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Home > Other Building Blocks > 2457-80-9
2457-80-9 | Adenosine, 5'-S-methyl-5'-thio-
CAS No: 2457-80-9 Catalog No: AG002OLP MDL No:MFCD00010533
Product Description
Catalog Number:
AG002OLP
Chemical Name:
Adenosine, 5'-S-methyl-5'-thio-
CAS Number:
2457-80-9
Molecular Formula:
C11H15N5O3S
Molecular Weight:
297.3335
MDL Number:
MFCD00010533
IUPAC Name:
(2R,3R,4S,5S)-2-(6-aminopurin-9-yl)-5-(methylsulfanylmethyl)oxolane-3,4-diol
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
InChI Key:
WUUGFSXJNOTRMR-IOSLPCCCSA-N
SMILES:
CSC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2N
UNII:
634Z2VK3UQ
Properties
Complexity:
352
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
4
Defined Bond Stereocenter Count:
0
Exact Mass:
297.09g/mol
Formal Charge:
0
Heavy Atom Count:
20
Hydrogen Bond Acceptor Count:
8
Hydrogen Bond Donor Count:
3
Isotope Atom Count:
0
Molecular Weight:
297.333g/mol
Monoisotopic Mass:
297.09g/mol
Rotatable Bond Count:
3
Topological Polar Surface Area:
145A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-0.3
Literature
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| The crystal structure of 5'-deoxy-5'-methylthioadenosine phosphorylase II from Sulfolobus solfataricus, a thermophilic enzyme stabilized by intramolecular disulfide bonds. | Journal of molecular biology 20060317 |
| EFA (9-beta-D-erythrofuranosyladenine) is an effective salvage agent for methylthioadenosine phosphorylase-selective therapy of T-cell acute lymphoblastic leukemia with L-alanosine. | Blood 20060201 |
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| A nucleosidase required for in vivo function of the S-adenosyl-L-methionine radical enzyme, biotin synthase. | Chemistry & biology 20050501 |
| Regulation of human methylthioadenosine phosphorylase gene by the CBF (CCAAT binding factor)/NF-Y (nuclear factor-Y). | The Biochemical journal 20050401 |
| Methylthioadenosine phosphorylase gene is silenced by promoter hypermethylation in human lymphoma cell line DHL-9: another mechanism of enzyme deficiency. | International journal of oncology 20050401 |
| Chemical mechanism and substrate specificity of RhlI, an acylhomoserine lactone synthase from Pseudomonas aeruginosa. | Biochemistry 20050301 |
| Ewing sarcomas with p53 mutation or p16/p14ARF homozygous deletion: a highly lethal subset associated with poor chemoresponse. | Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20050120 |
| Strong expression of methylthioadenosine phosphorylase (MTAP) in human colon carcinoma cells is regulated by TCF1/[beta]-catenin. | Laboratory investigation; a journal of technical methods and pathology 20050101 |
| Bayesian phylogenetic analysis reveals two-domain topology of S-adenosylhomocysteine hydrolase protein sequences. | Molecular phylogenetics and evolution 20050101 |
| Comparative analysis of RNA regulatory elements of amino acid metabolism genes in Actinobacteria. | BMC microbiology 20050101 |
| Natural history of S-adenosylmethionine-binding proteins. | BMC structural biology 20050101 |
| Design and evaluation of 5'-modified nucleoside analogs as prodrugs for an E. coli purine nucleoside phosphorylase mutant. | Nucleosides, nucleotides & nucleic acids 20050101 |
| Functional analysis of methylthioribose kinase genes in plants. | Plant physiology 20041201 |
| Methylthioadenosine phosphorylase from the archaeon Pyrococcus furiosus. Mechanism of the reaction and assignment of disulfide bonds. | European journal of biochemistry 20041201 |
| Methylthioadenosine phosphorylase gene expression is impaired in human liver cirrhosis and hepatocarcinoma. | Biochimica et biophysica acta 20041105 |
| Methylthioadenosine. | The international journal of biochemistry & cell biology 20041101 |
| Loss of methylthioadenosine phosphorylase and elevated ornithine decarboxylase is common in pancreatic cancer. | Clinical cancer research : an official journal of the American Association for Cancer Research 20041101 |
