Basic information
- CAS
68436-47-5- Standard SMILES
CC(C)=CCc1cc(-c2coc3cc(O)cc(O)c3c2=O)ccc1O- InChIKey
SWDSVBNAMCDHTF-UHFFFAOYSA-N- Molecular formula
- C20H18O5
- Average molar mass
- 338.4 g/mol
- Monoisotopic mass
- 338.11542367
Overview
Isowighteone is a member of the class of 7-hydroxyisoflavones that is isoflavone substituted by hydroxy groups at positions 5, 7 and 4' and a prenyl group at position 3'. It has been isolated from Ficus mucuso. It has a role as a plant metabolite. It is functionally related to an isoflavone.
Names & identifiers
- Preferred name
- Isowighteone
- IUPAC
- 5,7-dihydroxy-3-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]chromen-4-one
- English name
- Isowightenon
- Molecular formula
- C20H18O5
- Molecular weight
- 338.35
Names & synonyms
isowighteone5,7-dihydroxy-3-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]chromen-4-one3'-(gamma,gamma-dimethylallyl)genistein5,7-Dihydroxy-3-(4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl)-4H-chromen-4-oneCHEBI:697493'-(g,g-Dimethylallyl)genistein5,7-dihydroxy-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-4H-chromen-4-one5,7-Dihydroxy-3-[4-hydroxy-3-(3-methyl-2-butenyl)phenyl]-4H-1-benzopyran-4-one, 9CI5,7-dihydroxy-3-(4-hydroxy-3-(3-methylbut-2-enyl)phenyl)chromen-4-one5,7-Dihydroxy-3-(4-hydroxy-3-(3-methyl-2-butenyl)phenyl)-4H-1-benzopyran-4-one, 9ciRefChem:15014368436-47-5
Show more names
3'-Dimethylallylgenistein4',5,7-Trihydroxy-3'-prenylisoflavone4',5,7-Trihydroxy-3'-(3-methyl-2-butenyl)isoflavone3'-(3-Methyl-2-butenyl)-4',5,7-trihydroxyisoflavone4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-[4-hydroxy-3-(3-methyl-2-buten-1-yl)phenyl]-
IsowigtheoneIsowightenon3'-Prenylgenistein5,7,4'-Trihydroxy-3'-prenylisoflavoneCHEMBL18125933'-prenyl-5,7,4'-trihydroxyisoflavone3'-isoprenylgenistein3'Dimethylallylgenistein
Properties
Computed structural properties
- XLogP
- 4.6
- Topological polar surface area
- 87 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 3
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 562
Experimental & physicochemical properties
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Isoflavonoids [PK1205]
Melting Point171 - 172 °C
Physical DescriptionSolid
Physicochemical properties
- solubility
- Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
- form
- powder
- color
- Yellow
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 280 · P280-P305+P351+P338
Safety & regulation
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P280-P305+P351+P338
Chemistry & industry
Pharmacology
Cellular LocationsMembrane
Applications
UsesIsowighteone is a natural product derivative of Genistein (G350000). Genistein exhibits specific inhibitory activity against tyrosine kinases, including autophosphorylation of epidermal growth factor receptor kinase (IC50 - 2.6uM). Also inhibits other protein kinases through competitive inhibition of ATP. Inhibits tumor cell proliferation and induces tumor cell differentiation. Produces cell-cycle arrest and apoptosis in Jurat T-leukemia cells. However, it prevents anti-CD3 monoclonal antibody-induced thymic apoptosis. Genistein also inhibits topoisomerase II activity in vitro. Genistein has also been shown to inhibit the action of GABA on recombinant GABAA receptors 2. uv(max)ethanol: 262.5 nm (e= 138). moderately sol. in hot alcohol.
Suppliers19 total
成都彼样生物科技有限公司18108052721 · [email protected]
江苏艾康生物医药研发有限公司025-66061636 19370895928 · [email protected]
陕西缔都化学有限公司029-029-81123119 17391733320 · [email protected]
武汉众志诚生物技术有限公司13628624121 13628604890 · [email protected]
成都普思生物科技股份有限公司028-85370565-229 18080489829 · [email protected]
云南西力生物技术股份有限公司0871-65217109 · [email protected]
武汉天植生物技术有限公司18607101326 15172504745 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…