valategrast   Click here for help

GtoPdb Ligand ID: 11487

Synonyms: R-411 | RO-0272441
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Valategrast (RO-0272441) is an orally available, small molecule α4 integrin inhibitor that was developed by Roche [2]. It is active at α4β1 and α4β7 integrins.
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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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 7
Hydrogen bond donors 2
Rotatable bonds 15
Topological polar surface area 87.74
Molecular weight 603.15
XLogP 7.07
No. Lipinski's rules broken 2
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 CCN(CCOC(=O)[C@@H](NC(=O)c1c(C)cccc1Cl)Cc1ccc(cc1)NC(=O)c1c(Cl)cccc1Cl)CC
Isomeric SMILES CCN(CCOC(=O)[C@@H](NC(=O)c1c(C)cccc1Cl)Cc1ccc(cc1)NC(=O)c1c(Cl)cccc1Cl)CC
InChI InChI=1S/C30H32Cl3N3O4/c1-4-36(5-2)16-17-40-30(39)25(35-28(37)26-19(3)8-6-9-22(26)31)18-20-12-14-21(15-13-20)34-29(38)27-23(32)10-7-11-24(27)33/h6-15,25H,4-5,16-18H2,1-3H3,(H,34,38)(H,35,37)/t25-/m0/s1
InChI Key VZVNFRFMDNFPOM-VWLOTQADSA-N
References
1. Hijazi Y, Welker H, Dorr AE, Tang JP, Blain R, Renzetti LM, Abbas R. (2004)
Pharmacokinetics, safety, and tolerability of R411, a dual alpha4beta1-alpha4beta7 integrin antagonist after oral administration at single and multiple once-daily ascending doses in healthy volunteers.
J Clin Pharmacol, 44 (12): 1368-78. [PMID:15545307]
2. Woodside DG, Vanderslice P. (2008)
Cell adhesion antagonists: therapeutic potential in asthma and chronic obstructive pulmonary disease.
BioDrugs, 22 (2): 85-100. [PMID:18345706]