travoprost   Click here for help

GtoPdb Ligand ID: 7102

Synonyms: AL-6221 | Travatan®
Approved drug
travoprost is an approved drug (EMA and FDA (2001))
Compound class: Synthetic organic
Comment: Travoprost is an analogue of prostaglindin F2α (PGF2α). 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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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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 Click here for help
Compound class Synthetic organic
Approved drug? Yes (EMA and FDA (2001))
IUPAC Name Click here for help
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 Click here for help
INN number INN
7775 travoprost
Synonyms Click here for help
AL-6221 | Travatan®
Database Links Click here for help
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
Search Google for chemical match using the InChIKey MKPLKVHSHYCHOC-AHTXBMBWSA-N
Search Google for chemicals with the same backbone MKPLKVHSHYCHOC
Search PubMed clinical trials travoprost
Search PubMed titles travoprost
Search PubMed titles/abstracts travoprost
UniChem Compound Search for chemical match using the InChIKey MKPLKVHSHYCHOC-AHTXBMBWSA-N
UniChem Connectivity Search for chemical match using the InChIKey MKPLKVHSHYCHOC-AHTXBMBWSA-N
Wikipedia travoprost

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Tocris
Travaprost (links to external site)
Cat. No. 4218