  0
 12 43  1  0
 12 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 17 52  1  0
 20 53  1  0
 21 54  1  0
 22 55  1  0
 23 56  1  0
 23 57  1  0
 24 58  1  1
 25 59  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      40.784 -15.568   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      41.690 -14.322   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      41.690 -16.814   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      43.154 -14.798   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      43.154 -16.338   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      41.214 -12.857   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      44.400 -13.892   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      39.244 -15.568   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      38.474 -16.902   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      36.934 -16.902   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      36.164 -15.568   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      34.624 -15.568   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      33.854 -14.234   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      32.314 -14.234   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      31.544 -12.901   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      31.544 -15.568   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      42.244 -11.713   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      41.768 -10.248   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      42.799  -9.104   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      42.323  -7.639   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      43.353  -6.495   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      42.878  -5.030   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      43.908  -3.885   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      41.214 -18.278   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      40.262  -9.928   0.000  0.00  0.00           O+0
CONECT    1    2    3    8                                                  
CONECT    2    1    4    6                                                  
CONECT    3    1    5   24                                                  
CONECT    4    2    5    7                                                  
CONECT    5    3    4                                                       
CONECT    6    2   17                                                       
CONECT    7    4                                                            
CONECT    8    1    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    6   18                                                       
CONECT   18   17   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24    3                                                            
CONECT   25   18                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

COMPND    HMDB0011137
HETATM    1  C1  UNL     1      -6.281   1.882  -1.039  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.821   2.608   0.194  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.261   1.630   1.184  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.103   0.898   0.566  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.003   1.844   0.163  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.831   1.086  -0.446  1.00  0.00           C  
HETATM    7  O1  UNL     1      -2.359   0.421  -1.574  1.00  0.00           O  
HETATM    8  C7  UNL     1      -1.280   0.092   0.513  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.593  -0.987   0.164  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.043  -1.976   1.099  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.426  -2.174   1.012  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.079  -1.426  -0.117  1.00  0.00           C  
HETATM   13  C12 UNL     1       3.522  -1.619  -0.204  1.00  0.00           C  
HETATM   14  C13 UNL     1       4.471  -0.714  -0.120  1.00  0.00           C  
HETATM   15  C14 UNL     1       4.202   0.706   0.086  1.00  0.00           C  
HETATM   16  C15 UNL     1       4.757   1.530  -1.088  1.00  0.00           C  
HETATM   17  C16 UNL     1       4.448   2.988  -0.815  1.00  0.00           C  
HETATM   18  C17 UNL     1       4.976   3.801  -1.939  1.00  0.00           C  
HETATM   19  O2  UNL     1       4.858   5.052  -1.973  1.00  0.00           O  
HETATM   20  O3  UNL     1       5.640   3.216  -3.027  1.00  0.00           O  
HETATM   21  C18 UNL     1       1.633  -3.642   0.982  1.00  0.00           C  
HETATM   22  O4  UNL     1       1.895  -4.167  -0.269  1.00  0.00           O  
HETATM   23  C19 UNL     1       0.303  -4.263   1.437  1.00  0.00           C  
HETATM   24  C20 UNL     1      -0.676  -3.323   0.758  1.00  0.00           C  
HETATM   25  O5  UNL     1      -0.594  -3.502  -0.605  1.00  0.00           O  
HETATM   26  H1  UNL     1      -7.094   2.486  -1.538  1.00  0.00           H  
HETATM   27  H2  UNL     1      -5.444   1.790  -1.735  1.00  0.00           H  
HETATM   28  H3  UNL     1      -6.747   0.929  -0.756  1.00  0.00           H  
HETATM   29  H4  UNL     1      -5.066   3.368  -0.068  1.00  0.00           H  
HETATM   30  H5  UNL     1      -6.723   3.067   0.669  1.00  0.00           H  
HETATM   31  H6  UNL     1      -4.878   2.135   2.107  1.00  0.00           H  
HETATM   32  H7  UNL     1      -6.045   0.908   1.491  1.00  0.00           H  
HETATM   33  H8  UNL     1      -4.527   0.362  -0.332  1.00  0.00           H  
HETATM   34  H9  UNL     1      -3.733   0.080   1.221  1.00  0.00           H  
HETATM   35  H10 UNL     1      -2.725   2.519   0.970  1.00  0.00           H  
HETATM   36  H11 UNL     1      -3.395   2.475  -0.688  1.00  0.00           H  
HETATM   37  H12 UNL     1      -1.067   1.784  -0.829  1.00  0.00           H  
HETATM   38  H13 UNL     1      -2.540  -0.518  -1.297  1.00  0.00           H  
HETATM   39  H14 UNL     1      -1.452   0.261   1.567  1.00  0.00           H  
HETATM   40  H15 UNL     1      -0.429  -1.144  -0.896  1.00  0.00           H  
HETATM   41  H16 UNL     1      -0.362  -1.777   2.164  1.00  0.00           H  
HETATM   42  H17 UNL     1       1.882  -1.782   1.955  1.00  0.00           H  
HETATM   43  H18 UNL     1       1.668  -1.778  -1.117  1.00  0.00           H  
HETATM   44  H19 UNL     1       1.828  -0.363  -0.095  1.00  0.00           H  
HETATM   45  H20 UNL     1       3.900  -2.658  -0.363  1.00  0.00           H  
HETATM   46  H21 UNL     1       5.541  -0.995  -0.205  1.00  0.00           H  
HETATM   47  H22 UNL     1       4.786   1.091   0.973  1.00  0.00           H  
HETATM   48  H23 UNL     1       3.153   0.990   0.162  1.00  0.00           H  
HETATM   49  H24 UNL     1       5.863   1.440  -1.091  1.00  0.00           H  
HETATM   50  H25 UNL     1       4.284   1.231  -2.033  1.00  0.00           H  
HETATM   51  H26 UNL     1       4.928   3.325   0.122  1.00  0.00           H  
HETATM   52  H27 UNL     1       3.328   3.128  -0.777  1.00  0.00           H  
HETATM   53  H28 UNL     1       6.539   3.623  -3.293  1.00  0.00           H  
HETATM   54  H29 UNL     1       2.390  -4.008   1.719  1.00  0.00           H  
HETATM   55  H30 UNL     1       2.394  -4.999  -0.254  1.00  0.00           H  
HETATM   56  H31 UNL     1       0.164  -4.121   2.531  1.00  0.00           H  
HETATM   57  H32 UNL     1       0.211  -5.299   1.104  1.00  0.00           H  
HETATM   58  H33 UNL     1      -1.695  -3.416   1.162  1.00  0.00           H  
HETATM   59  H34 UNL     1      -1.301  -4.093  -0.958  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4   31   32
CONECT    4    5   33   34
CONECT    5    6   35   36
CONECT    6    7    8   37
CONECT    7   38
CONECT    8    9    9   39
CONECT    9   10   40
CONECT   10   11   24   41
CONECT   11   12   21   42
CONECT   12   13   43   44
CONECT   13   14   14   45
CONECT   14   15   46
CONECT   15   16   47   48
CONECT   16   17   49   50
CONECT   17   18   51   52
CONECT   18   19   19   20
CONECT   20   53
CONECT   21   22   23   54
CONECT   22   55
CONECT   23   24   56   57
CONECT   24   25   58
CONECT   25   59
END

