IMPPAT Phytochemical information: 
1-Methoxy-2-(3-methylbut-2-en-1-yl)-9H-carbazole-3-carbaldehyde

1-Methoxy-2-(3-methylbut-2-en-1-yl)-9H-carbazole-3-carbaldehyde
Summary

SMILES: O=Cc1cc2c(c(c1CC=C(C)C)OC)[nH]c1c2cccc1
InChI: InChI=1S/C19H19NO2/c1-12(2)8-9-14-13(11-21)10-16-15-6-4-5-7-17(15)20-18(16)19(14)22-3/h4-8,10-11,20H,9H2,1-3H3
InChIKey: FRQNYPFNOITCMV-UHFFFAOYSA-N
DeepSMILES: O=Ccccccc6CC=CC)C)))))OC)))[nH]cc5cccc6
Scaffold Graph/Node/Bond level: c1ccc2c(c1)[nH]c1ccccc12
Scaffold Graph/Node level: C1CCC2C(C1)NC1CCCCC12
Scaffold Graph level: C1CCC2C(C1)CC1CCCCC12
Functional groups: cC=O; CC=C(C)C; cOC; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Carbazoles
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Carbazole alkaloids
Synonymous chemical names:
indizoline
External chemical identifiers:
CID:CID_14282362; ZINC:ZINC000014516916
Chemical structure download


1-Methoxy-2-(3-methylbut-2-en-1-yl)-9H-carbazole-3-carbaldehyde
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 293.37
Log P RDKit 4.65
Topological polar surface area (Å2) RDKit 42.09
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 22
Number of heteroatoms RDKit 3
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 4
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-Methoxy-2-(3-methylbut-2-en-1-yl)-9H-carbazole-3-carbaldehyde
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 Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.56


1-Methoxy-2-(3-methylbut-2-en-1-yl)-9H-carbazole-3-carbaldehyde
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly 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 Yes
P-glycoprotein substrate SwissADME No