IMPPAT Phytochemical information: 
Methyl 2-O-tosyl-3-O-benzyl-alpha-L-rhamnopyranoside
Methyl 2-O-tosyl-3-O-benzyl-alpha-L-rhamnopyranoside
Summary

SMILES: CO[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1OS(=O)(=O)c1ccc(cc1)C)OCc1ccccc1)O
InChI: InChI=1S/C21H26O7S/c1-14-9-11-17(12-10-14)29(23,24)28-20-19(18(22)15(2)27-21(20)25-3)26-13-16-7-5-4-6-8-16/h4-12,15,18-22H,13H2,1-3H3/t15-,18-,19+,20+,21+/m0/s1
InChIKey: NBHVHPZZGDGHTG-NWRWZVFGSA-N
DeepSMILES: CO[C@@H]O[C@@H]C)[C@@H][C@H][C@H]6OS=O)=O)cccccc6))C))))))))OCcccccc6)))))))))O
Scaffold Graph/Node/Bond level: O=S(=O)(OC1COCCC1OCc1ccccc1)c1ccccc1
Scaffold Graph/Node level: OS(O)(OC1COCCC1OCC1CCCCC1)C1CCCCC1
Scaffold Graph level: CC(C)(CC1CCCCC1CCC1CCCCC1)C1CCCCC1
Functional groups: CO[C@@H](C)OC; cS(=O)(=O)OC; COC; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
Synonymous chemical names:
5-o-alpha-l-rhamnopyranoside-(s)-4,5,7-trihydroxyflavanone
External chemical identifiers:
CID:CID_16724794
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Methyl 2-O-tosyl-3-O-benzyl-alpha-L-rhamnopyranoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 422.5
Log P RDKit 2.41
Topological polar surface area (Å2) RDKit 91.29
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 1
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.24
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.43
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 2
Number of aromatic heterocycles RDKit 0
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
Methyl 2-O-tosyl-3-O-benzyl-alpha-L-rhamnopyranoside
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.685311
Methyl 2-O-tosyl-3-O-benzyl-alpha-L-rhamnopyranoside
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.10
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No