PGE1   Click here for help

GtoPdb Ligand ID: 1882

Synonyms: Alprostadil® | MR-256 | prostaglandin E1
Approved drug PDB Ligand
PGE1 is an approved drug (FDA (1981))
Compound class: Metabolite
Comment: PGE1 is an endogenous prostaglandin. Synthetic PGE1 is known as alprostadil. PGE1 activates prostanoid family GPCRs.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 13
Topological polar surface area 94.83
Molecular weight 354.24
XLogP 3.31
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES CCCCCC(C=CC1C(O)CC(=O)C1CCCCCCC(=O)O)O
Isomeric SMILES CCCCC[C@@H](/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)O)O
InChI 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/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16+,17+,19+/m0/s1
InChI Key GMVPRGQOIOIIMI-DWKJAMRDSA-N
Classification Click here for help
Compound class Metabolite
Approved drug? Yes (FDA (1981))
IUPAC Name Click here for help
7-[(1R,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]heptanoic acid
International Nonproprietary Names Click here for help
INN number INN
4425 alprostadil
Synonyms Click here for help
Alprostadil® | MR-256 | prostaglandin E1
Database Links Click here for help
Specialist databases
GPCRdb Ligand PGE1
Other databases
BindingDB Ligand 50101853
CAS Registry No. 745-65-3
ChEBI CHEBI:15544
ChEMBL Ligand CHEMBL495
DrugBank Ligand DB00770
DrugCentral Ligand 138
GtoPdb PubChem SID 135650814
LIPID MAPS LMFA03010134
PubChem CID 5280723
RCSB PDB Ligand XPG
Search Google for chemical match using the InChIKey GMVPRGQOIOIIMI-DWKJAMRDSA-N
Search Google for chemicals with the same backbone GMVPRGQOIOIIMI
Search PubMed clinical trials alprostadil
Search PubMed titles alprostadil
Search PubMed titles/abstracts alprostadil
UniChem Compound Search for chemical match using the InChIKey GMVPRGQOIOIIMI-DWKJAMRDSA-N
UniChem Connectivity Search for chemical match using the InChIKey GMVPRGQOIOIIMI-DWKJAMRDSA-N
Wikipedia Prostaglandin_E1

Product suppliers

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Tocris
Alprostadil (links to external site)
Cat. No. 1620