IMPPAT Phytochemical information: 
Donaxarine

Donaxarine
Summary

SMILES: CN1CCC2(OC1C)C(=O)Nc1c2cccc1
InChI: InChI=1S/C13H16N2O2/c1-9-15(2)8-7-13(17-9)10-5-3-4-6-11(10)14-12(13)16/h3-6,9H,7-8H2,1-2H3,(H,14,16)
InChIKey: YHAQQFNSEZLLPM-UHFFFAOYSA-N
DeepSMILES: CNCCCOC6C)))C=O)Ncc5cccc6
Scaffold Graph/Node/Bond level: O=C1Nc2ccccc2C12CCNCO2
Scaffold Graph/Node level: OC1NC2CCCCC2C12CCNCO2
Scaffold Graph level: CC1CC2CCCCC2C12CCCCC2
Functional groups: COC(C)N(C)C; cNC(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Indolines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Simple oxindole alkaloids
Synonymous chemical names:
donaxerine, donaxarine
External chemical identifiers:
CID:CID_10955426
Chemical structure download


Donaxarine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 232.28
Log P RDKit 1.53
Topological polar surface area (Å2) RDKit 41.57
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 13
Number of heavy atoms RDKit 17
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.15
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.46
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 3
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 3


Donaxarine
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 0.74


Donaxarine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.81
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes