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Human Metabolome Database Version 3.5

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Showing metabocard for Thymidine 5'-triphosphate (HMDB01342)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:10:21 -0700
HMDB ID HMDB01342
Secondary Accession Numbers None
Metabolite Identification
Common 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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C10H17N2O14P3
Average Molecular Weight 482.1683
Monoisotopic Molecular Weight 481.989262798
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 Number 365-08-2
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 Key NHVNXKFIZYSCEB-XLPZGREQSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Nucleosides, Nucleotides, and Analogues
Class Pyrimidine Nucleotides
Sub Class Pyrimidine 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 Parent Pyrimidine 2'-deoxyribonucleoside Triphosphates
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction
  • DNA component
Application Not Available
Cellular locations
  • Mitochondria
  • Nucleus
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 7.78 g/L ALOGPS
LogP -0.09 ALOGPS
LogP -2.1 ChemAxon
LogS -1.79 ALOGPS
pKa (strongest acidic) 0.9 ChemAxon
pKa (strongest basic) -3.2 ChemAxon
Hydrogen Acceptor Count 11 ChemAxon
Hydrogen Donor Count 6 ChemAxon
Polar Surface Area 238.69 A2 ChemAxon
Rotatable Bond Count 8 ChemAxon
Refractivity 88.03 ChemAxon
Polarizability 36.57 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -3 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Mitochondria
  • Nucleus
Biofluid Locations Not Available
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Pyrimidine Metabolism SMP00046 map00240 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022565
KNApSAcK ID Not Available
Chemspider ID 58493 Link_out
KEGG Compound ID C00459 Link_out
BioCyc ID TTP Link_out
BiGG ID 35032 Link_out
Wikipedia Link TTP Link_out
NuGOwiki Link HMDB01342 Link_out
Metagene Link HMDB01342 Link_out
METLIN ID Not Available
PubChem Compound 64968 Link_out
PDB ID TTP Link_out
ChEBI ID 18077 Link_out
References
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)
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 Link_out
  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 Link_out
  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 Link_out
Enzymes
Name: Ectonucleoside triphosphate diphosphohydrolase 1
Reactions:
  • ATP + 2 H2O = AMP + 2 phosphate [RN:R00085]
Gene Name: ENTPD1
Uniprot ID: P49961 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Soluble calcium-activated nucleotidase 1
Reactions:
  • a nucleoside diphosphate + H2O = a nucleotide + phosphate [RN:R00329]
Gene Name: CANT1
Uniprot ID: Q8WVQ1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ectonucleoside triphosphate diphosphohydrolase 3
Reactions:
  • ATP + 2 H2O = AMP + 2 phosphate [RN:R00085]
Gene Name: ENTPD3
Uniprot ID: O75355 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Uridine-cytidine kinase 1
Reactions:
  • ATP + uridine = ADP + UMP [RN:R00964]
Gene Name: UCK1
Uniprot ID: Q9HA47 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Nucleoside diphosphate kinase, mitochondrial
Reactions:
  • ATP + nucleoside diphosphate = ADP + nucleoside triphosphate [RN:R00331]
Gene Name: NME4
Uniprot ID: O00746 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Nucleoside diphosphate kinase A
Reactions:
  • ATP + nucleoside diphosphate = ADP + nucleoside triphosphate [RN:R00331]
Gene Name: NME1
Uniprot ID: P15531 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Nucleoside diphosphate kinase 7
Reactions:
  • ATP + nucleoside diphosphate = ADP + nucleoside triphosphate [RN:R00331]
Gene Name: NME7
Uniprot ID: Q9Y5B8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Nucleoside diphosphate kinase B
Reactions:
  • ATP + nucleoside diphosphate = ADP + nucleoside triphosphate [RN:R00331]
Gene Name: NME2
Uniprot ID: P22392 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Nucleoside diphosphate kinase 3
Reactions:
  • ATP + nucleoside diphosphate = ADP + nucleoside triphosphate [RN:R00331]
Gene Name: NME3
Uniprot ID: Q13232 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Nucleoside diphosphate kinase 6
Reactions:
  • ATP + nucleoside diphosphate = ADP + nucleoside triphosphate [RN:R00331]
Gene Name: NME6
Uniprot ID: O75414 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Inosine triphosphate pyrophosphatase
Reactions:
  • a nucleoside triphosphate + H2O = a nucleotide + diphosphate [RN:R01532]
Gene Name: ITPA
Uniprot ID: Q9BY32 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA-directed RNA polymerase II subunit RPB2
Reactions:
  • nucleoside triphosphate + RNAn = diphosphate + RNAn+1 [RN:R00444]
Gene Name: POLR2B
Uniprot ID: P30876 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA-directed RNA polymerase II subunit RPB1
Reactions:
  • nucleoside triphosphate + RNAn = diphosphate + RNAn+1 [RN:R00444]
Gene Name: POLR2A
Uniprot ID: P24928 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA-directed RNA polymerase, mitochondrial
Reactions:
  • nucleoside triphosphate + RNAn = diphosphate + RNAn+1 [RN:R00444]
Gene Name: POLRMT
Uniprot ID: O00411 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA-directed RNA polymerase I subunit RPA2
Reactions:
  • nucleoside triphosphate + RNAn = diphosphate + RNAn+1 [RN:R00444]
Gene Name: POLR1B
Uniprot ID: Q9H9Y6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA-directed RNA polymerase III subunit RPC2
Reactions:
  • nucleoside triphosphate + RNAn = diphosphate + RNAn+1 [RN:R00444]
Gene Name: POLR3B
Uniprot ID: Q9NW08 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA polymerase beta
Reactions:
  • deoxynucleoside triphosphate + DNAn = diphosphate + DNAn+1 [RN:R00379]
Gene Name: POLB
Uniprot ID: P06746 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA polymerase alpha catalytic subunit
Reactions:
  • deoxynucleoside triphosphate + DNAn = diphosphate + DNAn+1 [RN:R00379]
Gene Name: POLA1
Uniprot ID: P09884 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA polymerase delta subunit 3
Reactions:
    Gene Name: POLD3
    Uniprot ID: Q15054 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: DNA polymerase lambda
    Reactions:
    • deoxynucleoside triphosphate + DNAn = diphosphate + DNAn+1 [RN:R00379]
    Gene Name: POLL
    Uniprot ID: Q9UGP5 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: DNA polymerase epsilon subunit 4
    Reactions:
    • deoxynucleoside triphosphate + DNAn = diphosphate + DNAn+1 [RN:R00379]
    Gene Name: POLE4
    Uniprot ID: Q9NR33 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: DNA polymerase eta
    Reactions:
    • deoxynucleoside triphosphate + DNAn = diphosphate + DNAn+1 [RN:R00379]
    Gene Name: POLH
    Uniprot ID: Q9Y253 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: DNA polymerase delta catalytic subunit
    Reactions:
    • deoxynucleoside triphosphate + DNAn = diphosphate + DNAn+1 [RN:R00379]
    Gene Name: POLD1
    Uniprot ID: P28340 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: DNA polymerase zeta catalytic subunit
    Reactions:
    • deoxynucleoside triphosphate + DNAn = diphosphate + DNAn+1 [RN:R00379]
    Gene Name: REV3L
    Uniprot ID: O60673 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: DNA polymerase epsilon catalytic subunit A
    Reactions:
    • deoxynucleoside triphosphate + DNAn = diphosphate + DNAn+1 [RN:R00379]
    Gene Name: POLE
    Uniprot ID: Q07864 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: DNA polymerase mu
    Reactions:
    • deoxynucleoside triphosphate + DNAn = diphosphate + DNAn+1 [RN:R00379]
    Gene Name: POLM
    Uniprot ID: Q9NP87 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: DNA polymerase kappa
    Reactions:
    • deoxynucleoside triphosphate + DNAn = diphosphate + DNAn+1 [RN:R00379]
    Gene Name: POLK
    Uniprot ID: Q9UBT6 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: DNA polymerase epsilon subunit 3
    Reactions:
    • deoxynucleoside triphosphate + DNAn = diphosphate + DNAn+1 [RN:R00379]
    Gene Name: POLE3
    Uniprot ID: Q9NRF9 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: DNA polymerase subunit gamma-1
    Reactions:
    • deoxynucleoside triphosphate + DNAn = diphosphate + DNAn+1 [RN:R00379]
    Gene Name: POLG
    Uniprot ID: P54098 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: DNA polymerase iota
    Reactions:
    • deoxynucleoside triphosphate + DNAn = diphosphate + DNAn+1 [RN:R00379]
    Gene Name: POLI
    Uniprot ID: Q9UNA4 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: DNA polymerase epsilon subunit 2
    Reactions:
    • deoxynucleoside triphosphate + DNAn = diphosphate + DNAn+1 [RN:R00379]
    Gene Name: POLE2
    Uniprot ID: P56282 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Uridine-cytidine kinase 2
    Reactions:
    • ATP + uridine = ADP + UMP [RN:R00964]
    Gene Name: UCK2
    Uniprot ID: Q9BZX2 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Uridine-cytidine kinase-like 1
    Reactions:
    • ATP + uridine = ADP + UMP [RN:R00964]
    Gene Name: UCKL1
    Uniprot ID: Q9NWZ5 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Ectonucleoside triphosphate diphosphohydrolase 8
    Reactions:
    • ATP + 2 H2O = AMP + 2 phosphate [RN:R00085]
    Gene Name: ENTPD8
    Uniprot ID: Q5MY95 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Putative nucleoside diphosphate kinase
    Reactions:
    • ATP + nucleoside diphosphate = ADP + nucleoside triphosphate [RN:R00331]
    Gene Name: NME2P1
    Uniprot ID: O60361 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: DNA-directed RNA polymerase III subunit RPC1
    Reactions:
    • nucleoside triphosphate + RNAn = diphosphate + RNAn+1 [RN:R00444]
    Gene Name: POLR3A
    Uniprot ID: O14802 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: DNA-directed RNA polymerase I subunit RPA1
    Reactions:
    • nucleoside triphosphate + RNAn = diphosphate + RNAn+1 [RN:R00444]
    Gene Name: POLR1A
    Uniprot ID: O95602 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Myb-binding protein 1A
    Reactions:
      Gene Name: MYBBP1A
      Uniprot ID: Q9BQG0 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: DNA polymerase theta
      Reactions:
        Gene Name: POLQ
        Uniprot ID: O75417 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA