amelubant   Click here for help

GtoPdb Ligand ID: 8463

Synonyms: BIIL 284 | BIIL-284
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Amebulant is a leukotriene B4 (BLT1) receptor antagonist prodrug [1].
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 4
Hydrogen bond donors 3
Rotatable bonds 13
Topological polar surface area 100.87
Molecular weight 538.25
XLogP 8.45
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 CCOC(=O)NC(=N)c1ccc(cc1)OCc1cccc(c1)COc1ccc(cc1)C(c1ccc(cc1)O)(C)C
Isomeric SMILES CCOC(=O)NC(=N)c1ccc(cc1)OCc1cccc(c1)COc1ccc(cc1)C(c1ccc(cc1)O)(C)C
InChI InChI=1S/C33H34N2O5/c1-4-38-32(37)35-31(34)25-8-16-29(17-9-25)39-21-23-6-5-7-24(20-23)22-40-30-18-12-27(13-19-30)33(2,3)26-10-14-28(36)15-11-26/h5-20,36H,4,21-22H2,1-3H3,(H2,34,35,37)
InChI Key SBVYURPQULDJTI-UHFFFAOYSA-N
Immunopharmacology Disease
Disease X-Refs Comment References
Rheumatoid arthritis Disease Ontology: DOID:7148
OMIM: 180300
 No progress in development beyond Phase 2 trial in RA.
Asthma Disease Ontology: DOID:2841
OMIM: 600807
 No progress in development beyond Phase 2 trial in asthma.
Chronic obstructive pulmonary disease Disease Ontology: DOID:3083
 No progress in development beyond Phase 2 trial in COPD.