CHEBI:4357 - deguelin

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ChEBI Name deguelin
ChEBI ID CHEBI:4357
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB9431676, eMolecules:29547187, eMolecules:1935628, ZINC000003978987
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Formula C23H22O6
Net Charge 0
Average Mass 394.423
Monoisotopic Mass 394.14164
InChI InChI=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
InChIKey ORDAZKGHSNRHTD-UXHICEINSA-N
SMILES [H][C@@]12COC3=C(C=C(OC)C(OC)=C3)[C@]1([H])C(=O)C1=C(O2)C2=C(OC(C)(C)C=C2)C=C1
Metabolite of Species Details
Tephrosia vogelii (NCBI:txid1157238) See: PubMed
Tephrosia purpurea (NCBI:txid228354) See: PubMed
Mundulea sericea (NCBI:txid54460) See: PubMed
Roles Classification
Biological Role(s): 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.
mitochondrial NADH:ubiquinone reductase inhibitor

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.
Application(s): 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.
anti-inflammatory agent
Any compound that has anti-inflammatory effects.
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ChEBI Ontology
Outgoing 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 Sources
(−)-cis-deguelin KNApSAcK
(−)-deguelin ChEBI
(7aS,13aS)-13,13a-dihydro-9,10-dimethoxy-3,3-dimethyl-3H-bis[1]benzopyrano[3,4-b:6',5'-e]pyran-7(7aH)-one ChEBI
(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)-one IUPAC
Manual Xrefs Databases
97058 ChemSpider
C00002522 KNApSAcK
C10417 KEGG COMPOUND
CPD-12163 MetaCyc
Deguelin Wikipedia
HMDB0250941 HMDB
LMPK12060019 LIPID MAPS
LSM-3368 LINCS
View more database links
Registry Number Type Source
522-17-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations
Last Modified
18 October 2021