IMPPAT Phytochemical information: 
Vicine
Vicine
Summary

SMILES: OC[C@H]1O[C@@H](Oc2c(N)nc([nH]c2=O)N)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C10H16N4O7/c11-7-6(8(19)14-10(12)13-7)21-9-5(18)4(17)3(16)2(1-15)20-9/h2-5,9,15-18H,1H2,(H5,11,12,13,14,19)/t2-,3-,4+,5-,9+/m1/s1
InChIKey: KGNGTSCIQCLKEH-SYCVNHKBSA-N
DeepSMILES: OC[C@H]O[C@@H]OccN)nc[nH]c6=O)))N))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=c1[nH]cncc1OC1CCCCO1
Scaffold Graph/Node level: OC1NCNCC1OC1CCCCO1
Scaffold Graph level: CC1CCCCC1CC1CCCCC1
Functional groups: CO; cO[C@@H](C)OC; cN; cnc; c[nH]c; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
NP Classifier Biosynthetic pathway: Carbohydrates
NP Classifier Superclass: Nucleosides
Synonymous chemical names:
vicine, Vicine
External chemical identifiers:
CID:CID_135413566; Molport-046-156-408|Molport-028-720-570
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Vicine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 304.26
Log P RDKit -3.89
Topological polar surface area (Å2) RDKit 197.17
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 10
Number of heavy atoms RDKit 21
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 4
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
Shape complexity RDKit 0.6
Number of rotatable bonds RDKit 3
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 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 2
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 2
Vicine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 1
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.29
Vicine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Highly soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -10.80
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