IMPPAT Phytochemical information: 
20-Hydroxyrutacridone epoxide
20-Hydroxyrutacridone epoxide
Summary

SMILES: OCC1(CO1)C1Oc2c(C1)c1c(c(c2)O)c(=O)c2c(n1C)cccc2
InChI: InChI=1S/C19H17NO5/c1-20-12-5-3-2-4-10(12)18(23)16-13(22)7-14-11(17(16)20)6-15(25-14)19(8-21)9-24-19/h2-5,7,15,21-22H,6,8-9H2,1H3
InChIKey: OJJHKXKXZMBCHJ-UHFFFAOYSA-N
DeepSMILES: OCCCO3))COccC5)cccc6)O))c=O)ccn6C))cccc6
Scaffold Graph/Node/Bond level: O=c1c2ccccc2[nH]c2c3c(ccc12)OC(C1CO1)C3
Scaffold Graph/Node level: OC1C2CCCCC2NC2C3CC(C4CO4)OC3CCC12
Scaffold Graph level: CC1C2CCCCC2CC2C3CC(C4CC4)CC3CCC12
Functional groups: CO; CC1(C)CO1; cOC; cO; c=O; cn(C)c
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:
hydroxyrutacridone epoxide
External chemical identifiers:
CID:CID_100916216; ChEBI:CHEBI:174562
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
20-Hydroxyrutacridone epoxide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 339.35
Log P RDKit 1.46
Topological polar surface area (Å2) RDKit 84.22
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.11
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.32
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
20-Hydroxyrutacridone epoxide
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 0.545459
20-Hydroxyrutacridone epoxide
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.80
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
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