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CHEBI:4357 - deguelin

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 vogelii (ncbitaxon:1157238) - PubMed (32454059)
Tephrosia purpurea (ncbitaxon:228354) - PubMed (31504284)
Roles Classification
Biological Roles:
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.
antiviral agent  A substance that destroys or inhibits replication of viruses.
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:
angiogenesis inhibitor  An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
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
(−)-deguelinChEBI
(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
(−)-cis-deguelinKNApSAcK
(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
Manual XrefsDatabases
C10417KEGG COMPOUND
C00002522KNApSAcK
LSM-3368LINCS
LMPK12060019LIPID MAPS
CPD-12163MetaCyc
HMDB0250941HMDB
DeguelinWikipedia
97058ChemSpider
Registry NumbersSources
CAS:522-17-8ChemIDplus
Citations