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

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ChEBI Name (20R)-28-hydroxylupen-30-al-3-one
ChEBI ID CHEBI:66045
ChEBI ASCII Name (20R)-28-hydroxylupen-30-al-3-one
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C30H48O3
Net Charge 0
Average Mass 456.70030
Monoisotopic Mass 456.36035
InChI InChI=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
InChIKey CBDKCJANRGOIIK-URCKAGISSA-N
SMILES [H][C@]1(CC[C@]2(CO)CC[C@]3(C)[C@]([H])(CC[C@]4([H])[C@@]5(C)CCC(=O)C(C)(C)[C@]5([H])CC[C@@]34C)[C@@]12[H])[C@@H](C)C=O
Metabolite of Species Details
Acacia mellifera (NCBI:txid381101) Found in stem (BTO:0001300). Previous component: stem bark; See: PubMed
Roles Classification
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (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 Number Type Source
11155056 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
17873838 PubMed citation Europe PMC
Last Modified
14 April 2015