Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 22:36:32 UTC
HMDB IDHMDB01532
Secondary Accession NumbersNone
Metabolite Identification
Common NameDeoxyadenosine triphosphate
DescriptionDeoxyadenosine triphosphate (dATP) is a purine nucleoside triphosphate used in cells for DNA synthesis. A nucleoside triphosphate is a molecule type that contains a nucleoside with three phosphates bound to it. dATP contains the sugar deoxyribose, a precursor in DNA synthesis whereby the two existing phosphate groups are cleaved with the remaining deoxyadenosine monophosphate being incorporated into DNA during replication. Due to its enzymatic incorporation into DNA, photoreactive dATP analogs such as N6-[4-azidobenzoyl–(2-aminoethyl)]-2′-deoxyadenosine-5′-triphosphate (AB-dATP) and N6-[4-[3-(trifluoromethyl)-diazirin-3-yl]benzoyl-(2-aminoethyl)]-2′-deoxyadenosine-5′-triphosphate (DB-dATP) have been used for DNA photoaffinity labeling.
Structure
Thumb
Synonyms
  1. 2'-Deoxy-5'-ATP
  2. 2'-Deoxy-ATP
  3. 2'-Deoxyadenosine 5'-triphosphate
  4. 2'-Deoxyadenosine triphosphate
  5. dATP
  6. Deoxy-ATP
  7. Deoxyadenosine 5'-triphosphate
  8. Deoxyadenosine triphosphate
  9. Deoxyadenosine-triphosphate
Chemical FormulaC10H16N5O12P3
Average Molecular Weight491.1816
Monoisotopic Molecular Weight491.000830537
IUPAC Name({[({[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
Traditional IUPAC Name({[(2R,3S,5R)-5-(6-aminopurin-9-yl)-3-hydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxyphosphonic acid
CAS Registry Number1927-31-7
SMILES
NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O1
InChI Identifier
InChI=1S/C10H16N5O12P3/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(16)6(25-7)2-24-29(20,21)27-30(22,23)26-28(17,18)19/h3-7,16H,1-2H2,(H,20,21)(H,22,23)(H2,11,12,13)(H2,17,18,19)/t5-,6+,7+/m0/s1
InChI KeySUYVUBYJARFZHO-RRKCRQDMSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassNucleosides, Nucleotides, and Analogues
ClassPurine Nucleotides
Sub ClassPurine Deoxyribonucleotides
Other Descriptors
  • 2'-deoxyadenosine 5'-phosphate(ChEBI)
  • Aromatic Heteropolycyclic Compounds
  • Deoxyribonucleotides(KEGG)
  • Organic Compounds
  • purine 2'-deoxyribonucleoside 5'-triphosphate(ChEBI)
Substituents
  • Aminopyrimidine
  • Imidazole
  • Imidazopyrimidine
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxolane
  • Phosphoric Acid Ester
  • Purine
  • Pyrimidine
  • Secondary Alcohol
Direct ParentPurine 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 solubility3.83 g/LALOGPS
logP-0.66ALOGPS
logP-5.3ChemAxon
logS-2.1ALOGPS
pKa (strongest acidic)0.9ChemAxon
pKa (strongest basic)5.01ChemAxon
physiological charge-3ChemAxon
hydrogen acceptor count13ChemAxon
hydrogen donor count6ChemAxon
polar surface area258.9ChemAxon
rotatable bond count8ChemAxon
refractivity94.3ChemAxon
polarizability38.05ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Mitochondria
  • Nucleus
Biofluid LocationsNot Available
Tissue Location
  • Erythrocyte
  • Lymphocyte
  • T-Lymphocyte
Pathways
