travoprost   

GtoPdb Ligand ID: 7102

Synonyms: AL-6221 | Travatan®
travoprost is an approved drug (EMA and FDA (2001))
Comment: Travoprost is an analogue of prostaglindin F (PGF). The drug itself is a prodrug that is hydrolysed in vivo to an active free acid form.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 14
Topological polar surface area 96.22
Molecular weight 500.24
XLogP 4.57
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES CC(OC(=O)CCCC=CCC1C(O)CC(C1C=CC(COc1cccc(c1)C(F)(F)F)O)O)C
Isomeric SMILES CC(OC(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@H]([C@@H]1/C=C/[C@H](COc1cccc(c1)C(F)(F)F)O)O)C
InChI InChI=1S/C26H35F3O6/c1-17(2)35-25(33)11-6-4-3-5-10-21-22(24(32)15-23(21)31)13-12-19(30)16-34-20-9-7-8-18(14-20)26(27,28)29/h3,5,7-9,12-14,17,19,21-24,30-32H,4,6,10-11,15-16H2,1-2H3/b5-3-,13-12+/t19-,21-,22-,23+,24-/m1/s1
InChI Key MKPLKVHSHYCHOC-AHTXBMBWSA-N
Classification
Compound class Natural product or derivative
Approved drug? Yes (EMA and FDA (2001))
IUPAC Name
propan-2-yl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-en-1-yl]cyclopentyl]hept-5-enoate
International Nonproprietary Names
INN number INN
7775 travoprost
Synonyms
AL-6221 | Travatan®
Comments
Travoprost is an analogue of prostaglindin F (PGF). The drug itself is a prodrug that is hydrolysed in vivo to an active free acid form.
Database Links
CAS Registry No. 157283-68-6
ChEBI CHEBI:746859
ChEMBL Ligand CHEMBL1200799
DrugBank Ligand DB00287
DrugCentral Ligand 2716
GtoPdb PubChem SID 178103680
PubChem CID 5282226
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Tocris
Travaprost
Cat. No. 4218