latanoprost (free acid form)   

GtoPdb Ligand ID: 1960

Synonyms: latanoprost-free acid | PHXA85
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).
2D Structure
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Physico-chemical Properties
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
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
Compound class Synthetic organic
Approved drug? Yes (FDA (1996))
Prodrug latanoprost (isopropyl ester)
IUPAC Name
(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoic acid
Synonyms
latanoprost-free acid | PHXA85
Database Links
ChEBI CHEBI:63925
ChEMBL Ligand CHEMBL1050
GtoPdb PubChem SID 135650508
PubChem CID 6441636
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