Updated BioCyc iOS App now
available in iTunes store
Updated BioCyc iOS App now
available in iTunes store
Updated BioCyc iOS App now
available in iTunes store
Updated BioCyc iOS App now
available in iTunes store
Updated BioCyc iOS App now
available in iTunes store
twitter

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 componenta nucleotidea 2'-deoxyribonucleotidea 2'-deoxyribonucleoside 5'-monophosphatea pyrimidine 2'-deoxyribonucleoside 5'-monophosphate
a nucleic acid componenta nucleotidea 2'-deoxyribonucleotidea pyrimidine 2'-deoxyribonucleotidea pyrimidine 2'-deoxyribonucleoside 5'-monophosphate
a nucleic acid componenta nucleotidea nucleoside 5'-monophosphatea 2'-deoxyribonucleoside 5'-monophosphatea pyrimidine 2'-deoxyribonucleoside 5'-monophosphate
a nucleic acid componenta nucleotidea pyrimidine nucleotidea pyrimidine 2'-deoxyribonucleotidea pyrimidine 2'-deoxyribonucleoside 5'-monophosphate
an organic heterocyclic compoundan organonitrogen heterocyclic compounda diazinea pyrimidinea pyrimidine nucleotidea pyrimidine 2'-deoxyribonucleotidea pyrimidine 2'-deoxyribonucleoside 5'-monophosphate
an organic heterocyclic compoundan organonitrogen heterocyclic compounda diazinea 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[periplasm] + H2O[periplasm] → a nucleoside[periplasm] + phosphate[periplasm]

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


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
Page generated by Pathway Tools version 19.5 (software by SRI International) on Mon Feb 8, 2016, biocyc14.