You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-05-13 15:14:23 UTC
HMDB IDHMDB0001342
Secondary Accession Numbers
  • HMDB01342
Metabolite Identification
Common NameThymidine 5'-triphosphate
DescriptionThymidine 5'-triphosphate, also known as TTP or DTHD5'ppp, 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. Thymidine 5'-triphosphate or Thymidine 5'-triphosphate is one of the four nucleoside triphosphates that make up DNA. Thymidine 5'-triphosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Thymidine 5'-triphosphate exists in all living species, ranging from bacteria to humans. Outside of the human body, Thymidine 5'-triphosphate has been detected, but not quantified in, several different foods, such as elliott's blueberries, mamey sapotes, sesames, alliums, and sweet oranges. This could make thymidine 5'-triphosphate a potential biomarker for the consumption of these foods.
Structure
Data?1589382863
Synonyms
ValueSource
2'-Deoxythymidine triphosphateChEBI
5'-TTPChEBI
Deoxy-TTPChEBI
Deoxythymidine 5'-triphosphateChEBI
Deoxythymidine triphosphateChEBI
DTHD5'pppChEBI
PPPDTChEBI
THYMIDINE-5'-triphosphATEChEBI
TTPChEBI
2'-Deoxythymidine triphosphoric acidGenerator
Deoxythymidine 5'-triphosphoric acidGenerator
Deoxythymidine triphosphoric acidGenerator
THYMIDINE-5'-triphosphoric acidGenerator
Thymidine 5'-triphosphoric acidGenerator
2'-Deoxythymidine 5'-triphosphateHMDB
5-Methyl-dUTPHMDB
dTTPHMDB
Thymidine mono(tetrahydrogen triphosphate)HMDB
Thymidine triphosphateHMDB
Thymidine 5'-triphosphate, magnesium saltHMDB
Thymidine 5'-triphosphate, trisodium saltHMDB
2'-Deoxythymidine-5'-triphosphateHMDB
Thymidine 5'-triphosphate, p''-(32)p-labeledHMDB
2’-Deoxythymidine 5’-triphosphateHMDB
2’-Deoxythymidine triphosphateHMDB
5’-TTPHMDB
Deoxythymidine 5’-triphosphateHMDB
Thymidine 5'-triphosphateHMDB
Thymidine 5’-triphosphateHMDB
Chemical FormulaC10H17N2O14P3
Average Molecular Weight482.1683
Monoisotopic Molecular Weight481.989262798
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 NamedTTP
CAS Registry Number365-08-2
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
InChI Identifier
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
InChI KeyNHVNXKFIZYSCEB-XLPZGREQSA-N
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9742300000-c721ba5109dede8a518bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9305110000-bbc51754a929afc4eb54Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0000900000-d176c8e8a9bdb2d457e5Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-0000900000-d176c8e8a9bdb2d457e5Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-0900000000-970154df2a1ed9a84a2fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 15V, negativesplash10-001i-0000900000-50c7a1492866ca00359dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 18V, negativesplash10-001i-0200900000-dda4f6996cabd8db242fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 20V, negativesplash10-053r-0602900000-0390bef6ad193f2b5004Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 23V, negativesplash10-0a59-0902600000-2f2a5a489951a9c68992Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 26V, negativesplash10-0a4i-0912200000-1d8c5b170f87fa6f2c9bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 34V, negativesplash10-0a4i-1921100000-93f84465717aa16d3f7cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 41V, negativesplash10-0a4i-2920000000-6d1131e45ff20126cf41Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 50V, negativesplash10-0a6r-5910000000-2a9eb44864392efb37c3Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 59V, negativesplash10-056r-9700000000-71a33ac9eaf4e714b558Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 73V, negativesplash10-004i-9200000000-0667d2c3d019b5ca17bcSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 33V, negativesplash10-001i-0209200000-ed0d460f9e1d08011f06Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 33V, negativesplash10-004i-9000000000-5ef060d5ec4b80c35c1aSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 33V, negativesplash10-0a4i-0190000000-e8bf71168cfd7e675dcaSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 33V, negativesplash10-001r-0019000000-d84a6f61ca04e6970204Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 16V, negativesplash10-001i-0009000000-6f966eb3b101b9fadfbeSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 18V, negativesplash10-001i-0019000000-f7153b7fadabb2f7f79fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-9c496d7377af5eb651b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-2901000000-99a48a5d17f022d6494cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-4900000000-889ecd9966747af96efeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-053i-1410900000-cc4f8db45f53046b5380Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057r-9870100000-6cf02bd6b66f7b822525Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-cde9ec4f970230e9f180Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Mitochondria
  • Nucleus
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02452
Phenol Explorer Compound IDNot Available
FooDB IDFDB030841
KNApSAcK IDC00019695
Chemspider ID58493
KEGG Compound IDC00459
BioCyc IDTTP
BiGG ID35032
Wikipedia LinkDeoxythymidine_Triphosphate
METLIN IDNot Available
PubChem Compound64968
PDB IDNot Available
ChEBI ID18077
Food Biomarker OntologyNot Available
VMH IDDTTP
MarkerDB ID
References
Synthesis ReferenceIkehara, 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)
General References
  1. Dahlmann N: Human serum thymidine triphosphate nucleotidohydrolase: purification and properties of a new enzyme. Biochemistry. 1982 Dec 21;21(26):6634-9. [PubMed:6297538 ]
  2. 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 ]
  3. 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 ]

Only showing the first 10 proteins. There are 43 proteins in total.

