latanoprost (free acid form)   Click here for help

GtoPdb Ligand ID: 1960

Synonyms: latanoprost-free acid | PHXA85
Approved drug
latanoprost (free acid form) is an approved drug (FDA (1996))
Compound class: Synthetic organic
Comment: The active free acid form of latanoprost results from metabolism of the prodrug latanoprost (isopropyl ester).
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 5
Hydrogen bond donors 4
Rotatable bonds 12
Topological polar surface area 97.99
Molecular weight 390.24
XLogP 3.19
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES OC(CCc1ccccc1)CCC1C(O)CC(C1CC=CCCCC(=O)O)O
Isomeric SMILES O[C@@H](CCc1ccccc1)CC[C@H]1[C@H](O)C[C@@H]([C@@H]1C/C=C\CCCC(=O)O)O
InChI InChI=1S/C23H34O5/c24-18(13-12-17-8-4-3-5-9-17)14-15-20-19(21(25)16-22(20)26)10-6-1-2-7-11-23(27)28/h1,3-6,8-9,18-22,24-26H,2,7,10-16H2,(H,27,28)/b6-1-/t18-,19+,20+,21-,22+/m0/s1
InChI Key HNPFPERDNWXAGS-NFVOFSAMSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1996))
Prodrug latanoprost (isopropyl ester)
IUPAC Name Click here for help
(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoic acid
Synonyms Click here for help
latanoprost-free acid | PHXA85
Database Links Click here for help
ChEBI CHEBI:63925
ChEMBL Ligand CHEMBL1050
GtoPdb PubChem SID 135650508
PubChem CID 6441636
Search Google for chemical match using the InChIKey HNPFPERDNWXAGS-NFVOFSAMSA-N
Search Google for chemicals with the same backbone HNPFPERDNWXAGS
UniChem Compound Search for chemical match using the InChIKey HNPFPERDNWXAGS-NFVOFSAMSA-N
UniChem Connectivity Search for chemical match using the InChIKey HNPFPERDNWXAGS-NFVOFSAMSA-N