IMPPAT Phytochemical information: 
Dithymoquinone
Dithymoquinone
Summary

SMILES: CC(C1=CC(=O)C2(C(C1=O)C1(C2C(=O)C(=CC1=O)C(C)C)C)C)C
InChI: InChI=1S/C20H24O4/c1-9(2)11-7-13(21)19(5)17(15(11)23)20(6)14(22)8-12(10(3)4)16(24)18(19)20/h7-10,17-18H,1-6H3
InChIKey: FPRGRROJPRIHJP-UHFFFAOYSA-N
DeepSMILES: CCC=CC=O)CCC6=O))CC4C=O)C=CC6=O)))CC)C)))))C)))C)))))C
Scaffold Graph/Node/Bond level: O=C1C=CC(=O)C2C1C1C(=O)C=CC(=O)C21
Scaffold Graph/Node level: OC1CCC(O)C2C1C1C(O)CCC(O)C21
Scaffold Graph level: CC1CCC(C)C2C1C1C(C)CCC(C)C21
Functional groups: CC1=CC(=O)CCC1=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Diterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Diterpenoids
NP Classifier Class: Abeoabietane diterpenoids
Synonymous chemical names:
nigellone, Nigellone, dithymoquinone
External chemical identifiers:
CID:CID_398941
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Dithymoquinone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 328.41
Log P RDKit 2.71
Topological polar surface area (Å2) RDKit 68.28
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 4
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 8
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.6
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
Dithymoquinone
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 0.78
Dithymoquinone
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 -6.83
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No