NameSMPDB LinkKEGG Link
Purine MetabolismSMP00050map00230
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 IDFDB022674
KNApSAcK IDNot Available
Chemspider ID15194
KEGG Compound IDC00131
BioCyc IDDATP
BiGG ID33969
Wikipedia LinkDeoxyadenosine triphosphate
NuGOwiki LinkHMDB01532
Metagene LinkHMDB01532
METLIN ID6303
PubChem Compound15993
PDB IDDTP
ChEBI ID16284
References
Synthesis ReferenceMunch-Petersen, Agnete. Formation in vitro of deoxyadenosine triphosphate from deoxyadenosine in Ehrlich ascites cells. Biochemical and Biophysical Research Communications (1960), 3 392-6.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Nespoli L, Porta F, Locatelli F, Aversa F, Carotti A, Lanfranchi A, Gibardi A, Marchesi ME, Abate L, Martelli MF, et al.: Successful lectin-separated bone marrow transplantation in adenosine deaminase deficiency-related severe immunodeficiency. Haematologica. 1990 Nov-Dec;75(6):546-50. Pubmed: 2098297
  2. Hoffbrand AV, Ganeshaguru K, Hooton JW, Tattersall MH: Effect of iron deficiency and desferrioxamine on DNA synthesis in human cells. Br J Haematol. 1976 Aug;33(4):517-26. Pubmed: 1009024
  3. Waddell D, Ullman B: Characterization of a cultured human T-cell line with genetically altered ribonucleotide reductase activity. Model for immunodeficiency. J Biol Chem. 1983 Apr 10;258(7):4226-31. Pubmed: 6339493
  4. Bory C, Boulieu R, Souillet G, Chantin C, Guibaud P, Hershfield MS: Effect of polyethylene glycol-modified adenosine deaminase (PEG-ADA) therapy in two ADA-deficient children: measurement of erythrocyte deoxyadenosine triphosphate as a useful tool. Adv Exp Med Biol. 1991;309A:173-6. Pubmed: 1789201
  5. Dang-Vu AP, Olsen EA, Vollmer RT, Greenberg ML, Hershfield MS: Treatment of cutaneous T cell lymphoma with 2'-deoxycoformycin (pentostatin). J Am Acad Dermatol. 1988 Oct;19(4):692-8. Pubmed: 3263401
  6. Donofrio J, Coleman MS, Hutton JJ, Daoud A, Lampkin B, Dyminski J: Overproduction of adenine deoxynucleosides and deoxynucletides in adenosine deaminase deficiency with severe combined immunodeficiency disease. J Clin Invest. 1978 Oct;62(4):884-7. Pubmed: 308954
  7. Cowan MJ, Shannon KM, Wara DW, Ammann AJ: Rejection of bone marrow transplant and resistance of alloantigen reactive cells to in vivo deoxyadenosine in adenosine deaminase deficiency. Clin Immunol Immunopathol. 1988 Nov;49(2):242-50. Pubmed: 2971490
  8. Grever MR, Siaw MF, Jacob WF, Neidhart JA, Miser JS, Coleman MS, Hutton JJ, Balcerzak SP: The biochemical and clinical consequences of 2'-deoxycoformycin in refractory lymphoproliferative malignancy. Blood. 1981 Mar;57(3):406-17. Pubmed: 6970050
  9. Simmonds HA, Fairbanks LD, Morris GS, Webster DR, Harley EH: Altered erythrocyte nucleotide patterns are characteristic of inherited disorders of purine or pyrimidine metabolism. Clin Chim Acta. 1988 Feb 15;171(2-3):197-210. Pubmed: 3370820
  10. Hirschhorn R, Roegner V, Rubinstein A, Papageorgiou P: Plasma deoxyadenosine, adenosine, and erythrocyte deoxyATP are elevated at birth in an adenosine deaminase-deficient child. J Clin Invest. 1980 Mar;65(3):768-71. Pubmed: 6965496
