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Escherichia coli K-12 substr. MG1655 Compound: UTP

Synonyms: uridine-triphosphate, uridine-5'-triphosphate

Superclasses: a nucleic acid component a nucleotide a nucleoside triphosphate a ribonucleoside triphosphate a pyrimidine ribonucleoside 5'-triphosphate
a nucleic acid component a nucleotide a pyrimidine nucleotide a pyrimidine ribonucleotide a pyrimidine ribonucleoside 5'-triphosphate
a nucleic acid component a nucleotide a ribonucleotide a pyrimidine ribonucleotide a pyrimidine ribonucleoside 5'-triphosphate
a nucleic acid component a nucleotide a ribonucleotide a ribonucleoside triphosphate a pyrimidine ribonucleoside 5'-triphosphate
an organic heterocyclic compound an organonitrogen heterocyclic compound a diazine a pyrimidine a pyrimidine nucleotide a pyrimidine ribonucleotide a pyrimidine ribonucleoside 5'-triphosphate
an organic heterocyclic compound an organonitrogen heterocyclic compound a diazine a pyrimidine

Chemical Formula: C9H11N2O15P3

Molecular Weight: 480.11 Daltons

Monoisotopic Molecular Weight: 483.96852735339996 Daltons

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

InChI: InChI=1S/C9H15N2O15P3/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(24-8)3-23-28(19,20)26-29(21,22)25-27(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,21,22)(H,10,12,15)(H2,16,17,18)/p-4/t4-,6-,7-,8-/m1/s1

InChIKey: InChIKey=PGAVKCOVUIYSFO-XVFCMESISA-J

Unification Links: CAS:63-39-8 , ChEBI:46398 , ChemSpider:5414500 , HMDB:HMDB00285 , IAF1260:33760 , KEGG:C00075 , MetaboLights:MTBLC46398 , PubChem:7058168

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -726.38

Reactions known to consume the compound:

anhydromuropeptides recycling , UDP-N-acetyl-D-glucosamine biosynthesis I :
N-acetyl-α-D-glucosamine 1-phosphate + UTP + H+ → UDP-N-acetyl-α-D-glucosamine + diphosphate

galactose degradation I (Leloir pathway) , UDP-glucose biosynthesis :
α-D-glucose 1-phosphate + UTP + H+ → UDP-α-D-glucose + diphosphate

Nitrogen Regulation Two-Component System :
a PII protein + UTP → a uridylylated PII protein + diphosphate
GlnK + UTP → uridylyl-[GlnK] + diphosphate

pyrimidine deoxyribonucleotides de novo biosynthesis II , superpathway of pyrimidine deoxyribonucleotides de novo biosynthesis (E. coli) :
dUTP + an oxidized flavodoxin + H2O ← UTP + a reduced flavodoxin

UTP and CTP de novo biosynthesis :
ATP + UTP + L-glutamine + H2O → ADP + CTP + L-glutamate + phosphate + 2 H+

Not in pathways:
UTP + H2O → UMP + diphosphate + H+
ATP + UTP + ammonium → ADP + CTP + phosphate + 2 H+


a nucleoside triphosphate + H2O → a nucleoside 5'-monophosphate + diphosphate + H+

Reactions known to produce the compound:

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

Not in pathways:
a nucleoside diphosphate + ATP → a nucleoside triphosphate + ADP

In Reactions of unknown directionality:

Not in pathways:
a reduced flavodoxin + a ribonucleoside triphosphate = an oxidized flavodoxin + a deoxyribonucleoside triphosphate + H2O


a nucleoside triphosphate + RNA(n) = RNA(n+1) + diphosphate

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

Activator (Mechanism unknown) of: glutamine synthetase deadenylase [Shapiro69]

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

Inhibitor (Competitive) of: GTP cyclohydrolase [Yim76] , UMP kinase [Briozzo05, Serina95]

Inhibitor (Mechanism unknown) of: m7GTP pyrophosphatase [Tchigvintsev13] , thiamine phosphate synthase [Kayama & Kawasaki, 1973, Kawasaki, 1979] , uridine kinase [ValentinHansen78] , cytidine kinase [ValentinHansen78]

Regulated Transcription Units (3 total): ?

Notes:


References

Briozzo05: Briozzo P, Evrin C, Meyer P, Assairi L, Joly N, Barzu O, Gilles AM (2005). "Structure of Escherichia coli UMP kinase differs from that of other nucleoside monophosphate kinases and sheds new light on enzyme regulation." J Biol Chem 280(27);25533-40. PMID: 15857829

Kawasaki, 1979: Kawasaki T (1979). "Thiamine phosphate pyrophosphorylase." Methods Enzymol 1979;62;69-73. PMID: 374983

Kayama & Kawasaki, 1973: Kayama Y, Kawasaki T (1973). "Purification and properties of thiaminephosphate pyrophosphorylase of Escherichia coli." Arch Biochem Biophys 1973;158(1);242-8. PMID: 4580841

Serina95: Serina L, Blondin C, Krin E, Sismeiro O, Danchin A, Sakamoto H, Gilles AM, Barzu O (1995). "Escherichia coli UMP-kinase, a member of the aspartokinase family, is a hexamer regulated by guanine nucleotides and UTP." Biochemistry 1995;34(15);5066-74. PMID: 7711027

Shapiro69: Shapiro BM (1969). "The glutamine synthetase deadenylylating enzyme system from Escherichia coli. Resolution into two components, specific nucleotide stimulation, and cofactor requirements." Biochemistry 8(2);659-70. PMID: 4893578

Tchigvintsev13: Tchigvintsev A, Tchigvintsev D, Flick R, Popovic A, Dong A, Xu X, Brown G, Lu W, Wu H, Cui H, Dombrowski L, Joo JC, Beloglazova N, Min J, Savchenko A, Caudy AA, Rabinowitz JD, Murzin AG, Yakunin AF (2013). "Biochemical and structural studies of conserved maf proteins revealed nucleotide pyrophosphatases with a preference for modified nucleotides." Chem Biol 20(11);1386-98. PMID: 24210219

ValentinHansen78: Valentin-Hansen P (1978). "Uridine-cytidine kinase from Escherichia coli." Methods Enzymol 1978;51;308-14. PMID: 211379

Yim76: Yim JJ, Brown GM (1976). "Characteristics of guanosine triphosphate cyclohydrolase I purified from Escherichia coli." J Biol Chem 1976;251(16);5087-94. PMID: 821948


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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 18.5 on Mon Nov 24, 2014, BIOCYC13B.