6-Azaribine (CHEM016574)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:37:26 UTC
Update Date2016-11-09 01:15:26 UTC
Accession NumberCHEM016574
Identification
Common Name6-Azaribine
ClassSmall Molecule
DescriptionA N-glycosyl-1,2,4-triazine that is 6-azauridine acetylated at positions 2', 3' and 5' on the sugar ring. It is a prodrug for 6-azauridine and is used for treatment of psoriasis.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2',3',5'-Tri-O-acetyl-6-azauridineChEBI
2',3',5'-Triacetyl-6-azauridineChEBI
2-(2',3',5'-Triacetyl-beta-D-ribofuranosyl)-as-triazine-3,5-(2H,4H)-dioneChEBI
2-beta-D-Ribofuranosyl-as-triazine-3,5(2H,4H)-dione 2',3',5'-triacetateChEBI
6-Azauridine 2',3',5'-triacetateChEBI
AzaribinaChEBI
AzaribinumChEBI
Triacetyl-6-azauridineChEBI
TriazureChEBI
2-(2',3',5'-Triacetyl-b-D-ribofuranosyl)-as-triazine-3,5-(2H,4H)-dioneGenerator
2-(2',3',5'-Triacetyl-β-D-ribofuranosyl)-as-triazine-3,5-(2H,4H)-dioneGenerator
2-b-D-Ribofuranosyl-as-triazine-3,5(2H,4H)-dione 2',3',5'-triacetateGenerator
2-b-D-Ribofuranosyl-as-triazine-3,5(2H,4H)-dione 2',3',5'-triacetic acidGenerator
2-beta-D-Ribofuranosyl-as-triazine-3,5(2H,4H)-dione 2',3',5'-triacetic acidGenerator
2-Β-D-ribofuranosyl-as-triazine-3,5(2H,4H)-dione 2',3',5'-triacetateGenerator
2-Β-D-ribofuranosyl-as-triazine-3,5(2H,4H)-dione 2',3',5'-triacetic acidGenerator
6-Azauridine 2',3',5'-triacetic acidGenerator
6-Azauridine triacetateMeSH
Triacetyl azauridineMeSH
Chemical FormulaC14H17N3O9
Average Molecular Mass371.302 g/mol
Monoisotopic Mass371.096 g/mol
CAS Registry Number2169-64-4
IUPAC Name[(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(5-hydroxy-3-oxo-2,3-dihydro-1,2,4-triazin-2-yl)oxolan-2-yl]methyl acetate
Traditional Nameazaribine
SMILES[H][C@]1(COC(C)=O)O[C@@]([H])(N2N=CC(O)=NC2=O)[C@]([H])(OC(C)=O)[C@]1([H])OC(C)=O
InChI IdentifierInChI=1S/C14H17N3O9/c1-6(18)23-5-9-11(24-7(2)19)12(25-8(3)20)13(26-9)17-14(22)16-10(21)4-15-17/h4,9,11-13H,5H2,1-3H3,(H,16,21,22)/t9-,11-,12-,13-/m1/s1
InChI KeyQQOBRRFOVWGIMD-OJAKKHQRSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentGlycosylamines
Alternative Parents
Substituents
  • N-glycosyl compound
  • Tricarboxylic acid or derivatives
  • Monosaccharide
  • Triazine
  • 1,2,4-triazine
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Lactam
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Azacycle
  • Oxacycle
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.45 g/LALOGPS
logP-0.19ALOGPS
logP-0.7ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)5.76ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area153.39 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity78.39 m³·mol⁻¹ChemAxon
Polarizability33.68 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03k9-6659000000-b42ec6b468accd7fc8b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-2911000000-aea0317f696c3874ff21Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03k9-9370000000-8dd461c9bc23f7c70f97Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9101000000-beba90f37273cce226a1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0296-9300000000-b649b657253ddaee5287Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0296-9200000000-6279e09f2a539d26f27dSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID88272
PubChem Compound ID16574
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1036874
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=1096923
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11600283
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=1173747
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=1243822
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=14023746
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=203231
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=324277
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=5137963
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=5171778
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=5911950
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=6198500
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=766762
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=8570536