CHEBI:73058 - madecassic acid

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ChEBI Name madecassic acid
ChEBI ID CHEBI:73058
Definition 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).
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C30H48O6
Net Charge 0
Average Mass 504.69850
Monoisotopic Mass 504.34509
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
InChIKey PRAUVHZJPXOEIF-AOLYGAPISA-N
SMILES [H][C@]12CC=C3[C@]4([H])[C@@H](C)[C@H](C)CC[C@@]4(CC[C@@]3(C)[C@]1(C)C[C@@H](O)[C@@]1([H])[C@](C)(CO)[C@@H](O)[C@H](O)C[C@]21C)C(O)=O
Metabolite of Species Details
Centella asiatica (NCBI:txid48106) See: PubMed
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing madecassic acid (CHEBI:73058) has parent hydride ursane (CHEBI:35711)
madecassic acid (CHEBI:73058) has role antioxidant (CHEBI:22586)
madecassic acid (CHEBI:73058) has role plant metabolite (CHEBI:76924)
madecassic acid (CHEBI:73058) is a monocarboxylic acid (CHEBI:25384)
madecassic acid (CHEBI:73058) is a pentacyclic triterpenoid (CHEBI:25872)
madecassic acid (CHEBI:73058) is a tetrol (CHEBI:33573)
Incoming madecassoside (CHEBI:66651) has functional parent madecassic acid (CHEBI:73058)
IUPAC Name
(2α,3β,6β)-2,3,6,23-tetrahydroxyurs-12-en-28-oic acid
Synonyms Sources
6β-hydroxyasiatic acid ChemIDplus
brahmic acid ChemIDplus
Manual Xrefs Databases
CN101991578 Patent
FR2963553 Patent
HMDB0036670 HMDB
TW200938215 Patent
View more database links
Registry Numbers Types Sources
18449-41-7 CAS Registry Number ChemIDplus
3041357 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
22816768 PubMed citation Europe PMC
22966846 PubMed citation Europe PMC
23346217 PubMed citation Europe PMC
Last Modified
14 April 2015