dihydrobetulinic acid

CHEBI:65485 ·resolve ·ANTIPROTOZOAL ·EXACT SEEDED

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

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:25872 CHEBI:25872
CHEBI:35868 CHEBI:35868

Chemical structure

Computed structure properties
Molecular formula	C30H50O3
Charge	0
Average mass	458.727 Da
Monoisotopic mass	458.376 Da
Source	ChEBI
InChIKey	PZXJOHSZQAEJFE-FZFNOLFKSA-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](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

Equivalent identifiers for this same structure in other resources.

cas:25488-53-3
patent:US5679828
reaxys:2678211

Activity roles

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

CHEBI:64946 CHEBI:64946
CHEBI:70868 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.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:65485`	dihydrobetulinic acid	`antibioticmech:chebi-d89a7ded3b`	2026-08-30

Mechanism summary

Mode of action: NUCLEIC_ACID_SYNTHESIS_INHIBITION host shared target — Assigned from ChEBI role CHEBI:50750 (EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor). ChEBI asserts the role on the compound. The target it names is one the host has too, so the mechanism is true but is not evidence of selectivity — 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.