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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:46:10 UTC
HMDB IDHMDB0001342
Secondary Accession Numbers
  • HMDB01342
Metabolite Identification
Common NameThymidine 5'-triphosphate
DescriptionDeoxythymidine triphosphate (dTTP) is one of the four nucleoside triphosphates that are used in the in vivo synthesis of DNA. Unlike the other deoxyribonucleoside triphosphates, thymidine triphosphate does not always contain the "deoxy" prefix in its name. The corresponding ribonucleoside triphosphate is called uridine triphosphate. Thymidine 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 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.
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

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9742300000-c721ba5109dede8a518b2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9305110000-bbc51754a929afc4eb542017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0002-9742300000-c721ba5109dede8a518b2021-09-05View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0000900000-d176c8e8a9bdb2d457e52012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-0000900000-d176c8e8a9bdb2d457e52012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-0900000000-970154df2a1ed9a84a2f2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 15V, negativesplash10-001i-0000900000-50c7a1492866ca00359d2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 18V, negativesplash10-001i-0200900000-dda4f6996cabd8db242f2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 20V, negativesplash10-053r-0602900000-0390bef6ad193f2b50042020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 23V, negativesplash10-0a59-0902600000-2f2a5a489951a9c689922020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 26V, negativesplash10-0a4i-0912200000-1d8c5b170f87fa6f2c9b2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 34V, negativesplash10-0a4i-1921100000-93f84465717aa16d3f7c2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 41V, negativesplash10-0a4i-2920000000-6d1131e45ff20126cf412020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 50V, negativesplash10-0a6r-5910000000-2a9eb44864392efb37c32020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 59V, negativesplash10-056r-9700000000-71a33ac9eaf4e714b5582020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 73V, negativesplash10-004i-9200000000-0667d2c3d019b5ca17bc2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 33V, negativesplash10-001i-0209200000-ed0d460f9e1d08011f062020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 33V, negativesplash10-004i-9000000000-5ef060d5ec4b80c35c1a2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 33V, negativesplash10-0a4i-0190000000-e8bf71168cfd7e675dca2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 33V, negativesplash10-001r-0019000000-d84a6f61ca04e69702042020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 16V, negativesplash10-001i-0009000000-6f966eb3b101b9fadfbe2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 18V, negativesplash10-001i-0019000000-f7153b7fadabb2f7f79f2020-07-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-9c496d7377af5eb651b22016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-2901000000-99a48a5d17f022d6494c2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-4900000000-889ecd9966747af96efe2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-053i-1410900000-cc4f8db45f53046b53802016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057r-9870100000-6cf02bd6b66f7b8225252016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-cde9ec4f970230e9f1802016-09-12View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, predicted)2012-12-05View Spectrum
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 IDNot Available
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.