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3-[(Dimethylamino)methyl]indole

AlkaPlorer ID: AK002645

Synonym: N,N-Dimethyl-1H-indole-3-methanamine, Gramine, Donaxine, Doranine 

IUPAC Name: 1-(1H-indol-1-ium-3-yl)-N,N-dimethylmethanamine

Structure

SMILES: CN(C)CC1=C[NH2+]C2=CC=CC=C12

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InChI: InChI=1S/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3/p+1

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InChIKey: OCDGBSUVYYVKQZ-UHFFFAOYSA-O

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Hordeum vulgare Hordeum Poaceae Poales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Dioscorea althaeoides Dioscorea Dioscoreaceae Dioscoreales Magnoliopsida Streptophyta Viridiplantae Eukaryota
None Desmodium Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Dioscorea zingiberensis Dioscorea Dioscoreaceae Dioscoreales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Arundo donax Arundo Poaceae Poales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Smilax china Smilax Smilacaceae Liliales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Dioscorea septemloba Dioscorea Dioscoreaceae Dioscoreales Magnoliopsida Streptophyta Viridiplantae Eukaryota
None Lupinus Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Dioscorea parviflora Dioscorea Dioscoreaceae Dioscoreales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Tribulus terrestris Tribulus Zygophyllaceae Zygophyllales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Acer rubrum Acer Sapindaceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Dioscorea futschauensis Dioscorea Dioscoreaceae Dioscoreales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Brassica oleracea Brassica Brassicaceae Brassicales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Dioscorea gracillima Dioscorea Dioscoreaceae Dioscoreales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Acer saccharinum Acer Sapindaceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Loropetalum chinense Loropetalum Hamamelidaceae Saxifragales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Phalaris arundinacea Phalaris Poaceae Poales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 175.255

TPSA？: 19.85

MolLogP？: 0.7976

Number of H-Donors: 1

Number of H-Acceptors: 1

RingCount: 2

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bacillus anthracis Anthrax lethal factor Potency 31622.8 nM None
Caenorhabditis elegans Caenorhabditis elegans Activity 2.0 % 10.1038/nature05991
Caenorhabditis elegans Caenorhabditis elegans Activity 3.0 % 10.1038/nature05991
Electrophorus electricus Acetylcholinesterase Inhibition 15.3 % 10.1016/j.bmc.2012.09.040
Equus caballus Cholinesterase Inhibition 10.59 % 10.1016/j.bmc.2012.09.040
Homo sapiens Aldehyde dehydrogenase 1A1 Potency 15848.9 nM None
Homo sapiens Aldehyde dehydrogenase 1A1 Potency 39810.7 nM None
Homo sapiens BGC-823 IC50 62.8 ug.mL-1 10.1016/j.ejmech.2012.05.003
Homo sapiens Bromodomain adjacent to zinc finger domain protein 2B Potency 707.9 nM None
Homo sapiens Cytochrome P450 1A2 AC50 nan None None
Homo sapiens Cytochrome P450 2C19 AC50 nan None None
Homo sapiens Cytochrome P450 2C19 Potency 31622.8 nM None
Homo sapiens Cytochrome P450 2C9 AC50 nan None None
Homo sapiens Cytochrome P450 2D6 AC50 158.49 nM None
Homo sapiens Cytochrome P450 2D6 Potency 158.5 nM None
Homo sapiens Cytochrome P450 2D6 Potency 10000.0 nM None
Homo sapiens Cytochrome P450 3A4 AC50 3162.28 nM None
Homo sapiens Cytochrome P450 3A4 Potency 3162.3 nM None
Homo sapiens Cytochrome P450 3A4 Potency 15848.9 nM None
Homo sapiens Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Potency 31622.8 nM None
Homo sapiens HepG2 IC50 100.0 ug.mL-1 10.1016/j.ejmech.2012.05.003
Homo sapiens Lysine-specific demethylase 4D-like Potency 31622.8 nM None
Homo sapiens Menin/Histone-lysine N-methyltransferase MLL Potency 39810.7 nM None
Homo sapiens NCI-H460 IC50 74.5 ug.mL-1 10.1016/j.ejmech.2012.05.003
Homo sapiens Nuclear factor erythroid 2-related factor 2 Potency 6513.1 nM None
Homo sapiens SGC-7901 IC50 77.3 ug.mL-1 10.1016/j.ejmech.2012.05.003
Homo sapiens SH-SY5Y Activity 45.0 % 10.1021/acs.jmedchem.6b00478
Homo sapiens Thyroid stimulating hormone receptor Potency 15848.9 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 10322.5 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 11582.1 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 12995.3 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 29855.4 nM None
Homo sapiens Voltage-gated calcium channel Inhibition 25.0 % 10.1021/acs.jmedchem.6b00478
Plasmodium falciparum Plasmodium falciparum Potency 8275.3 nM None
Plasmodium falciparum Plasmodium falciparum Potency 9285.0 nM None
Rattus norvegicus Cortical neurone Activity 0.0 % 10.1021/acs.jmedchem.6b00478
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 19952.62 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 20000.0 nM 10.6019/CHEMBL4651402
None Unchecked Activity 76.0 % 10.1021/acs.jmedchem.6b00478
None Unchecked Activity 80.0 % 10.1021/acs.jmedchem.6b00478
None Unchecked Inhibition nan % 10.1021/acs.jmedchem.6b00478
None Unchecked Potency 2238.7 nM None
None Unchecked Potency 12589.3 nM None

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT010774 CNCc1c[nH]c2ccccc12.C[SAH]>>CN(C)Cc1c[nH]c2ccccc12 RXN-8687
AKRT014598 C[SAH].C[SAH].NCc1c[nH]c2ccccc12>>CN(C)Cc1c[nH]c2ccccc12 RXN-18224