davelizomib   Click here for help

GtoPdb Ligand ID: 12887

Compound class: Synthetic organic
Comment: The structure for davelizomib was obtained from proposed INN list 129 (August 2023) where it is described as a proteasome inhibitor and antineoplastic agent. It is example I-1 in patent JP2021531302A. This patent encompasses use of claimed compounds for the treatment of multiple myeloma, and identifies its potential in MM that is resistant to treatment with the existing proteasome inhibitor bortezomib.
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 CDK toolkit. 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 10
Hydrogen bond donors 3
Rotatable bonds 12
Topological polar surface area 134.27
Molecular weight 481.26
XLogP 1.52
No. Lipinski's rules broken 0
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.

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Canonical SMILES CC(C)C[C@@H](B1O[C@@H](CC(=O)O)C(=O)O1)NC(=O)CNC(=O)[C@@H]2CCN2C3=CC=C(C=C3F)F
Isomeric SMILES B1(O[C@H](C(=O)O1)CC(=O)O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@@H]2CCN2C3=C(C=C(C=C3)F)F
InChI InChI=1S/C21H26BF2N3O7/c1-11(2)7-17(22-33-16(9-19(29)30)21(32)34-22)26-18(28)10-25-20(31)15-5-6-27(15)14-4-3-12(23)8-13(14)24/h3-4,8,11,15-17H,5-7,9-10H2,1-2H3,(H,25,31)(H,26,28)(H,29,30)/t15-,16-,17-/m0/s1
InChI Key BMSAGHWUHGTMIV-ULQDDVLXSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
2-[(4S)-2-[(1R)-1-[[2-[[(2S)-1-(2,4-difluorophenyl)azetidine-2-carbonyl]amino]acetyl]amino]-3-methylbutyl]-5-oxo-1,3,2-dioxaborolan-4-yl]acetic acid
Database Links Click here for help
CAS Registry No. 2409841-51-4 (source: WHO INN record)
GtoPdb PubChem SID 485206008
PubChem CID 147112102
Search Google for chemical match using the InChIKey BMSAGHWUHGTMIV-ULQDDVLXSA-N
Search Google for chemicals with the same backbone BMSAGHWUHGTMIV
UniChem Compound Search for chemical match using the InChIKey BMSAGHWUHGTMIV-ULQDDVLXSA-N
UniChem Connectivity Search for chemical match using the InChIKey BMSAGHWUHGTMIV-ULQDDVLXSA-N