IMPPAT Phytochemical information: 
Maderone
Maderone
Summary

SMILES: COc1cc(OC)c2c(c1OC)C(=C(C(=O)C2=O)CC(OC(=O)C)C)O
InChI: InChI=1S/C18H20O8/c1-8(26-9(2)19)6-10-15(20)14-13(17(22)16(10)21)11(23-3)7-12(24-4)18(14)25-5/h7-8,20H,6H2,1-5H3
InChIKey: BBMJALGKCLSLAE-UHFFFAOYSA-N
DeepSMILES: COcccOC))ccc6OC)))C=CC=O)C6=O)))CCOC=O)C)))C))))O
Scaffold Graph/Node/Bond level: O=C1C=Cc2ccccc2C1=O
Scaffold Graph/Node level: OC1CCC2CCCCC2C1O
Scaffold Graph level: CC1CCC2CCCCC2C1C
Functional groups: cOC; CC1=C(O)ccC(=O)C1=O; COC(C)=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: Naphthoquinones
Synonymous chemical names:
maderone, 4-naphthaquinone (maderone), Maderone
External chemical identifiers:
CID:CID_90477921
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Maderone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 364.35
Log P RDKit 2.09
Topological polar surface area (Å2) RDKit 108.36
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.06
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.39
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 2
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 2
Maderone
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 Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.603705
Maderone
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.56
Number of PAINS structural alerts SwissADME 2
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes