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Escherichia coli K-12 substr. MG1655 Compound: CTP

Synonyms: cytidine-triphosphate, cytidine-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: C9H12N3O14P3

Molecular Weight: 479.13 Daltons

Monoisotopic Molecular Weight: 482.9845117686 Daltons

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

InChI: InChI=1S/C9H16N3O14P3/c10-5-1-2-12(9(15)11-5)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)(H2,10,11,15)(H2,16,17,18)/p-4/t4-,6-,7-,8-/m1/s1

InChIKey: InChIKey=PCDQPRRSZKQHHS-XVFCMESISA-J

Unification Links: CAS:65-47-4 , ChEBI:37563 , ChemSpider:5414498 , HMDB:HMDB00082 , IAF1260:33710 , KEGG:C00063 , MetaboLights:MTBLC37563 , PubChem:7058166

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -687.75

Reactions known to consume the compound:

CDP-diacylglycerol biosynthesis I , CDP-diacylglycerol biosynthesis II :
CTP + a 1,2-diacyl-sn-glycerol 3-phosphate + H+ → a CDP-diacylglycerol + diphosphate

CMP-KDO biosynthesis I :
3-deoxy-D-manno-octulosonate + CTP → CMP-3-deoxy-D-manno-octulosonate + diphosphate

coenzyme A biosynthesis I :
(R)-4'-phosphopantothenate + L-cysteine + CTP → CMP + R-4'-phosphopantothenoyl-L-cysteine + diphosphate + H+

cytidylyl molybdenum cofactor biosynthesis :
MoO2-molybdopterin cofactor + CTP + H+ → cytidylyl molybdenum cofactor + diphosphate

methylerythritol phosphate pathway I :
2-C-methyl-D-erythritol 4-phosphate + CTP + H+ → 4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol + diphosphate

pyrimidine deoxyribonucleotides de novo biosynthesis I :
CTP + H2O → CDP + phosphate + H+

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

Not in pathways:
CTP + hydroxyl radical → 5-hydroxy-CTP + H+
CTP + a 2,3,4-saturated L-phosphatidate + H+ → a CDP-2,3,4-saturated-diacylglycerol + diphosphate
CTP + H2O → CMP + diphosphate + H+
a tRNA precursor + 2 CTP + ATP → a tRNA containing a 3' CCA end + 3 diphosphate


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

Reactions known to produce the compound:

CMP phosphorylation , salvage pathways of pyrimidine ribonucleotides :
CDP + ATP → CTP + ADP

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

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


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 inhibited by CTP, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: CTP synthase [Long67] , CTP:2,3,4-saturated L-phosphatidate cytidylyltransferase [Langley78, Comment 1]

Inhibitor (Allosteric) of: aspartate transcarbamylase [Zhang91, Hoover83, Weitzman66, Gerhart62]

Inhibitor (Mechanism unknown) of: thiamine phosphate synthase [Kayama73, Kawasaki79] , glutamine synthetase [Woolfolk67, Comment 2] , uridine kinase [ValentinHansen78] , cytidine kinase [ValentinHansen78]


References

Gerhart62: Gerhart JC, Pardee AB (1962). "The enzymology of control by feedback inhibition." J Biol Chem 237;891-6. PMID: 13897943

Hoover83: Hoover TA, Roof WD, Foltermann KF, O'Donovan GA, Bencini DA, Wild JR (1983). "Nucleotide sequence of the structural gene (pyrB) that encodes the catalytic polypeptide of aspartate transcarbamoylase of Escherichia coli." Proc Natl Acad Sci U S A 1983;80(9);2462-6. PMID: 6302686

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

Langley78: Langley KE, Kennedy EP (1978). "Partial purification and properties of CTP:phosphatidic acid cytidylyltransferase from membranes of Escherichia coli." J Bacteriol 1978;136(1);85-95. PMID: 30751

Long67: Long CW, Pardee AB (1967). "Cytidine triphosphate synthetase of Escherichia coli B. I. Purification and kinetics." J Biol Chem 242(20);4715-21. PMID: 4862983

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

Weitzman66: Weitzman PD, Wilson IB (1966). "Studies on aspartate transcarbamylase and its allosteric interaction." J Biol Chem 241(23);5481-8. PMID: 5333198

Woolfolk67: Woolfolk CA, Stadtman ER (1967). "Regulation of glutamine synthetase. 3. Cumulative feedback inhibition of glutamine synthetase from Escherichia coli." Arch Biochem Biophys 118(3);736-55. PMID: 4860415

Zhang91: Zhang Y, Kantrowitz ER (1991). "The synergistic inhibition of Escherichia coli aspartate carbamoyltransferase by UTP in the presence of CTP is due to the binding of UTP to the low affinity CTP sites." J Biol Chem 1991;266(33);22154-8. PMID: 1939236


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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 Thu Dec 18, 2014, BIOCYC14B.