CHEBI:52717 - bortezomib

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ChEBI Name bortezomib
ChEBI ID CHEBI:52717
Definition L-Phenylalaninamide substituted at the amide nitrogen by a 1-(dihydroxyboranyl)-3-methylbutyl group and at Nα by a pyrazin-2-ylcarbonyl group. It is a dipeptidyl boronic acid that reversibly inhibits the 26S proteasome.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:41143
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Formula C19H25BN4O4
Net Charge 0
Average Mass 384.23700
Monoisotopic Mass 384.197
InChI InChI=1S/C19H25BN4O4/c1-13(2)10-17(20(27)28)24-18(25)15(11-14-6-4-3-5-7-14)23-19(26)16-12-21-8-9-22-16/h3-9,12-13,15,17,27-28H,10-11H2,1-2H3,(H,23,26)(H,24,25)/t15-,17-/m0/s1
InChIKey GXJABQQUPOEUTA-RDJZCZTQSA-N
SMILES CC(C)C[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)c1cnccn1)B(O)O
Roles Classification
Biological Role(s): protease inhibitor
A compound which inhibits or antagonizes the biosynthesis or actions of proteases (endopeptidases).
antiprotozoal drug
Any antimicrobial drug which is used to treat or prevent protozoal infections.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
antiprotozoal drug
Any antimicrobial drug which is used to treat or prevent protozoal infections.
proteasome inhibitor
A drug that blocks the action of proteasomes, cellular complexes that break down proteins.
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ChEBI Ontology
Outgoing bortezomib (CHEBI:52717) has functional parent boronic acid (CHEBI:38267)
bortezomib (CHEBI:52717) has role antineoplastic agent (CHEBI:35610)
bortezomib (CHEBI:52717) has role antiprotozoal drug (CHEBI:35820)
bortezomib (CHEBI:52717) has role protease inhibitor (CHEBI:37670)
bortezomib (CHEBI:52717) has role proteasome inhibitor (CHEBI:52726)
bortezomib (CHEBI:52717) is a L-phenylalanine derivative (CHEBI:84144)
bortezomib (CHEBI:52717) is a amino acid amide (CHEBI:22475)
bortezomib (CHEBI:52717) is a pyrazines (CHEBI:38314)
IUPAC Names
[(1R)-3-methyl-1-({(2S)-3-phenyl-2-[(pyrazin-2-ylcarbonyl)amino]propanoyl}amino)butyl]boronic acid
N-[(1R)-1-(dihydroxyboranyl)-3-methylbutyl]-Nα-(pyrazin-2-ylcarbonyl)-L-phenylalaninamide
INN Source
bortezomib ChemIDplus
Synonyms Sources
N-[(1R)-1-(DIHYDROXYBORYL)-3-METHYLBUTYL]-N-(PYRAZIN-2-YLCARBONYL)-L-PHENYLALANINAMIDE PDBeChem
PS 341 ChemIDplus
PS-341 ChemIDplus
Brand Name Source
Velcade DrugBank
Manual Xrefs Databases
391 DrugCentral
BO2 PDBeChem
Bortezomib Wikipedia
D03150 KEGG DRUG
DB00188 DrugBank
LSM-6281 LINCS
View more database links
Registry Numbers Types Sources
179324-69-7 CAS Registry Number ChemIDplus
8723817 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
18484921 PubMed citation Europe PMC
18980173 PubMed citation Europe PMC
21504411 PubMed citation Europe PMC
21865767 PubMed citation Europe PMC
Last Modified
22 February 2017