bevirimat

CHEBI:65484 ·resolve ·ANTIVIRAL ·EXACT REVIEWED

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

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:25384
Label unavailable CHEBI:25872
Label unavailable 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

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

cas:174022-42-5
reaxys:7504927

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

wikipedia.en:Bevirimat

Activity roles

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

HIV-1 maturation inhibitor 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

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

HIV-1 Gag CA-SP1 cleavage-site region in immature particles VIRAL_PROTEIN DIRECT_BINDING_TARGET

Photoaffinity bevirimat analog crosslinking in immature virus-like particles and mass spectrometry mapped interactions at or near CA-SP1 and in the major homology region. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2011-12 (retrieved 2026-09-02).

PMID:22151792 (Primary direct-interaction mapping study in immature Gag particles.)

Mechanism summary

Mode of action: VIRAL_ASSEMBLY_INHIBITION microbial target — CURATOR: PMID:22151792 used bevirimat photoaffinity analogs and mass spectrometry to demonstrate direct binding in immature HIV-1 Gag at or near the CA-SP1 cleavage site. This blocks the final protease-mediated Gag cleavage and produces immature, noninfectious particles; it does not inhibit the viral protease active site.

Resistance mechanisms

1 source-backed resistance determinants or associations, with ARO grounding where reported. Grouped by reported mechanism type.

ANTIBIOTIC_TARGET_ALTERATION 1

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
HIV-1 Gag CA-SP1 cleavage-site substitutions Resistance substitutions cluster at or near the CA-SP1 cleavage site. SP1-A1V remained robustly replicative under bevirimat, while SP1-V7A caused high-level resistance and V7M or T8 deletion caused intermediate resistance. Species-grounding update (2026-10-14): the existing HIV-1 claim is placed in Lentivirus humimdef1 (NCBITaxon:3418650). UniProt's Human immunodeficiency virus type 1 node NCBITaxon:11676 is unranked beneath that species, not itself a species-rank node. The 2010 paper's Results and Conclusions describe laboratory comparisons in the NL4-3 background; that background is not an exact identifier for the tested derivatives or a patient-isolate assignment. This update does not revalidate every inherited variant assertion or the tested compound's exact formulation. No protein accession, strain TaxID, experimental genome or normalized allele is assigned.	—	Lentivirus humimdef1 `NCBITaxon:3418650`	HIV-1 Gag CA-SP1	PMID:19279107 (Primary in-vitro resistance-evolution study.) PMID:20406463 (Primary mutational susceptibility study.) https://rest.uniprot.org/taxonomy/3418650 (Species context only: UniProt release 2026_03, retrieved 2026-10-14, identifies active species Lentivirus humimdef1, NCBITaxon:3418650. The separately pinned native taxonomy/11676 response (retrieved 2026-10-08, same release) identifies HIV-1 as an active unranked child of this species. These taxonomy records do not establish experimental strain, protein, allele, genome or patient identity.)

Record-level evidence

PMID:22151792 (Primary direct-target and maturation-mechanism study.)
PMID:19279107 (Primary in-vitro resistance-evolution study.)
PMID:20406463 (Primary CA-SP1 polymorphism and susceptibility study.)

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
REVIEWED 2026-09-02 · codex · LLM-assisted
Verified exact ChEBI identity, structure, and antiviral class; added direct HIV-1 Gag CA-SP1 binding, the maturation mechanism, and compound-specific target-alteration resistance evidence.
RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories
GROUNDED_RESISTANCE_TAXONOMY 2026-10-14 · codex · LLM-assisted
Grounded the existing bevirimat HIV-1 resistance claim at species rank as Lentivirus humimdef1 (NCBITaxon:3418650), using the cited 2010 primary organism context and UniProt taxonomy release 2026_03. Preserved the original mechanism, gene-family label, variant wording and primary citations. Distinguished the unranked HIV-1 node and laboratory background from experimental identities. Added no protein, strain, genome, normalized allele or numeric AST; whole-record review and exact compound formulation remain open.

Provenance

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

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