IMPPAT Phytochemical information: 
2-Methoxy-1-(9H-pyrido(3,4-b)indol-1-yl)ethanone

2-Methoxy-1-(9H-pyrido(3,4-b)indol-1-yl)ethanone
Summary

SMILES: COCC(=O)c1nccc2c1[nH]c1c2cccc1
InChI: InChI=1S/C14H12N2O2/c1-18-8-12(17)14-13-10(6-7-15-14)9-4-2-3-5-11(9)16-13/h2-7,16H,8H2,1H3
InChIKey: KGXNMZDNPKYEHN-UHFFFAOYSA-N
DeepSMILES: COCC=O)cncccc6[nH]cc5cccc6
Scaffold Graph/Node/Bond level: c1ccc2c(c1)[nH]c1cnccc12
Scaffold Graph/Node level: C1CCC2C(C1)NC1CNCCC12
Scaffold Graph level: C1CCC2C(C1)CC1CCCCC12
Functional groups: COC; cC(C)=O; cnc; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Harmala alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Carboline alkaloids
Synonymous chemical names:
arenarine a
External chemical identifiers:
CID:CID_183645
Chemical structure download


2-Methoxy-1-(9H-pyrido(3,4-b)indol-1-yl)ethanone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 240.26
Log P RDKit 2.55
Topological polar surface area (Å2) RDKit 54.98
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 14
Number of heavy atoms RDKit 18
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 2
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 12
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.14
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 2
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


2-Methoxy-1-(9H-pyrido(3,4-b)indol-1-yl)ethanone
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 0.715629


2-Methoxy-1-(9H-pyrido(3,4-b)indol-1-yl)ethanone
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.19
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No