HMDB0011137
     RDKit          3D
11-Epi-PGF2a
 59 59  0  0  0  0  0  0  0  0999 V2000
   -6.2807    1.8825   -1.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8207    2.6080    0.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2607    1.6297    1.1840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1033    0.8979    0.5660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0026    1.8440    0.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8313    1.0859   -0.4461 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3595    0.4209   -1.5745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2802    0.0920    0.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5931   -0.9866    0.1643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0430   -1.9764    1.0991 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4263   -2.1741    1.0120 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0789   -1.4263   -0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5224   -1.6186   -0.2042 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4709   -0.7141   -0.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2022    0.7056    0.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7571    1.5297   -1.0876 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4479    2.9877   -0.8149 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9764    3.8010   -1.9386 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8577    5.0518   -1.9729 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6396    3.2158   -3.0272 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6325   -3.6422    0.9820 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8947   -4.1669   -0.2686 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3030   -4.2625    1.4367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6759   -3.3227    0.7578 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5941   -3.5016   -0.6048 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0944    2.4860   -1.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4437    1.7899   -1.7353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7467    0.9292   -0.7555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0663    3.3678   -0.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7228    3.0670    0.6695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8779    2.1353    2.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0452    0.9076    1.4907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5265    0.3623   -0.3321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7330    0.0796    1.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7254    2.5185    0.9702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3952    2.4746   -0.6876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0667    1.7842   -0.8293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5405   -0.5180   -1.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4518    0.2611    1.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4287   -1.1437   -0.8956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3622   -1.7767    2.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8821   -1.7816    1.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6685   -1.7778   -1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8279   -0.3631   -0.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9003   -2.6583   -0.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5405   -0.9952   -0.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7857    1.0911    0.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1525    0.9900    0.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8626    1.4400   -1.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2841    1.2306   -2.0328 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9285    3.3252    0.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3283    3.1279   -0.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5388    3.6230   -3.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3903   -4.0077    1.7190 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3941   -4.9995   -0.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1636   -4.1206    2.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2106   -5.2992    1.1036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6949   -3.4163    1.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3009   -4.0935   -0.9580 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
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 11 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 24 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  6
  7 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  1
 11 42  1  0
 12 43  1  0
 12 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 17 52  1  0
 20 53  1  0
 21 54  1  0
 22 55  1  0
 23 56  1  0
 23 57  1  0
 24 58  1  1
 25 59  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
11-Epi-PGF2alpha	HMDB
11-Epi-prostaglandin F2a	HMDB
11-Epi-prostaglandin F2alpha	HMDB

Chemical Formula

C₂₀H₃₄O₅

Average Molecular Weight

354.481

Monoisotopic Molecular Weight

354.240624198

IUPAC Name

(5Z)-7-[(2R,3S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid

Traditional Name

(5Z)-7-[(2R,3S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid

CAS Registry Number

Not Available

SMILES

CCCCC[C@H](O)\C=C\[C@H]1[C@@H](O)CC(O)C1C\C=C/CCCC(O)=O

InChI Identifier

InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16?,17+,18?,19-/m0/s1

InChI Key

PXGPLTODNUVGFL-BTJIPTOOSA-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
Long-chain fatty acid
Hydroxy fatty acid
Cyclopentanol
Fatty acid
Unsaturated fatty acid
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0011137)
Membrane (HMDB: HMDB0011137)

Source

Exogenous

Exogenous (HMDB: HMDB0011137)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0011137)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

Leukotriene C4 Synthesis Deficiency (PathBank: SMP0120510)

Metabolic pathway

Arachidonic Acid Metabolism (PathBank: SMP0087315)

