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CHEBI:9442 - tephrosin

ChEBI IDCHEBI:9442
ChEBI Nametephrosin
Stars
DefinitionA 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.
Secondary ChEBI IDCHEBI:68052
Last Modified28 July 2014
DownloadsMolfile
FormulaC23H22O7
Net Charge0
Average Mass410.422
Monoisotopic Mass410.13655
SMILES[H][C@@]12COc3cc(OC)c(OC)cc3[C@]1(O)C(=O)c1ccc3c(c1O2)C=CC(C)(C)O3
InChIInChI=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
InChIKeyAQBZCCQCDWNNJQ-AUSIDOKSSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Antheroporum pierrei (IPNI:474590-1)
twig (BTO:0001411) PubMed (21452840) Dried leaves and twigs were extracted with CH2Cl2/MeOH (1:1)
leaf (BTO:0000713) PubMed (21452840) Dried leaves and twigs were extracted with CH2Cl2/MeOH (1:1)
Roles Classification
Biological Role:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Applications:
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.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
TephrosinKEGG COMPOUND
hydroxydeguelinChEBI
deguelinol IChEBI
(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)-oneChEBI
Manual XrefsDatabases
C10535KEGG COMPOUND
CPD-12165MetaCyc
LMPK12060047LIPID MAPS
TephrosinWikipedia
DE19707178Patent
GB350897Patent
GB437171Patent
C00002578KNApSAcK
Registry NumbersSources
Reaxys:5661956Reaxys
CAS:76-80-2KEGG COMPOUND
CAS:76-80-2ChemIDplus
Citations