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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-10-29 12:42:36 UTC
Update Date2022-03-07 02:51:03 UTC
HMDB IDHMDB0011137
Secondary Accession Numbers
  • HMDB11137
Metabolite Identification
Common Name11-Epi-PGF2a
Description11-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
Data?1582752872
Synonyms
ValueSource
11-Epi-PGF2alphaHMDB
11-Epi-prostaglandin F2aHMDB
11-Epi-prostaglandin F2alphaHMDB
Chemical FormulaC20H34O5
Average Molecular Weight354.481
Monoisotopic Molecular Weight354.240624198
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 NumberNot 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 KeyPXGPLTODNUVGFL-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentProstaglandins 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 FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP3.11ALOGPS
logP2.61ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)4.36ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity100.47 m³·mol⁻¹ChemAxon
Polarizability40.87 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+186.62931661259
DarkChem[M-H]-190.31731661259
DeepCCS[M+H]+199.00130932474
DeepCCS[M-H]-196.5630932474
DeepCCS[M-2H]-230.93430932474
DeepCCS[M+Na]+206.16230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
11-Epi-PGF2aCCCCC[C@H](O)\C=C\[C@H]1[C@@H](O)CC(O)C1C\C=C/CCCC(O)=O4432.8Standard polar33892256
11-Epi-PGF2aCCCCC[C@H](O)\C=C\[C@H]1[C@@H](O)CC(O)C1C\C=C/CCCC(O)=O2715.9Standard non polar33892256
11-Epi-PGF2aCCCCC[C@H](O)\C=C\[C@H]1[C@@H](O)CC(O)C1C\C=C/CCCC(O)=O2917.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
11-Epi-PGF2a,1TMS,isomer #1CCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)C(O)C[C@@H]1O)O[Si](C)(C)C2949.0Semi standard non polar33892256
11-Epi-PGF2a,1TMS,isomer #2CCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)C(O)C[C@@H]1O[Si](C)(C)C2859.6Semi standard non polar33892256
11-Epi-PGF2a,1TMS,isomer #3CCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)C(O[Si](C)(C)C)C[C@@H]1O2822.7Semi standard non polar33892256
11-Epi-PGF2a,1TMS,isomer #4CCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)C(O)C[C@@H]1O2856.2Semi standard non polar33892256
11-Epi-PGF2a,2TMS,isomer #1CCCCC[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)C2849.4Semi standard non polar33892256
11-Epi-PGF2a,2TMS,isomer #2CCCCC[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)C2825.3Semi standard non polar33892256
11-Epi-PGF2a,2TMS,isomer #3CCCCC[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)C2825.0Semi standard non polar33892256
11-Epi-PGF2a,2TMS,isomer #4CCCCC[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)C2795.4Semi standard non polar33892256
11-Epi-PGF2a,2TMS,isomer #5CCCCC[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)C2817.2Semi standard non polar33892256
11-Epi-PGF2a,2TMS,isomer #6CCCCC[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]1O2787.1Semi standard non polar33892256
11-Epi-PGF2a,3TMS,isomer #1CCCCC[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)C2764.6Semi standard non polar33892256
11-Epi-PGF2a,3TMS,isomer #2CCCCC[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)C2770.9Semi standard non polar33892256
11-Epi-PGF2a,3TMS,isomer #3CCCCC[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)C2760.5Semi standard non polar33892256
11-Epi-PGF2a,3TMS,isomer #4CCCCC[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)C2743.8Semi standard non polar33892256
11-Epi-PGF2a,4TMS,isomer #1CCCCC[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)C2751.0Semi standard non polar33892256
11-Epi-PGF2a,1TBDMS,isomer #1CCCCC[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)C3185.7Semi standard non polar33892256
11-Epi-PGF2a,1TBDMS,isomer #2CCCCC[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)C3078.4Semi standard non polar33892256
11-Epi-PGF2a,1TBDMS,isomer #3CCCCC[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]1O3047.3Semi standard non polar33892256
11-Epi-PGF2a,1TBDMS,isomer #4CCCCC[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]1O3118.5Semi standard non polar33892256
11-Epi-PGF2a,2TBDMS,isomer #1CCCCC[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)C3395.0Semi standard non polar33892256
11-Epi-PGF2a,2TBDMS,isomer #2CCCCC[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)C3281.7Semi standard non polar33892256
11-Epi-PGF2a,2TBDMS,isomer #3CCCCC[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)C3325.3Semi standard non polar33892256
11-Epi-PGF2a,2TBDMS,isomer #4CCCCC[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)C3293.6Semi standard non polar33892256
11-Epi-PGF2a,2TBDMS,isomer #5CCCCC[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)C3265.6Semi standard non polar33892256
11-Epi-PGF2a,2TBDMS,isomer #6CCCCC[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]1O3272.0Semi standard non polar33892256
11-Epi-PGF2a,3TBDMS,isomer #1CCCCC[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)C3511.3Semi standard non polar33892256
11-Epi-PGF2a,3TBDMS,isomer #2CCCCC[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)C3543.8Semi standard non polar33892256
11-Epi-PGF2a,3TBDMS,isomer #3CCCCC[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)C3485.0Semi standard non polar33892256
11-Epi-PGF2a,3TBDMS,isomer #4CCCCC[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)C3481.1Semi standard non polar33892256
11-Epi-PGF2a,4TBDMS,isomer #1CCCCC[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)C3668.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 11-Epi-PGF2a GC-MS (Non-derivatized) - 70eV, Positivesplash10-0019-6489000000-bf681ff653e664e9cde02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 11-Epi-PGF2a GC-MS (4 TMS) - 70eV, Positivesplash10-004i-9100177000-79583ccaf34002541a282017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 11-Epi-PGF2a GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 11-Epi-PGF2a GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Epi-PGF2a 10V, Positive-QTOFsplash10-014r-0019000000-3c46ffbee46021b809012017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Epi-PGF2a 20V, Positive-QTOFsplash10-01bi-2297000000-9fe530991fdc645e26f02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Epi-PGF2a 40V, Positive-QTOFsplash10-0103-9170000000-0fa33343bc482bd6f5a52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Epi-PGF2a 10V, Negative-QTOFsplash10-0udr-0009000000-a337fc1b13431013f06a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Epi-PGF2a 20V, Negative-QTOFsplash10-000i-1039000000-40b895b35529c4a817632017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Epi-PGF2a 40V, Negative-QTOFsplash10-0a4i-9631000000-8dc66a223446641955e62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Epi-PGF2a 10V, Negative-QTOFsplash10-0udi-0009000000-4f29fd22c6b0dfe3ac772021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Epi-PGF2a 20V, Negative-QTOFsplash10-0udr-0098000000-06ede09931efe0fba78e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Epi-PGF2a 40V, Negative-QTOFsplash10-00el-9182000000-f1a4c9aba7f705d2868d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Epi-PGF2a 10V, Positive-QTOFsplash10-014r-0019000000-ece58dc4c35634d7fe3f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Epi-PGF2a 20V, Positive-QTOFsplash10-014i-9255000000-c6aef7e365cba872a5582021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Epi-PGF2a 40V, Positive-QTOFsplash10-05mo-9300000000-552900f74505f7605b0b2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027915
KNApSAcK IDNot Available
Chemspider ID35032067
KEGG Compound IDC05959
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480669
PDB IDNot Available
ChEBI ID27595
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

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