IMPPAT Phytochemical information: 
Epoxysuberosin

Epoxysuberosin
Summary

SMILES: COc1cc2oc(=O)ccc2cc1[C@@H]1OC1(C)C
InChI: InChI=1S/C14H14O4/c1-14(2)13(18-14)9-6-8-4-5-12(15)17-10(8)7-11(9)16-3/h4-7,13H,1-3H3/t13-/m0/s1
InChIKey: ACDYKNCYYMDLKV-ZDUSSCGKSA-N
DeepSMILES: COcccoc=O)ccc6cc%10[C@@H]OC3C)C
Scaffold Graph/Node/Bond level: O=c1ccc2cc(C3CO3)ccc2o1
Scaffold Graph/Node level: OC1CCC2CC(C3CO3)CCC2O1
Scaffold Graph level: CC1CCC2CC(C3CC3)CCC2C1
Functional groups: cOC; coc; c=O; c[C@@H]1OC1(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Coumarins and derivatives
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Pyranocoumarins|Simple coumarins
Synonymous chemical names:
epoxysuberosin
External chemical identifiers:
CID:CID_101119215
Chemical structure download


Epoxysuberosin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 246.26
Log P RDKit 2.65
Topological polar surface area (Å2) RDKit 51.97
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 14
Number of heavy atoms RDKit 18
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.07
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.36
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
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 3


Epoxysuberosin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
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 Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.6


Epoxysuberosin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.41
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No