Bevirimat
(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-(3-carboxy-3-methylbutanoyl)oxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
Molecular Identity
Bevirimat
(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-(3-carboxy-3-methylbutanoyl)oxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
PubChem CID: 457928
Bevirimat is 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. It has a role as a metabolite and a HIV-1 maturation inhibitor. It is a monocarboxylic acid, a pentacyclic triterpenoid and a dicarboxylic acid monoester. It is functionally related to a betulinic acid.
2D Structure
Properties
C36H56O6
Molecular Formula
584.80
Molecular Weight
g/mol
584.4077
Exact Mass
Da
9.1
XLogP
Above Lipinski threshold
101
TPSA
Good oral absorption (< 140 A²)
2
H-Bond Donors
6
H-Bond Acceptors
1170
Complexity
SMILES
Canonical SMILES
SMILES: Synonyms(20)
Bevirimat174022-42-5PA-457YK-FH312bevirimatumS125DW66N83-O-(3',3'-Dimethylsuccinyl)betulinic acid3-O-(3',3'-dimethylsuccinyl) betulinic acidPA-103001CHEBI:65484DTXSID20169749(3beta)-3-[(3-carboxy-3-methylbutanoyl)oxy]lup-20(29)-en-28-oic acid(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-(3-carboxy-3-methylbutanoyl)oxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid(3beta)-3-((3-carboxy-3-methylbutanoyl)oxy)lup-20(29)-en-28-oic aciddsb-2nmg
Data from PubChem (NCBI)
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