madecassic acid

CHEBI:73058 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A pentacyclic triterpenoid that is ursane substituted by a carboxy group at position 28 and hydroxy groups at positions 2, 3, 6 and 23 (the 2α,3β,6β stereoisomer). — 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:25384 CHEBI:25384
CHEBI:25872 CHEBI:25872
CHEBI:33573 CHEBI:33573

Chemical structure

Computed structure properties
Molecular formula	C30H48O6
Charge	0
Average mass	504.708 Da
Monoisotopic mass	504.34509 Da
Source	ChEBI
InChIKey	PRAUVHZJPXOEIF-AOLYGAPISA-N

SMILES

[H][C@]12CC=C3[C@@](C)(CC[C@@]4(C(=O)O)CC[C@@H](C)[C@H](C)[C@@]34[H])[C@]1(C)C[C@@H](O)[C@]1([H])[C@]2(C)C[C@@H](O)[C@H](O)[C@@]1(C)CO

InChI

InChI=1S/C30H48O6/c1-16-9-10-30(25(35)36)12-11-28(5)18(22(30)17(16)2)7-8-21-26(3)13-20(33)24(34)27(4,15-31)23(26)19(32)14-29(21,28)6/h7,16-17,19-24,31-34H,8-15H2,1-6H3,(H,35,36)/t16-,17+,19-,20-,21-,22+,23-,24+,26-,27+,28-,29-,30+/m1/s1

Also called

(2α,3β,6β)-2,3,6,23-tetrahydroxyurs-12-en-28-oic acid (EXACT_SYNONYM)— chebi
6β-hydroxyasiatic acid (EXACT_SYNONYM)— chebi
brahmic acid (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:18449-41-7
drugbank:DB14037
hmdb:HMDB0036670
knapsack:C00051418
lipidmaps:LMPR0106180009
patent:CN101991578
patent:FR2963553
patent:TW200938215
reaxys:3041357

Activity roles

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

CHEBI:33282 CHEBI:33282

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:73058`	madecassic acid	`antibioticmech:chebi-ee8f1c47bb`	2026-08-30

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.