IMPPAT Phytochemical information: 
Cleistanthin B
Cleistanthin B
Summary

SMILES: OC[C@H]1O[C@@H](Oc2c3COC(=O)c3c(c3c2cc(OC)c(c3)OC)c2ccc3c(c2)OCO3)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C27H26O12/c1-33-16-6-12-13(7-17(16)34-2)25(39-27-24(31)23(30)22(29)19(8-28)38-27)14-9-35-26(32)21(14)20(12)11-3-4-15-18(5-11)37-10-36-15/h3-7,19,22-24,27-31H,8-10H2,1-2H3/t19-,22-,23+,24-,27+/m1/s1
InChIKey: BJGIWVGXMRUMNA-WBYCZGBQSA-N
DeepSMILES: OC[C@H]O[C@@H]OccCOC=O)c5ccc9ccOC))cc6)OC)))))))cccccc6)OCO5))))))))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C1OCc2c1c(-c1ccc3c(c1)OCO3)c1ccccc1c2OC1CCCCO1
Scaffold Graph/Node level: OC1OCC2C(OC3CCCCO3)C3CCCCC3C(C3CCC4OCOC4C3)C12
Scaffold Graph level: CC1CCC2C(CC3CCCCC3)C3CCCCC3C(C3CCC4CCCC4C3)C12
Functional groups: CO; c1cOCO1; cO[C@@H](C)OC; cC(=O)OC; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
ClassyFire Class: Lignan glycosides
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans
NP Classifier Class: Arylnaphthalene and aryltetralin lignans
Synonymous chemical names:
cleistanthin b
External chemical identifiers:
CID:CID_119458; ChEMBL:CHEMBL601587; ChEBI:CHEBI:84407
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Cleistanthin B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 542.49
Log P RDKit 1.1
Topological polar surface area (Å2) RDKit 162.6
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 27
Number of heavy atoms RDKit 39
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 0.19
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 17
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.37
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 3
Total number of rings RDKit 6
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 6
Cleistanthin B
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 0.33
Cleistanthin B
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -8.32
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 Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No