Thymidine 5'-triphosphate (PAMDB000346)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000346
Identification
Name: Thymidine 5'-triphosphate
Description:Thymidine triphosphate or TTP is one of the four nucleoside triphosphates that make up DNA. It can be used by DNA ligase to create overlapping "sticky ends" so that protruding ends of opened microbial plasmids maybe closed up.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 2'-Deoxythymidine 5'-triphosphate
  • 2'-Deoxythymidine 5'-triphosphoric acid
  • 2'-Deoxythymidine triphosphate
  • 2'-Deoxythymidine triphosphoric acid
  • 5'-TTP
  • 5-Methyl-dUTP
  • Deoxy-TTP
  • Deoxythymidine 5'-triphosphate
  • Deoxythymidine 5'-triphosphoric acid
  • Deoxythymidine triphosphate
  • Deoxythymidine triphosphoric acid
  • DTTP
  • Thymidine 5'-triphosphate
  • Thymidine 5'-triphosphoric acid
  • Thymidine mono(tetrahydrogen triphosphate)
  • Thymidine mono(tetrahydrogen triphosphoric acid)
  • Thymidine triphosphate
  • Thymidine triphosphoric acid
  • TTP
Chemical Formula: C10H17N2O14P3
Average Molecular Weight: 482.1683
Monoisotopic Molecular Weight: 481.989262798
InChI Key: NHVNXKFIZYSCEB-XLPZGREQSA-N
InChI:InChI=1S/C10H17N2O14P3/c1-5-3-12(10(15)11-9(5)14)8-2-6(13)7(24-8)4-23-28(19,20)26-29(21,22)25-27(16,17)18/h3,6-8,13H,2,4H2,1H3,(H,19,20)(H,21,22)(H,11,14,15)(H2,16,17,18)/t6-,7+,8+/m0/s1
CAS number: 365-08-2
IUPAC Name:{[hydroxy({[hydroxy({[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphoryl]oxy})phosphoryl]oxy}phosphonic acid
Traditional IUPAC Name: dTTP
SMILES:CC1=CN([C@H]2C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O2)C(=O)NC1=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleoside diphosphates. These are pyrimidine nucleotides with a diphosphate group linked to the ribose moiety lacking a hydroxyl group at position 2.
Kingdom Organic compounds
Super ClassNucleosides, nucleotides, and analogues
Class Pyrimidine nucleotides
Sub ClassPyrimidine deoxyribonucleotides
Direct Parent Pyrimidine 2'-deoxyribonucleoside diphosphates
Alternative Parents
Substituents
  • Pyrimidine 2'-deoxyribonucleoside diphosphate
  • Organic pyrophosphate
  • Monoalkyl phosphate
  • Pyrimidone
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Hydropyrimidine
  • Saccharide
  • Heteroaromatic compound
  • Vinylogous amide
  • Oxolane
  • Urea
  • Secondary alcohol
  • Lactam
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-3
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility7.78 mg/mLALOGPS
logP-0.09ALOGPS
logP-2.1ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)0.9ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area238.69 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity88.03 m3·mol-1ChemAxon
Polarizability36.57 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Adenosine triphosphate + dTDP <> ADP + Thymidine 5'-triphosphate
Thymidine 5'-triphosphate + Glucose 1-phosphate + Hydrogen ion <> dTDP-D-Glucose + Pyrophosphate
Thymidine 5'-triphosphate + Water > 5-Thymidylic acid + Hydrogen ion + Pyrophosphate
Thymidine 5'-triphosphate + DNA <> Pyrophosphate + DNA
Thymidine 5'-triphosphate + Cytidine <> dTDP + Cytidine monophosphate
Thymidine 5'-triphosphate + Uridine <> dTDP + Uridine 5'-monophosphate
Thymidine 5'-triphosphate + Glucose 1-phosphate <> Pyrophosphate + dTDP-D-Glucose
Adenosine triphosphate + dTDP > Adenosine diphosphate + Thymidine 5'-triphosphate + ADP
Thymidine 5'-triphosphate + Hydrogen ion + Glucose 1-phosphate > Pyrophosphate + dTDP-D-Glucose
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0000900000-d176c8e8a9bdb2d457e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-0000900000-d176c8e8a9bdb2d457e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-0900000000-970154df2a1ed9a84a2fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
  • Dahlmann N, Ueckermann C: Separation of deoxythymidine-5'-triphosphatase from unspecific hydrolases. A recommended micromethod in the diagnostic evaluation of human carcinoma. Anticancer Res. 1984 Jul-Oct;4(4-5):299-303. Pubmed: 6091528
  • Dahlmann N: Human serum thymidine triphosphate nucleotidohydrolase: purification and properties of a new enzyme. Biochemistry. 1982 Dec 21;21(26):6634-9. Pubmed: 6297538
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Schultes BC, Fischbach E, Dahlmann N: Purification and characterization of two different thymidine-5'-triphosphosphate-hydrolysing enzymes in human serum. Biol Chem Hoppe Seyler. 1992 May;373(5):237-47. Pubmed: 1320895
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference: Ikehara, Morio; Ohtsuka, Eiko. Coenzyme analogs. XXI. A new synthesis of thymidine 5'-triphosphate and the use of P1,P2-bis(2-cyanoethyl) pyrophosphate in the nucleoside triphosphate synthesis. Chemical & Pharmaceutical Bulletin (1963), 11(11), 1358-63.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID18077
HMDB IDHMDB01342
Pubchem Compound ID64968
Kegg IDC00459
ChemSpider ID58493
WikipediaTTP
BioCyc IDTTP
EcoCyc IDTTP
Ligand ExpoTTP