5'-Chloro-5'-deoxyadenosine - CAS 892-48-8
Catalog: |
BB039390 |
Product Name: |
5'-Chloro-5'-deoxyadenosine |
CAS: |
892-48-8 |
Synonyms: |
5'-Chloroadenosine; 5'-deoxy-5'-chloroadenosine |
IUPAC Name: | (2R,3R,4S,5S)-2-(6-aminopurin-9-yl)-5-(chloromethyl)oxolane-3,4-diol |
Description: | 5'-Chloro-5'-deoxyadenosine (CAS# 892-48-8) is an intermediate in the synthesis of 5'-Deoxy-5'-(methylthio)adenosine (D242600), a substrate to study the specificity and kinetics of 5'-methylthioadenosinephosphorylase (MTAP) (EC2.4.2.28), a tumor suppressor gene expressed enzyme that supports the S-adenosylmethionine (AdoMet) and methionine salvage pathways. |
Molecular Weight: | 285.69 |
Molecular Formula: | C10H12ClN5O3 |
Canonical SMILES: | C1=NC2=C(C(=N1)N)N=CN2C3C(C(C(O3)CCl)O)O |
InChI: | InChI=1S/C10H12ClN5O3/c11-1-4-6(17)7(18)10(19-4)16-3-15-5-8(12)13-2-14-9(5)16/h2-4,6-7,10,17-18H,1H2,(H2,12,13,14)/t4-,6-,7-,10-/m1/s1 |
InChI Key: | IYSNPOMTKFZDHZ-KQYNXXCUSA-N |
Boiling Point: | 645.6 °C at 760 mmHg |
Melting Point: | 187 °C |
Purity: | 96 % |
Density: | 2.03 g/cm3 |
Storage: | Store at 2-8 °C |
LogP: | -0.15230 |
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PMID | Publication Date | Title | Journal |
22579483 | 20120615 | S-Adenosylhomocysteine hydrolase of the protozoan parasite Trichomonas vaginalis: potent inhibitory activity of 9-(2-deoxy-2-fluoro-β,D-arabinofuranosyl)adenine | Bioorganic & medicinal chemistry letters |
19590008 | 20090728 | Biosynthesis of the salinosporamide A polyketide synthase substrate chloroethylmalonyl-coenzyme A from S-adenosyl-L-methionine | Proceedings of the National Academy of Sciences of the United States of America |
18083524 | 20080301 | Activation and inhibition of DNA methyltransferases by S-adenosyl-L-homocysteine analogues | Bioorganic & medicinal chemistry |
18059261 | 20080101 | Discovery and characterization of a marine bacterial SAM-dependent chlorinase | Nature chemical biology |
12161307 | 20020815 | Synthesis of adenosylcobinamide 2-chlorophenyl phosphate, a zwitterionic cobinamide phosphate analog of adenosylcobalamin en route to crystallizable cobinamides | Journal of inorganic biochemistry |
Complexity: | 338 |
Compound Is Canonicalized: | Yes |
Covalently-Bonded Unit Count: | 1 |
Defined Atom Stereocenter Count: | 4 |
Defined Bond Stereocenter Count: | 0 |
Exact Mass: | 285.062867 |
Formal Charge: | 0 |
Heavy Atom Count: | 19 |
Hydrogen Bond Acceptor Count: | 7 |
Hydrogen Bond Donor Count: | 3 |
Isotope Atom Count: | 0 |
Monoisotopic Mass: | 285.062867 |
Rotatable Bond Count: | 2 |
Topological Polar Surface Area: | 119 |
Undefined Atom Stereocenter Count: | 0 |
Undefined Bond Stereocenter Count: | 0 |
XLogP3: | -0.3 |
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