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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
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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
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
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discounted EARLY registration ends Dec 31, 2014
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MetaCyc Compound: dCTP

Systematic Name: 2'-deoxycytidine-5'-(tetrahydrogen triphosphate)

Synonyms: 2'-deoxycytidine-5'-triphosphate, deoxycytidine-triphosphate, deoxy-CTP

Superclasses: a nucleic acid component a nucleotide a 2'-deoxyribonucleotide a deoxyribonucleoside triphosphate a pyrimidine 2'-deoxyribonucleoside 5'-triphosphate
a nucleic acid component a nucleotide a 2'-deoxyribonucleotide a pyrimidine 2'-deoxyribonucleotide a pyrimidine 2'-deoxyribonucleoside 5'-triphosphate
a nucleic acid component a nucleotide a nucleoside triphosphate a deoxyribonucleoside triphosphate a pyrimidine 2'-deoxyribonucleoside 5'-triphosphate
a nucleic acid component a nucleotide a pyrimidine nucleotide a pyrimidine 2'-deoxyribonucleotide a pyrimidine 2'-deoxyribonucleoside 5'-triphosphate
an organic heterocyclic compound an organonitrogen heterocyclic compound a diazine a pyrimidine a pyrimidine nucleotide a pyrimidine 2'-deoxyribonucleotide a pyrimidine 2'-deoxyribonucleoside 5'-triphosphate
an organic heterocyclic compound an organonitrogen heterocyclic compound a diazine a pyrimidine

Chemical Formula: C9H12N3O13P3

Molecular Weight: 463.13 Daltons

Monoisotopic Molecular Weight: 466.98959714649993 Daltons

SMILES: C(C2(C(CC(N1(C(N=C(C=C1)N)=O))O2)O))OP(OP(OP([O-])([O-])=O)([O-])=O)([O-])=O

InChI: InChI=1S/C9H16N3O13P3/c10-7-1-2-12(9(14)11-7)8-3-5(13)6(23-8)4-22-27(18,19)25-28(20,21)24-26(15,16)17/h1-2,5-6,8,13H,3-4H2,(H,18,19)(H,20,21)(H2,10,11,14)(H2,15,16,17)/p-4/t5-,6+,8+/m0/s1

InChIKey: InChIKey=RGWHQCVHVJXOKC-SHYZEUOFSA-J

Unification Links: CAS:2056-98-6 , ChEBI:61481 , HMDB:HMDB00998 , IAF1260:35027 , KEGG:C00458 , PubChem:25244665

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -529.6495 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

pyrimidine deoxyribonucleotides de novo biosynthesis II , superpathway of pyrimidine deoxyribonucleotides de novo biosynthesis (E. coli) :
dCTP + H+ + H2O → ammonium + dUTP

pyrimidine deoxyribonucleotides de novo biosynthesis IV :
dCTP + 2 H2O → dUMP + ammonium + diphosphate

pyrimidine deoxyribonucleotides dephosphorylation :
dCTP + H2O → dCMP + diphosphate + H+

Not in pathways:
dCTP + H2O → dCDP + phosphate + H+
dCTP + 2 H2O → dCMP + 2 phosphate + 2 H+

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:

pyrimidine deoxyribonucleotide phosphorylation , pyrimidine deoxyribonucleotides biosynthesis from CTP , pyrimidine deoxyribonucleotides de novo biosynthesis I , pyrimidine deoxyribonucleotides de novo biosynthesis III , pyrimidine deoxyribonucleotides de novo biosynthesis IV :
dCDP + ATP → dCTP + ADP

pyrimidine deoxyribonucleotides de novo biosynthesis II :
dCTP + an oxidized flavodoxin + H2O ← CTP + a reduced flavodoxin

superpathway of pyrimidine deoxyribonucleotides de novo biosynthesis (E. coli) :
dCDP + ATP → dCTP + ADP
dCTP + an oxidized flavodoxin + H2O ← CTP + a reduced flavodoxin

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

In Reactions of unknown directionality:

Not in pathways:
a deoxyribonucleoside triphosphate + an oxidized thioredoxin + H2O = a ribonucleoside triphosphate + a reduced thioredoxin
a deoxyribonucleoside triphosphate + (deoxynucleotides)(n) = (deoxynucleotides)(n+1) + diphosphate
a deoxyribonucleoside triphosphate + (deoxynucleotides)(n) = (deoxynucleotides)(n+1) + diphosphate
a deoxyribonucleoside triphosphate + (deoxynucleotides)(n) = (deoxynucleotides)(n+1) + diphosphate
a reduced flavodoxin + a ribonucleoside triphosphate = an oxidized flavodoxin + a deoxyribonucleoside triphosphate + H2O


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 dCTP, sorted by the type of activation, are:

Activator (Allosteric) of: thymidine kinase [Iwatsuki67, Chen78] , deoxycytidylate deaminase [Weiner93] , dCMP deaminase [Hou08]

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

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

Inhibitor (Mechanism unknown) of: dTMP kinase [Helmward89, Nelson69, Comment 2] , deoxyribonucleoside 5'-monophosphate phosphatase [Proudfoot04]


References

Chen78: Chen MS, Prusoff WH (1978). "Thymidine kinase from Escherichia coli." Methods Enzymol 1978;51;354-60. PMID: 357898

Helmward89: Helmward Z "Handbook of Enzyme Inhibitors. 2nd, revised and enlarged edition." Weinheim, Federal Republic of Germany ; New York, NY, USA , 1989.

Hou08: Hou HF, Liang YH, Li LF, Su XD, Dong YH (2008). "Crystal structures of Streptococcus mutans 2'-deoxycytidylate deaminase and its complex with substrate analog and allosteric regulator dCTP x Mg2+." J Mol Biol 377(1);220-31. PMID: 18255096

Iwatsuki67: Iwatsuki N, Okazaki R (1967). "Mechanism of regulation of deoxythymidine kinase of Escherichia coli. I. Effect of regulatory deoxynucleotides on the state of aggregation of the enzyme." J Mol Biol 1967;29(1);139-54. PMID: 4861610

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

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

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

Proudfoot04: Proudfoot M, Kuznetsova E, Brown G, Rao NN, Kitagawa M, Mori H, Savchenko A, Yakunin AF (2004). "General enzymatic screens identify three new nucleotidases in Escherichia coli. Biochemical characterization of SurE, YfbR, and YjjG." J Biol Chem 279(52);54687-94. PMID: 15489502

Weiner93: Weiner KX, Weiner RS, Maley F, Maley GF (1993). "Primary structure of human deoxycytidylate deaminase and overexpression of its functional protein in Escherichia coli." J Biol Chem 268(17);12983-9. PMID: 7685356


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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
Page generated by SRI International Pathway Tools version 18.5 on Sat Dec 20, 2014, BIOCYC14B.