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Escherichia coli K-12 substr. MG1655 Compound: dUMP

Synonyms: U, deoxyurdine-phosphate, 2'-deoxyuridine 5-monophosphate, deoxyuridine-phosphate, 2'-deoxyuridine 5'-phosphate, 2'-deoxyuridylic acid, 2'-deoxy-5'-uridylic acid

Superclasses: a nucleic acid component a nucleotide a 2'-deoxyribonucleotide a 2'-deoxyribonucleoside 5'-monophosphate a pyrimidine 2'-deoxyribonucleoside 5'-monophosphate
a nucleic acid component a nucleotide a 2'-deoxyribonucleotide a pyrimidine 2'-deoxyribonucleotide a pyrimidine 2'-deoxyribonucleoside 5'-monophosphate
a nucleic acid component a nucleotide a nucleoside 5'-monophosphate a 2'-deoxyribonucleoside 5'-monophosphate a pyrimidine 2'-deoxyribonucleoside 5'-monophosphate
a nucleic acid component a nucleotide a pyrimidine nucleotide a pyrimidine 2'-deoxyribonucleotide a pyrimidine 2'-deoxyribonucleoside 5'-monophosphate
an organic heterocyclic compound an organonitrogen heterocyclic compound a diazine a pyrimidine a pyrimidine nucleotide a pyrimidine 2'-deoxyribonucleotide a pyrimidine 2'-deoxyribonucleoside 5'-monophosphate
an organic heterocyclic compound an organonitrogen heterocyclic compound a diazine a pyrimidine

Chemical Formula: C9H11N2O8P

Molecular Weight: 306.17 Daltons

Monoisotopic Molecular Weight: 308.0409519145 Daltons

dUMP compound structure

SMILES: C(OP(=O)([O-])[O-])C1(OC(CC(O)1)N2(C=CC(=O)NC(=O)2))

InChI: InChI=1S/C9H13N2O8P/c12-5-3-8(11-2-1-7(13)10-9(11)14)19-6(5)4-18-20(15,16)17/h1-2,5-6,8,12H,3-4H2,(H,10,13,14)(H2,15,16,17)/p-2/t5-,6+,8+/m0/s1

InChIKey: InChIKey=JSRLJPSBLDHEIO-SHYZEUOFSA-L

Unification Links: CAS:964-26-1 , ChEBI:246422 , ChemSpider:18555972 , HMDB:HMDB01409 , IAF1260:34762 , KEGG:C00365 , MetaboLights:MTBLC246422 , PubChem:18601100

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -366.94

Reactions known to consume the compound:

N10-formyl-tetrahydrofolate biosynthesis , pyrimidine deoxyribonucleotides de novo biosynthesis I , pyrimidine deoxyribonucleotides de novo biosynthesis II , superpathway of pyrimidine deoxyribonucleotides de novo biosynthesis (E. coli) :
a 5,10-methylene-tetrahydrofolate + dUMP → dTMP + a 7,8-dihydrofolate

Not in pathways:
dUMP + H2O → 2'-deoxyuridine + phosphate

Not in pathways:
a 2'-deoxyribonucleoside 5'-monophosphate + H2O → a 2'-deoxynucleoside + phosphate

Not in pathways:
a nucleoside 5'-monophosphate[periplasmic space] + H2O[periplasmic space] → a nucleoside[periplasmic space] + phosphate[periplasmic space]

Reactions known to produce the compound:

pyrimidine deoxyribonucleotides de novo biosynthesis I , pyrimidine deoxyribonucleotides de novo biosynthesis II , pyrimidine deoxyribonucleotides dephosphorylation , superpathway of pyrimidine deoxyribonucleotides de novo biosynthesis (E. coli) :
dUTP + H2O → dUMP + diphosphate + H+

salvage pathways of pyrimidine deoxyribonucleotides :
2'-deoxyuridine + ATP → dUMP + ADP + H+

Not in pathways:
DNAn + H2O → (deoxynucleotides)(n-1) + a 2'-deoxyribonucleoside 5'-monophosphate

tRNA processing :
a tRNA precursor with a 5' extension and a long 3' trailer + n H2O → a tRNA precursor with a 5' extension and a short 3' extension + n a nucleoside 5'-monophosphate
a tRNA precursor with a short 3' extension → an uncharged tRNA + n a nucleoside 5'-monophosphate

Not in pathways:
a nucleoside 3',5'-bisphosphate + H2O → a nucleoside 5'-monophosphate + phosphate
a tRNA precursor + H2O → a tRNA + a nucleoside 5'-monophosphate
RNase R degradation substrate RNA + n-1 H2O → n-2 a nucleoside 5'-monophosphate + a diribonucleotide
an oligonucleotide + H2O → n a nucleoside 5'-monophosphate
RNA + n H2O → n a nucleoside 5'-monophosphate
DNAn + n H2O → n a nucleoside 5'-monophosphate
a nucleoside diphosphate + H2O → a nucleoside 5'-monophosphate + phosphate + H+
a RNA-DNA hybrid + n H2O → DNA + n a nucleoside 5'-monophosphate
a nucleoside triphosphate + H2O → a nucleoside 5'-monophosphate + diphosphate + H+
RNase II degradation substrate mRNA + n H2O → n a nucleoside 5'-monophosphate
mutated tRNA + n H2O → n a nucleoside 5'-monophosphate
(deoxynucleotides)(n) + H2O → (deoxynucleotides)(n-1) + a nucleoside 5'-monophosphate

Enzymes inhibited by dUMP, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: dTMP kinase [Nelson69, Helmward89]

This compound has been characterized as an alternative substrate of the following enzymes: pyrimidine nucleotidase , dCMP kinase , deoxyribonucleoside 5'-monophosphate phosphatase , dTMP kinase


References

Helmward89: Helmward Z "Handbook of Enzyme Inhibitors. 2nd, revised and enlarged edition." Weinheim, Federal Republic of Germany ; New York, NY, USA , 1989.

Nelson69: Nelson DJ, Carter CE (1969). "Purification and characterization of Thymidine 5-monophosphate kinase from Escherichia coli B." J Biol Chem 1969;244(19);5254-62. PMID: 4899016


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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
Page generated by SRI International Pathway Tools version 19.0 on Fri Jul 31, 2015, biocyc11.