Grundinformationen
- CAS
3768-18-1- Standard-SMILES
CC(=O)Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)n1- InChIKey
NIDVTARKFBZMOT-PEBGCTIMSA-N- Summenformel
- C11H15N3O6
- Durchschnittliche Molmasse
- 285,25 g/mol
- Monoisotopische Masse
- 285,09608521
Überblick
N(4)-acetylcytidine is cytidine in which one of the exocyclic amino hydrogens is substituted by an acetyl group. It has a role as a metabolite. It is a secondary carboxamide, a member of acetamides and a member of cytidines.
Namen und Bezeichner
- Bevorzugter Name
- N4-Acetylcytidine
- IUPAC
- N-[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]acetamide
- Lokaler Name
- 4-Acetyl-1-(β-D-ribofuranosyl)cytosin
- Englischer Name
- N4-Acetylcytidine
- Summenformel
- C11H15N3O6
- Molmasse
- 285.25
Namen und Synonyme
N4-AcetylcytidineN-Acetylcytidine3768-18-1AcetylcytidineDTXSID40958718N-[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]acetamideN-{1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxo-1,2-dihydropyrimidin-4-yl}acetamideN-(1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)acetamideN-(1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)-2-oxopyrimidin-4-yl)acetamideRefChem:831612DTXCID301386616223-195-6
Weitere Namen anzeigen
rC(Ac)N4-Ac-rCN4-Ac-CrACETYL CYTOSINEn-acetyl-cytidin4-Acetylcytidine
Cytidine, N-acetyl-4-Acetyl-1-(beta-D-ribofuranosyl)cytosineN-4-Acetylcytidine4-N-acetyl-cytidineN4-Acetyl-D-cytidinen-acetyl-CytidineMFCD00006540Ac-rC
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -1,4
- Polarare Oberfläche (TPSA)
- 132 Ų
- H-Brücken-Donoren
- 4
- H-Brücken-Akzeptoren
- 6
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 20
- Formalladung
- 0
- Komplexität
- 477
Experimentelle und physikochemische Eigenschaften
Physical DescriptionSolid
Collision Cross Section162.7 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
Physikochemische Eigenschaften
- Schmelzpunkt
- 199 °C · 199 °C (dec.)(lit.)
- Dichte
- 1.72 · 1.72±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Sealed in dry,Store in freezer, under -20°C
- Löslichkeit
- DMSO (Slightly, Heated), Methanol (Slightly, Heated)
- Aggregatzustand
- Solid
- pka
- 10.21 · 10.21±0.20(Predicted)
- Farbe
- White to Pale Yellow
- PH
- 1.5 · <1.5
- InChI
- InChI=1S/C11H15N3O6/c1-5(16)12-7-2-3-14(11(19)13-7)10-9(18)8(17)6(4-15)20-10/h2-3,6,8-10,15,17-18H,4H2,1H3,(H,12,13,16,19)/t6-,8-,9-,10-/m1/s1
- InChIKey
- NIDVTARKFBZMOT-PEBGCTIMSA-N
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Sicherheitsdaten
- wgk
- 3
- hs_code
- 29335990
- risk_code
- 20/21/22-36/37/38
- hazard_code
- Xn
- safety_code
- 36-36/37/39-26
Chemie und Industrie
Pharmakologische Informationen
Tissue LocationsPlacenta
Anwendungen
BeschreibungN4-Acetylcytidine is a modified nucleoside and endogenous urinary nucleoside product of the degradation of tRNA. N4-Acetylcytidine is a biological marker for various cancers with elevated concentrations present in urine. tRNA has been shown to be excreted in abnormal amounts in the urine of cancer patients. tRNA from neoplastic tissue had a much more rapid turnover rate than the tRNA from the corresponding normal tissue. Evidence indicates that methylation of tRNA occurs only after synthesis of the intact macromolecule. Because there are no specific enzyme systems to incorporate the modified nucleosides into the macromolecular nucleic acid, these nucleosides once released in the process of tRNA turnover cannot be reutilized, nor are they further degraded, but are excreted in urine.N4-Acetylcytidine is also a partially protected cytidine and therefore can be used as a synthetic building block to prepare further derivatized nucleosides such as 2’,3’-dideoxycytidine.
VerwendenN4-Acetylcytidine (cas# 3768-18-1) is a nucleotide-derived metabolite used as biomarkers for diagnosis of inflammation-related diseases.
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