IMPPAT Phytochemical information: 
6-(1,8-Dihydroxy-6-methylnaphthalen-2-yl)-5-hydroxy-2-methylnaphthalene-1,4-dione

6-(1,8-Dihydroxy-6-methylnaphthalen-2-yl)-5-hydroxy-2-methylnaphthalene-1,4-dione
Summary

SMILES: Cc1cc(O)c2c(c1)ccc(c2O)c1ccc2c(c1O)C(=O)C=C(C2=O)C
InChI: InChI=1S/C22H16O5/c1-10-7-12-3-4-13(21(26)18(12)16(23)8-10)14-5-6-15-19(22(14)27)17(24)9-11(2)20(15)25/h3-9,23,26-27H,1-2H3
InChIKey: AUDXGGMYRPKMIO-UHFFFAOYSA-N
DeepSMILES: CcccO)ccc6)cccc6O))cccccc6O))C=O)C=CC6=O))C
Scaffold Graph/Node/Bond level: O=C1C=CC(=O)c2cc(-c3ccc4ccccc4c3)ccc21
Scaffold Graph/Node level: OC1CCC(O)C2CC(C3CCC4CCCCC4C3)CCC12
Scaffold Graph level: CC1CCC(C)C2CC(C3CCC4CCCCC4C3)CCC12
Functional groups: cO; CC1=CC(=O)ccC1=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Naphthalenes
ClassyFire Subclass: Naphthoquinones
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Naphthalenes
NP Classifier Class: Bisnaphthalenes|Naphthoquinones
Synonymous chemical names:
ebenone
External chemical identifiers:
CID:CID_86103922; ZINC:ZINC000015148896
Chemical structure download


6-(1,8-Dihydroxy-6-methylnaphthalen-2-yl)-5-hydroxy-2-methylnaphthalene-1,4-dione
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 360.37
Log P RDKit 4.26
Topological polar surface area (Å2) RDKit 94.83
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 20
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.09
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 3
Total number of rings RDKit 4
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 4


6-(1,8-Dihydroxy-6-methylnaphthalen-2-yl)-5-hydroxy-2-methylnaphthalene-1,4-dione
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 Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.6


6-(1,8-Dihydroxy-6-methylnaphthalen-2-yl)-5-hydroxy-2-methylnaphthalene-1,4-dione
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -4.88
Number of PAINS structural alerts SwissADME 2
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No