Deoxyadenosine triphosphate

Deoxyadenosine triphosphate (dATP) is a nucleotide used in cells for DNA synthesis (or replication), as a substrate of DNA polymerase.^[1]

Deoxyadenosine triphosphate

Names
IUPAC name [[(2R,3S,5R)-5-(6-aminopurin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
Other names dATP, 2'-deoxyadenosine triphosphate
Identifiers
CAS Number	1927-31-7 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16284 Y
ChEMBL	ChEMBL335538 Y
ChemSpider	15194 Y=  Y=  Y=  N
ECHA InfoCard	100.016.058
IUPHAR/BPS	1760
PubChem CID	15993
CompTox Dashboard (EPA)	DTXSID10895848
InChI 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 Y=  Y Key: SUYVUBYJARFZHO-RRKCRQDMSA-N Y=  Y InChI=1/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 Key: SUYVUBYJARFZHO-RRKCRQDMBD
SMILES O=P(O)(O)OP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n2cnc1c(ncnc12)N)C[C@@H]3O
Properties
Chemical formula	C10H16N5O12P3
Molar mass	491.181623
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Deoxyadenosine triphosphate is produced from DNA by the action of nuclease P1, adenylate kinase, and pyruvate kinase.^[2]

Health effects

High levels of dATP can be toxic and result in impaired immune function, since dATP acts as a noncompetitive inhibitor for the DNA synthesis enzyme ribonucleotide reductase. Patients with adenosine deaminase deficiency (ADA) tend to have elevated intracellular dATP concentrations because adenosine deaminase normally curbs adenosine levels by converting it into inosine.^[3][4] Deficiency of this deaminase also causes immunodeficiency.^[5]

In cardiac myosin, dATP is an alternative to ATP as an energy substrate for facilitating cross-bridge formation.^[6][7]

See also

• Adenosine triphosphate (ATP)
• Adenosine deaminase deficiency (ADA)
• Dilated cardiomyopathy (DCM)