IMPPAT Phytochemical information: 
2-Benzyl-1,3-dihydroxyanthracene-9,10-dione
2-Benzyl-1,3-dihydroxyanthracene-9,10-dione
Summary

SMILES: Oc1cc2C(=O)c3ccccc3C(=O)c2c(c1Cc1ccccc1)O
InChI: InChI=1S/C21H14O4/c22-17-11-16-18(20(24)14-9-5-4-8-13(14)19(16)23)21(25)15(17)10-12-6-2-1-3-7-12/h1-9,11,22,25H,10H2
InChIKey: FQURQNLGRCILOM-UHFFFAOYSA-N
DeepSMILES: OcccC=O)cccccc6C=O)c%10cc%14Ccccccc6))))))))O
Scaffold Graph/Node/Bond level: O=C1c2ccccc2C(=O)c2cc(Cc3ccccc3)ccc21
Scaffold Graph/Node level: OC1C2CCCCC2C(O)C2CC(CC3CCCCC3)CCC12
Scaffold Graph level: CC1C2CCCCC2C(C)C2CC(CC3CCCCC3)CCC12
Functional groups: cO; cC(=O)c
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:
2-benzylxanthopurpurin
External chemical identifiers:
CID:CID_630215; ZINC:ZINC000013376419
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
2-Benzyl-1,3-dihydroxyanthracene-9,10-dione
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 330.34
Log P RDKit 3.46
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 21
Number of heavy atoms RDKit 25
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 20
Number of sp3 hybridized carbon atoms RDKit 1
Shape complexity RDKit 0.05
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 0
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
2-Benzyl-1,3-dihydroxyanthracene-9,10-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 0.59
2-Benzyl-1,3-dihydroxyanthracene-9,10-dione
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.03
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No