Secondary metabolite: 3-[(2R,3R,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3H,4H,5H-imidazo[4,5-d][1,2,3]triazin-4-one

3-[(2R,3R,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3H,4H,5H-imidazo[4,5-d][1,2,3]triazin-4-one
Summary
Molecular formula: C10H13N5O6
SMILES: OCC1O[C@H]([C@@H]([C@H]([C@@H]1O)O)O)n1nnc2c(c1=O)[nH]cn2
InChI: InChI=1S/C10H13N5O6/c16-1-3-5(17)6(18)7(19)10(21-3)15-9(20)4-8(13-14-15)12-2-11-4/h2-3,5-7,10,16-19H,1H2,(H,11,12)/t3?,5-,6+,7-,10-/m1/s1
InChIKey: PYDYQIZPDUHKRL-HQFWVWBGSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Organic oxygen compounds
Class: Organooxygen compounds
Sub class: Carbohydrates and carbohydrate conjugates
Synonymous chemical names:
3-[(2R,3R,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3H,4H,5H-imidazo[4,5-d][1,2,3]triazin-4-one
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
3-[(2R,3R,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3H,4H,5H-imidazo[4,5-d][1,2,3]triazin-4-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 299.24
Log P RDKit -3.51
Topological polar surface area (Å2) RDKit 166.61
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 10
Number of heavy atoms RDKit 21
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 5
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.5
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 6
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.6
Shape complexity RDKit 0.6
Number of rotatable bonds SwissADME 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 2
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
3-[(2R,3R,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3H,4H,5H-imidazo[4,5-d][1,2,3]triazin-4-one
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 1
Ghose filter RDKit Failed
Veber filter RDKit Bad
Egan filter RDKit Bad
Pfizer’s 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Number of Leadlikeness violations SwissADME 0
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.38
3-[(2R,3R,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3H,4H,5H-imidazo[4,5-d][1,2,3]triazin-4-one
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -9.37
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No
Designed by R.P. Vivek-Ananth, M Karthikeyan and Ajaya Kumar Sahoo