CHEBI:2873 - asiatic acid

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ChEBI Name asiatic acid
ChEBI ID CHEBI:2873
Definition A pentacyclic triterpenoid that is ursane substituted by a carboxy group at position 28 and hydroxy groups at positions 2, 3 and 23 (the 2α,3β stereoisomer). It is isolated from Symplocos lancifolia and Vateria indica and exhibits anti-angiogenic activity.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:68382
Supplier Information ZINC000072142408
Download Molfile XML SDF
Formula C30H48O5
Net Charge 0
Average Mass 488.69910
Monoisotopic Mass 488.35017
InChI InChI=1S/C30H48O5/c1-17-9-12-30(25(34)35)14-13-28(5)19(23(30)18(17)2)7-8-22-26(3)15-20(32)24(33)27(4,16-31)21(26)10-11-29(22,28)6/h7,17-18,20-24,31-33H,8-16H2,1-6H3,(H,34,35)/t17-,18+,20-,21-,22-,23+,24+,26+,27+,28-,29-,30+/m1/s1
InChIKey JXSVIVRDWWRQRT-UYDOISQJSA-N
SMILES [H][C@@]12CC[C@]3(C)[C@]([H])(CC=C4[C@]5([H])[C@@H](C)[C@H](C)CC[C@@]5(CC[C@@]34C)C(O)=O)[C@@]1(C)C[C@@H](O)[C@H](O)[C@@]2(C)CO
Metabolite of Species Details
Combretum quadrangulare (IPNI:170410-1) Found in leaf (BTO:0000713). Methanolic extract of leaves See: PubMed
Vateria indica (IPNI:321552-1) Found in latex (BTO:0000710). Previous component: resin; See: PubMed
Symplocos lancifolia (NCBI:txid239704) Found in leaf (BTO:0000713). Dried, powdered leaves extracted with boiling 80% methanol See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): angiogenesis modulating agent
An agent that modulates the physiologic angiogenesis process. This is accomplished by endogenous angiogenic proteins and a variety of other chemicals and pharmaceutical agents.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing asiatic acid (CHEBI:2873) has parent hydride ursane (CHEBI:35711)
asiatic acid (CHEBI:2873) has role angiogenesis modulating agent (CHEBI:50926)
asiatic acid (CHEBI:2873) has role metabolite (CHEBI:25212)
asiatic acid (CHEBI:2873) is a monocarboxylic acid (CHEBI:25384)
asiatic acid (CHEBI:2873) is a pentacyclic triterpenoid (CHEBI:25872)
asiatic acid (CHEBI:2873) is a triol (CHEBI:27136)
Incoming 11α-hydroxyasiatic acid (CHEBI:68380) has functional parent asiatic acid (CHEBI:2873)
19α-hydroxyasiatic acid (CHEBI:67915) has functional parent asiatic acid (CHEBI:2873)
2α,3β,23α-trihydroxyurs-12-en-28-oic acid 28-O-β-D-glucopyranoside (CHEBI:67952) has functional parent asiatic acid (CHEBI:2873)
3-O-[β-D-glucopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl]asiatic acid (CHEBI:68379) has functional parent asiatic acid (CHEBI:2873)
IUPAC Name
(2α,3β)-2,3,23-trihydroxyurs-12-en-28-oic acid
Synonym Source
Asiatic acid KEGG COMPOUND
Manual Xrefs Databases
0AS PDBeChem
C00003739 KNApSAcK
C08617 KEGG COMPOUND
JP2012092110 Patent
TW200938215 Patent
View more database links
Registry Numbers Types Sources
2712715 Reaxys Registry Number Reaxys
464-92-6 CAS Registry Number ChemIDplus
Citations Types Sources
21265555 PubMed citation Europe PMC
21288041 PubMed citation Europe PMC
21561086 PubMed citation Europe PMC
23102509 PubMed citation Europe PMC
Last Modified
27 May 2015