IMPPAT Phytochemical information: 
Arborinine

Arborinine
Summary

SMILES: COc1cc2c(c(c1OC)O)c(=O)c1c(n2C)cccc1
InChI: InChI=1S/C16H15NO4/c1-17-10-7-5-4-6-9(10)14(18)13-11(17)8-12(20-2)16(21-3)15(13)19/h4-8,19H,1-3H3
InChIKey: ATBZZQPALSPNMF-UHFFFAOYSA-N
DeepSMILES: COcccccc6OC)))O))c=O)ccn6C))cccc6
Scaffold Graph/Node/Bond level: O=c1c2ccccc2[nH]c2ccccc12
Scaffold Graph/Node level: OC1C2CCCCC2NC2CCCCC21
Scaffold Graph level: CC1C2CCCCC2CC2CCCCC21
Functional groups: 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:
arborinine, 2,3-dimethoxy-1-hydroxy-10-methylacridone(arborinine)
External chemical identifiers:
CID:CID_5281832; ChEMBL:CHEMBL349609; ChEBI:CHEBI:2804; ZINC:ZINC000005783606; FDASRS:16XG8UE639; SureChEMBL:SCHEMBL1663913; MolPort-005-981-218
Chemical structure download


Arborinine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 285.3
Log P RDKit 2.41
Topological polar surface area (Å2) RDKit 60.69
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 21
Number of heteroatoms RDKit 5
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 13
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.19
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


Arborinine
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 Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.734522


Arborinine
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 -5.73
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
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