IMPPAT Phytochemical information: 
Isohernandin

Isohernandin
Summary

SMILES: COc1cc(cc(c1OC)OC)[C@@H]1[C@H]2C(=O)OC[C@@H]2Cc2c1c(OC)c1c(c2)OCO1
InChI: InChI=1S/C23H24O8/c1-25-14-6-12(7-15(26-2)20(14)27-3)17-18-11(5-13-9-29-23(24)19(13)17)8-16-21(22(18)28-4)31-10-30-16/h6-8,13,17,19H,5,9-10H2,1-4H3/t13-,17-,19-/m0/s1
InChIKey: SXYMZPDEDWTMMB-IXDGSTSKSA-N
DeepSMILES: COcccccc6OC)))OC))))[C@@H][C@H]C=O)OC[C@@H]5Ccc9cOC))ccc6)OCO5
Scaffold Graph/Node/Bond level: O=C1OCC2Cc3cc4c(cc3C(c3ccccc3)C12)OCO4
Scaffold Graph/Node level: OC1OCC2CC3CC4OCOC4CC3C(C3CCCCC3)C21
Scaffold Graph level: CC1CCC2CC3CC4CCCC4CC3C(C3CCCCC3)C12
Functional groups: cOC; COC(=O)C; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
ClassyFire Class: Lignan lactones
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans
NP Classifier Class: Arylnaphthalene and aryltetralin lignans
Synonymous chemical names:
isohernandin
External chemical identifiers:
CID:CID_14283388
Chemical structure download


Isohernandin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 428.44
Log P RDKit 2.93
Topological polar surface area (Å2) RDKit 81.68
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 31
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.13
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.43
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
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 5


Isohernandin
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 Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.672787


Isohernandin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.60
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 Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No