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Desmethylglycitein (Standard)

CAT: 0804-HY-N5072RSize: 1 EachDry Ice: NoHazardous: No
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Description
Desmethylglycitein (4',6,7-Trihydroxyisoflavone), a metabolite of daidzein, sourced from Glycine max with antioxidant, and anti-cancer activities. Desmethylglycitein binds directly to CDK1 and CDK2 in vivo, resulting in the suppresses CDK1 and CDK2 activity[1]. Desmethylglycitein is a direct inhibitor of protein kinase C (PKC) α, against solar UV (sUV) -induced matrix matrix metalloproteinase 1 (MMP1) [2]. Desmethylglycitein binds to PI3K in an ATP competitive manner in the cytosol, where it inhibits the activity of PI3K and downstream signaling cascades, leading to the suppression of adipogenesis in 3T3-L1 preadipocytes[3].
CAS Number
17817-31-1
UNSPSC
12352005
Target
CDK; PI3K; PKC
Related Pathways
Cell Cycle/DNA Damage; Epigenetics; PI3K/Akt/mTOR; TGF-beta/Smad
Field of Research
Cancer
Smiles
O=C1C(C2=CC=C(O)C=C2)=COC3=CC(O)=C(O)C=C13
Molecular Formula
C15H10O5
Molecular Weight
270.24
References & Citations
[1]Lee DE, et al. 6,7,4'-trihydroxyisoflavone inhibits HCT-116 human colon cancer cell proliferation by targeting CDK1 and CDK2. Carcinogenesis. 2011 Apr;32 (4) :629-35.|[2]Lim TG, et al. The daidzein metabolite, 6,7,4'-Trihydroxyisoflavone, is a novel inhibitor of PKCα in suppressing solar UV-induced matrix metalloproteinase 1. Int J Mol Sci. 2014 Nov 19;15 (11) :21419-32|[3]Seo SG, et al. A metabolite of daidzein, 6,7,4'-trihydroxyisoflavone, suppresses adipogenesis in 3T3-L1 preadipocytes via ATP-competitive inhibition of PI3K.
Shipping Conditions
Room temperature
Scientific Category
Reference Standards

Chemical Information

6,7,4'-Trihydroxyisoflavone

4',6,7-trihydroxyisoflavone is a hydroxyisoflavone that is daidzein bearing an additional hydroxy substituent at position 6. It has a role as a metabolite, an EC 1.14.18.1 (tyrosinase) inhibitor, an anti-inflammatory agent, a PPARalpha agonist, a PPARgamma agonist and an antimutagen. It is functionally related to a daidzein.

CAS Number17817-31-1
PubChem CID5284649
IUPAC Name6,7-dihydroxy-3-(4-hydroxyphenyl)chromen-4-one
Molecular FormulaC15H10O5
Molecular Weight270.24
XLogP2.1
Topological Polar Surface Area87
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count1
Heavy Atom Count20
Formal Charge0
Complexity410
SMILES
C1=CC(=CC=C1C2=COC3=CC(=C(C=C3C2=O)O)O)O
InChI
InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-14-6-13(18)12(17)5-10(14)15(11)19/h1-7,16-18H
InChIKey
GYLUFQJZYAJQDI-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of 6,7,4'-Trihydroxyisoflavone
CAS: 17817-31-1
CID: 5284649
Formula: C15H10O5
MW: 270.24
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight270.24
XLogP32.1
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count1
Exact Mass270.05282342
Monoisotopic Mass270.05282342
Topological Polar Surface Area87 Ų
Heavy Atom Count20
Formal Charge0
Complexity410
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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