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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:08 UTC
HMDB IDHMDB0001139
Secondary Accession Numbers
  • HMDB01139
Metabolite Identification
Common NameProstaglandin F2a
DescriptionProstaglandin F2a (PGF2) is one of the earliest discovered and most common prostaglandins. It is actively biosynthesized in various organs of mammals and exhibits a variety of biological activities, including contraction of pulmonary arteries. It is used in medicine to induce labor and as an abortifacient. PGF2a binds to the Prostaglandin F2 receptor (PTGFR) which is a member of the G-protein coupled receptor family. PGF2-alpha mediates luteolysis. Luteolysis is the structural and functional degradation of the corpus luteum (CL) that occurs at the end of the luteal phase of both the estrous and menstrual cycles in the absence of pregnancy. PGF2 may also be involved in modulating intraocular pressure and smooth muscle contraction in the uterus and gastrointestinal tract sphincters. PGF2 is mainly synthesized directly from PGH2 by PGH2 9,11-endoperoxide reductase. A small amount of PGF2 is also produced from PGE2 by PGE2 9-ketoreductase. A PGF2 epimer has been reported to exhibit various biological activities, and its levels are increased in bronchoalveolar lavage fluid, plasma, and urine in patients with mastocytosis and bronchial asthma. PGF2 is synthesized from PGD2 by PGD2 11-ketoreductase. (PMID: 16475787 ). 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?1582752179
Synonyms
ValueSource
(+)-Prostaglandin F2aHMDB
(5Z,13E)-(15S)-9-alpha,11-alpha,15-Trihydroxyprosta-5,13-dienoateHMDB
(5Z,13E)-(15S)-9-alpha,11-alpha,15-Trihydroxyprosta-5,13-dienoic acidHMDB
(5Z,13E,15S)-9a,11a,15-Trihydroxyprosta-5,13-dien-1-OateHMDB
(5Z,13E,15S)-9a,11a,15-Trihydroxyprosta-5,13-dien-1-Oic acidHMDB
(5Z,9a,11a,13E,15S)-9,11,15-Trihydroxy-prosta-5,13-dien-1-OateHMDB
(5Z,9a,11a,13E,15S)-9,11,15-Trihydroxy-prosta-5,13-dien-1-Oic acidHMDB
(9alpha,11alpha,15)-Trihydroxyprosta-(5Z,13E)-dien-1-OateHMDB
(9alpha,11alpha,15)-Trihydroxyprosta-(5Z,13E)-dien-1-Oic acidHMDB
7-[3,5-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoateHMDB
7-[3,5-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoic acidHMDB
9,11,15-Trihydroxy-(5Z,9a,11a,13E,15S)-prosta-5,13-dien-1-OateHMDB
9,11,15-Trihydroxy-(5Z,9a,11a,13E,15S)-prosta-5,13-dien-1-Oic acidHMDB
9,11,15-Trihydroxyprosta-5Z,13E-dien-1-OateHMDB
9,11,15-Trihydroxyprosta-5Z,13E-dien-1-Oic acidHMDB
9a,11a,15(S)-Trihydroxy-5-cis-13-trans-prostadienoateHMDB
9a,11a,15(S)-Trihydroxy-5-cis-13-trans-prostadienoic acidHMDB
9a,11a-PGF2HMDB
9a,11a-PGF2aHMDB
AmoglandinHMDB
CyclosinHMDB
DinifertinHMDB
DinoprostHMDB
EnzaprostHMDB
Enzaprost FHMDB
F2a IsoprostaneHMDB
Glandin NHMDB
L-PGF2-alphaHMDB
L-Prostaglandin F2-alphaHMDB
PanacelanHMDB
PGF2aHMDB
Prostaglandin F2HMDB
ProstamateHMDB
Prostarmon FHMDB
Prostin F 2 alphaHMDB
ProtamodinHMDB
9alpha,11beta PGF2HMDB
9alpha,11beta-PGF2HMDB
EstrofanHMDB
F2 alpha, ProstaglandinHMDB
F2alpha, ProstaglandinHMDB
PGF2HMDB
PGF2 alphaHMDB
PGF2alphaHMDB
Prostaglandin F2 alphaHMDB
Prostaglandin F2alphaHMDB
alpha, PGF2HMDB
Chemical FormulaC20H34O5
Average Molecular Weight354.481
Monoisotopic Molecular Weight354.240624198
IUPAC Name(5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid
Traditional Name5-trans-PGF2α
CAS Registry Number551-11-1
SMILES
CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\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-UAAPODJFSA-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 Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point30 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP4.39BODOR,H & HUANG,M (1992)
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
Polarizability41.7 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]+188.47331661259
DarkChem[M-H]-191.16231661259
AllCCS[M+H]+194.25232859911
AllCCS[M-H]-191.7832859911
DeepCCS[M+H]+198.17230932474
DeepCCS[M-H]-195.77630932474
DeepCCS[M-2H]-229.00830932474
DeepCCS[M+Na]+204.08530932474
AllCCS[M+H]+194.332859911
AllCCS[M+H-H2O]+191.632859911
AllCCS[M+NH4]+196.732859911
AllCCS[M+Na]+197.432859911
AllCCS[M-H]-191.832859911
AllCCS[M+Na-2H]-193.132859911
AllCCS[M+HCOO]-194.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Prostaglandin F2aCCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C\CCCC(O)=O4461.2Standard polar33892256
Prostaglandin F2aCCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C\CCCC(O)=O2708.1Standard non polar33892256
