IMPPAT Phytochemical information: 
Hypophyllanthin

Hypophyllanthin
Summary

SMILES: COC[C@@H]1Cc2cc(OC)c3c(c2[C@@H]([C@H]1COC)c1ccc(c(c1)OC)OC)OCO3
InChI: InChI=1S/C24H30O7/c1-25-11-16-8-15-10-20(29-5)23-24(31-13-30-23)22(15)21(17(16)12-26-2)14-6-7-18(27-3)19(9-14)28-4/h6-7,9-10,16-17,21H,8,11-13H2,1-5H3/t16-,17-,21+/m0/s1
InChIKey: LBJCUHLNHSKZBW-XGHQBKJUSA-N
DeepSMILES: COC[C@@H]CcccOC))ccc6[C@@H][C@H]%10COC))))cccccc6)OC)))OC))))))))OCO5
Scaffold Graph/Node/Bond level: c1ccc(C2CCCc3ccc4c(c32)OCO4)cc1
Scaffold Graph/Node level: C1CCC(C2CCCC3CCC4OCOC4C32)CC1
Scaffold Graph level: C1CCC(C2CCCC3CCC4CCCC4C32)CC1
Functional groups: COC; cOC; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
ClassyFire Class: Aryltetralin lignans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans
NP Classifier Class: Arylnaphthalene and aryltetralin lignans
Synonymous chemical names:
hypophyllanthin
External chemical identifiers:
CID:CID_182140; ChEMBL:CHEMBL510130; ZINC:ZINC000015778313; FDASRS:22ZZ21E33P
Chemical structure download


Hypophyllanthin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 430.5
Log P RDKit 3.65
Topological polar surface area (Å2) RDKit 64.61
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 24
Number of heavy atoms RDKit 31
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.12
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 8
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4


Hypophyllanthin
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 Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.63334


Hypophyllanthin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.36
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 Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No