  11. Schmalstieg FC, Mills GC, Tsuda H, Goldman AS: Severe combined immunodeficiency in a child with a healthy adenosine deaminase deficient mother. Pediatr Res. 1983 Dec;17(12):935-40. Pubmed: 6606796
  12. Simmonds HA, Webster DR, Perrett D, Reiter S, Levinsky RJ: Formation and degradation of deoxyadenosine nucleotides in inherited adenosine deaminase deficiency. Biosci Rep. 1982 May;2(5):303-14. Pubmed: 6980023
  13. Simmonds HA, Sahota A, Potter CF, Perrett D, Hugh-Jones K, Watson JG: Purine metabolism in adenosine deaminase deficiency. Ciba Found Symp. 1978;(68):255-62. Pubmed: 387357
  14. Hirschhorn R, Roegner-Maniscalco V, Kuritsky L, Rosen FS: Bone marrow transplantation only partially restores purine metabolites to normal in adenosine deaminase-deficient patients. J Clin Invest. 1981 Dec;68(6):1387-93. Pubmed: 7033281
  15. Goday A, Simmonds HA, Webster DR, Levinsky RJ, Watson AR, Hoffbrand AV: Importance of platelet-free preparations for evaluating lymphocyte nucleotide levels in inherited or acquired immunodeficiency syndromes. Clin Sci (Lond). 1983 Dec;65(6):635-43. Pubmed: 6414755
  16. Chen SH, Ochs HD, Scott CR, Giblett ER, Tingle AJ: Adenosine deaminase deficiency: disappearance of adenine deoxynucleotides from a patient's erythrocytes after successful marrow transplantation. J Clin Invest. 1978 Dec;62(6):1386-9. Pubmed: 372236
  17. Gruber HE, Cohen AH, Firestein GS, Redelman D, Bluestein HG: Deoxy-ATP accumulation in adenosine deaminase-inhibited human B and T lymphocytes. Adv Exp Med Biol. 1986;195 Pt A:503-7. Pubmed: 3487921
  18. Bory C, Boulieu R, Souillet G, Chantin C, Rolland MO, Mathieu M, Hershfield M: Comparison of red cell transfusion and polyethylene glycol-modified adenosine deaminase therapy in an adenosine deaminase-deficient child: measurement of erythrocyte deoxyadenosine triphosphate as a useful tool. Pediatr Res. 1990 Aug;28(2):127-30. Pubmed: 2395602
  19. Peters GJ, De Abreu RA, Oosterhof A, Veerkamp JH: Concentration of nucleotides and deoxynucleotides in peripheral and phytohemagglutinin-stimulated mammalian lymphocytes. Effects of adenosine and deoxyadenosine. Biochim Biophys Acta. 1983 Aug 23;759(1-2):7-15. Pubmed: 6603870
  20. Morgan G, Levinsky RJ, Hugh-Jones K, Fairbanks LD, Morris GS, Simmonds HA: Heterogeneity of biochemical, clinical and immunological parameters in severe combined immunodeficiency due to adenosine deaminase deficiency. Clin Exp Immunol. 1987 Dec;70(3):491-9. Pubmed: 3436096
  21. Zofall M, Bartholomew B: Two novel dATP analogs for DNA photoaffinity labeling. Nucleic Acids Res. 2000 Nov 1;28(21):4382-90. Pubmed: 11058139

Enzymes

Gene Name:
UCK1
Uniprot ID:
Q9HA47
Reactions
Deoxyadenosine triphosphate + Cytidine unknown dADP + Cytidine monophosphatedetails
Deoxyadenosine triphosphate + Uridine unknown dADP + Uridine 5'-monophosphatedetails
Gene Name:
NME4
Uniprot ID:
O00746
Reactions
Adenosine triphosphate + dADP unknown ADP + Deoxyadenosine triphosphatedetails
