IMPPAT Phytochemical information: 
[[2-(4-hydroxy-1H-indol-3-yl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanylethylidene]amino] sulfate
[[2-(4-hydroxy-1H-indol-3-yl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanylethylidene]amino] sulfate
Summary

SMILES: OC[C@H]1O[C@@H](SC(=NOS(=O)(=O)[O-])Cc2c[nH]c3c2c(O)ccc3)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C16H20N2O10S2/c19-6-10-13(21)14(22)15(23)16(27-10)29-11(18-28-30(24,25)26)4-7-5-17-8-2-1-3-9(20)12(7)8/h1-3,5,10,13-17,19-23H,4,6H2,(H,24,25,26)/p-1/t10-,13-,14+,15-,16+/m1/s1
InChIKey: CSMYCLLHRFFFLG-IRHMCKRBSA-M
DeepSMILES: OC[C@H]O[C@@H]SC=NOS=O)=O)[O-]))))Ccc[nH]cc5cO)ccc6))))))))))))[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; CC(=NOS(=O)(=O)[O-])S[C@@H](C)OC; c[nH]c; cO
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:
4-hydroxyglucobrassicin
External chemical identifiers:
CID:CID_656560; ChEBI:CHEBI:62724
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
[[2-(4-hydroxy-1H-indol-3-yl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanylethylidene]amino] sulfate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 463.47
Log P RDKit -1.26
Topological polar surface area (Å2) RDKit 204.96
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 30
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 0.31
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
[[2-(4-hydroxy-1H-indol-3-yl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanylethylidene]amino] sulfate
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 1
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.0979824
[[2-(4-hydroxy-1H-indol-3-yl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanylethylidene]amino] sulfate
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 -9.44
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 5
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