Drug action pathway

Piroxicam Action Pathway (PathBank: SMP0000077)
Acetylsalicylic Acid Action Pathway (PathBank: SMP0000083)
Etodolac Action Pathway (PathBank: SMP0000084)
Ketoprofen Action Pathway (PathBank: SMP0000085)
Ibuprofen Action Pathway (PathBank: SMP0000086)
Rofecoxib Action Pathway (PathBank: SMP0000087)
Diclofenac Action Pathway (PathBank: SMP0000093)
Sulindac Action Pathway (PathBank: SMP0000094)
Celecoxib Action Pathway (PathBank: SMP0000096)
Ketorolac Action Pathway (PathBank: SMP0000098)
Suprofen Action Pathway (PathBank: SMP0000101)
Bromfenac Action Pathway (PathBank: SMP0000102)
Indomethacin Action Pathway (PathBank: SMP0000104)
Mefenamic Acid Action Pathway (PathBank: SMP0000109)
Oxaprozin Action Pathway (PathBank: SMP0000113)
Nabumetone Action Pathway (PathBank: SMP0000114)
Naproxen Action Pathway (PathBank: SMP0000120)
Diflunisal Action Pathway (PathBank: SMP0000289)
Meloxicam Action Pathway (PathBank: SMP0000106)
Valdecoxib Action Pathway (PathBank: SMP0000116)
Antipyrine Action Pathway (PathBank: SMP0000692)
Antrafenine Action Pathway (PathBank: SMP0000693)
Carprofen Action Pathway (PathBank: SMP0000694)
Etoricoxib Action Pathway (PathBank: SMP0000695)
Fenoprofen Action Pathway (PathBank: SMP0000696)
Flurbiprofen Action Pathway (PathBank: SMP0000697)
Magnesium salicylate Action Pathway (PathBank: SMP0000698)
Lumiracoxib Action Pathway (PathBank: SMP0000699)
Lornoxicam Action Pathway (PathBank: SMP0000700)
Phenylbutazone Action Pathway (PathBank: SMP0000701)
Nepafenac Action Pathway (PathBank: SMP0000702)
Trisalicylate-choline Action Pathway (PathBank: SMP0000703)
Tolmetin Action Pathway (PathBank: SMP0000704)
Tiaprofenic Acid Action Pathway (PathBank: SMP0000705)
Tenoxicam Action Pathway (PathBank: SMP0000706)
Salsalate Action Pathway (PathBank: SMP0000707)
Salicylate-sodium Action Pathway (PathBank: SMP0000708)
Salicylic Acid Action Pathway (PathBank: SMP0000709)
Acetaminophen Action Pathway (PathBank: SMP0000710)

