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bevirimat

Go to external page http://purl.obolibrary.org/obo/CHEBI_65484

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.

Term info

Label

bevirimat

Synonyms
  • (3beta)-3-[(3-carboxy-3-methylbutanoyl)oxy]lup-20(29)-en-28-oic acid
database cross reference
Subsets

3_STAR

INN
bevirimatum [ WHO_MedNet ]

INN
bevirimat [ ChemIDplus ]

IUPAC NAME
(3beta)-3-[(3-carboxy-3-methylbutanoyl)oxy]lup-20(29)-en-28-oic acid [ IUPAC ]

INN
bevirimat [ WHO_MedNet ]

charge

0

formula

C36H56O6

has obo namespace

chebi_ontology

has related synonym

PA-457, bevirimatum, BVM, 3-O-(3',3'-dimethylsuccinyl) betulinic acid, bevirimat

id

CHEBI:65484

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

mass

584.82620

monoisotopicmass

584.40769

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