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CHEBI:6570 - lupeol

ChEBI IDCHEBI:6570
ChEBI Namelupeol
Stars
DefinitionA pentacyclic triterpenoid that is lupane in which the hydrogen at the 3β position is substituted by a hydroxy group. It occurs in the skin of lupin seeds, as well as in the latex of fig trees and of rubber plants. It is also found in many edible fruits and vegetables.
Secondary ChEBI IDCHEBI:132397
Last Modified12 July 2016
Submitterliuqingping
DownloadsMolfile
FormulaC30H50O
Net Charge0
Average Mass426.729
Monoisotopic Mass426.38617
SMILES[H][C@]12CC[C@@]3([H])[C@@](C)(CC[C@@]4(C)CC[C@@H](C(=C)C)[C@@]43[H])[C@]1(C)CC[C@@]1([H])C(C)(C)[C@@H](O)CC[C@]21C
InChIInChI=1S/C30H50O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-25,31H,1,9-18H2,2-8H3/t20-,21+,22-,23+,24-,25+,27+,28-,29+,30+/m0/s1
InChIKeyMQYXUWHLBZFQQO-QGTGJCAVSA-N
Species of MetaboliteComponentSourceComments
Juglans sinensis (ncbitaxon:442437-1)
twig (BTO:0001411) PubMed (21309591) 80% Methanolic extract of dried leaves and twigs
leaf (BTO:0000713) PubMed (21309591) 80% Methanolic extract of dried leaves and twigs
Breynia fruticosa (ncbitaxon:296042) root (BTO:0001188) PubMed (21428418) 90% Methanolic extract of air-dried, crushed roots.
Croton gratissimus (ncbitaxon:316784)
leaf (BTO:0000713) PubMed (22032651) Combined hexane,methylene chloride,ethyl acetate and methanol extract of Ground leaves
stem (BTO:0001300) PubMed (22032651) Previous component: stem bark; Combined hexane,methylene chloride,ethyl acetate and methanol extract of Ground leaves
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.
Application:
anti-inflammatory drug  A substance that reduces or suppresses inflammation.
ChEBI Ontology
Outgoing Relation(s)
lupeol (CHEBI:6570) has parent hydride lupane (CHEBI:36485)
lupeol (CHEBI:6570) has role anti-inflammatory drug (CHEBI:35472)
lupeol (CHEBI:6570) has role plant metabolite (CHEBI:76924)
lupeol (CHEBI:6570) is a pentacyclic triterpenoid (CHEBI:25872)
lupeol (CHEBI:6570) is a secondary alcohol (CHEBI:35681)
Incoming Relation(s)
3-(Z)-caffeoyllupeol (CHEBI:65549) has functional parent lupeol (CHEBI:6570)
IUPAC Name 
(3β)-lup-20(29)-en-3-ol
Synonyms  Source
beta-viscolChemIDplus
monogynol BChemIDplus
fagarasterolChemIDplus
UniProt Name  Source
lupeolUniProt
Manual XrefsDatabases
C08628KEGG COMPOUND
CPD-90MetaCyc
C00003749KNApSAcK
259846PubChem Compound
Registry NumbersSources
Reaxys:2063497Reaxys
CAS:545-47-1KEGG COMPOUND
CAS:545-47-1ChemIDplus
Citations