Deoxyuridine Triphosphate (HCID 65070)

Überblick

DUTP is a deoxyuridine phosphate having a triphosphate group at the 5'-position. It has a role as an Arabidopsis thaliana metabolite, a mouse metabolite, an Escherichia coli metabolite and a human metabolite. It is a deoxyuridine phosphate and a pyrimidine 2'-deoxyribonucleoside 5'-triphosphate. It is a conjugate acid of a dUTP(3-).

Namen und Bezeichner

Bevorzugter Name: Deoxyuridine Triphosphate
IUPAC: [[(2R,3S,5R)-5-(2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
Englischer Name: 2'-Deoxyuridine-5'-triphosphate trisodium salt
Summenformel: C9H16N2NaO14P3
Molmasse: 492.14

Namen und Synonyme

dUTPDeoxyuridine triphosphate1173-82-62'-Deoxyuridine 5'-triphosphatedeoxy-UTP[[(2R,3S,5R)-5-(2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphateCHEBI:176252'-deoxyuridine 5'-(tetrahydrogen triphosphate)2'-Deoxyuridine-5'-triphosphorate(((2R,3S,5R)-5-(2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl)methoxy-hydroxyphosphoryl) phosphono hydrogen phosphateRefChem:585755(((((((2R,3S,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl)methoxy)(hydroxy)phosphoryl)oxy)(hydroxy)phosphoryl)oxy)phosphonic acid

Weitere Namen anzeigen

2'-dUTP2’dUTP,3NadUTP.Na3-C-βAids052149Aids-052149-Deoxy-β-Epi 2&rsquo

2'-deoxyuridine-5'-triphosphate102814-08-4DEOXYURIDINE-5'-TRIPHOSPHATEDeoxyuridine 5'-triphosphate2'-Deoxyuridine-5'-triphosphoric acid2'-Deoxyuracil 5'-triphosphate2'-Deoxyuridine-5'-triphosphate trisodium saltCHEMBL374361

Datenbank-Bezeichner

CAS: 102814-08-4、1173-82-6、91918-34-2
PubChem CID: 65070
DTXSID: DTXSID60908053
ChEMBL: CHEMBL374361
ChEBI: CHEBI:17625
Nikkaji: J315.490D

Eigenschaften

Berechnete Struktureigenschaften

XLogP: -5,5
Polarare Oberfläche (TPSA): 239 Å²
H-Brücken-Donoren: 6
H-Brücken-Akzeptoren: 14
Frei drehbare Bindungen: 8
Schwere Atome: 28
Formalladung: 0
Komplexität: 808

Experimentelle und physikochemische Eigenschaften

Chemical ClassesBiological Agents -> Nucleic Acids and Derivatives

DrugsPharmaceuticals -> Listed in ZINC15

Physical DescriptionSolid

Collision Cross Section · 2 Einträge

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

188.9 Å² [M-2H+Na]-

Physikochemische Eigenschaften

Schmelzpunkt: 150 o · >150o C (Dec.)
storage temp.: -20 °C · -20°C
Löslichkeit: Methanol (Slightly), Water (Slightly)
Aggregatzustand: Powder
Farbe: White
Biologische Quelle: synthetic (organic)
Wasserlöslichkeit: Soluble in water.
Stabilität: Hygroscopic
InChIKey: FVFWWPFKJNTHIQ-BAJMBWAYNA-N
SMILES: O=C1NC(=O)C=CN1[C@H]1C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O1.[NaH] |&1:8,10,12,r|

Sicherheit und Regulatorisches

Toxikologische Informationen

Toxicity Summary · 1 Eintrag

Deoxyuridine triphosphate (dUTP) can be misincorporated into DNA and cause DNA damage. The extent of DNA damage caused by dUTP is dependent on the levels of the pyrophosphatase dUTPase and uracil-DNA glycosylase (UDG). DNA damage due to dUTP misincorporation is highly dependent on the levels of the pyrophosphatase dUTPase, which limits intracellular accumulation of dUTP. (A4337) Also, loss of viability following thymidylate synthase (TS) inhibition occurs as a consequence of accumulation of dUTP in some cell lines and subsequent misincorporation of uracil into DNA. (PMCID: PMC2364072)

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

Sicherheitsdaten

wgk: 1
hs_code: 29349990
risk_code: 36/37/38
safety_code: 26-36
Speicherklasse: 11 - Combustible Solids

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 LocationsEpidermis

Cellular LocationsMitochondria

Metabolite PathwaysBeta Ureidopropionase Deficiency

Verwendung und Herstellung

UsesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.

Anwendungen · 1 Eintrag

Verwenden2'-Deoxyuridine-5'-triphosphate trisodium salt may be used to study the distribution, specificity and kinetics of deoxyuridine 5′-triphosphate nucleotidohydrolase(s). 2'-Deoxyuridine-5'-triphosphate trisodium salt is important enzymes that protect cells from the incorporation of dUTP into DNA.