IMPPAT Phytochemical information: 
Phebalosin

Phebalosin
Summary

SMILES: COc1ccc2c(c1[C@H]1O[C@@H]1C(=C)C)oc(=O)cc2
InChI: InChI=1S/C15H14O4/c1-8(2)13-15(19-13)12-10(17-3)6-4-9-5-7-11(16)18-14(9)12/h4-7,13,15H,1H2,2-3H3/t13-,15-/m1/s1
InChIKey: YTDNHMHONBWCBV-UKRRQHHQSA-N
DeepSMILES: COcccccc6[C@H]O[C@@H]3C=C)C))))))oc=O)cc6
Scaffold Graph/Node/Bond level: O=c1ccc2cccc(C3CO3)c2o1
Scaffold Graph/Node level: OC1CCC2CCCC(C3CO3)C2O1
Scaffold Graph level: CC1CCC2CCCC(C3CC3)C2C1
Functional groups: cOC; c[C@H]1O[C@@H]1C(=C)C; coc; c=O
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: Simple coumarins
Synonymous chemical names:
Phebalosin, phebalosin, phebalosin [7-methoxy-8-(1,2-epoxy-3-methyl-3-butenyl)coumarin]
External chemical identifiers:
CID:CID_188300; ChEMBL:CHEMBL486409; ZINC:ZINC000005158373; FDASRS:57637245VY; MolPort-035-705-769
Chemical structure download


Phebalosin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 258.27
Log P RDKit 2.82
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 15
Number of heavy atoms RDKit 19
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.13
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.27
Number of rotatable bonds RDKit 3
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


Phebalosin
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 0.482337


Phebalosin
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 -6.00
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 3
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