dihydrobetulinic acid

CHEBI:65485 ·resolve ·ANTIPROTOZOAL ·EXACT REVIEWED

A pentacyclic triterpenoid that is lupane having a 3β-hydroxy and 28-carboxy substituents. Isolated from the leaves of Syzygium claviflorum, it exhibits anti-HIV and antileishmanial activity. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

• Label unavailable CHEBI:25872
• Label unavailable CHEBI:35868

Chemical structure

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](O)CC[C@]21C

InChI

InChI=1S/C30H50O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h18-24,31H,8-17H2,1-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1

Also called

• (3β)-3-hydroxylupan-28-oic acid (EXACT_SYNONYM)— chebi
• 20,29-dihydrobetulinic acid (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:25488-53-3
• reaxys:2678211

Patents and articles

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

• patent:US5679828

Activity roles

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

• anti-HIV agent CHEBI:64946
• antileishmanial agent CHEBI:70868

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.

Molecular targets

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

DNA topoisomerases I and II PROTEIN MEASURED_TARGET_ASSOCIATION

Relaxation, decatenation, and enzyme-DNA mobility assays showed dual topoisomerase inhibition and prevention of binary-complex formation, but did not directly measure compound-protein binding. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2003 (retrieved 2026-09-02).

Leishmania donovani NCBITaxon:5661

• PMID:12765337 (Primary dihydrobetulinic-acid antileishmanial and topoisomerase study.)

Mechanism summary

Mode of action

NUCLEIC_ACID_SYNTHESIS_INHIBITION host shared target — CURATOR: PMID:12765337 measured inhibition of Leishmania donovani DNA topoisomerase I relaxation and topoisomerase II decatenation. Dihydrobetulinic acid prevented formation of enzyme-DNA binary complexes without inducing DNA cleavage; it inhibited promastigotes and amastigotes and reduced hamster spleen and liver parasite burden by more than 92%.

Record-level evidence

• PMID:12765337 (Primary exact-dihydrobetulinic-acid cellular, enzyme, apoptosis, and hamster study.)

Curation history

1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Seeded from data/raw/ inventories (CHEBI)

2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

3. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

4. REVIEWED 2026-09-03 · codex · LLM-assisted

   Verified exact ChEBI identity, structure, antileishmanial role, and filing class; curator-confirmed nucleic-acid-synthesis inhibition and added the measured dual-topoisomerase association without overclaiming direct binding.

5. RESEEDED_FROM_SOURCES 2026-09-10 · 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 (YAML).

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