EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:4357 - deguelin

Default Structure
ChEBI IDCHEBI:4357
ChEBI Namedeguelin
Stars
DefinitionA rotenone that is 13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one substituted by methoxy groups at positions 9 and 10, and by two methyl groups at position 3 (the 7aS,13aS-stereoisomer). It exists in abundant quantities in the bark, roots, and leaves of the Leguminosae family of plants and reported to exert anti-tumour effects in various cancers.
Last Modified18 October 2021
DownloadsMolfile
FormulaC23H22O6
Net Charge0
Average Mass394.423
Monoisotopic Mass394.14164
SMILES[H][C@@]12COc3cc(OC)c(OC)cc3[C@]1([H])C(=O)c1ccc3c(c1O2)C=CC(C)(C)O3
InChIInChI=1S/C23H22O6/c1-23(2)8-7-12-15(29-23)6-5-13-21(24)20-14-9-17(25-3)18(26-4)10-16(14)27-11-19(20)28-22(12)13/h5-10,19-20H,11H2,1-4H3/t19-,20+/m1/s1
InChIKeyORDAZKGHSNRHTD-UXHICEINSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Mundulea sericea (ncbitaxon:54460) - PubMed (9270008)
Tephrosia purpurea (ncbitaxon:228354) - PubMed (31504284)
Tephrosia vogelii (ncbitaxon:1157238) - PubMed (32454059)
Roles Classification
Biological Roles:
antiviral agent  A substance that destroys or inhibits replication of viruses.
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor  An EC 2.7.11.* (protein-serine/threonine kinase) inhibitor that interferes with the action of non-specific serine/threonine protein kinase (EC 2.7.11.1), a kinase enzyme involved in phosphorylation of hydroxy group of serine or threonine.
Applications:
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
angiogenesis inhibitor  An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
ChEBI Ontology
Outgoing Relation(s)
deguelin (CHEBI:4357) has role angiogenesis inhibitor (CHEBI:48422)
deguelin (CHEBI:4357) has role anti-inflammatory agent (CHEBI:67079)
deguelin (CHEBI:4357) has role antineoplastic agent (CHEBI:35610)
deguelin (CHEBI:4357) has role antiviral agent (CHEBI:22587)
deguelin (CHEBI:4357) has role apoptosis inducer (CHEBI:68495)
deguelin (CHEBI:4357) has role EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor (CHEBI:50925)
deguelin (CHEBI:4357) has role mitochondrial NADH:ubiquinone reductase inhibitor (CHEBI:38498)
deguelin (CHEBI:4357) has role plant metabolite (CHEBI:76924)
deguelin (CHEBI:4357) is a aromatic ether (CHEBI:35618)
deguelin (CHEBI:4357) is a diether (CHEBI:46786)
deguelin (CHEBI:4357) is a organic heteropentacyclic compound (CHEBI:38164)
deguelin (CHEBI:4357) is a rotenones (CHEBI:72581)
IUPAC Name 
(7aS,13aS)-9,10-dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one
Synonyms  Source
(7aS,13aS)-13,13a-dihydro-9,10-dimethoxy-3,3-dimethyl-3H-bis[1]benzopyrano[3,4-b:6',5'-e]pyran-7(7aH)-oneChEBI
(7aS,13aS)-9,10-dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-pyrano[2',3':7,8][1]benzopyrano[2,3-c][1]benzopyran-7(7aH)-oneIUPAC
(−)-deguelinChEBI
(−)-cis-deguelinKNApSAcK
Manual XrefsDatabases
97058ChemSpider
C00002522KNApSAcK
C10417KEGG COMPOUND
CPD-12163MetaCyc
DeguelinWikipedia
HMDB0250941HMDB
LMPK12060019LIPID MAPS
LSM-3368LINCS
Registry NumbersSources
CAS:522-17-8ChemIDplus
Citations