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Identification
YMDB IDYMDB00279
NameCytidine triphosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionCytidine triphosphate, also known as 5'-CTP or H4CTP, belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. Cytidine triphosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Cytidine triphosphate exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
  • 5'-(tetrahydrogen triphosphate) cytidine
  • 5'-CTP
  • CTP
  • Cytidine 3'-triphosphate
  • Cytidine 5-Prime-Triphosphate
  • cytidine 5'-(tetrahydrogen triphosphate)
  • Cytidine 5'-triphosphate
  • Cytidine 5'-triphosphoric acid
  • Cytidine mono
  • Cytidine mono(tetrahydrogen triphosphate) (ester)
  • Cytidine Triphosphate
  • Cytidine triphosphic acid
  • cytidine-5'-triphosphate
  • Deoxycytosine triphosphate
  • H4ctp
  • CYTIDINE-5'-triphosphoric acid
  • Cytidine triphosphoric acid
  • Triphosphate, cytidine
  • CRPPP
  • Magnesium CTP
  • MG CTP
CAS number65-47-4
WeightAverage: 483.1563
Monoisotopic: 482.984511771
InChI KeyPCDQPRRSZKQHHS-XVFCMESISA-N
InChIInChI=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)/t4-,6-,7-,8-/m1/s1
IUPAC Name({[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
Traditional IUPAC NameCTP
Chemical FormulaC9H16N3O14P3
SMILES[H]O[C@]1([H])[C@]([H])(O[H])[C@]([H])(O[C@@]1([H])N1C([H])=C([H])C(=NC1=O)N([H])[H])C([H])([H])OP(=O)(O[H])OP(=O)(O[H])OP(=O)(O[H])O[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentose phosphates
Alternative Parents
Substituents
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Hydroxypyrimidine
  • Monoalkyl phosphate
  • Hydropyrimidine
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Phosphoric acid ester
  • Pyrimidine
  • Heteroaromatic compound
  • Tetrahydrofuran
  • 1,2-diol
  • Secondary alcohol
  • Azacycle
  • Oxacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point215-218 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility11.2 g/LALOGPS
logP-0.34ALOGPS
logP-4.3ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)0.91ChemAxon
pKa (Strongest Basic)-0.54ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area268.2 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity87.16 m³·mol⁻¹ChemAxon
Polarizability35.87 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
  • endoplasmic reticulum
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Cardiolipin BiosynthesisPW002431 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(10:0/10:0/10:0/28:0)PW003484 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(10:0/10:0/10:0/30:0)PW003501 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(10:0/10:0/12:0/26:0)PW003502 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(10:0/10:0/12:0/28:0)PW003503 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glycerophospholipid metabolismec00564 Map00564
N-Glycan biosynthesisec00510 Map00510
Pantothenate and CoA biosynthesisec00770 Map00770
Pyrimidine metabolismec00240 Map00240
beta-Alanine metabolismec00410 Map00410
SMPDB Reactions
D-4'-Phosphopantothenate + Cytidine triphosphate + L-CysteineCytidine monophosphate + Pyrophosphate + hydron + 4-Phosphopantothenoylcysteine
PA(16:0/16:0) + hydron + Cytidine triphosphatePyrophosphate + CDP-DG(16:0/16:0)
DG(16:0/16:0/0:0) + hydron + Cytidine triphosphateCDP-DG(16:0/16:0) + Pyrophosphate
PA(16:0/16:0) + hydron + Cytidine triphosphate Pyrophosphate + CDP-DG(16:0/16:0)
PA(16:0/16:0) + hydron + Cytidine triphosphatePyrophosphate + CDP-DG(14:0/14:0)
KEGG Reactions
LPA(16:0/0:0) + hydron + Cytidine triphosphatePyrophosphate + CDP-diacylglycerol
Phosphorylcholine + hydron + Cytidine triphosphatePyrophosphate + Citicoline
Uridine triphosphate + Adenosine triphosphate + water + L-Glutaminephosphate + L-Glutamic acid + hydron + ADP + Cytidine triphosphate
Uridine triphosphate + Adenosine triphosphate + Ammoniumphosphate + hydron + ADP + Cytidine triphosphate
Dolichol-20 + Cytidine triphosphatedolichyl phosphate + CDP + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Shen, H., Heacock, P. N., Clancey, C. J., Dowhan, W. (1996). "The CDS1 gene encoding CDP-diacylglycerol synthase in Saccharomyces cerevisiae is essential for cell growth." J Biol Chem 271:789-795.8557688
  • Marobbio, C. M., Di Noia, M. A., Palmieri, F. (2006). "Identification of a mitochondrial transporter for pyrimidine nucleotides in Saccharomyces cerevisiae: bacterial expression, reconstitution and functional characterization." Biochem J 393:441-446.16194150
Synthesis Reference:Simon, Ethan S.; Bednarski, Mark D.; Whitesides, George M. Synthesis of CMP-NeuAc from N-acetylglucosamine: generation of CTP from CMP using adenylate kinase. Journal of the American Chemical Society (1988), 110(21), 7159-63.
