IMPPAT Phytochemical information: 
Chitranone
Chitranone
Summary

SMILES: O=C1C(=CC(=O)c2c1ccc(c2O)C1=C(C)C(=O)c2c(C1=O)c(O)ccc2)C
InChI: InChI=1S/C22H14O6/c1-9-8-15(24)18-13(19(9)25)7-6-12(21(18)27)16-10(2)20(26)11-4-3-5-14(23)17(11)22(16)28/h3-8,23,27H,1-2H3
InChIKey: ITGPISXKMZIRAV-UHFFFAOYSA-N
DeepSMILES: O=CC=CC=O)cc6cccc6O))C=CC)C=O)ccC6=O))cO)ccc6))))))))))))))))C
Scaffold Graph/Node/Bond level: O=C1C=CC(=O)c2cc(C3=CC(=O)c4ccccc4C3=O)ccc21
Scaffold Graph/Node level: OC1CCC(O)C2CC(C3CC(O)C4CCCCC4C3O)CCC12
Scaffold Graph level: CC1CCC(C)C2CC(C3CC(C)C4CCCCC4C3C)CCC12
Functional groups: CC1=CC(=O)ccC1=O; cO; cC1=C(C)C(=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:
chitranone (binapthoquinone), 1,2-dihydro-1(s),5,5'-trihydroxy-2'-3( r )-dimethyl-2( r )-propyl-3,8'-bisnaphthalene-1',4'4'-trione (chitranone), chitranone
External chemical identifiers:
CID:CID_633072; ChEMBL:CHEMBL470658; ZINC:ZINC000044417732
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Chitranone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 374.35
Log P RDKit 3.28
Topological polar surface area (Å2) RDKit 108.74
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 6
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 2
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
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
Chitranone
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 0.79
Chitranone
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately 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 -5.92
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 Yes
P-glycoprotein substrate SwissADME No