| Comprehensive analysis of the 9p21 region in neuroblastoma suggests a role for genes mapping to 9p21-23 in the biology of favourable stage 4 tumours. | British journal of cancer 20040913 |
| Crystal structure of yeast Ypr118w, a methylthioribose-1-phosphate isomerase related to regulatory eIF2B subunits. | The Journal of biological chemistry 20040827 |
| Inhibition of lipopolysaccharide-stimulated TNF-alpha promoter activity by S-adenosylmethionine and 5'-methylthioadenosine. | American journal of physiology. Gastrointestinal and liver physiology 20040801 |
| Analogs of 1-phosphonooxy-2,2-dihydroxy-3-oxo-5-(methylthio)pentane, an acyclic intermediate in the methionine salvage pathway: a new preparation and characterization of activity with E1 enolase/phosphatase from Klebsiella oxytoca. | Bioorganic & medicinal chemistry 20040715 |
| S-adenosylmethionine and its metabolite induce apoptosis in HepG2 cells: Role of protein phosphatase 1 and Bcl-x(S). | Hepatology (Baltimore, Md.) 20040701 |
| Delivery systems and molecular targets of mechanism-based therapies for GBM. | Expert review of neurotherapeutics 20040701 |
| Metabolic and antiproliferative consequences of activated polyamine catabolism in LNCaP prostate carcinoma cells. | The Journal of biological chemistry 20040625 |
| [Expression and clinical significance of methylthioadenosine phosphorylase gene in patients with non-small cell lung cancer]. | Zhonghua yi xue za zhi 20040602 |
| Antioxidant properties of S-adenosyl-L-methionine in Fe(2+)-initiated oxidations. | Free radical biology & medicine 20040515 |
| Novel amino acid derived natural products from the ascidian Atriolum robustum: identification and pharmacological characterization of a unique adenosine derivative. | Journal of medicinal chemistry 20040422 |
| Synthesis and evaluation of analogues of S-adenosyl-L-methionine, as inhibitors of the E. coli cyclopropane fatty acid synthase. | Bioorganic & medicinal chemistry letters 20040405 |
| 5'-methylthioadenosine modulates the inflammatory response to endotoxin in mice and in rat hepatocytes. | Hepatology (Baltimore, Md.) 20040401 |
| Pharmacology and mechanism of action of pemetrexed. | Clinical lung cancer 20040401 |
| Heparan sulfate proteoglycans function as receptors for fibroblast growth factor-2 activation of extracellular signal-regulated kinases 1 and 2. | Circulation research 20040220 |
| Picomolar transition state analogue inhibitors of human 5'-methylthioadenosine phosphorylase and X-ray structure with MT-immucillin-A. | Biochemistry 20040113 |
| Bacterial variations on the methionine salvage pathway. | BMC microbiology 20040101 |
| Status of methylthioadenosine phosphorylase and its impact on cellular response to L-alanosine and methylmercaptopurine riboside in human soft tissue sarcoma cells. | Oncology research 20040101 |
| Branched-chain amino acid aminotransferase and methionine formation in Mycobacterium tuberculosis. | BMC microbiology 20040101 |
| Methylthioadenosine phosphorylase regulates ornithine decarboxylase by production of downstream metabolites. | The Journal of biological chemistry 20031212 |
| Altered gene expression in liver from a murine model of hyperhomocysteinemia. | The Journal of biological chemistry 20030822 |
| Identification of gene expression profiles predicting tumor cell response to L-alanosine. | Biochemical pharmacology 20030815 |
| Characterization of methylthioadenosin phosphorylase (MTAP) expression in malignant melanoma. | The American journal of pathology 20030801 |
| Anaplerotic reactions in tumour proliferation and apoptosis. | Biochemical pharmacology 20030801 |
| Homozygous deletion of CDKN2A and codeletion of the methylthioadenosine phosphorylase gene in the majority of pleural mesotheliomas. | Clinical cancer research : an official journal of the American Association for Cancer Research 20030601 |
| CDKN2A, CDKN2B, and MTAP gene dosage permits precise characterization of mono- and bi-allelic 9p21 deletions in childhood acute lymphoblastic leukemia. | Genes, chromosomes & cancer 20030501 |
