betulinic acid
CHEBI:3087
·resolve ·ANTIPROTOZOAL
·EXACT
SEEDED
A pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3β-hydroxy and 28-carboxy substituents. It is found in the bark and other plant parts of several species of plants including Syzygium claviflorum. It exhibits anti-HIV, antimalarial, antineoplastic and anti-inflammatory properties. — 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.
Chemical structure
Computed structure properties
| Molecular formula | C30H48O3 |
|---|
| Charge | 0 |
|---|
| Average mass | 456.711 Da |
|---|
| Monoisotopic mass | 456.36035 Da |
|---|
| Source | ChEBI |
|---|
| InChIKey | QGJZLNKBHJESQX-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/C30H48O3/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/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1
Also called
- 3β-hydroxylup-20(29)-en-28-oic acid (EXACT_SYNONYM)— chebi
- Betulinic acid (EXACT_SYNONYM)— chebi
- Mairin (EXACT_SYNONYM)— chebi
Cross-references
Equivalent identifiers for this same structure in other resources.
- cas:472-15-1
- hmdb:HMDB0030094
- kegg.compound:C08619
- knapsack:C00003741
- lipidmaps:LMPR0106140004
- patent:RU2445317
- patent:RU2458933
- patent:US2012237629
- reaxys:2711110
- wikipedia.en:Betulinic_acid
Activity roles
Every antimicrobial role a source asserts for this compound — the
unreduced evidence behind its antimicrobial_class.
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:3087 |
betulinic acid |
antibioticmech:chebi-11d66592fe |
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.