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
Supplier Information ChemicalBook:CB6851738
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Ozone () (or trioxygen) is an inorganic molecule with the chemical formula O3. It is a pale blue gas with a distinctively pungent smell. It is an allotrope of oxygen that is much less stable than the diatomic allotrope O2, breaking down in the lower atmosphere to O2 (dioxygen). Ozone is formed from dioxygen by the action of ultraviolet (UV) light and electrical discharges within the Earth's atmosphere. It is present in very low concentrations throughout the atmosphere, with its highest concentration high in the ozone layer of the stratosphere, which absorbs most of the Sun's ultraviolet (UV) radiation. Ozone's odor is reminiscent of chlorine, and detectable by many people at concentrations of as little as 0.1 ppm in air. Ozone's O3 structure was determined in 1865. The molecule was later proven to have a bent structure and to be weakly diamagnetic. At standard temperature and pressure, ozone is a pale blue gas that condenses at cryogenic temperatures to a dark blue liquid and finally a violet-black solid. Ozone's instability with regard to more common dioxygen is such that both concentrated gas and liquid ozone may decompose explosively at elevated temperatures, physical shock, or fast warming to the boiling point. It is therefore used commercially only in low concentrations. Ozone is a powerful oxidizing agent (far more so than dioxygen) and has many industrial and consumer applications related to oxidation. This same high oxidizing potential, however, causes ozone to damage mucous and respiratory tissues in animals, and also tissues in plants, above concentrations of about 0.1 ppm. While this makes ozone a potent respiratory hazard and pollutant near ground level, a higher concentration in the ozone layer (from two to eight ppm) is beneficial, preventing damaging UV light from reaching the Earth's surface.
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Formula C19H25BN4O4
Net Charge 0
Average Mass 384.23700
Monoisotopic Mass 384.19689
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
bortezomib UniProt
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 Types Sources
18484921 PubMed citation Europe PMC
18980173 PubMed citation Europe PMC
21504411 PubMed citation Europe PMC
21865767 PubMed citation Europe PMC
Last Modified
07 December 2021