Record Information
Version2.0
Creation Date2012-05-31 13:50:21 -0600
Update Date2015-09-13 12:56:10 -0600
Secondary Accession Numbers
  • ECMDB01342
Identification
Name:Thymidine 5'-triphosphate
DescriptionThymidine 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
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
Weight:Average: 482.1683
Monoisotopic: 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
Description belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleoside triphosphates. These are pyrimidine nucleotides with a triphosphate group linked to the ribose moiety lacking a hydroxyl group at position 2.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleotides
Sub ClassPyrimidine deoxyribonucleotides
Direct ParentPyrimidine 2'-deoxyribonucleoside triphosphates
Alternative Parents
Substituents
  • Pyrimidine 2'-deoxyribonucleoside triphosphate
  • Pyrimidone
  • Monoalkyl phosphate
  • Hydropyrimidine
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Heteroaromatic compound
  • Vinylogous amide
  • Tetrahydrofuran
  • Lactam
  • Secondary alcohol
  • Urea
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility7.78 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity88.03 m³·mol⁻¹ChemAxon
Polarizability36.6 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
O-antigen building blocks biosynthesisPW002089 ThumbThumb?image type=greyscaleThumb?image type=simple
Pyrimidine metabolismPW000942 ThumbThumb?image type=greyscaleThumb?image type=simple
Secondary Metabolites: enterobacterial common antigen biosynthesisPW000959 ThumbThumb?image type=greyscaleThumb?image type=simple
Secondary Metabolites: enterobacterial common antigen biosynthesis 2PW002045 ThumbThumb?image type=greyscaleThumb?image type=simple
Secondary Metabolites: enterobacterial common antigen biosynthesis 3PW002046 ThumbThumb?image type=greyscaleThumb?image type=simple
Starch and sucrose metabolismPW000941 ThumbThumb?image type=greyscaleThumb?image type=simple
purine nucleotides de novo biosynthesisPW000910 ThumbThumb?image type=greyscaleThumb?image type=simple
purine nucleotides de novo biosynthesis 1435709748PW000960 ThumbThumb?image type=greyscaleThumb?image type=simple
purine nucleotides de novo biosynthesis 2PW002033 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
4620± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucoseMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
525± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerolMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
667± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetateMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
Find out more about how we convert literature concentrations.
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9742300000-c721ba5109dede8a518bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9305110000-bbc51754a929afc4eb54View in MoNA
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, Positivesplash10-004i-0900000000-9c496d7377af5eb651b2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-2901000000-99a48a5d17f022d6494cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-4900000000-889ecd9966747af96efeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-053i-1410900000-cc4f8db45f53046b5380View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057r-9870100000-6cf02bd6b66f7b822525View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-cde9ec4f970230e9f180View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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

