2'-DEOXYADENOSINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H13N5O3
Molecular Weight	251.2419
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=NC=NC2=C1N=CN2[C@H]3C[C@H](O)[C@@H](CO)O3

InChI

InChIKey=OLXZPDWKRNYJJZ-RRKCRQDMSA-N

InChI=1S/C10H13N5O3/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)/t5-,6+,7+/m0/s1

HIDE SMILES / InChI

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23280131 | https://www.ncbi.nlm.nih.gov/pubmed/15705418

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

Targets

Primary Target	Pharmacology	Condition	Potency
Adenosine deaminase 14 Target ID: P00813 Gene ID: 100.0 Gene Symbol: ADA Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15705418	Substrate 661

Conditions

Condition	Modality	Targets	Highest Phase	Product
Adenosine deaminase deficiency 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23280131	Diagnostic		Natural Metabolite	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Polymerase Bypass of N(6)-Deoxyadenosine Adducts Derived from Epoxide Metabolites of 1,3-Butadiene.	2015-07-20	26098310
Utilization of CDKN1A/p21 gene for class discrimination of DNA damage-induced clastogenicity.	2014-01-06	24211769
Effects of substitutions at the 4' and 2 positions on the bioactivity of 4'-ethynyl-2-fluoro-2'-deoxyadenosine.	2013-12	24100493
Investigations into the origin of the molecular recognition of several adenosine deaminase inhibitors.	2011-01-13	21138280
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.	2010-03-15	20131875
Direct detection of 8-oxo-deoxyguanosine using UV resonance Raman spectroscopy.	2006-07-01	16808627
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	17042329
Characterization of glycine N-methyltransferase from rabbit liver.	2004-06	15181470
Telomerase activity, apoptosis and cell cycle progression in ataxia telangiectasia lymphocytes expressing TCL1.	2003-09-15	12966431
Selectivity of purine alkylation by a quinone methide. Kinetic or thermodynamic control?	2003-08-08	12895079
Adenine and deazaadenine nucleoside and deoxynucleoside analogues: inhibition of viral replication of sheep MVV (in vitro model for HIV) and bovine BHV-1.	2002-09	12110319
5'-Esters of 2'-deoxyadenosine and 2-chloro-2'-deoxyadenosine with cell differentiation-provoking agents.	2002	12136933
Cognitive and behavioral abnormalities in adenosine deaminase deficient severe combined immunodeficiency.	2001-07	11445793
Molecular cloning and functional characterization of inhibitor-sensitive (mENT1) and inhibitor-resistant (mENT2) equilibrative nucleoside transporters from mouse brain.	2000-12-01	11085929
Phosphorylation of the anti-HIV compound (S,S)-isodideoxyadenosine by human recombinant deoxycytidine kinase.	2000-11-15	11020453
1H-NMR spectroscopy of body fluids: inborn errors of purine and pyrimidine metabolism.	1999-04	10102915
Determination of adenosine and deoxyadenosine in urine by high-performance liquid chromatography with column switching.	1998-11-20	9869364
Rapid radioassay for metabolites of adenosine and deoxyadenosine in erythrocytes.	1995-12-01	8749261
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.	1993-04	8097528
Substrate specificity of human deoxycytidine kinase toward antiviral 2',3'-dideoxynucleoside analogs.	1992-01-22	1739408
Preclinical studies on deoxycoformycin and deoxyadenosine as pharmacologic T cell purging tools.	1989-09	2790329
Genetic analysis of deoxyadenosine toxicity in dividing human lymphoblasts.	1986	3020905
Analytical DNA flow cytometric analysis of deoxyadenosine toxicity in cultured human leukemic lymphoblasts.	1984-09	6332978
Purine metabolizing enzymes as predictors of lymphoblast sensitivity to deoxyadenosine.	1984-09	6147383
Nucleotide levels and metabolism of adenosine and deoxyadenosine in intact erythrocytes deficient in adenosine deaminase.	1984	6609529
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.	1983-07	6601986
Adenosine and deoxyadenosine toxicity in colony assay systems for human T-lymphocytes, B-lymphocytes, and granulocytes.	1982	6982786
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.	1981-12	7326805
Deoxycytidine kinase-mediated toxicity of deoxyadenosine analogs toward malignant human lymphoblasts in vitro and toward murine L1210 leukemia in vivo.	1980-11	6256765
Resistance of pokeweed mitogen-stimulated B cells to inhibition by deoxyadenosine.	1980-07	6969149
Antiviral, antimetabolic and antineoplastic activities of 2'- or 3'-amino or -azido-substituted deoxyribonucleosides.	1980-06-15	7406907
Altered deoxynucleoside triphosphate levels paralleling deoxyadenosine toxicity in adenosine deaminase inhibited human lymphocytes.	1980	6968502

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:48:08 GMT 2025` Edited by `admin` on `Mon Mar 31 17:48:08 GMT 2025`
Record UNII	P582C98ULC
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

2'-DEOXYADENOSINE

Systematic Name

English

NSC-141848

Preferred Name

English

.BETA.-D-RIBOFURANOSE, 1-(6-AMINO-9H-PURIN-9-YL)-1,2-DIDEOXY-

Systematic Name

English

NSC-143510

Code

English

DESOXYADENOSINE

Systematic Name

English

ADENOSINE, 2'-DEOXY-

Systematic Name

English

9-(2-DEOXY-.BETA.-D-ERYTHRO-PENTOFURANOSYL)ADENINE

Common Name

English

9H-PURIN-6-AMINE, 9-(2-DEOXY-.BETA.-D-RIBOFURANOSYL)-

Common Name

English

9H-PURIN-6-AMINE, 9-(2-DEOXY-.BETA.-D-ERYTHRO-PENTOFURANOSYL)-

Common Name

English

NSC-83258

Code

English

2'-DEOXYADENOSINE [USP IMPURITY]

Common Name

English

DEOXYADENOSINE

Systematic Name

English

Classification Tree Code System Code

LOINC

75122-2