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Kurarinone

CAT: 0013-GTR19156593-04Size: 25 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19156593-04Size:25 mg
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Description
Kurarinone, a flavanoid derived from shrub Sophora flavescens, Kurarinone exhibits anti-tumor, estrogenic, and anti-inflammatory activities, it also shows strong inhibitory effect on immune responses. Kurarinone may ameliorate chronic inflammatory skin diseases through the suppression of pathogenic CD4 (+) T-cell differentiation and the overall immune response.Kurarinone, a lavandulyl flavanone, was isolated from a polyphenolic extract of the roots of Sophora flavescens using fractionation guided by estrogenic activity, which was determined by recombinant yeast and Ishikawa Var-I bioassays. METHODS AND RESULTS:Kurarinone showed weak estrogenic activity both in the yeast screen and in the Ishikawa Var-I assay with EC (50) values of 4.6 and 1.66 microM, respectively. Furthermore, Kurarinone was found to have potent cytotoxic activity (IC (50) value = 22.2 microM) against human MCF-7/6 breast cancer cells in the sulforhodamine-B assay.
CAS Number
34981-26-5
Purity
>98% (HPLC)
Solubility
In Vitro: DMSO : 50 mg/mL (114.02 mM)
Smiles
O=C1C[C@@H] (C2=CC=C (O) C=C2O) OC3=C (C[C@H] (C (C) =C) C/C=C (C) \C) C (O) =CC (OC) =C13
Molecular Formula
C26H30O6
Molecular Weight
438.52
Storage Conditions
Storage temperature: -20°C. Stability: ≥ 2 years
Notes
For research use only.

Chemical Information

Kurarinone

(2S)-(-)-kurarinone is a trihydroxyflavanone that is (2S)-flavanone substituted by hydroxy groups at positions 7, 2' and 4', a lavandulyl group at position 8 and a methoxy group at position 5. Isolated from the roots of Sophora flavescens, it exhibits cytotoxicity against human myeloid leukemia HL-60 cells. It has a role as a metabolite and an antineoplastic agent. It is a member of 4'-hydroxyflavanones, a monomethoxyflavanone and a trihydroxyflavanone. It is functionally related to a (2S)-flavanone.

CAS Number34981-26-5
PubChem CID11982640
IUPAC Name(2S)-2-(2,4-dihydroxyphenyl)-7-hydroxy-5-methoxy-8-[(2R)-5-methyl-2-prop-1-en-2-ylhex-4-enyl]-2,3-dihydrochromen-4-one
Molecular FormulaC26H30O6
Molecular Weight438.5
XLogP5.6
Topological Polar Surface Area96.2
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count7
Heavy Atom Count32
Formal Charge0
Complexity698
SMILES
CC(=CC[C@H](CC1=C2C(=C(C=C1O)OC)C(=O)C[C@H](O2)C3=C(C=C(C=C3)O)O)C(=C)C)C
InChI
InChI=1S/C26H30O6/c1-14(2)6-7-16(15(3)4)10-19-21(29)12-24(31-5)25-22(30)13-23(32-26(19)25)18-9-8-17(27)11-20(18)28/h6,8-9,11-12,16,23,27-29H,3,7,10,13H2,1-2,4-5H3/t16-,23+/m1/s1
InChIKey
LTTQKYMNTNISSZ-MWTRTKDXSA-N
Chemical Structure
2D Structure
2D structure of Kurarinone
CAS: 34981-26-5
CID: 11982640
Formula: C26H30O6
MW: 438.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight438.5
XLogP35.6
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count7
Exact Mass438.20423867
Monoisotopic Mass438.20423867
Topological Polar Surface Area96.2 Ų
Heavy Atom Count32
Formal Charge0
Complexity698
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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