CHEBI:65484 - bevirimat

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ChEBI Name bevirimat
ChEBI ID CHEBI:65484
Definition A pentacyclic triterpenoid obtained by the formal condensation of 2,2-dimethylsuccinic acid with the 3-hydroxy group of betulinic acid. It is isolated from the Chinese herb Syzygium claviflorum. The first in the class of HIV-1 maturation inhibitors to be studied in humans, bevirimat was identified as a potent HIV drug candidate and several clinical trials were conducted, but development into a new drug was plagued by numerous resistance-related problems.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C36H56O6
Net Charge 0
Average Mass 584.82620
Monoisotopic Mass 584.40769
InChI InChI=1S/C36H56O6/c1-21(2)22-12-17-36(30(40)41)19-18-34(8)23(28(22)36)10-11-25-33(7)15-14-26(42-27(37)20-31(3,4)29(38)39)32(5,6)24(33)13-16-35(25,34)9/h22-26,28H,1,10-20H2,2-9H3,(H,38,39)(H,40,41)/t22-,23+,24-,25+,26-,28+,33-,34+,35+,36-/m0/s1
InChIKey YJEJKUQEXFSVCJ-WRFMNRASSA-N
SMILES [H][C@]12CC[C@]3([H])[C@@]4(C)CC[C@H](OC(=O)CC(C)(C)C(O)=O)C(C)(C)[C@]4([H])CC[C@@]3(C)[C@]1(C)CC[C@]1(CC[C@@H](C(C)=C)[C@]21[H])C(O)=O
Metabolite of Species Details
Syzygium claviflorum (NCBI:txid219860) Found in leaf (BTO:0000713). See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): HIV-1 maturation inhibitor
A compound that blocks the processing of the Gag precursor protein in HIV-1 by the viral protease enzyme, leading to the formation of noninfectious, immature virus particles that are incapable of infecting other cells.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing bevirimat (CHEBI:65484) has functional parent betulinic acid (CHEBI:3087)
bevirimat (CHEBI:65484) has role HIV-1 maturation inhibitor (CHEBI:71168)
bevirimat (CHEBI:65484) has role metabolite (CHEBI:25212)
bevirimat (CHEBI:65484) is a dicarboxylic acid monoester (CHEBI:36244)
bevirimat (CHEBI:65484) is a monocarboxylic acid (CHEBI:25384)
bevirimat (CHEBI:65484) is a pentacyclic triterpenoid (CHEBI:25872)
IUPAC Name
(3β)-3-[(3-carboxy-3-methylbutanoyl)oxy]lup-20(29)-en-28-oic acid
INNs Sources
bevirimat ChemIDplus
bévirimat WHO MedNet
bevirimat WHO MedNet
bevirimatum WHO MedNet
Synonyms Sources
3-O-(3',3'-dimethylsuccinyl) betulinic acid ChEBI
BVM ChEBI
PA-457 ChEBI
Manual Xref Database
Bevirimat Wikipedia
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Registry Numbers Types Sources
174022-42-5 CAS Registry Number ChemIDplus
7504927 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
16930665 PubMed citation Europe PMC
19024627 PubMed citation Europe PMC
19105849 PubMed citation Europe PMC
19195334 PubMed citation Europe PMC
19279107 PubMed citation Europe PMC
20154583 PubMed citation Europe PMC
20406463 PubMed citation Europe PMC
22151792 PubMed citation Europe PMC
22888428 PubMed citation Europe PMC
8176401 PubMed citation Europe PMC
Last Modified
16 November 2012