CAS 1927-31-7 Datp (HCID 15993)

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Basic information

CAS: 1927-31-7
Standard SMILES: Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O1
InChIKey: SUYVUBYJARFZHO-RRKCRQDMSA-N
Molecular formula: C10H16N5O12P3
Average molar mass: 491.18 g/mol
Monoisotopic mass: 491.00083084

Overview

DATP is a purine 2'-deoxyribonucleoside 5'-triphosphate having adenine as the nucleobase. It has a role as a mouse metabolite and an Escherichia coli metabolite. It is a 2'-deoxyadenosine 5'-phosphate and a purine 2'-deoxyribonucleoside 5'-triphosphate. It is a conjugate acid of a dATP(3-).

Names & identifiers

Preferred name: Datp
IUPAC: [[(2R,3S,5R)-5-(6-aminopurin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
English name: 2'-Deoxyadenosine 5'-triphosphate
Molecular formula: C10H16N5O12P3
Molecular weight: 491.18

Names & synonyms

dATP1927-31-72'-deoxyadenosine 5'-triphosphateDeoxyadenosine triphosphatedeoxy-ATP2'-deoxyadenosine triphosphateDeoxyadenosine 5'-triphosphate2'-Datp2'-Deoxy-ATPK8KCC8SH6N[[(2R,3S,5R)-5-(6-aminopurin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphateCHEBI:16284

Show more names

2'-Deoxyadenosine-5'-Triphosphate, Sodium Salt2’-datp5'-DATPDATP, LI2'-dATP·2NadATP SodiumDATP LI-SALTdATP.Free acid

deoxyadenosine-triphosphateDTXSID10895848({[({[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic aciddATP cpd(((((((2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxyoxolan-2-yl)methoxy)(hydroxy)phosphoryl)oxy)(hydroxy)phosphoryl)oxy)phosphonic acid(((2R,3S,5R)-5-(6-aminopurin-9-yl)-3-hydroxyoxolan-2-yl)methoxy-hydroxyphosphoryl) phosphono hydrogen phosphate((2R,3S,5R)-5-(6-aminopurin-9-yl)-3-hydroxyoxolan-2-yl)methyl (hydroxy-phosphonooxyphosphoryl) hydrogen phosphate[(2R,3S,5R)-5-(6-aminopurin-9-yl)-3-hydroxyoxolan-2-yl]methyl (hydroxy-phosphonooxyphosphoryl) hydrogen phosphate

Properties

Computed structural properties

XLogP: -4.4
Topological polar surface area: 259 Å²
Hydrogen bond donors: 6
Hydrogen bond acceptors: 16
Rotatable bonds: 8
Heavy atoms: 30
Formal charge: 0
Complexity: 769

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

Physical DescriptionSolid

Collision Cross Section · 3 items

183.78 Å² [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

185.9 Å² [M+Na-2H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

202 Å² [M+Na]+

Physicochemical properties

Boiling point: 913.3 · 913.3±75.0 °C(Predicted)
Density: 2.51 · 2.51±0.1 g/cm3(Predicted)
storage temp.: -20 °C · Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
pka: 0.97 · 0.97±0.50(Predicted)
form: Powder
color: colorless
PH: 7 · 7
Water Solubility: 50 mg/mL · ≥ 50mg/mL in Water

Safety & regulation

GHS classification

GHS ClassificationNot Classified

Hazard information

Hazard Classes and CategoriesNot Classified

Toxicology

Health EffectsChronically high levels of deoxyadenosine triphosphate are associated with Adenosine Deaminase Deficiency.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

wgk: 3
rtecs: AU7358800
hs_code: 29349990
Signal word: Warning
Symbol(GHS): GHS07
Storage Class: 10 - Combustible liquids
Hazard statements: H302-H315-H319-H332-H335
Precautionary statements: P280-P305+P351+P338-P310

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

Metabolism of organophosphates occurs principally by oxidation, by hydrolysis via esterases and by reaction with glutathione. Demethylation and glucuronidation may also occur. Oxidation of organophosphorus pesticides may result in moderately toxic products. In general, phosphorothioates are not directly toxic but require oxidative metabolism to the proximal toxin. The glutathione transferase reactions produce products that are, in most cases, of low toxicity. Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of organophosphate exposure.

Tissue LocationsErythrocyte

Cellular LocationsMitochondria

Metabolite PathwaysAdenine phosphoribosyltransferase deficiency (APRT)