2α,19α-dihydroxy-3-oxo-12-ursen-28-oic acid

CHEBI:65783 ·resolve ·ANTIVIRAL ·EXACT SEEDED

A pentacyclic triterpenoid that is urs-12-ene substituted by a carboxy group at position 28, α-configured hydroxy groups at positions 2 and 19 and an oxo group at position 3. Isolated from the whole plants of Geum japonicum, it exhibits activity against HIV-1 protease. — 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:23824 CHEBI:23824
CHEBI:2468 CHEBI:2468
CHEBI:25872 CHEBI:25872
CHEBI:35871 CHEBI:35871

Chemical structure

Computed structure properties
Molecular formula	C30H46O5
Charge	0
Average mass	486.693 Da
Monoisotopic mass	486.33452 Da
Source	ChEBI
InChIKey	LJORXTIGOHMBOS-OTRVPSFMSA-N

SMILES

[H][C@]12CC=C3[C@@]4([H])[C@](C(=O)O)(CC[C@@H](C)[C@@]4(C)O)CC[C@@]3(C)[C@]1(C)CC[C@@]1([H])C(C)(C)C(=O)[C@H](O)C[C@]21C

InChI

InChI=1S/C30H46O5/c1-17-10-13-30(24(33)34)15-14-27(5)18(22(30)29(17,7)35)8-9-21-26(4)16-19(31)23(32)25(2,3)20(26)11-12-28(21,27)6/h8,17,19-22,31,35H,9-16H2,1-7H3,(H,33,34)/t17-,19-,20+,21-,22-,26+,27-,28-,29-,30+/m1/s1

Also called

(2α)-2,19-dihydroxy-3-oxours-12-en-28-oic acid (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

chemspider:552868
reaxys:8885609

Activity roles

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

CHEBI:35660 CHEBI:35660

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:65783`	2α,19α-dihydroxy-3-oxo-12-ursen-28-oic acid	`antibioticmech:chebi-4c3af6600f`	2026-08-30

Mechanism summary

Mode of action: VIRAL_PROTEASE_INHIBITION microbial target — Assigned from ChEBI role CHEBI:35660 (HIV protease 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.