IMPPAT Phytochemical information: 
2,10a-Dihydro-8,10a-dihydroxy-3,11-dimethyl-1H-cyclopent(b)anthracene-5,10-dione
2,10a-Dihydro-8,10a-dihydroxy-3,11-dimethyl-1H-cyclopent(b)anthracene-5,10-dione
Summary

SMILES: Oc1ccc2c(c1)C(=O)C1(C(=CC3=C(CCC3=C1C)C)C2=O)O
InChI: InChI=1S/C19H16O4/c1-9-3-5-12-10(2)19(23)16(8-14(9)12)17(21)13-6-4-11(20)7-15(13)18(19)22/h4,6-8,20,23H,3,5H2,1-2H3
InChIKey: KPVZBJKXSXYQCW-UHFFFAOYSA-N
DeepSMILES: Occcccc6)C=O)CC=CC=CCCC5=C9C)))))C))))C6=O)))O
Scaffold Graph/Node/Bond level: O=C1C2=CC3=CCCC3=CC2C(=O)c2ccccc21
Scaffold Graph/Node level: OC1C2CCCCC2C(O)C2CC3CCCC3CC12
Scaffold Graph level: CC1C2CCCCC2C(C)C2CC3CCCC3CC12
Functional groups: cO; cC(=O)C; cC(=O)C1=CC2=C(C)CCC2=C(C)C1; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Anthracenes
ClassyFire Subclass: Anthraquinones
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Polycyclic aromatic polyketides
NP Classifier Class: Anthraquinones and anthrones
Synonymous chemical names:
kigelinol, Kigelinol
External chemical identifiers:
CID:CID_127683; ChEMBL:CHEMBL485983
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
2,10a-Dihydro-8,10a-dihydroxy-3,11-dimethyl-1H-cyclopent(b)anthracene-5,10-dione
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 308.33
Log P RDKit 2.87
Topological polar surface area (Å2) RDKit 74.6
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 23
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 0.05
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 14
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.26
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
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
2,10a-Dihydro-8,10a-dihydroxy-3,11-dimethyl-1H-cyclopent(b)anthracene-5,10-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 Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.77
2,10a-Dihydro-8,10a-dihydroxy-3,11-dimethyl-1H-cyclopent(b)anthracene-5,10-dione
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 -7.36
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes