CHEBI:9442 - tephrosin

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ChEBI Name tephrosin
ChEBI ID CHEBI:9442
Definition A member of the class of rotenones that is 13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one substituted with geminal methyl groups at position 3, hydroxy group at position 7a and methoxy groups at positions 9 and 10 (the 7aR,13aR stereoisomer). It is isolated from the leaves and twigs of Antheroporum pierrei and exhibits antineoplastic and pesticidal activities.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:68052
Supplier Information ChemicalBook:CB7463387, ChemicalBook:CB0463388, eMolecules:591516, Selleckchem:mirtazapine-remeron-avanza
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Wikipedia License
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 C23H22O7
Net Charge 0
Average Mass 410.41660
Monoisotopic Mass 410.13655
InChI InChI=1S/C23H22O7/c1-22(2)8-7-12-15(30-22)6-5-13-20(12)29-19-11-28-16-10-18(27-4)17(26-3)9-14(16)23(19,25)21(13)24/h5-10,19,25H,11H2,1-4H3/t19-,23-/m1/s1
InChIKey AQBZCCQCDWNNJQ-AUSIDOKSSA-N
SMILES [H][C@@]12COc3cc(OC)c(OC)cc3[C@]1(O)C(=O)c1ccc3OC(C)(C)C=Cc3c1O2
Metabolite of Species Details
Antheroporum pierrei (IPNI:474590-1) Found in leaf (BTO:0000713). Dried leaves and twigs were extracted with CH2Cl2/MeOH (1:1) See: PubMed
Antheroporum pierrei (IPNI:474590-1) Found in twig (BTO:0001411). Dried leaves and twigs were extracted with CH2Cl2/MeOH (1:1) See: PubMed
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): pesticide
Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing tephrosin (CHEBI:9442) has role antineoplastic agent (CHEBI:35610)
tephrosin (CHEBI:9442) has role metabolite (CHEBI:25212)
tephrosin (CHEBI:9442) has role pesticide (CHEBI:25944)
tephrosin (CHEBI:9442) is a aromatic ether (CHEBI:35618)
tephrosin (CHEBI:9442) is a cyclic ketone (CHEBI:3992)
tephrosin (CHEBI:9442) is a organic heteropentacyclic compound (CHEBI:38164)
tephrosin (CHEBI:9442) is a rotenones (CHEBI:72581)
Incoming 4',5'-dihydro-11,5'-dihydroxy-4'-methoxytephrosin (CHEBI:65772) has functional parent tephrosin (CHEBI:9442)
IUPAC Name
(7aR,13aR)-7a-hydroxy-9,10-dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one
Synonyms Sources
(7aR,13aR)-13,13a-dihydro-7a-hydroxy-9,10-dimethoxy-3,3-dimethyl-3H-bis(1)benzopyrano(3,4-b:6',5'-e)pyran-7(7aH)-one ChEBI
deguelinol I ChEBI
hydroxydeguelin ChEBI
Tephrosin KEGG COMPOUND
Manual Xrefs Databases
C00002578 KNApSAcK
C10535 KEGG COMPOUND
CPD-12165 MetaCyc
DE19707178 Patent
GB350897 Patent
GB437171 Patent
LMPK12060047 LIPID MAPS
Tephrosin Wikipedia
View more database links
Registry Numbers Types Sources
5661956 Reaxys Registry Number Reaxys
76-80-2 CAS Registry Number ChemIDplus
Citations Types Sources
17830264 PubMed citation Europe PMC
20572190 PubMed citation Europe PMC
21452840 PubMed citation Europe PMC
21966156 PubMed citation Europe PMC
22123175 PubMed citation Europe PMC
22237680 PubMed citation Europe PMC
22970736 PubMed citation Europe PMC
Last Modified
28 July 2014