misoprostol (free acid form)   

GtoPdb Ligand ID: 1935

Synonyms: misoprostol acid | SC 30695
Compound class: Synthetic organic
Comment: Active metabolite of the approved drug misoprostol (methyl ester).
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 13
Topological polar surface area 94.83
Molecular weight 368.26
XLogP 3.25
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES CCCCC(CC=CC1C(O)CC(=O)C1CCCCCCC(=O)O)(O)C
Isomeric SMILES CCCCC(C/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)O)(O)C
InChI InChI=1S/C21H36O5/c1-3-4-13-21(2,26)14-9-11-17-16(18(22)15-19(17)23)10-7-5-6-8-12-20(24)25/h9,11,16-17,19,23,26H,3-8,10,12-15H2,1-2H3,(H,24,25)/b11-9+/t16-,17-,19-,21?/m1/s1
InChI Key CNWGPXZGIIOYDL-MKYGPDKMSA-N
Classification
Compound class Synthetic organic
Prodrug misoprostol (methyl ester)
IUPAC Name
7-[(1R,2R,3R)-3-hydroxy-2-[(E)-4-hydroxy-4-methyloct-1-enyl]-5-oxocyclopentyl]heptanoic acid
International Nonproprietary Names
INN number INN
5154 misoprostol
Synonyms
misoprostol acid | SC 30695
Comments
Active metabolite of the approved drug misoprostol (methyl ester).
Database Links
CAS Registry No. 59122-46-2 (source: Scifinder)
ChEMBL Ligand CHEMBL1201377
GtoPdb PubChem SID 135650610
PubChem CID 6436406
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Wikipedia Misoprostol