IMPPAT Phytochemical information: 
[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1Z,3S)-3-hydroxy-3-methyl-N-sulfooxypentanimidothioate
[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1Z,3S)-3-hydroxy-3-methyl-N-sulfooxypentanimidothioate
Summary

SMILES: OC[C@H]1O[C@@H](S/C(=N\OS(=O)(=O)O)/C[C@](CC)(O)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C12H23NO10S2/c1-3-12(2,18)4-7(13-23-25(19,20)21)24-11-10(17)9(16)8(15)6(5-14)22-11/h6,8-11,14-18H,3-5H2,1-2H3,(H,19,20,21)/b13-7-/t6-,8-,9+,10-,11+,12+/m1/s1
InChIKey: JEOJIKMFKHSAJU-XVGGJBPNSA-N
DeepSMILES: OC[C@H]O[C@@H]S/C=N\OS=O)=O)O))))/C[C@]CC))O)C)))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: C1CCOCC1
Scaffold Graph/Node level: C1CCOCC1
Scaffold Graph level: C1CCCCC1
Functional groups: CO; C/C(=N/OS(=O)(=O)O)S[C@@H](C)OC
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:
glucocleomin
External chemical identifiers:
CID:CID_101003963; ZINC:ZINC000004097560
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1Z,3S)-3-hydroxy-3-methyl-N-sulfooxypentanimidothioate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 405.45
Log P RDKit -1.8
Topological polar surface area (Å2) RDKit 186.34
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 12
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 13
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 2
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.5
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 1
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.92
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 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
[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1Z,3S)-3-hydroxy-3-methyl-N-sulfooxypentanimidothioate
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
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 0.12
[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1Z,3S)-3-hydroxy-3-methyl-N-sulfooxypentanimidothioate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
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 -9.78
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