Human Metabolome Database Version 3.5

Showing metabocard for Deoxyadenosine triphosphate (HMDB01532)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 16:36:32 -0600
HMDB ID HMDB01532
Secondary Accession Numbers None
Metabolite Identification
Common Name Deoxyadenosine triphosphate
Description Deoxyadenosine 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C10H16N5O12P3
Average Molecular Weight 491.1816
Monoisotopic Molecular Weight 491.000830537
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 Number 1927-31-7
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 Key SUYVUBYJARFZHO-RRKCRQDMSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Nucleosides, Nucleotides, and Analogues
Class Purine Nucleotides
Sub Class Purine 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 Parent Purine 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 3.83 g/L ALOGPS
LogP -0.66 ALOGPS
LogP -5.3 ChemAxon
LogS -2.11 ALOGPS
pKa (strongest acidic) 0.9 ChemAxon
pKa (strongest basic) 5.01 ChemAxon
Hydrogen Acceptor Count 13 ChemAxon
Hydrogen Donor Count 6 ChemAxon
Polar Surface Area 258.9 A2 ChemAxon
Rotatable Bond Count 8 ChemAxon
Refractivity 94.3 ChemAxon
Polarizability 38.05 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
  • Lymphocyte
  • Erythrocyte
  • T-Lymphocyte
Pathways
Name SMPDB Link KEGG Link
Purine Metabolism SMP00050 map00230 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
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022674
KNApSAcK ID Not Available
Chemspider ID 15194 Link_out
KEGG Compound ID C00131 Link_out
BioCyc ID DATP Link_out
BiGG ID 33969 Link_out
Wikipedia Link Deoxyadenosine triphosphate Link_out
NuGOwiki Link HMDB01532 Link_out
Metagene Link HMDB01532 Link_out
METLIN ID 6303 Link_out
PubChem Compound 15993 Link_out
PDB ID DTP Link_out
ChEBI ID 16284 Link_out
References
Synthesis Reference Munch-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) Download (PDF)
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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out

Enzymes
Name: Uridine-cytidine kinase 1
Reactions:
Deoxyadenosine triphosphate + Cytidine unknown dADP + Cytidine monophosphate details
Deoxyadenosine triphosphate + Uridine unknown dADP + Uridine 5'-monophosphate details
Gene Name: UCK1
Uniprot ID: Q9HA47 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Nucleoside diphosphate kinase, mitochondrial
Reactions:
Adenosine triphosphate + dADP unknown ADP + Deoxyadenosine triphosphate details
Gene Name: NME4
Uniprot ID: O00746 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Nucleoside diphosphate kinase A
Reactions:
Adenosine triphosphate + dADP unknown ADP + Deoxyadenosine triphosphate details
Gene Name: NME1
Uniprot ID: P15531 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Nucleoside diphosphate kinase 7
Reactions:
Adenosine triphosphate + dADP unknown ADP + Deoxyadenosine triphosphate details
Gene Name: NME7
Uniprot ID: Q9Y5B8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Nucleoside diphosphate kinase B
Reactions:
Adenosine triphosphate + dADP unknown ADP + Deoxyadenosine triphosphate details
Gene Name: NME2
Uniprot ID: P22392 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Nucleoside diphosphate kinase 3
Reactions:
Adenosine triphosphate + dADP unknown ADP + Deoxyadenosine triphosphate details
Gene Name: NME3
Uniprot ID: Q13232 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Nucleoside diphosphate kinase 6
Reactions:
Adenosine triphosphate + dADP unknown ADP + Deoxyadenosine triphosphate details
Gene Name: NME6
Uniprot ID: O75414 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glucokinase
Reactions: Not Available
Gene Name: GCK
Uniprot ID: P35557 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hexokinase-3
Reactions: Not Available
Gene Name: HK3
Uniprot ID: P52790 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hexokinase-2
Reactions: Not Available
Gene Name: HK2
Uniprot ID: P52789 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Pyruvate kinase isozymes M1/M2
Reactions:
Deoxyadenosine triphosphate + Pyruvic acid unknown dADP + Phosphoenolpyruvic acid details
Gene Name: PKM
Uniprot ID: P14618 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Pyruvate kinase isozymes R/L
Reactions:
