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discounted EARLY registration ends Dec 31, 2014
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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
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for maintenance.
Metabolic Modeling Tutorial
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BioCyc websites down
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Metabolic Modeling Tutorial
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MetaCyc 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): -618.39075 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

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

UTP and CTP dephosphorylation I :
ATP + UTP + L-glutamine + H2O → ADP + CTP + L-glutamate + phosphate + 2 H+
UTP + H2O → UDP + phosphate + H+

UTP and CTP dephosphorylation II :
ATP + UTP + L-glutamine + H2O → ADP + CTP + L-glutamate + phosphate + 2 H+
UTP + 2 H2O → UMP + 2 phosphate + 2 H+

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


a pyrimidine ribonucleotide + H2O → D-ribose 5-phosphate + a pyrimidine base


ribonucleotiden + ribonucleotiden + ATP → ribonucleotidem+n + AMP + diphosphate

jadomycin biosynthesis :
α-D-glucose 1-phosphate + a nucleoside triphosphate + H+ → an NDP-α-D-glucose + diphosphate

phytol salvage pathway :
phytyl monophosphate + a nucleoside triphosphate → phytyl diphosphate + a nucleoside diphosphate

pyrimidine deoxyribonucleosides salvage :
2'-deoxycytidine + a nucleoside triphosphate → dCMP + a nucleoside diphosphate + H+


a nucleoside triphosphate + H2O → a nucleoside diphosphate + phosphate + H+
a nucleoside triphosphate + H2O → a nucleoside 5'-monophosphate + diphosphate + H+
a nucleoside triphosphate + 2 H2O → a nucleoside 5'-monophosphate + 2 phosphate + 2 H+


a nucleotide + H2O → a nucleoside + phosphate

Reactions known to produce the compound:

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

Not in pathways:
a tRNA precursor + H2O → a tRNA + a ribonucleotide


a nucleoside diphosphate + ATP → a nucleoside triphosphate + ADP

Reactions known to both consume and produce the compound:

chitin biosynthesis , sucrose biosynthesis II , sucrose degradation II (sucrose synthase) , UDP-glucose biosynthesis :
α-D-glucose 1-phosphate + UTP + H+ ↔ UDP-α-D-glucose + diphosphate

galactose degradation III :
α-D-galactose 1-phosphate + UTP + H+ ↔ UDP-α-D-galactose + diphosphate

stachyose degradation :
α-D-glucose 1-phosphate + UTP + H+ ↔ UDP-α-D-glucose + diphosphate
α-D-galactose 1-phosphate + UTP + H+ ↔ UDP-α-D-galactose + diphosphate

UDP-α-D-glucuronate biosynthesis (from myo-inositol) :
α-D-glucuronate 1-phosphate + UTP + H+ ↔ UDP-α-D-glucuronate + diphosphate

UDP-D-galacturonate biosynthesis II (from D-galacturonate) :
α-D-galacturonate 1-phosphate + UTP + H+ ↔ UDP-α-D-galacturonate + diphosphate

UDP-L-arabinose biosynthesis II (from L-arabinose) :
β-L-arabinose 1-phosphate + UTP + H+ ↔ UDP-β-L-arabinopyranose + diphosphate

Not in pathways:
α-D-xylose 1-phosphate + UTP + H+ ↔ UDP-α-D-xylose + diphosphate

In Reactions of unknown directionality:

Not in pathways:
CTP + H+ + H2O = UTP + ammonium
2'-deoxycytidine + UTP = dCMP + UDP + H+
2'-deoxyadenosine + UTP = dAMP + UDP + H+
2'-deoxyguanosine + UTP = dGMP + UDP + H+
UTP + N-acetyl-α-D-galactosamine 1-phosphate + H+ = UDP-N-acetyl-α-D-galactosamine + diphosphate
UTP + a sugar 1-phosphate = a UDP-sugar + diphosphate
RNA(n) + UTP = RNA(n+1) + diphosphate


a reduced flavodoxin + a ribonucleoside triphosphate = an oxidized flavodoxin + a deoxyribonucleoside triphosphate + H2O
a deoxyribonucleoside triphosphate + an oxidized thioredoxin + H2O = a ribonucleoside triphosphate + a reduced thioredoxin


a nucleoside triphosphate + AMP = a nucleoside diphosphate + ADP
a nucleoside triphosphate + RNA(n) = RNA(n+1) + diphosphate
RNA(n) + a nucleoside triphosphate = RNA(n+1) + diphosphate
a nucleoside triphosphate + an α-D-aldose 1-phosphate + H+ = a nucleoside diphosphate-hexose + diphosphate
a gentamicin + a nucleoside triphosphate = a 2-nucleotidylgentamicin + diphosphate


a nucleotide + a 2'-deoxynucleoside = a nucleoside + a 2'-deoxyribonucleoside 5'-monophosphate

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

Activator (Mechanism unknown) of: glutamine synthetase deadenylase [Shapiro69] , oleanolate UDP-glucuronosyltransferase [Wojciechowski75] , phytyl-P kinase [Ischebeck06]

