IMPPAT Phytochemical information: 
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Summary

SMILES: OC[C@H]1O[C@@H](OCCc2cc(O)c(cc2O)O)[C@@H]([C@H]([C@@H]1O)O)OC(=O)Cc1ccc(c(c1)O)O
InChI: InChI=1S/C22H26O12/c23-9-17-19(30)20(31)21(34-18(29)6-10-1-2-12(24)14(26)5-10)22(33-17)32-4-3-11-7-15(27)16(28)8-13(11)25/h1-2,5,7-8,17,19-28,30-31H,3-4,6,9H2/t17-,19-,20+,21-,22-/m1/s1
InChIKey: OHBCQZHHEGRATF-MIUGBVLSSA-N
DeepSMILES: OC[C@H]O[C@@H]OCCcccO)ccc6O)))O))))))))[C@@H][C@H][C@@H]6O))O))OC=O)Ccccccc6)O))O
Scaffold Graph/Node/Bond level: O=C(Cc1ccccc1)OC1CCCOC1OCCc1ccccc1
Scaffold Graph/Node level: OC(CC1CCCCC1)OC1CCCOC1OCCC1CCCCC1
Scaffold Graph level: CC(CC1CCCCC1)CC1CCCCC1CCCC1CCCCC1
Functional groups: CO; cO; CO[C@@H](C)OC; CC(=O)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: Shikimates and Phenylpropanoids
NP Classifier Superclass: Phenylethanoids (C6-C2)
NP Classifier Class: Phenylethanoids
Synonymous chemical names:
tetraacetate,3,acyl-3,4-dehydrogentiopicroside
External chemical identifiers:
CID:CID_16091524; ChEBI:CHEBI:66208; ZINC:ZINC000035066243
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
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Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 482.44
Log P RDKit -0.63
Topological polar surface area (Å2) RDKit 206.6
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 8
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 34
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.23
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.41
Number of rotatable bonds RDKit 9
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
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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 2
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 0.13
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ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
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 -9.03
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 2
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