IMPPAT Phytochemical information: 
Isoshinanolone

Isoshinanolone
Summary

SMILES: C[C@@H]1CC(=O)c2c([C@@H]1O)cccc2O
InChI: InChI=1S/C11H12O3/c1-6-5-9(13)10-7(11(6)14)3-2-4-8(10)12/h2-4,6,11-12,14H,5H2,1H3/t6-,11-/m1/s1
InChIKey: YUPNHTWYVBHLMG-KSBSHMNSSA-N
DeepSMILES: C[C@@H]CC=O)cc[C@@H]6O))cccc6O
Scaffold Graph/Node/Bond level: O=C1CCCc2ccccc21
Scaffold Graph/Node level: OC1CCCC2CCCCC12
Scaffold Graph level: CC1CCCC2CCCCC12
Functional groups: CO; cC(=O)C; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Tetralins
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Naphthalenes
NP Classifier Class: Naphthoquinones
Synonymous chemical names:
isoshinanolone, Isoshinanolone
External chemical identifiers:
CID:CID_443777; ChEMBL:CHEMBL2023569; ChEBI:CHEBI:31733
Chemical structure download


Isoshinanolone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 192.21
Log P RDKit 1.65
Topological polar surface area (Å2) RDKit 57.53
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 11
Number of heavy atoms RDKit 14
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.18
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.36
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 2
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 2


Isoshinanolone
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.656681


Isoshinanolone
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.38
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No