bavdegalutamide   Click here for help

GtoPdb Ligand ID: 11512

Synonyms: ARV-110 | ARV110 | compound 406 [WO2018071606A1]
Compound class: Synthetic organic
Comment: Bavdegalutamide (ARV110) is a bifunctional degarder class compound (PROTAC). One end of the molecule binds to the androgen receptor and the other binds to the cereblon E3 ligase and directs the AR for proteasome-mediated degradation [1]. It has clinical potential as an oral therapy for metastatic castration-resistant prostate cancer. PubChem CID 134414307 represents the molecule without specified stereo chemistry.

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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 14
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 181.17
Molecular weight 811.3
XLogP 4.78
No. Lipinski's rules broken 1

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#Cc1ccc(cc1Cl)O[C@@H]1CC[C@H](CC1)NC(=O)c1ccc(nn1)N1CCC(CC1)CN1CCN(CC1)c1cc2C(=O)N(C(=O)c2cc1F)C1CCC(=O)NC1=O
Isomeric SMILES N#Cc1ccc(cc1Cl)O[C@@H]1CC[C@H](CC1)NC(=O)c1ccc(nn1)N1CCC(CC1)CN1CCN(CC1)c1cc2C(=O)N(C(=O)c2cc1F)C1CCC(=O)NC1=O
InChI InChI=1S/C41H43ClFN9O6/c42-31-19-28(4-1-25(31)22-44)58-27-5-2-26(3-6-27)45-38(54)33-7-9-36(48-47-33)51-13-11-24(12-14-51)23-49-15-17-50(18-16-49)35-21-30-29(20-32(35)43)40(56)52(41(30)57)34-8-10-37(53)46-39(34)55/h1,4,7,9,19-21,24,26-27,34H,2-3,5-6,8,10-18,23H2,(H,45,54)(H,46,53,55)/t26-,27-,34?
InChI Key CLCTZVRHDOAUGJ-SYVGMNBRSA-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
Ligand families/groups PROTACs, molecular glues and other degraders
IUPAC Name Click here for help
6-[4-({4-[2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxo-2,3-dihydro-1H-isoindol-5-yl]piperazin-1-yl}methyl)piperidin-1-yl]-N-[(1r,4r)-4-(3-chloro-4-cyanophenoxy)cyclohexyl]pyridazine-3-carboxamide
International Nonproprietary Names Click here for help
INN number INN
11542 bavdegalutamide
Synonyms Click here for help
ARV-110 | ARV110 | compound 406 [WO2018071606A1]
Database Links Click here for help
GtoPdb PubChem SID 441604884
PubChem CID 134414307
Search Google for chemical match using the InChIKey CLCTZVRHDOAUGJ-SYVGMNBRSA-N
Search Google for chemicals with the same backbone CLCTZVRHDOAUGJ
Search PubMed clinical trials bavdegalutamide
Search PubMed titles bavdegalutamide
Search PubMed titles/abstracts bavdegalutamide
UniChem Compound Search for chemical match using the InChIKey CLCTZVRHDOAUGJ-SYVGMNBRSA-N
UniChem Connectivity Search for chemical match using the InChIKey CLCTZVRHDOAUGJ-SYVGMNBRSA-N

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MedChemExpress
Bavdegalutamide (links to external site)
Cat. No. HY-138641