Tricirbine (CHEM018516)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:18:18 UTC
Update Date2016-11-09 01:15:49 UTC
Accession NumberCHEM018516
Identification
Common NameTricirbine
ClassSmall Molecule
DescriptionA nucleoside analogue in which the nucleobase portion is a 1,4,5,6,8-pentaazaacenaphthylene ring system substituted with an amino group at position 3, and a methyl group at position 5 and is bound to the beta-D-ribofuranosyl moiety by an N(1)-glycosidic linkage.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
TCNChEBI
6-ARPPPMeSH
3-amino-1,5-dihydro-5-Methyl-I-beta-D-ribofuranosyl-1,4,5,6,8- pentaazaacenaphthyleneMeSH
6-amino-4-Methyl-8-(beta-D-ribofuranosyl)-(4H,8H)pyrrolo(4,3,2-de)pyrimido(4,5-c)pyridazineMeSH
Chemical FormulaC13H16N6O4
Average Molecular Mass320.309 g/mol
Monoisotopic Mass320.123 g/mol
CAS Registry Number35943-35-2
IUPAC Name(2R,3S,4R,5R)-2-(hydroxymethyl)-5-{5-imino-7-methyl-2,6,7,9,11-pentaazatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),3,8(12),9-tetraen-2-yl}oxolane-3,4-diol
Traditional Name(2R,3S,4R,5R)-2-(hydroxymethyl)-5-{5-imino-7-methyl-2,6,7,9,11-pentaazatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),3,8(12),9-tetraen-2-yl}oxolane-3,4-diol
SMILES[H][C@]1(CO)O[C@@]([H])(N2C=C3C4=C(N=CN=C24)N(C)NC3=N)[C@]([H])(O)[C@]1([H])O
InChI IdentifierInChI=1S/C13H16N6O4/c1-18-11-7-5(10(14)17-18)2-19(12(7)16-4-15-11)13-9(22)8(21)6(3-20)23-13/h2,4,6,8-9,13,20-22H,3H2,1H3,(H2,14,17)/t6-,8-,9-,13-/m1/s1
InChI KeyHOGVTUZUJGHKPL-HTVVRFAVSA-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
  • Pentose monosaccharide
  • Pyrrolo[2,3-d]pyrimidine
  • Pyrrolo[3,4-d]pyridazine
  • Pyrrolopyrimidine
  • Monosaccharide
  • Pyridazine
  • Pyrimidine
  • Imidolactam
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Tetrahydrofuran
  • Carboxylic acid amidrazone
  • Secondary alcohol
  • Azacycle
  • Oxacycle
  • Organoheterocyclic compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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 Solubility9.02 g/LALOGPS
logP-1.7ALOGPS
logP-1.3ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)12.46ChemAxon
pKa (Strongest Basic)8.35ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area139.75 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity110.26 m³·mol⁻¹ChemAxon
Polarizability31.21 ųChemAxon
Number of Rings4ChemAxon
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, Positivesplash10-0079-0916000000-73dd86cbe2e15c326525Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1900000000-d53846d65c6152b02424Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-1900000000-e553be1c9d0d3bb6310cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014r-0529000000-c5134d63d7bc50a0dc30Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0910000000-bb38f9b89df6d2778644Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dr-0900000000-a0466d1a7c9fe1956cd0Spectrum
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 IDDB12405
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 LinkTriciribine
Chemspider IDNot Available
ChEBI ID65310
PubChem Compound ID65399
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=22075556
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22728437
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22773664