Gene Name:
NME1
Uniprot ID:
P15531
Reactions
Adenosine triphosphate + dADP unknown ADP + Deoxyadenosine triphosphatedetails
Gene Name:
NME7
Uniprot ID:
Q9Y5B8
Reactions
Adenosine triphosphate + dADP unknown ADP + Deoxyadenosine triphosphatedetails
Gene Name:
NME2
Uniprot ID:
P22392
Reactions
Adenosine triphosphate + dADP unknown ADP + Deoxyadenosine triphosphatedetails
Gene Name:
NME3
Uniprot ID:
Q13232
Reactions
Adenosine triphosphate + dADP unknown ADP + Deoxyadenosine triphosphatedetails
Gene Name:
NME6
Uniprot ID:
O75414
Reactions
Adenosine triphosphate + dADP unknown ADP + Deoxyadenosine triphosphatedetails
Gene Name:
GCK
Uniprot ID:
P35557
Gene Name:
HK3
Uniprot ID:
P52790
Gene Name:
HK2
Uniprot ID:
P52789
Gene Name:
PKM
Uniprot ID:
P14618
Reactions
Deoxyadenosine triphosphate + Pyruvic acid unknown dADP + Phosphoenolpyruvic aciddetails
Gene Name:
PKLR
Uniprot ID:
P30613
Reactions
Deoxyadenosine triphosphate + Pyruvic acid unknown dADP + Phosphoenolpyruvic aciddetails
Gene Name:
POLB
Uniprot ID:
P06746
Gene Name:
POLA1
Uniprot ID:
P09884
Reactions
Deoxyadenosine triphosphate + DNA unknown Pyrophosphate + DNAdetails
Gene Name:
POLD3
Uniprot ID:
Q15054
Gene Name:
POLL
Uniprot ID:
Q9UGP5
Gene Name:
POLE4
Uniprot ID:
Q9NR33
Reactions
Deoxyadenosine triphosphate + DNA unknown Pyrophosphate + DNAdetails
Gene Name:
POLH
Uniprot ID:
Q9Y253
Gene Name:
POLD1
Uniprot ID:
P28340
Reactions
Deoxyadenosine triphosphate + DNA unknown Pyrophosphate + DNAdetails
Gene Name:
REV3L
Uniprot ID:
O60673
Gene Name:
POLE
Uniprot ID:
Q07864
Reactions
Deoxyadenosine triphosphate + DNA unknown Pyrophosphate + DNAdetails
Gene Name:
POLM
Uniprot ID:
Q9NP87
Gene Name:
POLK
Uniprot ID:
Q9UBT6
Gene Name:
POLE3
Uniprot ID:
Q9NRF9
Reactions
Deoxyadenosine triphosphate + DNA unknown Pyrophosphate + DNAdetails
Gene Name:
POLG
Uniprot ID:
P54098
Gene Name:
POLI
Uniprot ID:
Q9UNA4
Gene Name:
POLE2
Uniprot ID:
P56282
Reactions
Deoxyadenosine triphosphate + DNA unknown Pyrophosphate + DNAdetails
Gene Name:
APAF1
Uniprot ID:
O14727
Gene Name:
UCK2
Uniprot ID:
Q9BZX2
Reactions
Deoxyadenosine triphosphate + Cytidine unknown dADP + Cytidine monophosphatedetails
Deoxyadenosine triphosphate + Uridine unknown dADP + Uridine 5'-monophosphatedetails
Gene Name:
UCKL1
Uniprot ID:
Q9NWZ5
Reactions
Deoxyadenosine triphosphate + Cytidine unknown dADP + Cytidine monophosphatedetails
Deoxyadenosine triphosphate + Uridine unknown dADP + Uridine 5'-monophosphatedetails
Gene Name:
MYBBP1A
Uniprot ID:
Q9BQG0
Gene Name:
POLQ
Uniprot ID:
O75417
Gene Name:
POLD2
Uniprot ID:
P49005
Reactions
Deoxyadenosine triphosphate + DNA unknown Pyrophosphate + DNAdetails
Gene Name:
NME5
Uniprot ID:
P56597
Reactions
Adenosine triphosphate + dADP unknown ADP + Deoxyadenosine triphosphatedetails
Gene Name:
PRIM1
Uniprot ID:
P49642
Reactions
Deoxyadenosine triphosphate + DNA unknown Pyrophosphate + DNAdetails
Gene Name:
PRIM2
Uniprot ID:
P49643
Reactions
Deoxyadenosine triphosphate + DNA unknown Pyrophosphate + DNAdetails