cobicistat   Click here for help

GtoPdb Ligand ID: 7535

Synonyms: GS-9350
Approved drug PDB Ligand
cobicistat is an approved drug (FDA (2012), EMA (2013))
Compound class: Synthetic organic
Comment: This compound is approved as a component of the so-called 'Quad pill' (Stribild®), an anti-HIV therapy which contains cobicistat, elvitegravir, emtricitabine, and tenofovir.
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 12
Hydrogen bond donors 3
Rotatable bonds 24
Topological polar surface area 194.5
Molecular weight 775.35
XLogP 3.7
No. Lipinski's rules broken 2

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 O=C(NC(Cc1ccccc1)CCC(Cc1ccccc1)NC(=O)C(NC(=O)N(Cc1csc(n1)C(C)C)C)CCN1CCOCC1)OCc1cncs1
Isomeric SMILES O=C(N[C@@H](Cc1ccccc1)CC[C@H](Cc1ccccc1)NC(=O)[C@@H](NC(=O)N(Cc1csc(n1)C(C)C)C)CCN1CCOCC1)OCc1cncs1
InChI InChI=1S/C40H53N7O5S2/c1-29(2)38-43-34(27-53-38)25-46(3)39(49)45-36(16-17-47-18-20-51-21-19-47)37(48)42-32(22-30-10-6-4-7-11-30)14-15-33(23-31-12-8-5-9-13-31)44-40(50)52-26-35-24-41-28-54-35/h4-13,24,27-29,32-33,36H,14-23,25-26H2,1-3H3,(H,42,48)(H,44,50)(H,45,49)/t32-,33-,36+/m1/s1
InChI Key ZCIGNRJZKPOIKD-CQXVEOKZSA-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
Approved drug? Yes (FDA (2012), EMA (2013))
IUPAC Name Click here for help
1,3-thiazol-5-ylmethyl N-[(2R,5R)-5-[[(2S)-2-[[methyl-[(2-propan-2-yl-1,3-thiazol-4-yl)methyl]carbamoyl]amino]-4-morpholin-4-ylbutanoyl]amino]-1,6-diphenylhexan-2-yl]carbamate
International Nonproprietary Names Click here for help
INN number INN
9266 cobicistat
Synonyms Click here for help
GS-9350
Database Links Click here for help
CAS Registry No. 1004316-88-4
ChEBI CHEBI:72291
ChEMBL Ligand CHEMBL2095208
DrugCentral Ligand 4299
GtoPdb PubChem SID 187051836
PubChem CID 25151504
RCSB PDB Ligand A1APA
Search Google for chemical match using the InChIKey ZCIGNRJZKPOIKD-CQXVEOKZSA-N
Search Google for chemicals with the same backbone ZCIGNRJZKPOIKD
Search PubMed clinical trials cobicistat
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UniChem Compound Search for chemical match using the InChIKey ZCIGNRJZKPOIKD-CQXVEOKZSA-N
UniChem Connectivity Search for chemical match using the InChIKey ZCIGNRJZKPOIKD-CQXVEOKZSA-N
Wikipedia Cobicistat