crenigacestat   Click here for help

GtoPdb Ligand ID: 11359

Synonyms: LY-3039478 | LY3039478
PDB Ligand
Compound class: Synthetic organic
Comment: Crenigacestat (LY3039478) is an oral γ-secretase/NOTCH pathway inhibitor that was developed for anti-tumour potential [1]. Structurally, it is a modified four amino acid peptide. It shows some selectivity for NOTCH 1 signalling [4].

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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 8
Hydrogen bond donors 3
Rotatable bonds 10
Topological polar surface area 111.63
Molecular weight 464.17
XLogP 2.59
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 OCCN1C(=O)[C@@H](NC(=O)[C@@H](NC(=O)CCC(F)(F)F)C)c2c(c3c1nccc3)cccc2
Isomeric SMILES OCCN1C(=O)[C@@H](NC(=O)[C@@H](NC(=O)CCC(F)(F)F)C)c2c(c3c1nccc3)cccc2
InChI InChI=1S/C22H23F3N4O4/c1-13(27-17(31)8-9-22(23,24)25)20(32)28-18-15-6-3-2-5-14(15)16-7-4-10-26-19(16)29(11-12-30)21(18)33/h2-7,10,13,18,30H,8-9,11-12H2,1H3,(H,27,31)(H,28,32)/t13-,18-/m0/s1
InChI Key YCBAQKQAINQRFW-UGSOOPFHSA-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
4,4,4-trifluoro-N-[(2S)-1-[[(7S)-5-(2-hydroxyethyl)-6-oxo-7H-pyrido[2,3-d][3]benzazepin-7-yl]amino]-1-oxopropan-2-yl]butanamide
International Nonproprietary Names Click here for help
INN number INN
10655 crenigacestat
Synonyms Click here for help
LY-3039478 | LY3039478
Database Links Click here for help
CAS Registry No. 1421438-81-4 (source: WHO INN record)
ChEMBL Ligand CHEMBL2338397
DrugBank Ligand DB12050
GtoPdb PubChem SID 440816728
PubChem CID 71236992
RCSB PDB Ligand N9C
Search Google for chemical match using the InChIKey YCBAQKQAINQRFW-UGSOOPFHSA-N
Search Google for chemicals with the same backbone YCBAQKQAINQRFW
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UniChem Compound Search for chemical match using the InChIKey YCBAQKQAINQRFW-UGSOOPFHSA-N
UniChem Connectivity Search for chemical match using the InChIKey YCBAQKQAINQRFW-UGSOOPFHSA-N

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MedChemExpress
Crenigacestat (links to external site)
Cat. No. HY-12449