Deoxyadenosine triphosphate + Pyruvic acid unknown dADP + Phosphoenolpyruvic acid details
Gene Name: PKLR
Uniprot ID: P30613 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA polymerase beta
Reactions: Not Available
Gene Name: POLB
Uniprot ID: P06746 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA polymerase alpha catalytic subunit
Reactions:
Deoxyadenosine triphosphate + DNA unknown Pyrophosphate + DNA details
Gene Name: POLA1
Uniprot ID: P09884 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA polymerase delta subunit 3
Reactions: Not Available
Gene Name: POLD3
Uniprot ID: Q15054 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA polymerase lambda
Reactions: Not Available
Gene Name: POLL
Uniprot ID: Q9UGP5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA polymerase epsilon subunit 4
Reactions:
Deoxyadenosine triphosphate + DNA unknown Pyrophosphate + DNA details
Gene Name: POLE4
Uniprot ID: Q9NR33 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA polymerase eta
Reactions: Not Available
Gene Name: POLH
Uniprot ID: Q9Y253 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA polymerase delta catalytic subunit
Reactions:
Deoxyadenosine triphosphate + DNA unknown Pyrophosphate + DNA details
Gene Name: POLD1
Uniprot ID: P28340 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA polymerase zeta catalytic subunit
Reactions: Not Available
Gene Name: REV3L
Uniprot ID: O60673 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA polymerase epsilon catalytic subunit A
Reactions:
Deoxyadenosine triphosphate + DNA unknown Pyrophosphate + DNA details
Gene Name: POLE
Uniprot ID: Q07864 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA-directed DNA/RNA polymerase mu
Reactions: Not Available
Gene Name: POLM
Uniprot ID: Q9NP87 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA polymerase kappa
Reactions: Not Available
Gene Name: POLK
Uniprot ID: Q9UBT6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA polymerase epsilon subunit 3
Reactions:
Deoxyadenosine triphosphate + DNA unknown Pyrophosphate + DNA details
Gene Name: POLE3
Uniprot ID: Q9NRF9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA polymerase subunit gamma-1
Reactions: Not Available
Gene Name: POLG
Uniprot ID: P54098 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA polymerase iota
Reactions: Not Available
Gene Name: POLI
Uniprot ID: Q9UNA4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA polymerase epsilon subunit 2
Reactions:
Deoxyadenosine triphosphate + DNA unknown Pyrophosphate + DNA details
Gene Name: POLE2
Uniprot ID: P56282 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Apoptotic protease-activating factor 1
Reactions: Not Available
Gene Name: APAF1
Uniprot ID: O14727 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Uridine-cytidine kinase 2
Reactions:
Deoxyadenosine triphosphate + Cytidine unknown dADP + Cytidine monophosphate details
Deoxyadenosine triphosphate + Uridine unknown dADP + Uridine 5'-monophosphate details
Gene Name: UCK2
Uniprot ID: Q9BZX2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Uridine-cytidine kinase-like 1
Reactions:
Deoxyadenosine triphosphate + Cytidine unknown dADP + Cytidine monophosphate details
Deoxyadenosine triphosphate + Uridine unknown dADP + Uridine 5'-monophosphate details
Gene Name: UCKL1
Uniprot ID: Q9NWZ5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Myb-binding protein 1A
Reactions: Not Available
Gene Name: MYBBP1A
Uniprot ID: Q9BQG0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA polymerase theta
Reactions: Not Available
Gene Name: POLQ
Uniprot ID: O75417 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA polymerase delta subunit 2
Reactions:
Deoxyadenosine triphosphate + DNA unknown Pyrophosphate + DNA details
Gene Name: POLD2
Uniprot ID: P49005 Link_out
Protein Sequence: FASTA
Name: Nucleoside diphosphate kinase homolog 5
Reactions:
Adenosine triphosphate + dADP unknown ADP + Deoxyadenosine triphosphate details
Gene Name: NME5
Uniprot ID: P56597 Link_out
Name: DNA primase small subunit
Reactions:
Deoxyadenosine triphosphate + DNA unknown Pyrophosphate + DNA details
Gene Name: PRIM1
Uniprot ID: P49642 Link_out
Name: DNA primase large subunit
Reactions:
Deoxyadenosine triphosphate + DNA unknown Pyrophosphate + DNA details
Gene Name: PRIM2
Uniprot ID: P49643 Link_out