IMPPAT Phytochemical information: 
1,3-Dihydroxy-10-methyl-4-(3-methylbut-2-enyl)acridin-9-one
1,3-Dihydroxy-10-methyl-4-(3-methylbut-2-enyl)acridin-9-one
Summary

SMILES: CC(=CCc1c(O)cc(c2c1n(C)c1ccccc1c2=O)O)C
InChI: InChI=1S/C19H19NO3/c1-11(2)8-9-13-15(21)10-16(22)17-18(13)20(3)14-7-5-4-6-12(14)19(17)23/h4-8,10,21-22H,9H2,1-3H3
InChIKey: ZVEGIYHOVGYFQS-UHFFFAOYSA-N
DeepSMILES: CC=CCccO)cccc6nC)cccccc6c%10=O)))))))))))O)))))))C
Scaffold Graph/Node/Bond level: O=c1c2ccccc2[nH]c2ccccc12
Scaffold Graph/Node level: OC1C2CCCCC2NC2CCCCC21
Scaffold Graph level: CC1C2CCCCC2CC2CCCCC21
Functional groups: CC=C(C)C; cO; cn(C)c; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Quinolines and derivatives
ClassyFire Subclass: Benzoquinolines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Anthranilic acid alkaloids
NP Classifier Class: Acridone alkaloids
Synonymous chemical names:
glycocitrine ii, Glycocitrine II
External chemical identifiers:
CID:CID_11781835; ChEMBL:CHEMBL451704
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
1,3-Dihydroxy-10-methyl-4-(3-methylbut-2-enyl)acridin-9-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 309.37
Log P RDKit 3.61
Topological polar surface area (Å2) RDKit 62.46
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 1
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 15
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.21
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
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
1,3-Dihydroxy-10-methyl-4-(3-methylbut-2-enyl)acridin-9-one
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 0.56
1,3-Dihydroxy-10-methyl-4-(3-methylbut-2-enyl)acridin-9-one
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately 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 -4.72
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No