Role

Not Available

Physical Properties

State

Solid

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
Water Solubility	0.12 g/L	ALOGPS
logP	3.11	ALOGPS
logP	2.61	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	4.36	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	100.47 m³·mol⁻¹	ChemAxon
Polarizability	40.87 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	186.629	31661259
DarkChem	[M-H]-	190.317	31661259
DeepCCS	[M+H]+	199.001	30932474
DeepCCS	[M-H]-	196.56	30932474
DeepCCS	[M-2H]-	230.934	30932474
DeepCCS	[M+Na]+	206.162	30932474
AllCCS	[M+H]+	194.3	32859911
AllCCS	[M+H-H2O]+	191.6	32859911
AllCCS	[M+NH4]+	196.7	32859911
AllCCS	[M+Na]+	197.4	32859911
AllCCS	[M-H]-	191.8	32859911
AllCCS	[M+Na-2H]-	193.1	32859911
AllCCS	[M+HCOO]-	194.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
11-Epi-PGF2a	CCCCC[C@H](O)\C=C\[C@H]1[C@@H](O)CC(O)C1C\C=C/CCCC(O)=O	4432.8	Standard polar	33892256
11-Epi-PGF2a	CCCCC[C@H](O)\C=C\[C@H]1[C@@H](O)CC(O)C1C\C=C/CCCC(O)=O	2715.9	Standard non polar	33892256
11-Epi-PGF2a	CCCCC[C@H](O)\C=C\[C@H]1[C@@H](O)CC(O)C1C\C=C/CCCC(O)=O	2917.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
11-Epi-PGF2a,1TMS,isomer #1	CCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)C(O)C[C@@H]1O)O[Si](C)(C)C	2949.0	Semi standard non polar	33892256
11-Epi-PGF2a,1TMS,isomer #2	CCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)C(O)C[C@@H]1O[Si](C)(C)C	2859.6	Semi standard non polar	33892256
11-Epi-PGF2a,1TMS,isomer #3	CCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)C(O[Si](C)(C)C)C[C@@H]1O	2822.7	Semi standard non polar	33892256
11-Epi-PGF2a,1TMS,isomer #4	CCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)C(O)C[C@@H]1O	2856.2	Semi standard non polar	33892256
11-Epi-PGF2a,2TMS,isomer #1	CCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)C(O)C[C@@H]1O)O[Si](C)(C)C	2849.4	Semi standard non polar	33892256
11-Epi-PGF2a,2TMS,isomer #2	CCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)C(O[Si](C)(C)C)C[C@@H]1O)O[Si](C)(C)C	2825.3	Semi standard non polar	33892256
11-Epi-PGF2a,2TMS,isomer #3	CCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)C(O)C[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C	2825.0	Semi standard non polar	33892256
11-Epi-PGF2a,2TMS,isomer #4	CCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)C(O)C[C@@H]1O[Si](C)(C)C	2795.4	Semi standard non polar	33892256
11-Epi-PGF2a,2TMS,isomer #5	CCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)C(O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C	2817.2	Semi standard non polar	33892256
11-Epi-PGF2a,2TMS,isomer #6	CCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)C[C@@H]1O	2787.1	Semi standard non polar	33892256
11-Epi-PGF2a,3TMS,isomer #1	CCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)C[C@@H]1O)O[Si](C)(C)C	2764.6	Semi standard non polar	33892256
11-Epi-PGF2a,3TMS,isomer #2	CCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)C(O)C[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C	2770.9	Semi standard non polar	33892256
11-Epi-PGF2a,3TMS,isomer #3	CCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)C(O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C	2760.5	Semi standard non polar	33892256
11-Epi-PGF2a,3TMS,isomer #4	CCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C	2743.8	Semi standard non polar	33892256
11-Epi-PGF2a,4TMS,isomer #1	CCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C	2751.0	Semi standard non polar	33892256
11-Epi-PGF2a,1TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)C(O)C[C@@H]1O)O[Si](C)(C)C(C)(C)C	3185.7	Semi standard non polar	33892256
11-Epi-PGF2a,1TBDMS,isomer #2	CCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)C(O)C[C@@H]1O[Si](C)(C)C(C)(C)C	3078.4	Semi standard non polar	33892256
11-Epi-PGF2a,1TBDMS,isomer #3	CCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)C(O[Si](C)(C)C(C)(C)C)C[C@@H]1O	3047.3	Semi standard non polar	33892256
11-Epi-PGF2a,1TBDMS,isomer #4	CCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)C(O)C[C@@H]1O	3118.5	Semi standard non polar	33892256
11-Epi-PGF2a,2TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)C(O)C[C@@H]1O)O[Si](C)(C)C(C)(C)C	3395.0	Semi standard non polar	33892256
11-Epi-PGF2a,2TBDMS,isomer #2	CCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)C(O[Si](C)(C)C(C)(C)C)C[C@@H]1O)O[Si](C)(C)C(C)(C)C	3281.7	Semi standard non polar	33892256
11-Epi-PGF2a,2TBDMS,isomer #3	CCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)C(O)C[C@@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3325.3	Semi standard non polar	33892256
11-Epi-PGF2a,2TBDMS,isomer #4	CCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)C(O)C[C@@H]1O[Si](C)(C)C(C)(C)C	3293.6	Semi standard non polar	33892256
11-Epi-PGF2a,2TBDMS,isomer #5	CCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)C(O[Si](C)(C)C(C)(C)C)C[C@@H]1O[Si](C)(C)C(C)(C)C	3265.6	Semi standard non polar	33892256
11-Epi-PGF2a,2TBDMS,isomer #6	CCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C[C@@H]1O	3272.0	Semi standard non polar	33892256
11-Epi-PGF2a,3TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C[C@@H]1O)O[Si](C)(C)C(C)(C)C	3511.3	Semi standard non polar	33892256
11-Epi-PGF2a,3TBDMS,isomer #2	CCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)C(O)C[C@@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3543.8	Semi standard non polar	33892256
11-Epi-PGF2a,3TBDMS,isomer #3	CCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)C(O[Si](C)(C)C(C)(C)C)C[C@@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3485.0	Semi standard non polar	33892256
11-Epi-PGF2a,3TBDMS,isomer #4	CCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C[C@@H]1O[Si](C)(C)C(C)(C)C	3481.1	Semi standard non polar	33892256
11-Epi-PGF2a,4TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C[C@@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3668.8	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 - 11-Epi-PGF2a GC-MS (Non-derivatized) - 70eV, Positive	splash10-0019-6489000000-bf681ff653e664e9cde0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11-Epi-PGF2a GC-MS (4 TMS) - 70eV, Positive	splash10-004i-9100177000-79583ccaf34002541a28	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11-Epi-PGF2a GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11-Epi-PGF2a GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - 11-Epi-PGF2a 10V, Positive-QTOF	splash10-014r-0019000000-3c46ffbee46021b80901	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Epi-PGF2a 20V, Positive-QTOF	splash10-01bi-2297000000-9fe530991fdc645e26f0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Epi-PGF2a 40V, Positive-QTOF	splash10-0103-9170000000-0fa33343bc482bd6f5a5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Epi-PGF2a 10V, Negative-QTOF	splash10-0udr-0009000000-a337fc1b13431013f06a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Epi-PGF2a 20V, Negative-QTOF	splash10-000i-1039000000-40b895b35529c4a81763	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Epi-PGF2a 40V, Negative-QTOF	splash10-0a4i-9631000000-8dc66a223446641955e6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Epi-PGF2a 10V, Negative-QTOF	splash10-0udi-0009000000-4f29fd22c6b0dfe3ac77	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Epi-PGF2a 20V, Negative-QTOF	splash10-0udr-0098000000-06ede09931efe0fba78e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Epi-PGF2a 40V, Negative-QTOF	splash10-00el-9182000000-f1a4c9aba7f705d2868d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Epi-PGF2a 10V, Positive-QTOF	splash10-014r-0019000000-ece58dc4c35634d7fe3f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Epi-PGF2a 20V, Positive-QTOF	splash10-014i-9255000000-c6aef7e365cba872a558	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Epi-PGF2a 40V, Positive-QTOF	splash10-05mo-9300000000-552900f74505f7605b0b	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Arachidonic Acid Metabolism
Leukotriene C4 Synthesis Deficiency		Not Available
Piroxicam Action Pathway		Not Available
Acetylsalicylic Acid Action Pathway		Not Available
Etodolac Action Pathway		Not Available

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

FDB027915

KNApSAcK ID

Not Available

Chemspider ID

35032067

KEGG Compound ID

C05959

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53480669

PDB ID

Not Available

ChEBI ID

27595

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

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details

1. Aldo-keto reductase family 1 member C3

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the conversion of aldehydes and ketones to alcohols. Catalyzes the reduction of prostaglandin (PG) D2, PGH2 and phenanthrenequinone (PQ) and the oxidation of 9-alpha,11-beta-PGF2 to PGD2. Functions as a bi-directional 3-alpha-, 17-beta- and 20-alpha HSD. Can interconvert active androgens, estrogens and progestins with their cognate inactive metabolites. Preferentially transforms androstenedione (4-dione) to testosterone.
Gene Name:: AKR1C3
Uniprot ID:: P42330
Molecular weight:: 36866.91

Showing metabocard for 11-Epi-PGF2a (HMDB0011137)

MOL for HMDB0011137 (11-Epi-PGF2a)

3D MOL for HMDB0011137 (11-Epi-PGF2a)

3D SDF for HMDB0011137 (11-Epi-PGF2a)

3D-SDF for HMDB0011137 (11-Epi-PGF2a)

PDB for HMDB0011137 (11-Epi-PGF2a)

3D PDB for HMDB0011137 (11-Epi-PGF2a)

SMILES for HMDB0011137 (11-Epi-PGF2a)

INCHI for HMDB0011137 (11-Epi-PGF2a)

Structure for HMDB0011137 (11-Epi-PGF2a)

3D Structure for HMDB0011137 (11-Epi-PGF2a)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes