IMPPAT Phytochemical information: 
Bergenin
Bergenin
Summary

SMILES: OC[C@H]1O[C@@H]2[C@@H]([C@H]([C@@H]1O)O)OC(=O)c1c2c(O)c(c(c1)O)OC
InChI: InChI=1S/C14H16O9/c1-21-11-5(16)2-4-7(9(11)18)12-13(23-14(4)20)10(19)8(17)6(3-15)22-12/h2,6,8,10,12-13,15-19H,3H2,1H3/t6-,8-,10+,12+,13-/m1/s1
InChIKey: YWJXCIXBAKGUKZ-HJJNZUOJSA-N
DeepSMILES: OC[C@H]O[C@@H][C@@H][C@H][C@@H]6O))O))OC=O)cc6cO)ccc6)O))OC
Scaffold Graph/Node/Bond level: O=C1OC2CCCOC2c2ccccc21
Scaffold Graph/Node level: OC1OC2CCCOC2C2CCCCC12
Scaffold Graph level: CC1CC2CCCCC2C2CCCCC12
Functional groups: CO; COC; cC(=O)OC; cO; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Benzene and substituted derivatives
ClassyFire Subclass: Benzoic acids and derivatives
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Isocoumarins
Synonymous chemical names:
berginin, corylopsin, cuscutin, vakerin, 3β,14β,16α,17β-tetrahydroxypregn-5-en-20-one (bergenin), bergenin
External chemical identifiers:
CID:CID_66065; ChEMBL:CHEMBL273019; ChEBI:CHEBI:69499; ZINC:ZINC000004046820; FDASRS:L84RBE4IDC; SureChEMBL:SCHEMBL893721; MolPort-002-507-606
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Bergenin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 328.27
Log P RDKit -1.2
Topological polar surface area (Å2) RDKit 145.91
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 14
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.36
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
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
Bergenin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 1
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.42
Bergenin
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 -8.99
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 No