Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C10H13N5O3.H2O |
| Molecular Weight | 269.2572 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.NC1=NC=NC2=C1N=CN2[C@H]3C[C@H](O)[C@@H](CO)O3
InChI
InChIKey=WZJWHIMNXWKNTO-VWZUFWLJSA-N
InChI=1S/C10H13N5O3.H2O/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(17)6(2-16)18-7;/h3-7,16-17H,1-2H2,(H2,11,12,13);1H2/t5-,6+,7+;/m0./s1
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C10H13N5O3 |
| Molecular Weight | 251.2419 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
2′-Deoxyadenosine, a pair of deoxythymidine (T) in double-stranded DNA, is a substrate of adenosine deaminase. In case of absence of this enzyme, 2′-deoxyadenosine accumulates in T lymphocytes and kills these cells resulting in a genetic disorder known as adenosine deaminase severe combined immunodeficiency disease (ADA-SCID).
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Altered deoxynucleoside triphosphate levels paralleling deoxyadenosine toxicity in adenosine deaminase inhibited human lymphocytes. | 1980 |
|
| Resistance of pokeweed mitogen-stimulated B cells to inhibition by deoxyadenosine. | 1980 Jul |
|
| Antiviral, antimetabolic and antineoplastic activities of 2'- or 3'-amino or -azido-substituted deoxyribonucleosides. | 1980 Jun 15 |
|
| Deoxycytidine kinase-mediated toxicity of deoxyadenosine analogs toward malignant human lymphoblasts in vitro and toward murine L1210 leukemia in vivo. | 1980 Nov |
|
| A comparison of the carcinogen-DNA adducts formed in rat liver in vivo after administration of single or multiple doses of N-methyl-4-aminoazobenzene. | 1981 Dec |
|
| Adenosine and deoxyadenosine toxicity in colony assay systems for human T-lymphocytes, B-lymphocytes, and granulocytes. | 1982 |
|
| S-adenosylhomocysteine catabolism and basis for acquired resistance during treatment of T-cell acute lymphoblastic leukemia with 2'-deoxycoformycin alone and in combination with 9-beta-D-arabinofuranosyladenine. | 1983 Jul |
|
| Nucleotide levels and metabolism of adenosine and deoxyadenosine in intact erythrocytes deficient in adenosine deaminase. | 1984 |
|
| Analytical DNA flow cytometric analysis of deoxyadenosine toxicity in cultured human leukemic lymphoblasts. | 1984 Sep |
|
| Purine metabolizing enzymes as predictors of lymphoblast sensitivity to deoxyadenosine. | 1984 Sep |
|
| Genetic analysis of deoxyadenosine toxicity in dividing human lymphoblasts. | 1986 |
|
| Preclinical studies on deoxycoformycin and deoxyadenosine as pharmacologic T cell purging tools. | 1989 Sep |
|
| Substrate specificity of human deoxycytidine kinase toward antiviral 2',3'-dideoxynucleoside analogs. | 1992 Jan 22 |
|
| High complete remission rate from 2-chloro-2'-deoxyadenosine in previously treated patients with B-cell chronic lymphocytic leukemia: response predicted by rapid decrease of blood lymphocyte count. | 1993 Apr |
|
| Rapid radioassay for metabolites of adenosine and deoxyadenosine in erythrocytes. | 1995 Dec 1 |
|
| Determination of adenosine and deoxyadenosine in urine by high-performance liquid chromatography with column switching. | 1998 Nov 20 |
|
| 1H-NMR spectroscopy of body fluids: inborn errors of purine and pyrimidine metabolism. | 1999 Apr |
|
| Molecular cloning and functional characterization of inhibitor-sensitive (mENT1) and inhibitor-resistant (mENT2) equilibrative nucleoside transporters from mouse brain. | 2000 Dec 1 |
|
| Phosphorylation of the anti-HIV compound (S,S)-isodideoxyadenosine by human recombinant deoxycytidine kinase. | 2000 Nov 15 |
|
| Cognitive and behavioral abnormalities in adenosine deaminase deficient severe combined immunodeficiency. | 2001 Jul |
|
| 5'-Esters of 2'-deoxyadenosine and 2-chloro-2'-deoxyadenosine with cell differentiation-provoking agents. | 2002 |
|
| Adenine and deazaadenine nucleoside and deoxynucleoside analogues: inhibition of viral replication of sheep MVV (in vitro model for HIV) and bovine BHV-1. | 2002 Sep |
|
| Selectivity of purine alkylation by a quinone methide. Kinetic or thermodynamic control? | 2003 Aug 8 |
|
| Telomerase activity, apoptosis and cell cycle progression in ataxia telangiectasia lymphocytes expressing TCL1. | 2003 Sep 15 |
|
| Characterization of glycine N-methyltransferase from rabbit liver. | 2004 Jun |
|
| Inhibition of hepatitis C replicon RNA synthesis by beta-D-2'-deoxy-2'-fluoro-2'-C-methylcytidine: a specific inhibitor of hepatitis C virus replication. | 2006 |
|
| Direct detection of 8-oxo-deoxyguanosine using UV resonance Raman spectroscopy. | 2007 May-Jun |
|
| A 13-Oxo-9,10-epoxytridecenoate phospholipid analogue of the genotoxic 4,5-epoxy-2E-decenal: detection in vivo, chemical synthesis, and adduction with DNA. | 2010 Mar 15 |
|
| Investigations into the origin of the molecular recognition of several adenosine deaminase inhibitors. | 2011 Jan 13 |
|
| Effects of substitutions at the 4' and 2 positions on the bioactivity of 4'-ethynyl-2-fluoro-2'-deoxyadenosine. | 2013 Dec |
|
| Utilization of CDKN1A/p21 gene for class discrimination of DNA damage-induced clastogenicity. | 2014 Jan 6 |
|
| Polymerase Bypass of N(6)-Deoxyadenosine Adducts Derived from Epoxide Metabolites of 1,3-Butadiene. | 2015 Jul 20 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:55:37 UTC 2023
by
admin
on
Fri Dec 15 15:55:37 UTC 2023
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| Record UNII |
F79D3BS9UH
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| Record Status |
Validated (UNII)
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| Record Version |
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F79D3BS9UH
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DTXSID801036040
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16373-93-6
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9549172
Created by
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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ANHYDROUS->SOLVATE | |||
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PARENT -> SALT/SOLVATE |
