2'-deoxyuridine (CHEBI:16450)

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ChEBI Name	2'-deoxyuridine

ChEBI ID	CHEBI:16450

Definition	A pyrimidine 2'-deoxyribonucleoside having uracil as the nucleobase.

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

Secondary ChEBI IDs	CHEBI:11398, CHEBI:42178, CHEBI:46165, CHEBI:46289, CHEBI:46293, CHEBI:4434, CHEBI:11572, CHEBI:14123, CHEBI:19261, CHEBI:23640, CHEBI:29113

Supplier Information	ChemicalBook:CB2117111, eMolecules:24627778, eMolecules:537627, ZINC000000895228

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Wikipedia	License
Deoxyuridine (dU) is a compound and a nucleoside. It belongs to a class of compounds known as Pyrimidine 2'-deoxyribonucleosides and closely resembles the chemical composition of uridine but without the presence of the 2' hydroxyl group. Idoxuridine and Trifluridine are variants of deoxyuridine used as antiviral drugs. They are similar enough to be incorporated as part of DNA replication, but they possess side groups on the uracil component (an iodine and a CF3 group, respectively), that prevent base pairing. A known use of dU is as a precursor in the synthesis of Edoxudine. This compound exists in all living organisms and can become part of DNA in both prokaryotic and eukaryotic cells through two mechanisms. The first is the removal of an amino group from cytosine to result in uracil and the second is the non-intentional incorporation of pyrimidine where thymine belongs in the DNA, resulting in dUMP. UMP synthase deficiency is a metabolic disorder in humans that involves deoxyuridine. Deoxyuridine can be toxic. It has also been found in several foods, which makes it a useful indicator for diseases through consumption of those foods.
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Formula

C9H12N2O5

Net Charge

Average Mass

228.20200

Monoisotopic Mass

228.07462

InChI

InChI=1S/C9H12N2O5/c12-4-6-5(13)3-8(16-6)11-2-1-7(14)10-9(11)15/h1-2,5-6,8,12-13H,3-4H2,(H,10,14,15)/t5-,6+,8+/m0/s1

InChIKey

MXHRCPNRJAMMIM-SHYZEUOFSA-N

SMILES

OC[C@H]1O[C@H](C[C@@H]1O)n1ccc(=O)[nH]c1=O

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):	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). 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.

ChEBI Ontology
Outgoing	2'-deoxyuridine (CHEBI:16450) has functional parent uracil (CHEBI:17568) 2'-deoxyuridine (CHEBI:16450) has role Escherichia coli metabolite (CHEBI:76971) 2'-deoxyuridine (CHEBI:16450) has role Saccharomyces cerevisiae metabolite (CHEBI:75772) 2'-deoxyuridine (CHEBI:16450) has role human metabolite (CHEBI:77746) 2'-deoxyuridine (CHEBI:16450) has role mouse metabolite (CHEBI:75771) 2'-deoxyuridine (CHEBI:16450) is a pyrimidine 2'-deoxyribonucleoside (CHEBI:19255)

Incoming	2'-deoxy-5-(4,5-dihydroxypentyl)uridine (CHEBI:132191) has functional parent 2'-deoxyuridine (CHEBI:16450) 5,6-dihydroxy-2'-deoxyuridine (CHEBI:132189) has functional parent 2'-deoxyuridine (CHEBI:16450) 5-(2-aminoethyl)-2'-deoxyuridine (CHEBI:142166) has functional parent 2'-deoxyuridine (CHEBI:16450)

IUPAC Name

1-(2-deoxy-β-D-erythro-pentofuranosyl)uracil

Citation

Last Modified

11 January 2019