PGI2   

GtoPdb Ligand ID: 1915

Synonyms: prostacyclin | prostacyclin I2 | prostaglandin I2 | vasocyclin
PGI2 is an approved drug (FDA (1995))
Comment: PGI2 is an endogenous prostaglandin. Synthetic PGI2 is known as epoprostenol. PG12 activates prostanoid family GPCRs.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 10
Topological polar surface area 86.99
Molecular weight 352.22
XLogP 2.98
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CCCCCC(C=CC1C(O)CC2C1CC(=CCCCC(=O)O)O2)O
Isomeric SMILES CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@H]2[C@@H]1C/C(=C/CCCC(=O)O)/O2)O
InChI InChI=1S/C20H32O5/c1-2-3-4-7-14(21)10-11-16-17-12-15(8-5-6-9-20(23)24)25-19(17)13-18(16)22/h8,10-11,14,16-19,21-22H,2-7,9,12-13H2,1H3,(H,23,24)/b11-10+,15-8-/t14-,16+,17+,18+,19-/m0/s1
InChI Key KAQKFAOMNZTLHT-OZUDYXHBSA-N
Classification
Compound class Metabolite or derivative
Approved drug? Yes (FDA (1995))
IUPAC Name
(5Z)-5-[(3aR,4R,5R,6aS)-5-hydroxy-4-[(E,3S)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[d]furan-2-ylidene]pentanoic acid
International Nonproprietary Names
INN number INN
4725 epoprostenol
Synonyms
prostacyclin | prostacyclin I2 | prostaglandin I2 | vasocyclin
Database Links
CAS Registry No. 35121-78-9 (source: Scifinder)
ChEBI CHEBI:15552
ChEMBL Ligand CHEMBL1139
DrugBank Ligand DB01240
DrugCentral Ligand 1034
GtoPdb PubChem SID 135651541
PubChem CID 5282411
Search Google for chemical match using the InChIKey KAQKFAOMNZTLHT-OZUDYXHBSA-N
Search Google for chemicals with the same backbone KAQKFAOMNZTLHT
Search PubMed clinical trials epoprostenol
Search PubMed titles epoprostenol
Search PubMed titles/abstracts epoprostenol
Search UniChem for chemical match using the InChIKey KAQKFAOMNZTLHT-OZUDYXHBSA-N
Search UniChem for chemicals with the same backbone KAQKFAOMNZTLHT
Wikipedia Prostacyclin