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N6-Benzyladenosine

CAT: 0804-HY-N7844-01Size: 10 mM - 1 mLDry Ice: NoHazardous: No
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CAT#:0804-HY-N7844-01Size:10 mM - 1 mL
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
N6-Benzyladenosine is an adenosine receptor agonist, has a cytoactive activity. N6-Benzyladenosine arrests cell cycle at G0/G1 phase and induces cell apoptosis. N6-Benzyladenosine also exerts inhibitory effect on T. gondii adenosine kinase and glioma[1]-[5].
CAS Number
4294-16-0
Product Name Alternative
Benzyladenosine
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Adenosine Receptor; Apoptosis; Phytohormone
Type
Natural Products
Related Pathways
Apoptosis; GPCR/G Protein; Others
Applications
COVID-19-immunoregulation
Field of Research
Cancer; Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/n6-benzyladenosine.html
Purity
99.72
Solubility
DMSO : 125 mg/mL (ultrasonic)
Smiles
O[C@H]1[C@@H](O)[C@H](N2C(N=CN=C3NCC4=CC=CC=C4)=C3N=C2)O[C@@H]1CO
Molecular Formula
C17H19N5O4
Molecular Weight
357.36
Precautions
H302, H315, H319, H335
References & Citations
[1]Kaminek M, et al. Cytokinin activities of N6-benzyladenosine derivatives hydroxylated on the side-chain phenyl ring. Journal of Plant Growth Regulation. 1987. 6 (2) :113.|[2]Castiglioni S, et al. N6-isopentenyladenosine and its analogue N6-benzyladenosine induce cell cycle arrest and apoptosis in bladder carcinoma T24 cells. Anticancer Agents Med Chem. 2013 May;13 (4) :672-8. |[3]Mlejnek P. Caspase inhibition and N6-benzyladenosine-induced apoptosis in HL-60 cells. J Cell Biochem. 2001;83 (4) :678-89.|[4]Kim YA, et al. Synthesis, biological evaluation and molecular modeling studies of N6-benzyladenosine analogues as potential anti-toxoplasma agents. Biochem Pharmacol. 2007 May 15;73 (10) :1558-72. |[5]Grimaldi M, et al. NMR for screening and a biochemical assay: Identification of new FPPS inhibitors exerting anticancer activity. Bioorg Chem. 2020 May;98:103449.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, protect from light)
Scientific Category
Natural Products
Clinical Information
No Development Reported
Isoform
Cytokinin

Chemical Information

Benzyladenosine

RN given refers to parent cpd

CAS Number4294-16-0
PubChem CID92208
IUPAC Name(2R,3R,4S,5R)-2-[6-(benzylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
Molecular FormulaC17H19N5O4
Molecular Weight357.4
XLogP1.1
Topological Polar Surface Area126
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count8
Rotatable Bond Count5
Heavy Atom Count26
Formal Charge0
Complexity466
SMILES
C1=CC=C(C=C1)CNC2=C3C(=NC=N2)N(C=N3)[C@H]4[C@@H]([C@@H]([C@H](O4)CO)O)O
InChI
InChI=1S/C17H19N5O4/c23-7-11-13(24)14(25)17(26-11)22-9-21-12-15(19-8-20-16(12)22)18-6-10-4-2-1-3-5-10/h1-5,8-9,11,13-14,17,23-25H,6-7H2,(H,18,19,20)/t11-,13-,14-,17-/m1/s1
InChIKey
MRPKNNSABYPGBF-LSCFUAHRSA-N
Chemical Structure
2D Structure
2D structure of Benzyladenosine
CAS: 4294-16-0
CID: 92208
Formula: C17H19N5O4
MW: 357.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight357.4
XLogP31.1
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count8
Rotatable Bond Count5
Exact Mass357.14370410
Monoisotopic Mass357.14370410
Topological Polar Surface Area126 Ų
Heavy Atom Count26
Formal Charge0
Complexity466
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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