Deoxyuridine Triphosphate
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Grundinformationen
- CAS
102814-08-4- Standard-SMILES
O=c1ccn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O2)c(=O)[nH]1- InChIKey
AHCYMLUZIRLXAA-SHYZEUOFSA-N- Summenformel
- C9H15N2O14P3
- Durchschnittliche Molmasse
- 468,14 g/mol
- Monoisotopische Masse
- 467,97361305
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
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- -5,5
- Polarare Oberfläche (TPSA)
- 239 Ų
- 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
188.9 Ų [M+Na-2H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
188.9 Ų [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.
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Toxikologische Informationen
Toxicity Summary
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
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
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.
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