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5'-Methylthioadenosine-d3

CAT: 0804-HY-16938S1-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-16938S1-01Size:1 mg
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Description
5'-Methylthioadenosine-d3 is the deuterium labeled 5'-Methylthioadenosine[1]. 5'-Methylthioadenosine (5'- (Methylthio) -5'-deoxyadenosine) is a nucleoside generated from S-adenosylmethionine (SAM) during polyamine synthesis. 5'-Methylthioadenosine suppresses tumors by inhibiting tumor cell proliferation, invasion, and the induction of apoptosis while controlling the inflammatory micro-environments of tumor tissue. 5'-Methylthioadenosine and its associated materials have striking regulatory effects on tumorigenesis[2][3][4].
CAS Number
174838-38-1
Product Name Alternative
5'- (Methylthio) -5'-deoxyadenosine-d3; 5'-S-Methyl-5'-thioadenosine-d3
UNSPSC
12352005
Hazard Statement
H302
Target
Apoptosis; Endogenous Metabolite; Parasite
Type
Isotope-Labeled Compounds
Related Pathways
Anti-infection; Apoptosis; Metabolic Enzyme/Protease
Applications
Metabolism-protein/nucleotide metabolism
Field of Research
Inflammation/Immunology
Purity
99.90
Solubility
DMF : 2.5mg/mL (ultrasonic) |DMSO : 50mg/mL (ultrasonic) |H2O : 1mg/mL (ultrasonic)
Smiles
NC1=C2N([C@]3([H])O[C@@H]([C@H]([C@H]3O)O)CSC([2H])([2H])[2H])C=NC2=NC=N1
Molecular Formula
C11H12D3N5O3S
Molecular Weight
300.35
Precautions
H302
References & Citations
[1]Russak EM, et al. Impact of Deuterium Substitution on the Pharmacokinetics of Pharmaceuticals. Ann Pharmacother. 2019 Feb;53 (2) :211-216.|[2]Tang Y, et al. 5'-Methylthioadenosine attenuates ischemia reperfusion injury after liver transplantation in rats. Inflammation. 2014;37 (5) :1366-1373.2018;78 (15) :4386-4395.|[3]Li Y, et al. 5'-Methylthioadenosine and Cancer: old molecules, new understanding. J Cancer. 2019;10 (4) :927-936.|[4]Tang B, et al. Specific Targeting of MTAP-Deleted Tumors with a Combination of 2'-Fluoroadenine and 5'-Methylthioadenosine. Cancer Res.|[5]Yaofeng Li, et al. 5'-Methylthioadenosine and Cancer: old molecules, new understanding. J Cancer. 2019;10 (4) :927-936.
Shipping Conditions
Blue Ice
Storage Conditions
-20°C, 3 years (Powder)
Scientific Category
Isotope-Labeled Compounds
Clinical Information
No Development Reported

Chemical Information

5'-Deoxy-5'-methylthioadenosine-d3

See also: 5'-Methylthioadenosine (annotation moved to).

CAS Number174838-38-1
PubChem CID163332392
IUPAC Name(2R,3R,4S,5S)-2-(6-aminopurin-9-yl)-5-(trideuteriomethylsulfanylmethyl)oxolane-3,4-diol
Molecular FormulaC11H15N5O3S
Molecular Weight300.35
XLogP-0.3
Topological Polar Surface Area145
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count8
Rotatable Bond Count3
Heavy Atom Count20
Formal Charge0
Complexity352
SMILES
[2H]C([2H])([2H])SC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)O
InChI
InChI=1S/C11H15N5O3S/c1-20-2-5-7(17)8(18)11(19-5)16-4-15-6-9(12)13-3-14-10(6)16/h3-5,7-8,11,17-18H,2H2,1H3,(H2,12,13,14)/t5-,7-,8-,11-/m1/s1/i1D3
InChIKey
WUUGFSXJNOTRMR-YZLHILBGSA-N
Chemical Structure
2D Structure
2D structure of 5'-Deoxy-5'-methylthioadenosine-d3
CAS: 174838-38-1
CID: 163332392
Formula: C11H15N5O3S
MW: 300.35
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight300.35
XLogP3-0.3
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count8
Rotatable Bond Count3
Exact Mass300.10839077
Monoisotopic Mass300.10839077
Topological Polar Surface Area145 Ų
Heavy Atom Count20
Formal Charge0
Complexity352
Isotope Atom Count3
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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