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CHEBI:66045 - (20R)-28-hydroxylupen-30-al-3-one

ChEBI IDCHEBI:66045
ChEBI Name(20R)-28-hydroxylupen-30-al-3-one
Stars
ASCII Name(20R)-28-hydroxylupen-30-al-3-one
DefinitionA pentacyclic triterpenoid that is lupan-30-al with a hydroxy substituent at position 28 and an oxo group at position 3 (the 20R stereoisomer) . Isolated from Acacia mellifera, it exhibits cytotoxicity activity against the NSCLC-N6 cell line, derived from a human non-small-cell bronchopulmonary carcinoma.
Last Modified14 April 2015
DownloadsMolfile
FormulaC30H48O3
Net Charge0
Average Mass456.711
Monoisotopic Mass456.36035
SMILES[H][C@]12CC[C@@]3([H])[C@@](C)(CC[C@@]4(CO)CC[C@@]([H])([C@@H](C)C=O)[C@@]43[H])[C@]1(C)CC[C@@]1([H])C(C)(C)C(=O)CC[C@]21C
InChIInChI=1S/C30H48O3/c1-19(17-31)20-9-14-30(18-32)16-15-28(5)21(25(20)30)7-8-23-27(4)12-11-24(33)26(2,3)22(27)10-13-29(23,28)6/h17,19-23,25,32H,7-16,18H2,1-6H3/t19-,20-,21+,22-,23+,25+,27-,28+,29+,30+/m0/s1
InChIKeyCBDKCJANRGOIIK-URCKAGISSA-N
Species of MetaboliteComponentSourceComments
Acacia mellifera (ncbitaxon:381101) stem (BTO:0001300) PubMed (17873838) Previous component: stem bark;
Roles Classification
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)
(20R)-28-hydroxylupen-30-al-3-one (CHEBI:66045) has parent hydride lupane (CHEBI:36485)
(20R)-28-hydroxylupen-30-al-3-one (CHEBI:66045) has role plant metabolite (CHEBI:76924)
(20R)-28-hydroxylupen-30-al-3-one (CHEBI:66045) is a aldehyde (CHEBI:17478)
(20R)-28-hydroxylupen-30-al-3-one (CHEBI:66045) is a pentacyclic triterpenoid (CHEBI:25872)
(20R)-28-hydroxylupen-30-al-3-one (CHEBI:66045) is a primary alcohol (CHEBI:15734)
IUPAC Name 
(20R)-28-hydroxy-3-oxolupan-29-al
Registry NumbersSources
Reaxys:11155056Reaxys
Citations