IMPPAT Phytochemical information: 
Tomentoside

Tomentoside
Summary

SMILES: OC[C@H]1O[C@@H](O[C@@H]2OC=CC3=CC[C@]([C@@H]23)(C)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C15H22O8/c1-15(20)4-2-7-3-5-21-13(9(7)15)23-14-12(19)11(18)10(17)8(6-16)22-14/h2-3,5,8-14,16-20H,4,6H2,1H3/t8-,9-,10-,11+,12-,13+,14+,15+/m1/s1
InChIKey: CRKMUAHMCAMOAU-AMTOUNBVSA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@@H]OC=CC=CC[C@][C@@H]95)C)O))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: C1=CC2=CCCC2C(OC2CCCCO2)O1
Scaffold Graph/Node level: C1CCC(OC2OCCC3CCCC32)OC1
Scaffold Graph level: C1CCC(CC2CCCC3CCCC32)CC1
Functional groups: CO; CC=C1C=CO[C@@H](O[C@@H](C)OC)C1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene glycosides
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Monoterpenoids
NP Classifier Class: Iridoids monoterpenoids
Synonymous chemical names:
Tomentoside, tomentoside
External chemical identifiers:
CID:CID_101664499; ZINC:ZINC000238754231
Chemical structure download


Tomentoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 330.33
Log P RDKit -1.63
Topological polar surface area (Å2) RDKit 128.84
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 8
Stereochemical complexity RDKit 0.53
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.73
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
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


Tomentoside
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 1
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.417139


Tomentoside
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
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 -9.44
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
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