| Structure of Escherichia coli 5'-methylthioadenosine/ S-adenosylhomocysteine nucleosidase inhibitor complexes provide insight into the conformational changes required for substrate binding and catalysis. | The Journal of biological chemistry 20030307 |
| Characterisation of methionine adenosyltransferase from Mycobacterium smegmatis and M. tuberculosis. | BMC microbiology 20030101 |
| Modeling and experiment yields the structure of acireductone dioxygenase from Klebsiella pneumoniae. | Nature structural biology 20021201 |
| Methylthioadenosine phosphorylase, a gene frequently codeleted with p16(cdkN2a/ARF), acts as a tumor suppressor in a breast cancer cell line. | Cancer research 20021115 |
| Chemotherapy targeting methylthioadenosine phosphorylase (MTAP) deficiency in adult T cell leukemia (ATL). | Leukemia 20020901 |
| S-adenosylmethionine conformations in solution and in protein complexes: conformational influences of the sulfonium group. | Biochemistry 20020618 |
| Deletion of dinucleotide repeat (Delta 14 allele) in the methylthioadenosine phosphorylase (MTAP) promoter and the allelotype of MTAP promoter in the Japanese population. | Japanese journal of cancer research : Gann 20020401 |
| Methylthioadenosine phosphorylase gene deletions are common in osteosarcoma. | Clinical cancer research : an official journal of the American Association for Cancer Research 20020301 |
| S-adenosylmethionine decarboxylase from Leishmania donovani. Molecular, genetic, and biochemical characterization of null mutants and overproducers. | The Journal of biological chemistry 20020222 |
| S-adenosylmethionine and methylthioadenosine are antiapoptotic in cultured rat hepatocytes but proapoptotic in human hepatoma cells. | Hepatology (Baltimore, Md.) 20020201 |
| Protein repair methyltransferase from the hyperthermophilic archaeon Pyrococcus furiosus. Unusual methyl-accepting affinity for D-aspartyl and N-succinyl-containing peptides. | The Journal of biological chemistry 20020111 |
| Methylthioadenosine phosphorylase as target for chemoselective treatment of T-cell acute lymphoblastic leukemic cells. | Blood cells, molecules & diseases 20020101 |
| The methionine salvage pathway in Bacillus subtilis. | BMC microbiology 20020101 |
| Isolation and properties of arginase from a shade plant, ginseng (Panax ginseng C.A. Meyer) roots. | Phytochemistry 20011201 |
| Glutamate 47 in 1-aminocyclopropane-1-carboxylate synthase is a major specificity determinant. | Biochemistry 20011016 |
| Mechanistic studies of two dioxygenases in the methionine salvage pathway of Klebsiella pneumoniae. | Biochemistry 20010529 |
| Arginine methylation of STAT1 modulates IFNalpha/beta-induced transcription. | Cell 20010309 |
| 5'-Methylthioadenosine administration prevents lipid peroxidation and fibrogenesis induced in rat liver by carbon-tetrachloride intoxication. | Journal of hepatology 20010301 |
| In situ kinetic characterization of methylthioadenosine transport by the adenosine transporter (P2) of the African Trypanosoma brucei brucei and Trypanosoma brucei rhodesiense. | Biochemical pharmacology 20010215 |
| Expression, purification, crystallization and preliminary X-ray analysis of Escherichia coli 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase. | Acta crystallographica. Section D, Biological crystallography 20010101 |
| Extracting biological information from DNA arrays: an unexpected link between arginine and methionine metabolism in Bacillus subtilis. | Genome biology 20010101 |
| MtnK, methylthioribose kinase, is a starvation-induced protein in Bacillus subtilis. | BMC microbiology 20010101 |
| Functional characterization of the A2b adenosine receptor in NIH 3T3 fibroblasts. | Biochemical pharmacology 19940302 |
| Antimicrobial and antiviral activity of xylosyl-methylthio-adenosine, a naturally occurring analogue of methylthio-adenosine from Doris verrucosa. | Experientia 19911201 |
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