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CHEBI:65484 - bevirimat

Default Structure
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:
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.
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
bévirimatWHO MedNet
bevirimatumWHO MedNet
Synonyms  Source
3-O-(3',3'-dimethylsuccinyl) betulinic acidChEBI
BVMChEBI
PA-457ChEBI
Manual XrefsDatabases
BevirimatWikipedia
Registry NumbersSources
Reaxys:7504927Reaxys
CAS:174022-42-5ChemIDplus
Citations