IMPPAT Phytochemical information: 
Scabequinone

Scabequinone
Summary

SMILES: CC([C@@H]1COC2=C(C1)C(=O)c1c(C2=O)occ1C)C
InChI: InChI=1S/C15H16O4/c1-7(2)9-4-10-12(16)11-8(3)5-18-15(11)13(17)14(10)19-6-9/h5,7,9H,4,6H2,1-3H3/t9-/m0/s1
InChIKey: SXLMNABKMWMBRO-VIFPVBQESA-N
DeepSMILES: CC[C@@H]COC=CC6)C=O)ccC6=O))occ5C))))))))))))C
Scaffold Graph/Node/Bond level: O=C1C2=C(OCCC2)C(=O)c2occc21
Scaffold Graph/Node level: OC1C2CCCOC2C(O)C2OCCC12
Scaffold Graph level: CC1C2CCCCC2C(C)C2CCCC12
Functional groups: COC1=C(C)C(=O)ccC1=O; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbonyl compounds
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesquiterpenoids
NP Classifier Class: Cadinane sesquiterpenoids
Synonymous chemical names:
Scabequinone, scabequinone
External chemical identifiers:
CID:CID_10801302; ZINC:ZINC000137474527
Chemical structure download


Scabequinone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 260.29
Log P RDKit 2.91
Topological polar surface area (Å2) RDKit 56.51
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 1
Stereochemical complexity RDKit 0.07
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.47
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 3
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 3


Scabequinone
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 0.778643


Scabequinone
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
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 -5.74
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 Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No