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:CB9431676, eMolecules:29547187, eMolecules:1935628, ZINC000003978987
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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.
View more via ChEBI Ontology
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