Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:10:21 UTC
HMDB IDHMDB01342
Secondary Accession NumbersNone
Metabolite Identification
Common NameThymidine 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
  1. 2'-Deoxythymidine 5'-triphosphate
  2. 2'-Deoxythymidine triphosphate
  3. 5'-TTP
  4. 5-Methyl-dUTP
  5. Deoxy-TTP
  6. Deoxythymidine 5'-triphosphate
  7. Deoxythymidine triphosphate
  8. dTTP
  9. Thymidine 5'-triphosphate
  10. Thymidine mono(tetrahydrogen triphosphate)
  11. Thymidine triphosphate
  12. TTP
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 IUPAC Name[hydroxy({hydroxy[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3H-pyrimidin-1-yl)oxolan-2-yl]methoxyphosphoryl}oxy)phosphoryl]oxyphosphonic acid
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
KingdomOrganic Compounds
Super ClassNucleosides, Nucleotides, and Analogues
ClassPyrimidine Nucleotides
Sub ClassPyrimidine Deoxyribonucleotides
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Deoxyribonucleotides(KEGG)
  • Pyrimidine Deoxyribonucleotides
  • pyrimidine 2'-deoxyribonucleoside 5'-triphosphate(ChEBI)
  • thymidine phosphate(ChEBI)
Substituents
  • Hydropyrimidine
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxolane
  • Phosphoric Acid Ester
  • Pyrimidine
  • Pyrimidone
  • Secondary Alcohol
Direct ParentPyrimidine 2'-deoxyribonucleoside Triphosphates
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
Biofunction
  • DNA component
ApplicationNot Available
Cellular locations
  • Mitochondria
  • Nucleus
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 area238.69ChemAxon
rotatable bond count8ChemAxon
refractivity88.03ChemAxon
polarizability36.57ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Mitochondria
  • Nucleus
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Pyrimidine MetabolismSMP00046map00240
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022565
KNApSAcK IDNot Available
Chemspider ID58493
KEGG Compound IDC00459
BioCyc IDTTP
BiGG ID35032
Wikipedia LinkTTP
NuGOwiki LinkHMDB01342
Metagene LinkHMDB01342
METLIN IDNot Available
PubChem Compound64968
PDB IDTTP
ChEBI ID18077
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)Not Available
General References
  1. 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
  2. Dahlmann N: Human serum thymidine triphosphate nucleotidohydrolase: purification and properties of a new enzyme. Biochemistry. 1982 Dec 21;21(26):6634-9. Pubmed: 6297538
  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

Enzymes

Gene Name:
ENTPD1
Uniprot ID:
P49961
Reactions
Thymidine 5'-triphosphate + Water unknown dTDP + Phosphoric aciddetails
Gene Name:
ENTPD3
Uniprot ID:
O75355
Reactions
Thymidine 5'-triphosphate + Water unknown dTDP + Phosphoric aciddetails
Gene Name:
UCK1
Uniprot ID:
Q9HA47
Reactions
Thymidine 5'-triphosphate + Cytidine unknown dTDP + Cytidine monophosphatedetails
Thymidine 5'-triphosphate + Uridine unknown dTDP + Uridine 5'-monophosphatedetails
Gene Name:
NME4
Uniprot ID:
O00746
Reactions
Adenosine triphosphate + dTDP unknown ADP + Thymidine 5'-triphosphatedetails
Gene Name:
NME1
Uniprot ID:
P15531
Reactions
Adenosine triphosphate + dTDP unknown ADP + Thymidine 5'-triphosphatedetails
Gene Name:
NME7
Uniprot ID:
Q9Y5B8
Reactions
Adenosine triphosphate + dTDP unknown ADP + Thymidine 5'-triphosphatedetails
Gene Name:
NME2
Uniprot ID:
P22392
Reactions
Adenosine triphosphate + dTDP unknown ADP + Thymidine 5'-triphosphatedetails
Gene Name:
NME3
Uniprot ID:
Q13232
Reactions
Adenosine triphosphate + dTDP unknown ADP + Thymidine 5'-triphosphatedetails
Gene Name:
NME6
Uniprot ID:
O75414
Reactions
Adenosine triphosphate + dTDP unknown ADP + Thymidine 5'-triphosphatedetails
Gene Name:
ITPA
Uniprot ID:
Q9BY32
Gene Name:
POLB
Uniprot ID:
P06746
Gene Name:
POLA1
Uniprot ID:
P09884
Reactions
Thymidine 5'-triphosphate + DNA unknown Pyrophosphate + DNAdetails
Gene Name:
POLD3
Uniprot ID:
Q15054
Gene Name:
POLL
Uniprot ID:
Q9UGP5
Gene Name:
POLE4
Uniprot ID:
Q9NR33
Reactions
Thymidine 5'-triphosphate + DNA unknown Pyrophosphate + DNAdetails
Gene Name:
POLH
Uniprot ID:
Q9Y253
Gene Name:
POLD1
Uniprot ID:
P28340
Reactions
Thymidine 5'-triphosphate + DNA unknown Pyrophosphate + DNAdetails
Gene Name:
REV3L
Uniprot ID:
O60673
Gene Name:
POLE
Uniprot ID:
Q07864
Reactions
Thymidine 5'-triphosphate + DNA unknown Pyrophosphate + DNAdetails
Gene Name:
POLM
Uniprot ID:
Q9NP87
Gene Name:
POLK
Uniprot ID:
Q9UBT6
Gene Name:
POLE3
Uniprot ID:
Q9NRF9
Reactions
Thymidine 5'-triphosphate + DNA unknown Pyrophosphate + DNAdetails
Gene Name:
POLG
Uniprot ID:
P54098
Gene Name:
POLI
Uniprot ID:
Q9UNA4
Gene Name:
POLE2
Uniprot ID:
P56282
Reactions
Thymidine 5'-triphosphate + DNA unknown Pyrophosphate + DNAdetails
Gene Name:
UCK2
Uniprot ID:
Q9BZX2
Reactions
Thymidine 5'-triphosphate + Cytidine unknown dTDP + Cytidine monophosphatedetails
Thymidine 5'-triphosphate + Uridine unknown dTDP + Uridine 5'-monophosphatedetails
Gene Name:
UCKL1
Uniprot ID:
Q9NWZ5
Reactions
Thymidine 5'-triphosphate + Cytidine unknown dTDP + Cytidine monophosphatedetails
Thymidine 5'-triphosphate + Uridine unknown dTDP + Uridine 5'-monophosphatedetails
Gene Name:
ENTPD8
Uniprot ID:
Q5MY95
Reactions
Thymidine 5'-triphosphate + Water unknown dTDP + Phosphoric aciddetails
Gene Name:
NME2P1
Uniprot ID:
O60361
Gene Name:
MYBBP1A
Uniprot ID:
Q9BQG0
Gene Name:
POLQ
Uniprot ID:
O75417
Gene Name:
POLD2
Uniprot ID:
P49005
Reactions
Thymidine 5'-triphosphate + DNA unknown Pyrophosphate + DNAdetails
Gene Name:
NME5
Uniprot ID:
P56597
Reactions
Adenosine triphosphate + dTDP unknown ADP + Thymidine 5'-triphosphatedetails
Gene Name:
PRIM1
Uniprot ID:
P49642
Reactions
Thymidine 5'-triphosphate + DNA unknown Pyrophosphate + DNAdetails
Gene Name:
PRIM2
Uniprot ID:
P49643
Reactions
Thymidine 5'-triphosphate + DNA unknown Pyrophosphate + DNAdetails