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 13 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
Altered deoxynucleoside triphosphate levels paralleling deoxyadenosine toxicity in adenosine deaminase inhibited human lymphocytes.	1980	6968502
Resistance of pokeweed mitogen-stimulated B cells to inhibition by deoxyadenosine.	1980 Jul	6969149
Deoxycytidine kinase-mediated toxicity of deoxyadenosine analogs toward malignant human lymphoblasts in vitro and toward murine L1210 leukemia in vivo.	1980 Nov	6256765
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	7326805
Adenosine and deoxyadenosine toxicity in colony assay systems for human T-lymphocytes, B-lymphocytes, and granulocytes.	1982	6982786
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	6601986
Nucleotide levels and metabolism of adenosine and deoxyadenosine in intact erythrocytes deficient in adenosine deaminase.	1984	6609529
Analytical DNA flow cytometric analysis of deoxyadenosine toxicity in cultured human leukemic lymphoblasts.	1984 Sep	6332978
Purine metabolizing enzymes as predictors of lymphoblast sensitivity to deoxyadenosine.	1984 Sep	6147383
Genetic analysis of deoxyadenosine toxicity in dividing human lymphoblasts.	1986	3020905
Preclinical studies on deoxycoformycin and deoxyadenosine as pharmacologic T cell purging tools.	1989 Sep	2790329
Substrate specificity of human deoxycytidine kinase toward antiviral 2',3'-dideoxynucleoside analogs.	1992 Jan 22	1739408
Rapid radioassay for metabolites of adenosine and deoxyadenosine in erythrocytes.	1995 Dec 1	8749261
Determination of adenosine and deoxyadenosine in urine by high-performance liquid chromatography with column switching.	1998 Nov 20	9869364
1H-NMR spectroscopy of body fluids: inborn errors of purine and pyrimidine metabolism.	1999 Apr	10102915
Cognitive and behavioral abnormalities in adenosine deaminase deficient severe combined immunodeficiency.	2001 Jul	11445793
5'-Esters of 2'-deoxyadenosine and 2-chloro-2'-deoxyadenosine with cell differentiation-provoking agents.	2002	12136933
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	12110319
Selectivity of purine alkylation by a quinone methide. Kinetic or thermodynamic control?	2003 Aug 8	12895079
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
Direct detection of 8-oxo-deoxyguanosine using UV resonance Raman spectroscopy.	2007 May-Jun	16808627
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	20131875
Investigations into the origin of the molecular recognition of several adenosine deaminase inhibitors.	2011 Jan 13	21138280
Utilization of CDKN1A/p21 gene for class discrimination of DNA damage-induced clastogenicity.	2014 Jan 6	24211769

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 `Fri Dec 15 15:08:58 UTC 2023` Edited by `admin` on `Fri Dec 15 15:08:58 UTC 2023`
Record UNII	P582C98ULC
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

2'-DEOXYADENOSINE

Systematic Name

English

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

Systematic Name

English

NSC-143510

Code

English

2'-DEOXYADENOSINE [INCI]

Common Name

English

DESOXYADENOSINE

Systematic Name

English

ADENOSINE, 2'-DEOXY-

Systematic Name

English

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

Common Name

English

NSC-141848

Code

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