cilomilast   Click here for help

GtoPdb Ligand ID: 7407

Synonyms: SB-207499
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: There is some ambiguity in the literature and on other database as to the exact structure of Cilomilast. The structure shown here matches that of the INN document, but the compound is represented on PubChem without specified stereochemistry by CID 151170.

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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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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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 3
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 79.55
Molecular weight 343.18
XLogP 3.09
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES N#CC1(CCC(CC1)C(=O)O)c1ccc(c(c1)OC1CCCC1)OC
Isomeric SMILES N#C[C@@]1(CC[C@@H](CC1)C(=O)O)c1ccc(c(c1)OC1CCCC1)OC
InChI InChI=1S/C20H25NO4/c1-24-17-7-6-15(12-18(17)25-16-4-2-3-5-16)20(13-21)10-8-14(9-11-20)19(22)23/h6-7,12,14,16H,2-5,8-11H2,1H3,(H,22,23)/t14-,20-
InChI Key CFBUZOUXXHZCFB-OYOVHJISSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(1s,4s)-4-cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]cyclohexane-1-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
7960 cilomilast
Synonyms Click here for help
SB-207499
Database Links Click here for help
CAS Registry No. 153259-65-5
ChEMBL Ligand CHEMBL511115
GtoPdb PubChem SID 178103979
PubChem CID 151170
RCSB PDB Ligand CIO
Search Google for chemical match using the InChIKey CFBUZOUXXHZCFB-OYOVHJISSA-N
Search Google for chemicals with the same backbone CFBUZOUXXHZCFB
Search PubMed clinical trials cilomilast
Search PubMed titles cilomilast
Search PubMed titles/abstracts cilomilast
UniChem Compound Search for chemical match using the InChIKey CFBUZOUXXHZCFB-OYOVHJISSA-N
UniChem Connectivity Search for chemical match using the InChIKey CFBUZOUXXHZCFB-OYOVHJISSA-N
Wikipedia Cilomilast

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MedChemExpress
Cilomilast (links to external site)
Cat. No. HY-10790