Enzymes

General function:
Involved in hydrolase activity
Specific function:
In the nervous system, could hydrolyze ATP and other nucleotides to regulate purinergic neurotransmission. Could also be implicated in the prevention of platelet aggregation by hydrolyzing platelet-activating ADP to AMP. Hydrolyzes ATP and ADP equally well.
Gene Name:
ENTPD1
Uniprot ID:
P49961
Molecular weight:
58706.0
Reactions
Thymidine 5'-triphosphate + Water → dTDP + Phosphatedetails
General function:
Involved in calcium ion binding
Specific function:
Calcium-dependent nucleotidase with a preference for UDP. The order of activity with different substrates is UDP > GDP > UTP > GTP. Has very low activity towards ADP and even lower activity towards ATP. Does not hydrolyze AMP and GMP. Involved in proteoglycan synthesis.
Gene Name:
CANT1
Uniprot ID:
Q8WVQ1
Molecular weight:
44839.24
General function:
Involved in hydrolase activity
Specific function:
Has a threefold preference for the hydrolysis of ATP over ADP.
Gene Name:
ENTPD3
Uniprot ID:
O75355
Molecular weight:
59104.76
Reactions
Thymidine 5'-triphosphate + Water → dTDP + Phosphatedetails
General function:
Involved in ATP binding
Specific function:
Phosphorylates uridine and cytidine to uridine monophosphate and cytidine monophosphate. Does not phosphorylate deoxyribonucleosides or purine ribonucleosides. Can use ATP or GTP as a phosphate donor. Can also phosphorylate cytidine and uridine nucleoside analogs such as 6-azauridine, 5-fluorouridine, 4-thiouridine, 5-bromouridine, N(4)-acetylcytidine, N(4)-benzoylcytidine, 5-fluorocytidine, 2-thiocytidine, 5-methylcytidine, and N(4)-anisoylcytidine.
Gene Name:
UCK1
Uniprot ID:
Q9HA47
Molecular weight:
22760.43
Reactions
Thymidine 5'-triphosphate + Cytidine → dTDP + Cytidine monophosphatedetails
Thymidine 5'-triphosphate + Uridine → dTDP + Uridine 5'-monophosphatedetails
General function:
Involved in nucleoside diphosphate kinase activity
Specific function:
Major role in the synthesis of nucleoside triphosphates other than ATP (By similarity).
Gene Name:
NME4
Uniprot ID:
O00746
Molecular weight:
20658.45
Reactions
Adenosine triphosphate + dTDP → ADP + Thymidine 5'-triphosphatedetails
General function:
Involved in nucleoside diphosphate kinase activity
Specific function:
Major role in the synthesis of nucleoside triphosphates other than ATP. Possesses nucleoside-diphosphate kinase, serine/threonine-specific protein kinase, geranyl and farnesyl pyrophosphate kinase, histidine protein kinase and 3'-5' exonuclease activities. Involved in cell proliferation, differentiation and development, signal transduction, G protein-coupled receptor endocytosis, and gene expression. Required for neural development including neural patterning and cell fate determination.
Gene Name:
NME1
Uniprot ID:
P15531
Molecular weight:
17148.635
Reactions
Adenosine triphosphate + dTDP → ADP + Thymidine 5'-triphosphatedetails
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:
NME7
Uniprot ID:
Q9Y5B8
Molecular weight:
42491.365
Reactions
Adenosine triphosphate + dTDP → ADP + Thymidine 5'-triphosphatedetails
General function:
Involved in nucleoside diphosphate kinase activity
Specific function:
Major role in the synthesis of nucleoside triphosphates other than ATP. Negatively regulates Rho activity by interacting with AKAP13/LBC. Acts as a transcriptional activator of the MYC gene; binds DNA non-specifically (PubMed:8392752). Exhibits histidine protein kinase activity.
Gene Name:
NME2
Uniprot ID:
P22392
Molecular weight:
30136.92
Reactions
Adenosine triphosphate + dTDP → ADP + Thymidine 5'-triphosphatedetails
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. Probably has a role in normal hematopoiesis by inhibition of granulocyte differentiation and induction of apoptosis.
Gene Name:
NME3
Uniprot ID:
Q13232
Molecular weight:
19014.85
Reactions
Adenosine triphosphate + dTDP → ADP + Thymidine 5'-triphosphatedetails
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. Inhibitor of p53-induced apoptosis.
Gene Name:
NME6
Uniprot ID:
O75414
Molecular weight:
22002.965
Reactions
Adenosine triphosphate + dTDP → ADP + Thymidine 5'-triphosphatedetails

Only showing the first 10 proteins. There are 43 proteins in total.