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CHEBI:67914 - euscaphic acid

ChEBI IDCHEBI:67914
ChEBI Nameeuscaphic acid
Stars
DefinitionA 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.
Last Modified27 May 2015
DownloadsMolfile
FormulaC30H48O5
Net Charge0
Average Mass488.709
Monoisotopic Mass488.35017
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@H](O)[C@H](O)C[C@]21C
InChIInChI=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
InChIKeyOXVUXGFZHDKYLS-QUFHAEKXSA-N
Species of MetaboliteComponentSourceComments
Rosa laevigata (ncbitaxon:74652) leaf (BTO:0000713) PubMed (21384845) 70% EtOH extract of dried leaves
Euscaphis japonica (ncbitaxon:210332) twig (BTO:0001411) DOI (10.1021/np1003593) 95% ethanolic extract of twigs
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
ChEBI Ontology
Outgoing Relation(s)
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  Source
Jacarandic acidChemIDplus
Tormentic acidChemIDplus
Manual XrefsDatabases
C17890KEGG COMPOUND
HMDB0036651HMDB
C00019491KNApSAcK
Registry NumbersSources
Reaxys:4912896Reaxys
CAS:53155-25-2ChemIDplus
CAS:53155-25-2KEGG COMPOUND
Citations