Basic information
- CAS
51225-30-0- Standard SMILES
CC(C)=CCc1c(O)cc2occ(-c3ccc(O)cc3)c(=O)c2c1O- InChIKey
KIMDVVKVNNSHGZ-UHFFFAOYSA-N- Molecular formula
- C20H18O5
- Average molar mass
- 338.4 g/mol
- Monoisotopic mass
- 338.11542367
Overview
Wighteone 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 6. It has been isolated from Ficus mucuso. It has a role as an antifungal agent and a plant metabolite. It is functionally related to an isoflavone.
Names & identifiers
- Preferred name
- Wighteone
- IUPAC
- 5,7-dihydroxy-3-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)chromen-4-one
- English name
- 3-(4-Hydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one
- Molecular formula
- C20H18O5
- Molecular weight
- 338.35
Names & synonyms
Wighteone51225-30-0Erythrinin B5,7,4'-Trihydroxy-6-prenylisoflavone5,7-Dihydroxy-3-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)chromen-4-one48ZS74CB9ACHEBI:10038DTXSID30199239RefChem:1101049DTXCID101217305,7-dihydroxy-3-(4-hydroxyphenyl)-6-(3-methylbut-2-en-1-yl)-4H-chromen-4-one3-(4-hydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-butenyl)-4h-1-benzopyran-4-one
Show more names
Erythrinin B|||6-Isopentenylgenistein4',5,7-Trihydroxy-6-prenyl-isoflavone4',5,7-Trihydroxy-6-(3-methyl-2-butenyl)isoflavone5,7-dihydroxy-3-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)-1-benzopyran-4-one
5,7-dihydroxy-3-(4-hydroxyphenyl)-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-hydroxyphenyl)-6-(3-methyl-2-butenyl)-UNII-48ZS74CB9ACHEMBL393222orb1681466orb2900227SCHEMBL1170652SCHEMBL35556596
Database identifiers
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
- 554
Experimental & physicochemical properties
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Isoflavonoids [PK1205]
Physicochemical properties
- Melting point
- 227 °C · 227 °C(Solv: methanol (67-56-1))
- Boiling point
- 586.1 · 586.1±50.0 °C(Predicted)
- Density
- 1.351 · 1.351±0.06 g/cm3(Predicted)
- solubility
- Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
- form
- powder
- pka
- 7.03 · 7.03±0.20(Predicted)
- color
- Yellow
- Stability
- Light Sensitive
- FDA UNII
- 48 ZS74CB9A · 48ZS74CB9A
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 310 · H310+H330-H302-H315-H319-H412
- Precautionary statements
Safety & regulation
Safety data
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- Hazard statements
- H310+H330-H302-H315-H319-H412
- Precautionary statements
- P501-P273-P260-P270-P262-P271-P264-P280-P284-P337+P313-P305+P351+P338-P361+P364-P332+P313-P301+P312+P330-P302+P352+P310-P304+P340+P310-P403+P233-P405
Chemistry & industry
Applications
UsesWighteone 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.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers56 total
陕西缔都医药有限责任公司029-81124775 17791530730 · [email protected]
陕西格列弗生物科技研究有限责任公司13892423764 · [email protected]
武汉敬康恩生物医药科技有限公司13720134139 086-15871494362 13720134139 · [email protected]
上海毕得医药科技股份有限公司
Related reactions
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Compound notes
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