Prostaglandin F2aCCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C\CCCC(O)=O2924.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Prostaglandin F2a,1TMS,isomer #1CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@H](O)[C@@H]1C/C=C/CCCC(=O)O)O[Si](C)(C)C2883.7Semi standard non polar33892256
Prostaglandin F2a,1TMS,isomer #2CCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C)C[C@H](O)[C@@H]1C/C=C/CCCC(=O)O2784.6Semi standard non polar33892256
Prostaglandin F2a,1TMS,isomer #3CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C/CCCC(=O)O2765.8Semi standard non polar33892256
Prostaglandin F2a,1TMS,isomer #4CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C[C@H](O)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C2816.1Semi standard non polar33892256
Prostaglandin F2a,2TMS,isomer #1CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C)C[C@H](O)[C@@H]1C/C=C/CCCC(=O)O)O[Si](C)(C)C2755.7Semi standard non polar33892256
Prostaglandin F2a,2TMS,isomer #2CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C/CCCC(=O)O)O[Si](C)(C)C2746.0Semi standard non polar33892256
Prostaglandin F2a,2TMS,isomer #3CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@H](O)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2827.9Semi standard non polar33892256
Prostaglandin F2a,2TMS,isomer #4CCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C/CCCC(=O)O2750.7Semi standard non polar33892256
Prostaglandin F2a,2TMS,isomer #5CCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C)C[C@H](O)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C2762.8Semi standard non polar33892256
Prostaglandin F2a,2TMS,isomer #6CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C2742.2Semi standard non polar33892256
Prostaglandin F2a,3TMS,isomer #1CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C/CCCC(=O)O)O[Si](C)(C)C2718.1Semi standard non polar33892256
Prostaglandin F2a,3TMS,isomer #2CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C)C[C@H](O)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2744.9Semi standard non polar33892256
Prostaglandin F2a,3TMS,isomer #3CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2730.6Semi standard non polar33892256
Prostaglandin F2a,3TMS,isomer #4CCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C2713.7Semi standard non polar33892256
Prostaglandin F2a,4TMS,isomer #1CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2746.0Semi standard non polar33892256
Prostaglandin F2a,1TBDMS,isomer #1CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@H](O)[C@@H]1C/C=C/CCCC(=O)O)O[Si](C)(C)C(C)(C)C3139.4Semi standard non polar33892256
Prostaglandin F2a,1TBDMS,isomer #2CCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C[C@H](O)[C@@H]1C/C=C/CCCC(=O)O2997.0Semi standard non polar33892256
Prostaglandin F2a,1TBDMS,isomer #3CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C/CCCC(=O)O2980.6Semi standard non polar33892256
Prostaglandin F2a,1TBDMS,isomer #4CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C[C@H](O)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C(C)(C)C3080.5Semi standard non polar33892256
Prostaglandin F2a,2TBDMS,isomer #1CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C[C@H](O)[C@@H]1C/C=C/CCCC(=O)O)O[Si](C)(C)C(C)(C)C3245.1Semi standard non polar33892256
Prostaglandin F2a,2TBDMS,isomer #2CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C/CCCC(=O)O)O[Si](C)(C)C(C)(C)C3232.7Semi standard non polar33892256
Prostaglandin F2a,2TBDMS,isomer #3CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@H](O)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3363.9Semi standard non polar33892256
Prostaglandin F2a,2TBDMS,isomer #4CCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C/CCCC(=O)O3197.2Semi standard non polar33892256
Prostaglandin F2a,2TBDMS,isomer #5CCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C[C@H](O)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C(C)(C)C3243.4Semi standard non polar33892256
Prostaglandin F2a,2TBDMS,isomer #6CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C(C)(C)C3227.3Semi standard non polar33892256
Prostaglandin F2a,3TBDMS,isomer #1CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C/CCCC(=O)O)O[Si](C)(C)C(C)(C)C3429.7Semi standard non polar33892256
Prostaglandin F2a,3TBDMS,isomer #2CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C[C@H](O)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3490.6Semi standard non polar33892256
Prostaglandin F2a,3TBDMS,isomer #3CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3479.2Semi standard non polar33892256
Prostaglandin F2a,3TBDMS,isomer #4CCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C(C)(C)C3432.6Semi standard non polar33892256
Prostaglandin F2a,4TBDMS,isomer #1CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3625.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Prostaglandin F2a GC-MS (Non-derivatized) - 70eV, Positivesplash10-0019-6489000000-bf681ff653e664e9cde02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prostaglandin F2a GC-MS (4 TMS) - 70eV, Positivesplash10-004i-9300188000-0fc1fbcf7464fb00c07e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prostaglandin F2a GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prostaglandin F2a GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Prostaglandin F2a LC-ESI-QQ , negative-QTOFsplash10-0udi-0009000000-cd642664d59adb85ae592017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin F2a 10V, Positive-QTOFsplash10-014r-0019000000-3c46ffbee46021b809012017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin F2a 20V, Positive-QTOFsplash10-01bi-2297000000-9fe530991fdc645e26f02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin F2a 40V, Positive-QTOFsplash10-0103-9170000000-0fa33343bc482bd6f5a52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin F2a 10V, Negative-QTOFsplash10-0udr-0009000000-a337fc1b13431013f06a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin F2a 20V, Negative-QTOFsplash10-000i-1039000000-40b895b35529c4a817632017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin F2a 40V, Negative-QTOFsplash10-0a4i-9631000000-8dc66a223446641955e62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin F2a 10V, Negative-QTOFsplash10-0udi-0009000000-4f29fd22c6b0dfe3ac772021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin F2a 20V, Negative-QTOFsplash10-0udr-0098000000-06ede09931efe0fba78e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin F2a 40V, Negative-QTOFsplash10-00el-9182000000-f1a4c9aba7f705d2868d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin F2a 10V, Positive-QTOFsplash10-014r-0019000000-ece58dc4c35634d7fe3f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin F2a 20V, Positive-QTOFsplash10-014i-9255000000-c6aef7e365cba872a5582021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin F2a 40V, Positive-QTOFsplash10-05mo-9300000000-552900f74505f7605b0b2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Locations
  • Adipose Tissue
  • Adrenal Gland
  • Epidermis
  • Placenta
  • Platelet
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000053 +/- 0.000012 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000371 +/- 0.000144 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.00033 +/- 0.000018 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.000248 +/- 0.00013 uMAdult (>18 years old)Both
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified7.340e-05 +/- 8.469e-06 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00007340 +/- 0.000008469 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.002 (0.0-0.004) uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00091 +/- 0.00008 uMAdult (>18 years old)Both
Normal
    • John W. Newman, U...
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothNormal details
UrineDetected and Quantified0.00013 +/- 0.00020 umol/mmol creatinineNewborn (0-30 days old)Both
Normal
details
UrineDetected and Quantified0.00021 +/- 0.000053 umol/mmol creatinineAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified0.00031 +/- 0.00012 umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified0.0000924 (0.0000588-0.000126) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0010 +/- 0.0002 uMAdult (>18 years old)Both
Cardiac arrest
details
BloodDetected and Quantified0.0005 +/- 0.0001 uMAdult (>18 years old)Both
Cardiac arrest
details
BloodDetected and Quantified0.0016 +/- 0.0004 uMAdult (>18 years old)Both
Cardiac arrest
details
BloodDetected and Quantified0.0007 +/- 0.0001 uMAdult (>18 years old)Both
Cardiac arrest
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000545 0.0000(4799 uMNot SpecifiedNot SpecifiedHIV-Seropositive, Dementia details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000500 (0.000452-0.000545) uMNot SpecifiedNot SpecifiedHIV-Seropositive (Neurologically normal) details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothCCD details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothIleal Crohn's disease details
