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Escherichia coli K-12 substr. MG1655 Compound: UMP

Abbrev Name: UMP

Synonyms: uridylate, 5'-UMP, U, uridine 5'-phosphate, 5'-uridylic acid (8CI)(9CI), uridine monophosphate, uridine 5'-monophosphate

Superclasses: a nucleic acid componenta nucleotidea nucleoside 5'-monophosphatea ribonucleoside 5'-monophosphatea pyrimidine ribonucleoside 5'-monophosphate
a nucleic acid componenta nucleotidea pyrimidine nucleotidea pyrimidine ribonucleotidea pyrimidine ribonucleoside 5'-monophosphate
a nucleic acid componenta nucleotidea ribonucleotidea pyrimidine ribonucleotidea pyrimidine ribonucleoside 5'-monophosphate
a nucleic acid componenta nucleotidea ribonucleotidea ribonucleoside 5'-monophosphatea pyrimidine ribonucleoside 5'-monophosphate
an organic heterocyclic compoundan organonitrogen heterocyclic compounda diazinea pyrimidinea pyrimidine nucleotidea pyrimidine ribonucleotidea pyrimidine ribonucleoside 5'-monophosphate


Chemical Formula: C9H11N2O9P

Molecular Weight: 322.17 Daltons

Monoisotopic Molecular Weight: 324.0358665366 Daltons

UMP compound structure

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

InChI: InChI=1S/C9H13N2O9P/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,10,12,15)(H2,16,17,18)/p-2/t4-,6-,7-,8-/m1/s1

InChIKey: InChIKey=DJJCXFVJDGTHFX-XVFCMESISA-L

Unification Links: CAS:58-97-9, ChEBI:57865, ChemSpider:1399139, HMDB:HMDB00288, IAF1260:33873, KEGG:C00105, MetaboLights:MTBLC57865, PubChem:1778309

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): -406.78

Reactions known to consume the compound:

UTP and CTP de novo biosynthesis :
ATP + UMP → ADP + UDP

Not in pathways:
UMP + H2O → uridine + phosphate

Not in pathways:
a ribonucleoside 5'-monophosphate + H2O → a ribonucleoside + phosphate

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

Reactions known to produce the compound:

enterobacterial common antigen biosynthesis :
di-trans,octa-cis-undecaprenyl phosphate + UDP-N-acetyl-α-D-glucosamine → N-acetyl-α-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol + UMP

lipid IVA biosynthesis :
UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine + H2O → 2,3-bis[(3R)-3-hydroxymyristoyl]-α-D-glucosaminyl 1-phosphate + UMP + 2 H+

Nitrogen Regulation Two-Component System :
uridylyl-[protein PII] → PII + UMP
uridylyl-[GlnK] → UMP + GlnK

peptidoglycan biosynthesis I (meso-diaminopimelate containing) :
UDP-N-acetyl-α-D-muramoyl-L-alanyl-γ-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine + di-trans,octa-cis-undecaprenyl phosphate → undecaprenyldiphospho-N-acetylmuramoyl-L-alanyl-γ-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine + UMP

pyrimidine nucleobases salvage I :
UMP + diphosphate ← 5-phospho-α-D-ribose 1-diphosphate + uracil

pyrimidine ribonucleosides salvage I :
uridine + ATP → UMP + ADP + H+

salvage pathways of pyrimidine ribonucleotides :
uridine + GTP → UMP + GDP + H+
UMP + diphosphate ← 5-phospho-α-D-ribose 1-diphosphate + uracil

UMP biosynthesis :
orotidine 5'-phosphate + H+ → CO2 + UMP

Not in pathways:
UDP + H2O → UMP + phosphate + H+
a UDP-sugar[periplasm] + H2O[periplasm]UMP[periplasm] + an α-D-aldose 1-phosphate[periplasm] + 2 H+[periplasm]
UTP + H2O → UMP + diphosphate + H+
a uridylylated PII protein + H2O → a PII protein + UMP

tRNA processing :
a tRNA precursor with a 5' extension and a long 3' trailer + H2O → a tRNA precursor with a 5' extension + a ribonucleoside 5'-monophosphate
a tRNA precursor with a 5' extension and a short 3' extension → a tRNA precursor with a 5' extension + a ribonucleoside 5'-monophosphate

Not in pathways:
a single stranded DNA + H2O → a ribonucleoside 5'-monophosphate + a single-stranded oligodeoxyribonucleotide

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

In Reactions of unknown directionality:

Not in pathways:
UDP-α-D-glucose + di-trans,octa-cis-undecaprenyl phosphate = UMP + α-D-glucopyranosyl-diphosphoundecaprenol

Enzymes activated by UMP, sorted by the type of activation, are:

Activator (Mechanism unknown) of: guanosine kinase [Kawasaki00]

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

Inhibitor (Competitive) of: UDP-glucose 4-epimerase [Wong77] Inhibitor (Allosteric) of: carbamoyl phosphate synthetase [Trotta74]

This compound has been characterized as an alternative substrate of the following enzymes: CMP kinase, pyrimidine nucleotidase, alkaline phosphatase, UMP phosphatase

In Growth Media: PMA phosphorus source test + UMP


References

Kawasaki00: Kawasaki H, Shimaoka M, Usuda Y, Utagawa T (2000). "End-product regulation and kinetic mechanism of guanosine-inosine kinase from Escherichia coli." Biosci Biotechnol Biochem 2000;64(5);972-9. PMID: 10879466

Trotta74: Trotta PP, Pinkus LM, Haschemeyer RH, Meister A (1974). "Reversible dissociation of the monomer of glutamine-dependent carbamyl phosphate synthetase into catalytically active heavy and light subunits." J Biol Chem 1974;249(2);492-9. PMID: 4358555

Wong77: Wong SS, Frey PA (1977). "Fluorescence and nucleotide binding properties of Escherichia coli uridine diphosphate galactose 4-epimerase: support for a model for nonstereospedific action." Biochemistry 16(2);298-305. PMID: 189796


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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
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