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))
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 Natural product or derivative
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
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
PubChem CID 5280723
RCSB PDB Ligand XPG
Search Google for chemical match using the InChIKey GMVPRGQOIOIIMI-DWKJAMRDSA-N
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Search PubMed clinical trials alprostadil
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Search PubMed titles/abstracts alprostadil
Search UniChem for chemical match using the InChIKey GMVPRGQOIOIIMI-DWKJAMRDSA-N
Search UniChem for chemicals with the same backbone GMVPRGQOIOIIMI
Wikipedia Prostaglandin_E1

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Tocris
Alprostadil
Cat. No. 1620