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CHEBI:65484 - bevirimat

ChEBI IDCHEBI:65484
ChEBI Namebevirimat
Stars
DefinitionA 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.
Last Modified16 November 2012
DownloadsMolfile
FormulaC36H56O6
Net Charge0
Average Mass584.838
Monoisotopic Mass584.40769
SMILES[H][C@]12CC[C@@]3([H])[C@@](C)(CC[C@@]4(C(=O)O)CC[C@@H](C(=C)C)[C@@]43[H])[C@]1(C)CC[C@@]1([H])C(C)(C)[C@@H](OC(=O)CC(C)(C)C(=O)O)CC[C@]21C
InChIInChI=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
InChIKeyYJEJKUQEXFSVCJ-WRFMNRASSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Syzygium claviflorum (ncbitaxon:219860) leaf (BTO:0000713) PubMed (8176401)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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.
ChEBI Ontology
Outgoing Relation(s)
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  Source
bevirimatChemIDplus
bevirimatWHO MedNet
bevirimatumWHO MedNet
bévirimatWHO MedNet
Synonyms  Source
3-O-(3',3'-dimethylsuccinyl) betulinic acidChEBI
PA-457ChEBI
BVMChEBI
Manual XrefsDatabases
BevirimatWikipedia
Registry NumbersSources
Reaxys:7504927Reaxys
CAS:174022-42-5ChemIDplus
Citations