CHEBI:6570 - lupeol

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name lupeol
ChEBI ID CHEBI:6570
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter qingping liu
Secondary ChEBI IDs CHEBI:132397
Supplier Information
Download Molfile XML SDF
Formula C30H50O
Net Charge 0
Average Mass 426.71740
Monoisotopic Mass 426.386
InChI InChI=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
InChIKey MQYXUWHLBZFQQO-QGTGJCAVSA-N
SMILES [H][C@]12CC[C@]3([H])[C@@]4(C)CC[C@H](O)C(C)(C)[C@]4([H])CC[C@@]3(C)[C@]1(C)CC[C@@]1(C)CC[C@@H](C(C)=C)[C@]21[H]
Metabolite of Species Details
Breynia fruticosa (NCBI:txid296042) Found in root (BTO:0001188). 90% Methanolic extract of air-dried, crushed roots. See: PubMed
Croton gratissimus (NCBI:txid316784) Found in leaf (BTO:0000713). Combined hexane,methylene chloride,ethyl acetate and methanol extract of Ground leaves See: PubMed
Croton gratissimus (NCBI:txid316784) Found in stem (BTO:0001300). Previous component: stem bark; Combined hexane,methylene chloride,ethyl acetate and methanol extract of Ground leaves See: PubMed
Juglans sinensis (NCBI:txid442437-1) Found in leaf (BTO:0000713). 80% Methanolic extract of dried leaves and twigs See: PubMed
Juglans sinensis (NCBI:txid442437-1) Found in twig (BTO:0001411). 80% Methanolic extract of dried leaves and twigs 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.
Application(s): anti-inflammatory drug
A substance that reduces or suppresses inflammation.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 3-(Z)-caffeoyllupeol (CHEBI:65549) has functional parent lupeol (CHEBI:6570)
IUPAC Name
(3β)-lup-20(29)-en-3-ol
Synonyms Sources
beta-viscol ChemIDplus
fagarasterol ChemIDplus
lupeol UniProt
monogynol B ChemIDplus
Manual Xrefs Databases
259846 PubChem
C00003749 KNApSAcK
C08628 KEGG COMPOUND
CPD-90 MetaCyc
View more database links
Registry Numbers Types Sources
2063497 Reaxys Registry Number Reaxys
545-47-1 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10930257 PubMed citation Europe PMC
16445885 PubMed citation Europe PMC
17107079 PubMed citation Europe PMC
21118697 PubMed citation Europe PMC
21467639 PubMed citation Europe PMC
21712449 PubMed citation Europe PMC
9883589 PubMed citation Europe PMC
Last Modified
12 July 2016