obicetrapib   Click here for help

GtoPdb Ligand ID: 12205

Synonyms: AMG-899 | DEZ-001 | TA-8995 | TA8995
Compound class: Synthetic organic
Comment: Obicetrapib is a clinical lead, orally bioavailable, small molecule, cholesterol ester transfer protein (CETP; P11597) inhibitor [1]. It was developed as a treament for dyslipidemia. Agents of the CETP inhibitor class are proposed to increase HDL cholesterol, lower LDL cholesterol, and enhance reverse cholesterol transport, as a mechanism to reduce the risks of elevated cholesterol on atherosclerosis. Prior to the re-launching of trials involving obicetrapib by NewAmsterdam Pharma, no CETP inhibitor had demonstrated sufficient safety and/or efficacy in a clinical study to warrant continued development [2].
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 8
Hydrogen bond donors 1
Rotatable bonds 16
Topological polar surface area 105.09
Molecular weight 722.22
XLogP 7.73
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 CCOC(=O)N1[C@H](CC)C[C@@H](c2c1ccc(c2)C(F)(F)F)N(c1ncc(cn1)OCCCC(=O)O)Cc1cc(cc(c1)C(F)(F)F)C(F)(F)F
Isomeric SMILES CC[C@@H]1C[C@@H](c2c(N1C(=O)OCC)ccc(c2)C(F)(F)F)N(Cc1cc(cc(c1)C(F)(F)F)C(F)(F)F)c1ncc(cn1)OCCCC(=O)O
InChI InChI=1S/C32H31F9N4O5/c1-3-22-14-26(24-13-19(30(33,34)35)7-8-25(24)45(22)29(48)49-4-2)44(28-42-15-23(16-43-28)50-9-5-6-27(46)47)17-18-10-20(31(36,37)38)12-21(11-18)32(39,40)41/h7-8,10-13,15-16,22,26H,3-6,9,14,17H2,1-2H3,(H,46,47)/t22-,26+/m1/s1
InChI Key NRWORBQAOQVYBJ-GJZUVCINSA-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
4-[2-[[3,5-bis(trifluoromethyl)phenyl]methyl-[(2R,4S)-1-ethoxycarbonyl-2-ethyl-6-(trifluoromethyl)-3,4-dihydro-2H-quinolin-4-yl]amino]pyrimidin-5-yl]oxybutanoic acid
International Nonproprietary Names Click here for help
INN number INN
9979 obicetrapib
Synonyms Click here for help
AMG-899 | DEZ-001 | TA-8995 | TA8995
Database Links Click here for help
CAS Registry No. 866399-87-3 (source: WHO INN record)
ChEMBL Ligand CHEMBL3785197
DrugBank Ligand DB14890
GtoPdb PubChem SID 472319325
PubChem CID 11498596
Search Google for chemical match using the InChIKey NRWORBQAOQVYBJ-GJZUVCINSA-N
Search Google for chemicals with the same backbone NRWORBQAOQVYBJ
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UniChem Compound Search for chemical match using the InChIKey NRWORBQAOQVYBJ-GJZUVCINSA-N
UniChem Connectivity Search for chemical match using the InChIKey NRWORBQAOQVYBJ-GJZUVCINSA-N