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

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
Antiviral, antimetabolic and antineoplastic activities of 2'- or 3'-amino or -azido-substituted deoxyribonucleosides.	1980 Jun 15	7406907
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
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
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	8097528
Determination of adenosine and deoxyadenosine in urine by high-performance liquid chromatography with column switching.	1998 Nov 20	9869364
Molecular cloning and functional characterization of inhibitor-sensitive (mENT1) and inhibitor-resistant (mENT2) equilibrative nucleoside transporters from mouse brain.	2000 Dec 1	11085929
Characterization of glycine N-methyltransferase from rabbit liver.	2004 Jun	15181470
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
Effects of substitutions at the 4' and 2 positions on the bioactivity of 4'-ethynyl-2-fluoro-2'-deoxyadenosine.	2013 Dec	24100493
Utilization of CDKN1A/p21 gene for class discrimination of DNA damage-induced clastogenicity.	2014 Jan 6	24211769
Polymerase Bypass of N(6)-Deoxyadenosine Adducts Derived from Epoxide Metabolites of 1,3-Butadiene.	2015 Jul 20	26098310

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

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