| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:10:43 -0700 |
| HMDB ID |
HMDB01532 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
dATP |
| Description |
Animals obtain their energy by oxidation of foods, plants do so by trapping the sunlight using chlorophyll. However, before the energy can be used, it is first transformed into a form which the organism can handle easily. This special carrier of energy is the molecule adenosine triphosphate, or ATP. The ATP molecule is composed of three components. At the centre is a sugar molecule, [[ribose] (the same sugar that forms the basis of DNA). Attached to one side of this is a base (a group consisting of linked rings of carbon and nitrogen atoms); in this case the base is adenine. The other side of the sugar is attached to a string of phosphate groups. These phosphates are the key to the activity of ATP. ATP consists of a base, in this case adenine (red), a ribose (magenta) and a phosphate chain (blue). ATP works by losing the endmost phosphate group when instructed to do so by an enzyme. This reaction releases a lot of energy, which the organism can then use to build proteins, contact muscles, etc. |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- 2'-Deoxy-5'-ATP
- 2'-Deoxy-ATP
- 2'-Deoxyadenosine 5'-triphosphate
- 2'-Deoxyadenosine triphosphate
- Deoxy-ATP
- Deoxyadenosine 5'-triphosphate
- Deoxyadenosine triphosphate
- 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 |
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| Biofunction |
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| Application |
Not Available |
| Cellular locations |
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| 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 |
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| Predicted Properties |
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| Spectra |
|---|
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| Biological Properties |
|---|
| Cellular Locations |
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| Biofluid Locations |
Not Available
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| Tissue Location |
- Lymphocyte
- Erythrocyte
- T-Lymphocyte
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| Pathways |
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| Normal Concentrations |
|---|
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Not Available |
| Abnormal Concentrations |
|---|
|
Not Available |
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank 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  |
| KEGG Compound ID |
C00131 |
| BioCyc ID |
DATP |
| BiGG ID |
33969 |
| Wikipedia Link |
Deoxyadenosine triphosphate |
| NuGOwiki Link |
HMDB01532 |
| Metagene Link |
HMDB01532 |
| METLIN ID |
6303 |
| PubChem Compound |
15993 |
| PDB ID |
DTP |
| ChEBI ID |
16284 |
| 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 |
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
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| Enzymes |
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| Name: |
Glucokinase
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| Reactions: |
- ATP + D-glucose = ADP + D-glucose 6-phosphate [RN:R00299]
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| Gene Name: |
GCK |
| Uniprot ID: |
P35557 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Hexokinase-3
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| Reactions: |
- ATP + D-hexose = ADP + D-hexose 6-phosphate [RN:R02848]
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| Gene Name: |
HK3 |
| Uniprot ID: |
P52790 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Hexokinase-2
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| Reactions: |
- ATP + D-hexose = ADP + D-hexose 6-phosphate [RN:R02848]
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| Gene Name: |
HK2 |
| Uniprot ID: |
P52789 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
DNA polymerase beta
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| Reactions: |
- deoxynucleoside triphosphate + DNAn = diphosphate + DNAn+1 [RN:R00379]
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| Gene Name: |
POLB |
| Uniprot ID: |
P06746 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
DNA polymerase lambda
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| Reactions: |
- deoxynucleoside triphosphate + DNAn = diphosphate + DNAn+1 [RN:R00379]
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| Gene Name: |
POLL |
| Uniprot ID: |
Q9UGP5 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
DNA polymerase eta
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| Reactions: |
- deoxynucleoside triphosphate + DNAn = diphosphate + DNAn+1 [RN:R00379]
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| Gene Name: |
POLH |
| Uniprot ID: |
Q9Y253 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
DNA polymerase mu
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| Reactions: |
- deoxynucleoside triphosphate + DNAn = diphosphate + DNAn+1 [RN:R00379]
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| Gene Name: |
POLM |
| Uniprot ID: |
Q9NP87 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
DNA polymerase kappa
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| Reactions: |
- deoxynucleoside triphosphate + DNAn = diphosphate + DNAn+1 [RN:R00379]
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| Gene Name: |
POLK |
| Uniprot ID: |
Q9UBT6 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
DNA polymerase iota
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| Reactions: |
- deoxynucleoside triphosphate + DNAn = diphosphate + DNAn+1 [RN:R00379]
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| Gene Name: |
POLI |
| Uniprot ID: |
Q9UNA4 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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