IMPPAT Phytochemical information: 
Isosophoranone

Isosophoranone
Summary

SMILES: COc1c(ccc(c1CC=C(C)C)O)C1COc2c(C1=O)c(O)c(c(c2)O)CC=C(C)C
InChI: InChI=1S/C26H30O6/c1-14(2)6-8-17-21(28)12-22-23(24(17)29)25(30)19(13-32-22)16-10-11-20(27)18(26(16)31-5)9-7-15(3)4/h6-7,10-12,19,27-29H,8-9,13H2,1-5H3
InChIKey: ARNVYCOTFWJTBS-UHFFFAOYSA-N
DeepSMILES: COcccccc6CC=CC)C)))))O))))CCOccC6=O))cO)ccc6)O))CC=CC)C
Scaffold Graph/Node/Bond level: O=C1c2ccccc2OCC1c1ccccc1
Scaffold Graph/Node level: OC1C(C2CCCCC2)COC2CCCCC21
Scaffold Graph level: CC1C2CCCCC2CCC1C1CCCCC1
Functional groups: cOC; CC=C(C)C; cO; cC(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Isoflavonoids
ClassyFire Subclass: Isoflavans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Isoflavonoids
NP Classifier Class: Isoflavanones
Synonymous chemical names:
Isosophoranone, isosophoranone
External chemical identifiers:
CID:CID_10478290; ChEMBL:CHEMBL3747601; MolPort-028-610-188
Chemical structure download


Isosophoranone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 438.52
Log P RDKit 5.19
Topological polar surface area (Å2) RDKit 96.22
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 26
Number of heavy atoms RDKit 32
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.04
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 17
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.35
Number of rotatable bonds RDKit 6
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 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


Isosophoranone
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.54


Isosophoranone
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly 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 -4.45
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
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