Associated Disorders and Diseases
Disease References
Cardiac arrest
  1. Strohmenger HU, Lindner KH, Keller A, Lindner IM, Bothner U, Georgieff M: Concentrations of prolactin and prostaglandins during and after cardiopulmonary resuscitation. Crit Care Med. 1995 Aug;23(8):1347-55. [PubMed:7634804 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022448
KNApSAcK IDNot Available
Chemspider ID4446204
KEGG Compound IDC00639
BioCyc IDNot Available
BiGG ID35568
Wikipedia LinkProstaglandin F2alpha
METLIN ID6032
PubChem Compound5283078
PDB IDNot Available
ChEBI ID15553
Food Biomarker OntologyNot Available
VMH IDPROSTGF2
MarkerDB IDMDB00000302
Good Scents IDNot Available
References
Synthesis ReferenceChen, Shaoqing; Janda, Kim D. Total synthesis of naturally occurring prostaglandin F2a on a non-crosslinked polystyrene support. Tetrahedron Letters (1998), 39(23), 3943-3946.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Grinsted J, Byskov AG: Meiosis-inducing and meiosis-preventing substances in human male reproductive organs. Fertil Steril. 1981 Feb;35(2):199-204. [PubMed:7202743 ]
  2. Catanzarite VA: Prophylactic intramyometrial carboprost tromethamine does not substantially reduce blood loss relative to intramyometrial oxytocin at routine cesarean section. Am J Perinatol. 1990 Jan;7(1):39-42. [PubMed:2403792 ]
  3. Carr BR, Milburn J Jr, Wright EE, Simpson ER: Adenylate cyclase activity in neocortex and fetal zone membrane fractions of the human fetal adrenal gland. J Clin Endocrinol Metab. 1985 Apr;60(4):718-22. [PubMed:2982905 ]
  4. Negrel R, Gaillard D, Ailhaud G: Prostacyclin as a potent effector of adipose-cell differentiation. Biochem J. 1989 Jan 15;257(2):399-405. [PubMed:2539085 ]
  5. Hammarstrom S, Hamberg M, Samuelsson B, Duell EA, Stawiski M, Voorhees JJ: Increased concentrations of nonesterified arachidonic acid, 12L-hydroxy-5,8,10,14-eicosatetraenoic acid, prostaglandin E2, and prostaglandin F2alpha in epidermis of psoriasis. Proc Natl Acad Sci U S A. 1975 Dec;72(12):5130-4. [PubMed:1061097 ]
  6. Steele GL, Leung PC: Intragonadal signalling mechanisms in the control of steroid hormone production. J Steroid Biochem Mol Biol. 1992 Mar;41(3-8):515-22. [PubMed:1562522 ]
  7. Ciabattoni G, Pugliese F, Spaldi M, Cinotti GA, Patrono C: Radioimmunoassay measurement of prostaglandins E2 and F2alpha in human urine. J Endocrinol Invest. 1979 Apr-Jun;2(2):173-82. [PubMed:489926 ]
  8. Davi G, Chiarelli F, Santilli F, Pomilio M, Vigneri S, Falco A, Basili S, Ciabattoni G, Patrono C: Enhanced lipid peroxidation and platelet activation in the early phase of type 1 diabetes mellitus: role of interleukin-6 and disease duration. Circulation. 2003 Jul 1;107(25):3199-203. Epub 2003 Jun 16. [PubMed:12810609 ]
  9. Komoto J, Yamada T, Watanabe K, Woodward DF, Takusagawa F: Prostaglandin F2alpha formation from prostaglandin H2 by prostaglandin F synthase (PGFS): crystal structure of PGFS containing bimatoprost. Biochemistry. 2006 Feb 21;45(7):1987-96. [PubMed:16475787 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
NADPH-dependent reductase with broad substrate specificity. Catalyzes the reduction of a wide variety of carbonyl compounds including quinones, prostaglandins, menadione, plus various xenobiotics. Catalyzes the reduction of the antitumor anthracyclines doxorubicin and daunorubicin to the cardiotoxic compounds doxorubicinol and daunorubicinol. Can convert prostaglandin E2 to prostaglandin F2-alpha. Can bind glutathione, which explains its higher affinity for glutathione-conjugated substrates. Catalyzes the reduction of S-nitrosoglutathione.
Gene Name:
CBR1
Uniprot ID:
P16152
Molecular weight:
30374.73
Reactions
Prostaglandin F2a + NADP → Prostaglandin E2 + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Has low NADPH-dependent oxidoreductase activity towards 4-benzoylpyridine and menadione (in vitro).
Gene Name:
CBR3
Uniprot ID:
O75828
Molecular weight:
30849.97
Reactions
Prostaglandin F2a + NADP → Prostaglandin E2 + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Prostaglandin inactivation. Contributes to the regulation of events that are under the control of prostaglandin levels. Catalyzes the NAD-dependent dehydrogenation of lipoxin A4 to form 15-oxo-lipoxin A4. Inhibits in vivo proliferation of colon cancer cells.
Gene Name:
HPGD
Uniprot ID:
P15428
Molecular weight:
28977.105