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CHEBI:67600 - 2α,3β-dihydroxy-20(29)-lupen-28-oic acid

ChEBI IDCHEBI:67600
ChEBI Name2α,3β-dihydroxy-20(29)-lupen-28-oic acid
Stars
ASCII Name2alpha,3beta-dihydroxy-20(29)-lupen-28-oic acid
DefinitionA pentacyclic triterpenoid that is betulinic acid carrying an additional α-hydroxy group at position 2. It has been isolated from Breynia fruticosa.
Last Modified1 June 2015
DownloadsMolfile
FormulaC30H48O4
Net Charge0
Average Mass472.710
Monoisotopic Mass472.35526
SMILES[H][C@]12CC[C@@]3([H])[C@@](C)(CC[C@@]4(C(=O)O)CC[C@@H](C(=C)C)[C@@]43[H])[C@]1(C)CC[C@@]1([H])C(C)(C)[C@@H](O)[C@H](O)C[C@]21C
InChIInChI=1S/C30H48O4/c1-17(2)18-10-13-30(25(33)34)15-14-28(6)19(23(18)30)8-9-22-27(5)16-20(31)24(32)26(3,4)21(27)11-12-29(22,28)7/h18-24,31-32H,1,8-16H2,2-7H3,(H,33,34)/t18-,19+,20+,21-,22+,23+,24-,27-,28+,29+,30-/m0/s1
InChIKeyPFCVZKFJHRCLCC-PGOIBATFSA-N
Species of MetaboliteComponentSourceComments
Breynia fruticosa (ncbitaxon:296042) root (BTO:0001188) PubMed (21428418) 90% Methanolic extract of air-dried, crushed roots.
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-dihydroxy-20(29)-lupen-28-oic acid (CHEBI:67600) has functional parent betulinic acid (CHEBI:3087)
2α,3β-dihydroxy-20(29)-lupen-28-oic acid (CHEBI:67600) has parent hydride lupane (CHEBI:36485)
2α,3β-dihydroxy-20(29)-lupen-28-oic acid (CHEBI:67600) has role plant metabolite (CHEBI:76924)
2α,3β-dihydroxy-20(29)-lupen-28-oic acid (CHEBI:67600) is a dihydroxy monocarboxylic acid (CHEBI:35972)
2α,3β-dihydroxy-20(29)-lupen-28-oic acid (CHEBI:67600) is a pentacyclic triterpenoid (CHEBI:25872)
IUPAC Name 
2α,3β-dihydroxylup-20(29)-en-28-oic acid
Synonym  Source
2α-hydroxybetulinic acidChEBI
Manual XrefsDatabases
C16912KEGG COMPOUND
Registry NumbersSources
Reaxys:5648545Reaxys
CAS:19533-92-7KEGG COMPOUND
CAS:19533-92-7ChemIDplus
Citations