Metabolite Card

Formula: C20H34O5 (354.2406)
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

Synonyms [en]

Prostaglandin F2a; Prostaglandin F2alpha; cyclosin; PGF2a; Dinoprost; amoglandin

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Prostaglandin F2alpha. 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000016786). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Prostaglandin 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.

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 13535-33-6
  • CAS Registry Number: 23518-25-4
  • CAS Registry Number: 36150-01-3
  • CAS Registry Number: 551-11-1
  • PubChem: 44208919
  • PubChem: 5280363
  • PubChem: 5283078
  • ChEBI: ChEBI:15553
  • ChEBI: ChEBI:187232
  • HMDB: HMDB0001139
  • HMDB: HMDB01139
  • HMDB: HMDB0302209
  • LipidMaps: LMFA03010002
  • LipidMaps: LMFA03010077
  • KEGG: C00639
  • BioCyc: 5Z13E-15S-9-ALPHA11-ALPHA15-TRIHY
  • NCBI MeSH: Dinoprost
  • Wikipedia: Dinoprost
  • Wikipedia: Prostaglandin F2alpha
  • Wikipedia: Prostaglandin_F2alpha
  • DrugBank: DB12789
  • RefMet: RM0153757
  • MoNA: IA000010
  • MoNA: IA000011
  • MoNA: IA000012
  • MoNA: IA000184
  • MoNA: IA000185
  • MoNA: IA000186
  • MoNA: IA000397
  • MoNA: IA000398
  • MoNA: IA000399
  • MoNA: KO001656
  • MoNA: KO001657
  • MoNA: KO001658
  • MoNA: KO001659
  • MoNA: KO001660
  • MoNA: MSJ00046
  • MoNA: UT000352
  • MoNA: UT000353
  • MoNA: UT000354
  • MoNA: UT000355
  • MoNA: UT000356
  • MoNA: UT000357
  • MoNA: UT000358
  • MoNA: UT000359
  • MoNA: UT000360
  • Metlin: METLIN_36085
  • Coconut NaturalProduct: CNP0212610.1
  • Coconut NaturalProduct: CNP0248684.1
  • Coconut NaturalProduct: CNP0248684.5

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R02264 1.1.1.- C00427 + C00005 + C00080<=>C00639 + C00006
KEGG:R02581 1.1.1.184 (5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate:NADP+ 9-oxidoreductase;
KEGG:R02683 1.1.1.141 (5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate:NAD+ 15-oxidoreductase
KEGG:R02684 1.1.1.188 (5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate:NADP+ 11-oxidoreductase
KEGG:R09506 1.11.1.20 thioredoxin:(5Z,9alpha,11alpha,13E,15S)-9,11-epidioxy-15-hydroxy-prosta-5,13-dienoate oxidoreductase
BioCyc:PROSTAGLANDIN-E2-9-REDUCTASE-RXN 1.1.1.189 NADPH + 5Z13E-15S-1115-DIHYDROXY-9-OXOPROS + PROTON --> 5Z13E-15S-9-ALPHA11-ALPHA15-TRIHY + NADP
BioCyc:RXN-21136 1.1.1.188 PROSTAGLANDIN-H2 + NADPH + PROTON --> 5Z13E-15S-9-ALPHA11-ALPHA15-TRIHY + NADP
BioCyc:RXN-12122 1.11.1.20 Red-Thioredoxin + PROSTAGLANDIN-H2 --> Ox-Thioredoxin + 5Z13E-15S-9-ALPHA11-ALPHA15-TRIHY
BioCyc:RXN-21138 1.1.1.141 5Z13E-15S-9-ALPHA11-ALPHA15-TRIHY + NAD --> CPD-22745 + NADH + PROTON
BioCyc:1.1.1.188-RXN 1.1.1.188 5Z13E-15S-9-ALPHA15-DIHYDROXY-11-O + NADPH + PROTON --> 5Z13E-15S-9-ALPHA11-ALPHA15-TRIHY + NADP
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Organism Source

Taxonomy Source

  1. Gersemia fruticosa [ncbi taxid: 134440]
  2. Homo sapiens [ncbi taxid: 9606]
  3. Mus musculus [ncbi taxid: 10090]
  4. Hydropuntia edulis [ncbi taxid: ]

Pathway Synthetic

pathway id name
WikiPathways:WP1311 Folic acid network
WikiPathways:WP1272 Selenium micronutrient network
WikiPathways:WP318 Eicosanoid synthesis
WikiPathways:WP1075 Folate metabolism
WikiPathways:WP3167 Quercetin and Nf-kB / AP-1 induced cell apoptosis
WikiPathways:WP3193 Vitamin B12 metabolism
WikiPathways:WP15 Selenium micronutrient network
WikiPathways:WP1533 Vitamin B12 metabolism
WikiPathways:WP1310 Selenium micronutrient network
WikiPathways:WP374 Prostaglandin synthesis and regulation
WikiPathways:WP854 Eicosanoid synthesis
WikiPathways:WP1090 Eicosanoid synthesis
WikiPathways:WP995 Prostaglandin synthesis and regulation
WikiPathways:WP1318 Eicosanoid synthesis
WikiPathways:WP293 Eicosanoid synthesis
WikiPathways:WP303 Prostaglandin synthesis and regulation
WikiPathways:WP1273 Folic acid network
WikiPathways:WP176 Folate metabolism
WikiPathways:WP98 Prostaglandin synthesis and regulation
WikiPathways:WP2435 Quercetin and Nf-kB / AP-1 induced apoptosis
View All Pathways