Prostaglandin F2alpha (BioCAD00000016786)
blood cerebrospinal fluid (csf) feces urine adipose tissue adrenal gland epidermis placenta platelet testis
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
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.
DBLinks
- CAS Registry Number: 551-11-1
- PubChem CID: 5283078
- ChEBI: 15553
- HMDB: HMDB0001139
- LipidMaps: LMFA03010002
- KEGG: C00639
- BioCyc: 5Z13E-15S-9-ALPHA11-ALPHA15-TRIHY
- NCBI MeSH: Dinoprost
- Wikipedia: Prostaglandin F2alpha
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
- WishartLab ClassyFire: [Eicosanoids] Eicosanoids
- RefMet: [Prostaglandins] Prostaglandins
- LipidMaps: [Prostaglandins [FA0301]] Prostaglandins [FA0301]
- ChEBI: [CHEBI:15553] prostaglandin F2alpha
- ChEBI: [CHEBI:187232] 5-trans-PGF2alpha
- Coconut NaturalProduct: [Isoprostanes] Isoprostanes
| 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 |
Taxonomy Source
- Gersemia fruticosa [ncbi taxid: 134440]
- Homo sapiens [ncbi taxid: 9606]
- Mus musculus [ncbi taxid: 10090]
- 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 |