2'-Desoxyadenosin-5'-(tetrahydrogentriphosphat)

Datp

HCID 15993CAS 1927-31-7

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Grundinformationen

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
Summenformel: C10H16N5O12P3
Durchschnittliche Molmasse: 491,18 g/mol
Monoisotopische Masse: 491,00083084

Überblick

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-).

Namen und Bezeichner

Bevorzugter Name: Datp
IUPAC: [[(2R,3S,5R)-5-(6-aminopurin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
Lokaler Name: 2'-Desoxyadenosin-5'-(tetrahydrogentriphosphat)
Englischer Name: 2'-Deoxyadenosine 5'-triphosphate
Summenformel: C10H16N5O12P3
Molmasse: 491.18

Namen und Synonyme

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

Weitere Namen anzeigen

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

Datenbank-Bezeichner

CAS: 1927-31-7、67460-17-7
PubChem CID: 15993
DTXSID: DTXSID10895848
ChEMBL: CHEMBL335538
ChEBI: CHEBI:16284
UNII: K8KCC8SH6N
EC Number: 217-662-3
Nikkaji: J90.479A

Eigenschaften

Berechnete Struktureigenschaften

XLogP: -4,4
Polarare Oberfläche (TPSA): 259 Å²
H-Brücken-Donoren: 6
H-Brücken-Akzeptoren: 16
Frei drehbare Bindungen: 8
Schwere Atome: 30
Formalladung: 0
Komplexität: 769

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15

Physical DescriptionSolid

Collision Cross Section · 3 Einträge

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]+

Physikochemische Eigenschaften

Siedepunkt: 913.3 · 913.3±75.0 °C(Predicted)
Dichte: 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)
Aggregatzustand: Powder
Farbe: colorless
PH: 7 · 7
Wasserlöslichkeit: 50 mg/mL · ≥ 50mg/mL in Water
InChIKey: VBEYWLZRUINVRS-KGXNBXOZSA-M
SMILES: C(OP(=O)(O)OP(O)(=O)OP(O)(O)=O)[C@H]1O[C@@H](N2C3C(=C(N=CN=3)N)N=C2)C[C@@H]1O
CAS Datenbank: 1927 · 1927-31-7(CAS DataBase Reference)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS ClassificationNot Classified

Gefahrenhinweise

Hazard Classes and CategoriesNot Classified

Toxikologische Informationen

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

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

Sicherheitsdaten

wgk: 3
hs_code: 29349990
RTECS-Nr.: AU7358800
Speicherklasse: 10 - Combustible liquids

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

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)