bevirimat

CHEBI:65484 ·resolve ·ANTIVIRAL ·EXACT SEEDED

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. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:25384 CHEBI:25384
CHEBI:25872 CHEBI:25872
CHEBI:36244 CHEBI:36244

Chemical structure

Computed structure properties
Molecular formula	C36H56O6
Charge	0
Average mass	584.838 Da
Monoisotopic mass	584.40769 Da
Source	ChEBI
InChIKey	YJEJKUQEXFSVCJ-WRFMNRASSA-N

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

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

Also called

bevirimatum (INN)— chebi
bévirimat (INN)— chebi
(3β)-3-[(3-carboxy-3-methylbutanoyl)oxy]lup-20(29)-en-28-oic acid (EXACT_SYNONYM)— chebi
3-O-(3',3'-dimethylsuccinyl) betulinic acid (EXACT_SYNONYM)— chebi
BVM (EXACT_SYNONYM)— chebi
PA-457 (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:174022-42-5
reaxys:7504927
wikipedia.en:Bevirimat

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:71168 CHEBI:71168

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:65484`	bevirimat	`antibioticmech:chebi-009a7f7ad5`	2026-08-30

Mechanism summary

Mode of action: VIRAL_ASSEMBLY_INHIBITION microbial target — Assigned from ChEBI role CHEBI:71168 (HIV-1 maturation inhibitor). ChEBI asserts the role on the compound. The role names a target specific to the microbe or virus — see mode_of_action_target_scope. Not a curator's mechanistic review.

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.