IMPPAT Phytochemical information: 
3-Indolylmethyl glucosinolate
3-Indolylmethyl glucosinolate
Summary

SMILES: OC[C@H]1O[C@@H](S/C(=N\OS(=O)(=O)O)/Cc2c[nH]c3c2cccc3)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C16H20N2O9S2/c19-7-11-13(20)14(21)15(22)16(26-11)28-12(18-27-29(23,24)25)5-8-6-17-10-4-2-1-3-9(8)10/h1-4,6,11,13-17,19-22H,5,7H2,(H,23,24,25)/b18-12-/t11-,13-,14+,15-,16+/m1/s1
InChIKey: DNDNWOWHUWNBCK-PIAXYHQTSA-N
DeepSMILES: OC[C@H]O[C@@H]S/C=N\OS=O)=O)O))))/Ccc[nH]cc5cccc6))))))))))))[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; c[nH]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:
Glucobrassicin, 3-indolylmethyl-glucosinolate (glucobrassicin), glucobrassicin
External chemical identifiers:
CID:CID_6602378; ZINC:ZINC000004096928; FDASRS:EA6EH0IU89
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
3-Indolylmethyl glucosinolate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 448.48
Log P RDKit -0.62
Topological polar surface area (Å2) RDKit 181.9
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 13
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 2
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.31
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.44
Number of rotatable bonds RDKit 7
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
3-Indolylmethyl glucosinolate
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
3-Indolylmethyl glucosinolate
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 -9.10
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 No