2'-deoxyadenosine (CHEBI:17256)

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CHEBI:17256 - 2'-deoxyadenosine

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ChEBI Name	2'-deoxyadenosine

ChEBI ID	CHEBI:17256

Definition	A purine 2'-deoxyribonucleoside having adenine as the nucleobase.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:39863, CHEBI:40535, CHEBI:19234, CHEBI:40560, CHEBI:40565, CHEBI:4405, CHEBI:14112

Supplier Information	ChemicalBook:CB9375521, ChemicalBook:CB7162318, eMolecules:496860, ZINC000001081581

Download	Molfile XML SDF

more structures >>

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31 33 0 0 0 0 999 V2000

-4.6460 1.7090 -1.0590 O 0 0 0 0 0 0 0 0 0 0 0 0

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-3.1800 -0.0580 -0.3040 C 0 0 1 0 0 0 0 0 0 0 0 0

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0.3430 0.1980 -0.1310 N 0 0 0 0 0 0 0 0 0 0 0 0

1.6080 -0.3000 -0.3190 C 0 0 0 0 0 0 0 0 0 0 0 0

2.1110 -1.3920 -0.8850 N 0 0 0 0 0 0 0 0 0 0 0 0

3.4110 -1.5960 -0.9100 C 0 0 0 0 0 0 0 0 0 0 0 0

4.2730 -0.7440 -0.3850 N 0 0 0 0 0 0 0 0 0 0 0 0

3.8630 0.3760 0.2010 C 0 0 0 0 0 0 0 0 0 0 0 0

4.7730 1.2630 0.7480 N 0 0 0 0 0 0 0 0 0 0 0 0

2.4830 0.6350 0.2580 C 0 0 0 0 0 0 0 0 0 0 0 0

1.7220 1.6410 0.7530 N 0 0 0 0 0 0 0 0 0 0 0 0

0.4660 1.3850 0.5280 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.3800 -1.4390 0.5070 C 0 0 0 0 0 0 0 0 0 0 0 0

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3.7880 -2.4940 -1.3770 H 0 0 0 0 0 0 0 0 0 0 0 0

5.7230 1.0710 0.7060 H 0 0 0 0 0 0 0 0 0 0 0 0

4.4620 2.0790 1.1700 H 0 0 0 0 0 0 0 0 0 0 0 0

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5 16 1 0 0 0 0

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Wikipedia	License
Deoxyadenosine (symbol dA or dAdo) is a deoxyribonucleoside. It is a derivative of the nucleoside adenosine, differing from the latter by the replacement of a hydroxyl group (-OH) by hydrogen (-H) at the 2′ position of its ribose sugar moiety. Deoxyadenosine is the DNA nucleoside A, which pairs with deoxythymidine (T) in double-stranded DNA. In absence of adenosine deaminase (ADA) it accumulates in T lymphocytes and kills these cells resulting in a genetic disorder known as adenosine deaminase severe combined immunodeficiency disease (ADA-SCID).
Read full article at Wikipedia

Formula

C10H13N5O3

Net Charge

Average Mass

251.24212

Monoisotopic Mass

251.10184

InChI

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

InChIKey

OLXZPDWKRNYJJZ-RRKCRQDMSA-N

SMILES

Nc1ncnc2n(cnc12)[C@H]1C[C@H](O)[C@@H](CO)O1

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Saccharomyces cerevisiae (NCBI:txid4932)	Source: yeast.sf.net See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed
Homo sapiens (NCBI:txid9606)	See: DOI

Roles Classification
Biological Role(s):	Saccharomyces cerevisiae metabolite Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ). Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	2'-deoxyadenosine (CHEBI:17256) has role Escherichia coli metabolite (CHEBI:76971) 2'-deoxyadenosine (CHEBI:17256) has role Saccharomyces cerevisiae metabolite (CHEBI:75772) 2'-deoxyadenosine (CHEBI:17256) has role human metabolite (CHEBI:77746) 2'-deoxyadenosine (CHEBI:17256) has role mouse metabolite (CHEBI:75771) 2'-deoxyadenosine (CHEBI:17256) is a purine 2'-deoxyribonucleoside (CHEBI:19254) 2'-deoxyadenosine (CHEBI:17256) is a purines 2'-deoxy-D-ribonucleoside (CHEBI:142361)

Incoming	8,5'-cyclo-2'-deoxyadenosine (CHEBI:131825) has functional parent 2'-deoxyadenosine (CHEBI:17256)

IUPAC Name

2'-deoxyadenosine

Synonyms	Sources
(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol	IUPAC
2'-Deoxyadenosine	KEGG COMPOUND
2'-deoxyadenosine	UniProt
5-(6-AMINO-PURIN-9-YL)-2-HYDROXYMETHYL-TETRAHYDRO-FURAN-3-OL	PDBeChem
9-(2-Deoxy-β-D-erythro-pentofuranosyl)adenine	NIST Chemistry WebBook
9-(2-deoxy-β-D-ribofuranosyl)-9H-purin-6-amine	NIST Chemistry WebBook
adenine deoxyribonucleoside	ChemIDplus
adenyldeoxyriboside	ChemIDplus
dA	ChEBI
Deoxyadenosine	KEGG COMPOUND

Manual Xrefs	Databases
3D1	PDBeChem
C00019281	KNApSAcK
C00559	KEGG COMPOUND
Deoxyadenosine	Wikipedia
DEOXYADENOSINE	MetaCyc
HMDB0000101	HMDB
View more database links

Registry Numbers	Types	Sources
283189	Gmelin Registry Number	Gmelin
91015	Reaxys Registry Number	Reaxys
958-09-8	CAS Registry Number	KEGG COMPOUND
958-09-8	CAS Registry Number	ChemIDplus
958-09-8	CAS Registry Number	NIST Chemistry WebBook

Citations

Yuan Y, Tian JM, Xiao J, Shao Q, Gao JM (2014)
Bioactive metabolites isolated from Penicillium sp. YY-20, the endophytic fungus from Ginkgo biloba.
Natural product research 28, 278-281 [PubMed:24144081]
[show Abstract]

Bose A, Sarkar AK, Basu S (2008)
Interaction of 9,10-anthraquinone with adenine and 2'-deoxyadenosine.
Biophysical chemistry 136, 59-65 [PubMed:18508186]
[show Abstract]

Yamamoto T, Moriwaki Y, Takahashi S, Fujita T, Tsutsumi Z, Yamakita J, Shimizu K, Shiota M, Ohta S, Higashino K (1998)
Determination of adenosine and deoxyadenosine in urine by high-performance liquid chromatography with column switching.
Journal of chromatography. B, Biomedical sciences and applications 719, 55-61 [PubMed:9869364]
[show Abstract]

Gao X, Blackburn MR, Knudsen TB (1994)
Activation of apoptosis in early mouse embryos by 2'-deoxyadenosine exposure.
Teratology 49, 1-12 [PubMed:8171392]
[show Abstract]

BUTLER VP, TANENBAUM SW, BEISER SM (1965)
A STUDY OF THE CROSS-REACTIVITY OF ANTIPURIN-6-OYL SERUM WITH DEOXYRIBONUCLEIC ACID (DNA).
The Journal of experimental medicine 121, 19-38 [PubMed:14253484]
[show Abstract]

Last Modified

21 April 2016

CHEBI:17256 - 2'-deoxyadenosine

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