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

Inhibitor (Competitive) of: UMP kinase [Briozzo05, Serina95] , GTP cyclohydrolase [Yim76] , cytidine 5'-monophosphate N-acetylneuraminate synthetase [RodriguezAparic92]

Inhibitor (Mechanism unknown) of: cytidine kinase [ValentinHansen78] , uridine kinase [ValentinHansen78] , thiamine phosphate synthase [Kayama73, Kawasaki79] , m7GTP pyrophosphatase [Tchigvintsev13] , UDP-L-rhamnose synthase [Martinez12] , UDP-glucose 4,6-dehydratase [Martinez12] , UDP-glucuronate 4-epimerase [Munoz99] , ornithine carbamoyltransferase, catabolic [Ruepp95] , UDP-glucuronate decarboxylase [Pattathil05] , UDP-glucuronate decarboxylase [Harper02] , phosphoribosylamidoimidazole-succinocarboxamide synthetase [Comment 1] , L-lactate dehydrogenase [Davies72] , UDP-D-xylose synthase [Baron72] , UDP-D-apiose synthase [Baron72] , UDP-α-D-glucose:glycogenin α-D-glucosyltransferase [Cao93] , UDP-α-D-glucose:glucosyl-glycogenin α-D-glucosyltransferase [Cao93]


References

Baron72: Baron D, Wellmann E, Grisebach H (1972). "Purification and properties of an enzyme from cell suspension cultures of parsley catalyzing the synthesis of UDP-apiose and UDP-D-xylose from UDP-D-glucuronic acid." Biochim Biophys Acta 258(1);310-8. PMID: 4333589

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

Cao93: Cao Y, Mahrenholz AM, DePaoli-Roach AA, Roach PJ (1993). "Characterization of rabbit skeletal muscle glycogenin. Tyrosine 194 is essential for function." J Biol Chem 268(20);14687-93. PMID: 8325847

Davies72: Davies DD, Davies S (1972). "Purification and properties of L(+)-lactate dehydrogenase from potato tubers." Biochem J 129(4);831-9. PMID: 4144124

Harper02: Harper AD, Bar-Peled M (2002). "Biosynthesis of UDP-xylose. Cloning and characterization of a novel Arabidopsis gene family, UXS, encoding soluble and putative membrane-bound UDP-glucuronic acid decarboxylase isoforms." Plant Physiol 130(4);2188-98. PMID: 12481102

Ischebeck06: Ischebeck T, Zbierzak AM, Kanwischer M, Dormann P (2006). "A salvage pathway for phytol metabolism in Arabidopsis." J Biol Chem 281(5);2470-7. PMID: 16306049

Kawasaki79: Kawasaki T (1979). "Thiamine phosphate pyrophosphorylase." Methods Enzymol 1979;62;69-73. PMID: 374983

Kayama73: Kayama Y, Kawasaki T (1973). "Purification and properties of thiaminephosphate pyrophosphorylase of Escherichia coli." Arch Biochem Biophys 1973;158(1);242-8. PMID: 4580841

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Martinez12: Martinez V, Ingwers M, Smith J, Glushka J, Yang T, Bar-Peled M (2012). "Biosynthesis of UDP-4-keto-6-deoxyglucose and UDP-rhamnose in pathogenic fungi Magnaporthe grisea and Botryotinia fuckeliana." J Biol Chem 287(2);879-92. PMID: 22102281

Munoz99: Munoz R, Lopez R, de Frutos M, Garcia E (1999). "First molecular characterization of a uridine diphosphate galacturonate 4-epimerase: an enzyme required for capsular biosynthesis in Streptococcus pneumoniae type 1." Mol Microbiol 31(2);703-13. PMID: 10027985

Ostanin89: Ostanin KV, Alenin VV, Domkin VD, Smirnov MN (1989). "[Isolation and properties of phosphoribosyl-aminoimidazole-succinocarboxyamide-synthestase from Saccharomyces cerevisiae yeasts]." Biokhimiia 1989;54(8);1265-73. PMID: 2684279

Pattathil05: Pattathil S, Harper AD, Bar-Peled M (2005). "Biosynthesis of UDP-xylose: characterization of membrane-bound AtUxs2." Planta 221(4);538-48. PMID: 15655675

RodriguezAparic92: Rodriguez-Aparicio LB, Luengo JM, Gonzalez-Clemente C, Reglero A (1992). "Purification and characterization of the nuclear cytidine 5'-monophosphate N-acetylneuraminic acid synthetase from rat liver." J Biol Chem 267(13);9257-63. PMID: 1577759

Ruepp95: Ruepp A, Muller HN, Lottspeich F, Soppa J (1995). "Catabolic ornithine transcarbamylase of Halobacterium halobium (salinarium): purification, characterization, sequence determination, and evolution." J Bacteriol 1995;177(5);1129-36. PMID: 7868583

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

Wojciechowski75: Wojciechowski, ZdzisImageaw A. (1975). "Biosynthesis of oleanolic acid glycosides by subcellular fractions of Calendula officinalis seedlings." Phytochemistry. 14:1749-1753.

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 MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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