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Vanicoside B

CAT: 0804-HY-N9561-02Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N9561-02Size:5 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Vanicoside B is a phenylpropanoyl sucrose derivative, can be isolated from the herb Persicaria dissitiflora. Vanicoside B targets cyclin-dependent kinase 8 (CDK8) and exhibits anti-tumor activity. The potential mechanism is Vanicoside B blocks CDK8-mediated signaling pathways and decreases the expression of epithelial-mesenchymal transition proteins, so that it leads to cell cycle arrest and apoptosis[1][2].
CAS Number
155179-21-8
UNSPSC
12352005
Target
CDK; STAT
Type
Natural Products
Related Pathways
Cell Cycle/DNA Damage; JAK/STAT Signaling; Stem Cell/Wnt
Applications
Cancer-Kinase/protease
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/vanicoside-b.html
Purity
99.82
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
OC(C=C1)=CC=C1/C=C/C(OC[C@@]2([C@H]([C@@H]([C@H](O2)COC(/C=C/C3=CC=C(C=C3)O)=O)O)OC(/C=C/C4=CC=C(C=C4)O)=O)O[C@H]5O[C@@H]([C@H]([C@@H]([C@H]5O)O)O)COC(/C=C/C6=CC(OC)=C(C=C6)O)=O)=O
Molecular Formula
C49H48O20
Molecular Weight
956.89
References & Citations
[1]Kim D, et al. Antitumor Activity of Vanicoside B Isolated from Persicaria dissitiflora by Targeting CDK8 in Triple-Negative Breast Cancer Cells. J Nat Prod. 2019 Nov 22;82 (11) :3140-3149. |[2]Takasaki M, et al. Cancer chemopreventive activity of phenylpropanoid esters of sucrose, vanicoside B and lapathoside A, from Polygonum lapathifolium. Cancer Lett. 2001 Nov 28;173 (2) :133-8.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, protect from light)
Scientific Category
Natural Products
Clinical Information
No Development Reported
Isoform
CDK3; STAT3

Chemical Information

Vanicoside B

Vanicoside B has been reported in Persicaria pensylvanica and Persicaria perfoliata with data available.

CAS Number155179-21-8
PubChem CID10033855
IUPAC Name[(2R,3R,4S,5S)-3-hydroxy-4-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-5-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxyoxolan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
Molecular FormulaC49H48O20
Molecular Weight956.9
XLogP3.7
Topological Polar Surface Area304
Hydrogen Bond Donor Count8
Hydrogen Bond Acceptor Count20
Rotatable Bond Count22
Heavy Atom Count69
Formal Charge0
Complexity1780
SMILES
COC1=C(C=CC(=C1)/C=C/C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@H](O2)O[C@]3([C@H]([C@@H]([C@H](O3)COC(=O)/C=C/C4=CC=C(C=C4)O)O)OC(=O)/C=C/C5=CC=C(C=C5)O)COC(=O)/C=C/C6=CC=C(C=C6)O)O)O)O)O
InChI
InChI=1S/C49H48O20/c1-62-36-24-31(8-19-35(36)53)12-22-40(55)63-25-37-43(58)45(60)46(61)48(66-37)69-49(27-65-41(56)21-10-29-4-15-33(51)16-5-29)47(67-42(57)23-11-30-6-17-34(52)18-7-30)44(59)38(68-49)26-64-39(54)20-9-28-2-13-32(50)14-3-28/h2-24,37-38,43-48,50-53,58-61H,25-27H2,1H3/b20-9+,21-10+,22-12+,23-11+/t37-,38-,43-,44-,45+,46-,47+,48-,49+/m1/s1
InChIKey
ALSDWGAQQGXOHC-PWYSLETCSA-N
Chemical Structure
2D Structure
2D structure of Vanicoside B
CAS: 155179-21-8
CID: 10033855
Formula: C49H48O20
MW: 956.9
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight956.9
XLogP33.7
Hydrogen Bond Donor Count8
Hydrogen Bond Acceptor Count20
Rotatable Bond Count22
Exact Mass956.27389392
Monoisotopic Mass956.27389392
Topological Polar Surface Area304 Ų
Heavy Atom Count69
Formal Charge0
Complexity1780
Isotope Atom Count0
Defined Atom Stereocenter Count9
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count4
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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