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Isosilybin B (Standard)

CAT: 0804-HY-N7045RSize: 1 EachDry Ice: NoHazardous: No
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Description
Isosilybin B (Standard) is the analytical standard of Isosilybin B. This product is intended for research and analytical applications. Isosilybin B is a flavonolignan. Isosilybin B can be isolated from Silybum marianum. Isosilybin B can regulate cell cycle-related proteins (e.g., reduce cyclins (D3, D1, A, E), Cdk4, Cdk2, Cdc25A), and activate Caspases (Caspase-9 and Caspase-3). Isosilybin B can promote Apoptosis, reduce androgen receptor (AR) and PSA. Isosilybin B has anticancer activity against prostate cancer[1][2].
CAS Number
142796-22-3
UNSPSC
12352005
Target
Androgen Receptor; Apoptosis; Caspase; CDK; PSMA; Reference Standards
Type
Reference compound
Related Pathways
Apoptosis; Cell Cycle/DNA Damage; Immunology/Inflammation; Others; Vitamin D Related/Nuclear Receptor
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/isosilybin-b-standard.html
Smiles
O=C1[C@H](O)[C@@H](C2=CC=C(O[C@@H](C3=CC=C(O)C(OC)=C3)[C@H](CO)O4)C4=C2)OC5=CC(O)=CC(O)=C15
Molecular Formula
C25H22O10
Molecular Weight
482.44
References & Citations
[1]Deep G, et al. Isosilybin B and isosilybin A inhibit growth, induce G1 arrest and cause apoptosis in human prostatecancer LNCaP and 22Rv1 cells. Carcinogenesis. 2007 Jul;28 (7) :1533-42.|[2]Deep G, et al. Isosilybin B causes androgen receptor degradation in human prostate carcinoma cells via PI3K-Akt-Mdm2-mediated pathway. Oncogene. 2008 Jun 26;27 (28) :3986-98.|[3]Deep G, et al. Isosilybin B and isosilybin A inhibit growth, induce G1 arrest and cause apoptosis in human prostatecancer LNCaP and 22Rv1 cells. Carcinogenesis. 2007 Jul;28 (7) :1533-42.|[4]Deep G, et al. Isosilybin B causes androgen receptor degradation in human prostate carcinoma cells via PI3K-Akt-Mdm2-mediated pathway. Oncogene. 2008 Jun 26;27 (28) :3986-98.
Shipping Conditions
Room temperature
Scientific Category
Reference Standards
Isoform
Caspase 3; Caspase 9; CDK2; CDK4

Chemical Information

Isosilybin B

isosilybin b has been reported in Anastatica hierochuntica and Silybum marianum with data available.

CAS Number142796-22-3
PubChem CID10885340
IUPAC Name(2R,3R)-3,5,7-trihydroxy-2-[(2S,3S)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one
Molecular FormulaC25H22O10
Molecular Weight482.4
XLogP2.4
Topological Polar Surface Area155
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count10
Rotatable Bond Count4
Heavy Atom Count35
Formal Charge0
Complexity750
SMILES
COC1=C(C=CC(=C1)[C@H]2[C@@H](OC3=C(O2)C=CC(=C3)[C@@H]4[C@H](C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O
InChI
InChI=1S/C25H22O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-18-7-12(3-5-16(18)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,23-29,31H,10H2,1H3/t20-,23-,24-,25+/m0/s1
InChIKey
FDQAOULAVFHKBX-WAABAYLZSA-N
Chemical Structure
2D Structure
2D structure of Isosilybin B
CAS: 142796-22-3
CID: 10885340
Formula: C25H22O10
MW: 482.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight482.4
XLogP32.4
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count10
Rotatable Bond Count4
Exact Mass482.12129689
Monoisotopic Mass482.12129689
Topological Polar Surface Area155 Ų
Heavy Atom Count35
Formal Charge0
Complexity750
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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