IMPPAT Phytochemical information: 
Toddacoumaquinone
Toddacoumaquinone
Summary

SMILES: COC1=CC(=O)c2c(C1=O)c(cc(c2)C)c1c(OC)cc(c2c1oc(=O)cc2)OC
InChI: InChI=1S/C23H18O7/c1-11-7-13-15(24)9-18(29-4)22(26)20(13)14(8-11)21-17(28-3)10-16(27-2)12-5-6-19(25)30-23(12)21/h5-10H,1-4H3
InChIKey: SQTLGMZYHSFVGI-UHFFFAOYSA-N
DeepSMILES: COC=CC=O)ccC6=O))cccc6)C)))ccOC))cccc6oc=O)cc6))))))OC
Scaffold Graph/Node/Bond level: O=C1C=CC(=O)c2c1cccc2-c1cccc2ccc(=O)oc12
Scaffold Graph/Node level: OC1CCC2CCCC(C3CCCC4C(O)CCC(O)C43)C2O1
Scaffold Graph level: CC1CCC2CCCC(C3CCCC4C(C)CCC(C)C43)C2C1
Functional groups: COC1=CC(=O)ccC1=O; cOC; coc; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Naphthalenes
ClassyFire Subclass: Naphthoquinones
NP Classifier Biosynthetic pathway: Polyketides|Shikimates and Phenylpropanoids
NP Classifier Superclass: Naphthalenes|Coumarins
NP Classifier Class: Naphthoquinones|Simple coumarins
Synonymous chemical names:
toddacoumaquinone, Toddacoumaquinone
External chemical identifiers:
CID:CID_10046907; ChEMBL:CHEMBL3236000; MolPort-044-754-148
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Toddacoumaquinone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 406.39
Log P RDKit 3.69
Topological polar surface area (Å2) RDKit 92.04
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 30
Number of heteroatoms RDKit 7
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 19
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.17
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
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
Toddacoumaquinone
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 0.61
Toddacoumaquinone
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
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 -6.26
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 1
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