CHEBI:67914 - euscaphic acid

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ChEBI Name euscaphic acid
ChEBI ID CHEBI:67914
Definition A pentacyclic triterpenoid that is urs-12-en-28-oic acid substituted by hydroxy groups at positions 2, 3 and 19 respectively (the 2α,3α-stereoisomer). It has been isolated from the leaves of Rosa laevigata.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C30H48O5
Net Charge 0
Average Mass 488.69910
Monoisotopic Mass 488.35017
InChI InChI=1S/C30H48O5/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/h8,17,19-23,31-32,35H,9-16H2,1-7H3,(H,33,34)/t17-,19-,20+,21-,22-,23-,26+,27-,28-,29-,30+/m1/s1
InChIKey OXVUXGFZHDKYLS-QUFHAEKXSA-N
SMILES C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@@H](O)[C@@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]2[C@]1(C)O)C(O)=O
Metabolite of Species Details
Euscaphis japonica (NCBI:txid210332) Found in twig (BTO:0001411). 95% ethanolic extract of twigs See: DOI
Rosa laevigata (NCBI:txid74652) Found in leaf (BTO:0000713). 70% EtOH extract of dried leaves 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): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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ChEBI Ontology
Outgoing euscaphic acid (CHEBI:67914) has parent hydride ursane (CHEBI:35711)
euscaphic acid (CHEBI:67914) has role plant metabolite (CHEBI:76924)
euscaphic acid (CHEBI:67914) is a hydroxy monocarboxylic acid (CHEBI:35868)
euscaphic acid (CHEBI:67914) is a pentacyclic triterpenoid (CHEBI:25872)
euscaphic acid (CHEBI:67914) is a triol (CHEBI:27136)
IUPAC Name
(2α,3α)-2,3,19-trihydroxyurs-12-en-28-oic acid
Synonyms Sources
Jacarandic acid ChemIDplus
Tormentic acid ChemIDplus
Manual Xrefs Databases
C00019491 KNApSAcK
C17890 KEGG COMPOUND
HMDB0036651 HMDB
View more database links
Registry Numbers Types Sources
4912896 Reaxys Registry Number Reaxys
53155-25-2 CAS Registry Number KEGG COMPOUND
53155-25-2 CAS Registry Number ChemIDplus
Citation Waiting for Citations Type Source
21384845 PubMed citation Europe PMC
Last Modified
27 May 2015