Enzymes

General function:
Involved in nucleic acid binding
Specific function:
In addition to polymerase activity, this DNA polymerase exhibits 3' to 5' and 5' to 3' exonuclease activity. It is able to utilize nicked circular duplex DNA as a template and can unwind the parental DNA strand from its template
Gene Name:
polA
Uniprot ID:
P00582
Molecular weight:
103117
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1).
General function:
Involved in DNA binding
Specific function:
DNA polymerase III is a complex, multichain enzyme responsible for most of the replicative synthesis in bacteria. The epsilon subunit contain the editing function and is a proofreading 3'-5' exonuclease
Gene Name:
dnaQ
Uniprot ID:
P03007
Molecular weight:
27099
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1).
General function:
Involved in nucleotide binding
Specific function:
The gamma chain seems to interact with the delta subunit to transfer the beta subunit on the DNA
Gene Name:
dnaX
Uniprot ID:
P06710
Molecular weight:
71137
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1).
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
Gene Name:
ndk
Uniprot ID:
P0A763
Molecular weight:
15463
Reactions
ATP + nucleoside diphosphate = ADP + nucleoside triphosphate.
General function:
Involved in ATP binding
Specific function:
ATP + uridine = ADP + UMP
Gene Name:
udk
Uniprot ID:
P0A8F4
Molecular weight:
24353
Reactions
ATP + uridine = ADP + UMP.
ATP + cytidine = ADP + CMP.
General function:
Involved in DNA binding
Specific function:
DNA polymerase III is a complex, multichain enzyme responsible for most of the replicative synthesis in bacteria. This DNA polymerase also exhibits 3' to 5' exonuclease activity. The beta chain is required for initiation of replication once it is clamped onto DNA, it slides freely (bidirectional and ATP- independent) along duplex DNA
Gene Name:
dnaN
Uniprot ID:
P0A988
Molecular weight:
40586
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1).
General function:
Involved in DNA binding
Specific function:
The exact function of the theta subunit is unknown
Gene Name:
holE
Uniprot ID:
P0ABS8
Molecular weight:
8846
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1).
General function:
Involved in nucleoside-triphosphate diphosphatase activity
Specific function:
Specific function unknown
Gene Name:
mazG
Uniprot ID:
P0AEY3
Molecular weight:
30412
Reactions
ATP + H(2)O = AMP + diphosphate.
General function:
Involved in 3'-5' exonuclease activity
Specific function:
DNA polymerase III is a complex, multichain enzyme responsible for most of the replicative synthesis in bacteria. This DNA polymerase also exhibits 3' to 5' exonuclease activity. The alpha chain is the DNA polymerase
Gene Name:
dnaE
Uniprot ID:
P10443
Molecular weight:
129903
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1).
General function:
Involved in DNA binding
Specific function:
DNA polymerase III is a complex, multichain enzyme responsible for most of the replicative synthesis in bacteria. This DNA polymerase also exhibits 3' to 5' exonuclease activity. The delta subunit seems to interact with the gamma subunit to transfer the beta subunit on the DNA
Gene Name:
holA
Uniprot ID:
P28630
Molecular weight:
38703
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1).
General function:
Involved in DNA binding
Specific function:
DNA polymerase III is a complex, multichain enzyme responsible for most of the replicative synthesis in bacteria. This DNA polymerase also exhibits 3' to 5' exonuclease activity
Gene Name:
holB
Uniprot ID:
P28631
Molecular weight:
36936
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1).
General function:
Involved in DNA-directed DNA polymerase activity
Specific function:
DNA polymerase III is a complex, multichain enzyme responsible for most of the replicative synthesis in bacteria. This DNA polymerase also exhibits 3' to 5' exonuclease activity. The exact function of the psi subunit is unknown
Gene Name:
holD
Uniprot ID:
P28632
Molecular weight:
15174
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1).
General function:
Involved in DNA binding
Specific function:
DNA polymerase III is a complex, multichain enzyme responsible for most of the replicative synthesis in bacteria. This DNA polymerase also exhibits 3' to 5' exonuclease activity
Gene Name:
holC
Uniprot ID:
P28905
Molecular weight:
16633
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1).
General function:
Involved in glucose-1-phosphate thymidylyltransferase activity
Specific function:
Catalyzes the formation of dTDP-glucose, from dTTP and glucose 1-phosphate, as well as its pyrophosphorolysis
Gene Name:
rmlA1
Uniprot ID:
P37744
Molecular weight:
32693
Reactions
dTTP + alpha-D-glucose 1-phosphate = diphosphate + dTDP-glucose.
General function:
Involved in hydrolase activity, acting on acid anhydrides, in phosphorus-containing anhydrides
Specific function:
Catalyzes the hydrolysis of nucleoside triphosphates, with a preference for pyrimidine deoxynucleoside triphosphates (dUTP, dTTP and dCTP)
Gene Name:
nudI
Uniprot ID:
P52006
Molecular weight:
16371
Reactions
Nucleoside triphosphate + H(2)O = nucleoside monophosphate + diphosphate.
General function:
Involved in glucose-1-phosphate thymidylyltransferase activity
Specific function:
Catalyzes the formation of dTDP-glucose, from dTTP and glucose 1-phosphate, as well as its pyrophosphorolysis
Gene Name:
rmlA2
Uniprot ID:
P61887
Molecular weight:
32734
Reactions
dTTP + alpha-D-glucose 1-phosphate = diphosphate + dTDP-glucose.
General function:
Involved in ATP binding
Specific function:
Catalyzes the reversible transfer of the terminal phosphate group between ATP and AMP. This small ubiquitous enzyme involved in the energy metabolism and nucleotide synthesis, is essential for maintenance and cell growth
Gene Name:
adk
Uniprot ID:
P69441
Molecular weight:
23586
Reactions
ATP + AMP = 2 ADP.

Transporters

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
Gene Name:
ndk
Uniprot ID:
P0A763
Molecular weight:
15463
Reactions
ATP + nucleoside diphosphate = ADP + nucleoside triphosphate.