IMPPAT Phytochemical information: 
Neoglucobrassicin
Neoglucobrassicin
Summary

SMILES: OC[C@H]1O[C@@H](S/C(=N\OS(=O)(=O)O)/Cc2cn(c3c2cccc3)OC)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C17H22N2O10S2/c1-27-19-7-9(10-4-2-3-5-11(10)19)6-13(18-29-31(24,25)26)30-17-16(23)15(22)14(21)12(8-20)28-17/h2-5,7,12,14-17,20-23H,6,8H2,1H3,(H,24,25,26)/b18-13-/t12-,14-,15+,16-,17+/m1/s1
InChIKey: PKKMITFKYRCCOL-JMZFCNQTSA-N
DeepSMILES: OC[C@H]O[C@@H]S/C=N\OS=O)=O)O))))/Cccncc5cccc6))))))OC))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: N=C(Cc1c[nH]c2ccccc12)SC1CCCCO1
Scaffold Graph/Node level: NC(CC1CNC2CCCCC12)SC1CCCCO1
Scaffold Graph level: CC(CC1CCCCC1)CC1CCC2CCCCC21
Functional groups: CO; C/C(=N/OS(=O)(=O)O)S[C@@H](C)OC; cn(OC)c
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: Amino acids and Peptides
NP Classifier Superclass: Amino acid glycosides
NP Classifier Class: Glucosinolates
Synonymous chemical names:
Neoglucobrassicin, 1-methoxy-3-indolylmethyl-glucosinolate (neoglucobrassicin), neoglucobrassicin
External chemical identifiers:
CID:CID_9576416; ZINC:ZINC000013550565
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Neoglucobrassicin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 478.5
Log P RDKit -1.09
Topological polar surface area (Å2) RDKit 180.27
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 31
Number of heteroatoms RDKit 14
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 2
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.29
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.47
Number of rotatable bonds RDKit 8
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
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
Neoglucobrassicin
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 Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.14
Neoglucobrassicin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -9.03
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 4
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