CHEBI:69355 - casticin

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ChEBI Name casticin
ChEBI ID CHEBI:69355
Definition A tetramethoxyflavone that consists of quercetagetin in which the hydroxy groups at positions 3, 6, 7 and 4' have been replaced by methoxy groups. It has been isolated from Eremophila mitchellii.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB22464309, Selleckchem:ly-411575, ZINC000028824948
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Ecdysone is a prohormone of the major insect molting hormone 20-hydroxyecdysone, secreted from the prothoracic glands. It is of steroidal structure. Insect molting hormones (ecdysone and its homologues) are generally called ecdysteroids. Ecdysteroids act as moulting hormones of arthropods but also occur in other related phyla where they can play different roles. In Drosophila melanogaster, an increase in ecdysone concentration induces the expression of genes coding for proteins that the larva requires. It causes chromosome puffs (sites of high expression) to form in polytene chromosomes. Recent findings in the laboratory of Chris Q. Doe have found a novel role of this hormone in regulating temporal gene transitions within neural stem cells of the fruit fly. Ecdysone and other ecdysteroids also appear in many plants mostly as a protection agent (toxins or antifeedants) against herbivorous insects. These phytoecdysteroids have been reputed to have medicinal value. They are part of herbal adaptogenic remedies like Cordyceps, yet an ecdysteroid precursor in plants has been shown to have cytotoxic properties as well as antioxidant properties on lipid peroxidation. Tebufenozide, sold under the Bayer trademark MIMIC, has ecdysteroid activity although its chemical structure has little resemblance to the ecdysteroids.
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Formula C19H18O8
Net Charge 0
Average Mass 374.34140
Monoisotopic Mass 374.10017
InChI InChI=1S/C19H18O8/c1-23-11-6-5-9(7-10(11)20)17-19(26-4)16(22)14-12(27-17)8-13(24-2)18(25-3)15(14)21/h5-8,20-21H,1-4H3
InChIKey PJQLSMYMOKWUJG-UHFFFAOYSA-N
SMILES COc1ccc(cc1O)-c1oc2cc(OC)c(OC)c(O)c2c(=O)c1OC
Metabolite of Species Details
Eremophila mitchellii (IPNI:585196-1) Found in leaf (BTO:0000713). n-Hexane,Methylene dichloride and methanolic extarct of airdried and ground leaves 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.
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ChEBI Ontology
Outgoing casticin (CHEBI:69355) has functional parent quercetagetin (CHEBI:8695)
casticin (CHEBI:69355) has role apoptosis inducer (CHEBI:68495)
casticin (CHEBI:69355) has role plant metabolite (CHEBI:76924)
casticin (CHEBI:69355) is a dihydroxyflavone (CHEBI:38686)
casticin (CHEBI:69355) is a tetramethoxyflavone (CHEBI:76875)
IUPAC Name
5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,6,7-trimethoxy-4H-chromen-4-one
Synonyms Sources
3',5-dihydroxy-3,4',6,7-tetramethoxyflavone ChemIDplus
3,6,7,4'-tetra-O-methyl-5,3'-dihydroxyflavone LIPID MAPS
5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,6,7-trimethoxy-4H-1-benzopyran-4-one ChemIDplus
quercetagetin 3,6,7,4'-tetramethyl ether LIPID MAPS
vitexicarpin ChemIDplus
Manual Xrefs Databases
Casticin Wikipedia
CN101028261 Patent
CN102743373 Patent
HMDB0030660 HMDB
LMPK12113010 LIPID MAPS
View more database links
Registry Numbers Types Sources
1300392 Reaxys Registry Number Reaxys
479-91-4 CAS Registry Number ChemIDplus
Citations
Last Modified
15 January 2014