External Links:
ResourceLink
CHEBI ID17677
HMDB IDHMDB00082
Pubchem Compound ID6176
Kegg IDC00063
ChemSpider ID5941
FOODB IDFDB012833
WikipediaCytidine_triphosphate
BioCyc IDCTP

Enzymes

General function:
Involved in transferase activity, transferring phosphorus-containing groups
Specific function:
Involved in the synthesis of the sugar donor Dol-P-Man which is required in the synthesis of N-linked and O-linked oligosaccharides and for that of GPI anchors. It is required for spore germination. Has an essential role in cellular metabolism
Gene Name:
SEC59
Uniprot ID:
P20048
Molecular weight:
58905.39844
Reactions
CTP + dolichol → CDP + dolichyl phosphate.
General function:
Involved in CTP synthase activity
Specific function:
Catalyzes the ATP-dependent amination of UTP to CTP with either L-glutamine or ammonia as the source of nitrogen
Gene Name:
URA7
Uniprot ID:
P28274
Molecular weight:
64709.80078
Reactions
ATP + UTP + NH(3) → ADP + phosphate + CTP.
General function:
Involved in CTP synthase activity
Specific function:
Catalyzes the ATP-dependent amination of UTP to CTP with either L-glutamine or ammonia as the source of nitrogen. Plays an important role in the regulation of phospholipid synthesis
Gene Name:
URA8
Uniprot ID:
P38627
Molecular weight:
63055.69922
Reactions
ATP + UTP + NH(3) → ADP + phosphate + CTP.
General function:
Coenzyme transport and metabolism
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
P40506
Molecular weight:
41892.69922
Reactions
CTP + (R)-4'-phosphopantothenate + L-cysteine → CMP + PPi + N-((R)-4'-phosphopantothenoyl)-L-cysteine.
General function:
Involved in transferase activity, transferring phosphorus-containing groups
Specific function:
Involved in pre-tRNA splicing. CTP- dependent diacylglycerol kinase that catalyzes the phosphorylation of diacylglycerol (DAG) to phosphatidate (PA). Controls phosphatidate levels at the nuclear envelope. Counteracts the activity of PAH1/SMP2. Involved in the resistance to nickel chloride and nalidixic acid. May be involved in vesicle trafficking between the endoplasmic reticulum and the Golgi apparatus
Gene Name:
DGK1
Uniprot ID:
Q12382
Molecular weight:
32839.80078
Reactions
CTP + 1,2-diacyl-sn-glycerol → CDP + 1,2-diacyl-sn-glycerol 3-phosphate.
General function:
Involved in nucleoside diphosphate kinase activity
Specific function:
Major role in the synthesis of nucleoside triphosphates other than ATP. The ATP gamma phosphate is transferred to the NDP beta phosphate via a ping-pong mechanism, using a phosphorylated active-site intermediate. Required for repair of UV radiation- and etoposide-induced DNA damage
Gene Name:
YNK1
Uniprot ID:
P36010
Molecular weight:
17166.59961
Reactions
ATP + nucleoside diphosphate → ADP + nucleoside triphosphate.
General function:
Involved in ATP binding
Specific function:
RAR (regulation of autonomous replication) is a protein whose activity increases the mitotic stability of plasmids
Gene Name:
ERG12
Uniprot ID:
P07277
Molecular weight:
48458.89844
Reactions
ATP + (R)-mevalonate → ADP + (R)-5-phosphomevalonate.
General function:
Involved in catalytic activity
Specific function:
CTP + choline phosphate = diphosphate + CDP- choline
Gene Name:
PCT1
Uniprot ID:
P13259
Molecular weight:
49405.80078
Reactions
CTP + choline phosphate → diphosphate + CDP-choline.
