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Showing Compound Prostaglandin F2a (FDB022448)

Record Information
Version1.0
Creation date2011-09-21 00:14:11 UTC
Update date2015-07-21 06:57:12 UTC
Primary IDFDB022448
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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 signaling pathways. [HMDB]
CAS Number551-11-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(+)-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
(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,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,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
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
l-PGF2-alphahmdb
l-Prostaglandin F2-alphahmdb
Prostaglandin F2ahmdb
Predicted PropertiesNot Available
Chemical FormulaC20H34O5
IUPAC name
InChI IdentifierInChI=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
Isomeric SMILESCCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C\CCCC(O)=O
Average Molecular Weight354.481
Monoisotopic Molecular Weight354.240624198
Classification
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

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Process

Naturally occurring process:

Role

Industrial application:

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Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MSNot Available
NMRNot Available
ChemSpider ID4446204
ChEMBL IDNot Available
KEGG Compound IDC00639
Pubchem Compound ID5283078
Pubchem Substance IDNot Available
ChEBI ID15553
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01139
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID35568
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Carbonyl reductase [NADPH] 1CBR1P16152
Carbonyl reductase [NADPH] 3CBR3O75828
Pathways
NameSMPDB LinkKEGG Link
Arachidonic Acid MetabolismSMP00075 map00590
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference