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CHEBI:67916 - 2α,3β,23-trihydroxylup-20(29)-en-28-oic acid

ChEBI IDCHEBI:67916
ChEBI Name2α,3β,23-trihydroxylup-20(29)-en-28-oic acid
Stars
ASCII Name2alpha,3beta,23-trihydroxylup-20(29)-en-28-oic acid
DefinitionA pentacyclic triterpenoid that is lup-20(29)-en-28-oic acid substituted by hydroxy groups at positions 2, 3 and 23 respectively (the 2α,3β-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[C@]3([H])[C@@]4(C)C[C@@H](O)[C@H](O)[C@@](C)(CO)[C@]4([H])CC[C@@]3(C)[C@]1(C)CC[C@@]1(C(=O)O)CC[C@@H](C(=C)C)[C@@]12[H]
InChIInChI=1S/C30H48O5/c1-17(2)18-9-12-30(25(34)35)14-13-28(5)19(23(18)30)7-8-22-26(3)15-20(32)24(33)27(4,16-31)21(26)10-11-29(22,28)6/h18-24,31-33H,1,7-16H2,2-6H3,(H,34,35)/t18-,19+,20+,21+,22+,23+,24-,26-,27-,28+,29+,30-/m0/s1
InChIKeyBHOYLWIIJSSSSI-STNOFSRUSA-N
Species of MetaboliteComponentSourceComments
Rosa laevigata (ncbitaxon:74652) leaf (BTO:0000713) PubMed (21384845) 70% EtOH extract of dried leaves
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)
2α,3β,23-trihydroxylup-20(29)-en-28-oic acid (CHEBI:67916) has parent hydride lupane (CHEBI:36485)
2α,3β,23-trihydroxylup-20(29)-en-28-oic acid (CHEBI:67916) has role plant metabolite (CHEBI:76924)
2α,3β,23-trihydroxylup-20(29)-en-28-oic acid (CHEBI:67916) is a hydroxy monocarboxylic acid (CHEBI:35868)
2α,3β,23-trihydroxylup-20(29)-en-28-oic acid (CHEBI:67916) is a pentacyclic triterpenoid (CHEBI:25872)
2α,3β,23-trihydroxylup-20(29)-en-28-oic acid (CHEBI:67916) is a triol (CHEBI:27136)
IUPAC Name 
(2α,3β)-2,3,23-trihydroxylup-20(29)-en-28-oic acid
Registry NumbersSources
Reaxys:8088063Reaxys
Citations