General function:
Involved in RNA binding
Specific function:
This enzyme carries out synthesis of the tRNA CCA terminus without the direction of a template using the multiple accepting and donating subsites within its active site
Gene Name:
CCA1
Uniprot ID:
P21269
Molecular weight:
62484.39844
Reactions
A tRNA precursor + 2 CTP + ATP → a tRNA with a 3' CCA end + 3 diphosphate.
General function:
Involved in catalytic activity
Specific function:
CTP + ethanolamine phosphate = diphosphate + CDP-ethanolamine
Gene Name:
MUQ1
Uniprot ID:
P33412
Molecular weight:
36862.60156
Reactions
CTP + ethanolamine phosphate → diphosphate + CDP-ethanolamine.
General function:
Involved in electron carrier activity
Specific function:
Participates as a hydrogen donor in redox reactions through the reversible oxidation of its active center dithiol to a disulfide, accompanied by the transfer of 2 electrons and 2 protons. It is involved in many cellular processes, including deoxyribonucleotide synthesis, repair of oxidatively damaged proteins, protein folding, sulfur metabolism, and redox homeostasis. Thioredoxin-dependent enzymes include phosphoadenosine-phosphosulfate reductase MET16, alkyl- hydroperoxide reductase DOT5, thioredoxin peroxidases TSA1 and TSA2, alkyl hydroperoxide reductase AHP1, and peroxiredoxin HYR1. Thioredoxin is also involved in protection against reducing stress. As part of the LMA1 complex, it is involved in the facilitation of vesicle fusion such as homotypic vacuole and ER- derived COPII vesicle fusion with the Golgi. This activity does not require the redox mechanism. Through its capacity to inactivate the stress response transcription factor YAP1 and its regulator the hydroperoxide stress sensor HYR1, it is involved in feedback regulation of stress response gene expression upon oxidative stress
Gene Name:
TRX2
Uniprot ID:
P22803
Molecular weight:
11203.7998
Reactions
General function:
Involved in electron carrier activity
Specific function:
Participates as a hydrogen donor in redox reactions through the reversible oxidation of its active center dithiol to a disulfide, accompanied by the transfer of 2 electrons and 2 protons. It is involved in many cellular processes, including deoxyribonucleotide synthesis, repair of oxidatively damaged proteins, protein folding, sulfur metabolism, and redox homeostasis. Thioredoxin-dependent enzymes include phosphoadenosine-phosphosulfate reductase MET16, alkyl- hydroperoxide reductase DOT5, thioredoxin peroxidases TSA1 and TSA2, alkyl hydroperoxide reductase AHP1, and peroxiredoxin HYR1. Thioredoxin is also involved in protection against reducing stress. As part of the LMA1 complex, it is involved in the facilitation of vesicle fusion such as homotypic vacuole and ER- derived COPII vesicle fusion with the Golgi. This activity does not require the redox mechanism
Gene Name:
TRX1
Uniprot ID:
P22217
Molecular weight:
11234.90039
Reactions
General function:
Involved in transferase activity, transferring phosphorus-containing groups
Specific function:
Supplies CDP-diacylglycerol, which may play an important role as both a precursor to phosphoinositide biosynthesis in the plasma membrane and as a negative effector of phosphatidylinositol 4-kinase activity, thereby exerting an effect on cell proliferation via a lipid-dependent signal transduction cascade
Gene Name:
CDS1
Uniprot ID:
P38221
Molecular weight:
51822.39844
Reactions
CTP + phosphatidate → diphosphate + CDP-diacylglycerol.
General function:
CDP-diacylglycerol biosynthetic process
Specific function:
Catalyzes the formation of CDP-diacylglycerol (CDP-DAG) from phosphatidic acid (PA) in the mitochondrial inner membrane. Required for the biosynthesis of the dimeric phospholipid cardiolipin, which stabilizes supercomplexes of the mitochondrial respiratory chain in the mitochondrial inner membrane.
Gene Name:
TAM41
Uniprot ID:
P53230
Molecular weight:
44199.33
Reactions

Transporters

General function:
Involved in binding
Specific function:
Not Available
Gene Name:
RIM2
Uniprot ID:
P38127
Molecular weight:
42101.39844