CHEBI:4357 - deguelin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
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:CB7463387, ChemicalBook:CB0463388, eMolecules:591516, Selleckchem:mirtazapine-remeron-avanza
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Mirtazapine, sold under the brand name Remeron among others, is an atypical tetracyclic antidepressant, and as such is used primarily to treat depression. Its effects may take up to four weeks but can also manifest as early as one to two weeks. It is often used in cases of depression complicated by anxiety or insomnia. The effectiveness of mirtazapine is comparable to other commonly prescribed antidepressants. It is taken by mouth. Common side effects include sleepiness, dizziness, increased appetite and weight gain. Serious side effects may include mania, low white blood cell count, and increased suicide among children. Withdrawal symptoms may occur with stopping. It is not recommended together with a monoamine oxidase inhibitor, although evidence supporting the danger of this combination has been challenged. It is unclear if use during pregnancy is safe. How it works is not clear, but it may involve blocking certain adrenergic and serotonin receptors. Chemically, it is a tetracyclic antidepressant, and is closely related to mianserin. It also has strong antihistaminergic effects. Mirtazapine came into medical use in the United States in 1996. The patent expired in 2004, and generic versions are available. In 2022, it was the 105th most commonly prescribed medication in the United States, with more than 6 million prescriptions.
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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
McGowan KE, March KL, Finch CK (2021)
The Hunger for Mirtazapine: A Discontinuation Syndrome.
Journal of pain & palliative care pharmacotherapy 35, 113-116 [PubMed:33856954]
[show Abstract]
Last Modified
18 October 2021