IMPPAT Phytochemical information: 
Karakin
Karakin
Summary

SMILES: O=C(OC[C@H]1O[C@@H](OC(=O)CC[N+](=O)[O-])[C@@H]([C@H]([C@@H]1O)O)OC(=O)CC[N+](=O)[O-])CC[N+](=O)[O-]
InChI: InChI=1S/C15H21N3O15/c19-9(1-4-16(24)25)30-7-8-12(22)13(23)14(32-10(20)2-5-17(26)27)15(31-8)33-11(21)3-6-18(28)29/h8,12-15,22-23H,1-7H2/t8-,12-,13+,14-,15+/m1/s1
InChIKey: CNURKUNYCXCBEK-WMNSZERYSA-N
DeepSMILES: O=COC[C@H]O[C@@H]OC=O)CC[N+]=O)[O-]))))))[C@@H][C@H][C@@H]6O))O))OC=O)CC[N+]=O)[O-]))))))))))))CC[N+]=O)[O-]
Scaffold Graph/Node/Bond level: C1CCOCC1
Scaffold Graph/Node level: C1CCOCC1
Scaffold Graph level: C1CCCCC1
Functional groups: COC(C)=O; CC(=O)O[C@@H](C)OC; C[N+](=O)[O-]; CO; CC(=O)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Carboxylic acids and derivatives
ClassyFire Subclass: Tricarboxylic acids and derivatives
Synonymous chemical names:
karakin, karakin (1,2,6-tri-o-(3-nitropropanoyl)-beta-d-glucose), Karakin
External chemical identifiers:
CID:CID_100274; ChEBI:CHEBI:6112; ZINC:ZINC000008221162; FDASRS:I84581BGZY
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Karakin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 483.34
Log P RDKit -2.57
Topological polar surface area (Å2) RDKit 258.01
Number of hydrogen bond acceptors RDKit 15
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 33
Number of heteroatoms RDKit 18
Number of nitrogen atoms RDKit 3
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.33
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.8
Number of rotatable bonds RDKit 16
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 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 1
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 1
Karakin
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 2
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.12
Karakin
ADME 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 -10.82
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 3
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes