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5-Methoxytryptamine

AlkaPlorer ID: AK011873

Synonym: 5-Methoxy-1H-indole-3-ethanamine, 3-(2-Aminoethyl)-5-methoxyindole 

IUPAC Name: 2-(5-methoxy-1H-indol-3-yl)ethanamine

Structure

SMILES: COC1=CC=C2NC=C(CCN)C2=C1

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InChI: InChI=1S/C11H14N2O/c1-14-9-2-3-11-10(6-9)8(4-5-12)7-13-11/h2-3,6-7,13H,4-5,12H2,1H3

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InChIKey: JTEJPPKMYBDEMY-UHFFFAOYSA-N

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Properties Information

Molecule Weight: 190.24599999999995

TPSA？: 51.04

MolLogP？: 1.6777

Number of H-Donors: 2

Number of H-Acceptors: 2

RingCount: 2

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Acinetobacter baumannii Acinetobacter baumannii Inhibition 13.31 % 10.6019/CHEMBL4513141
Acinetobacter baumannii Acinetobacter baumannii MIC 60.8 ug.mL-1 10.1016/j.bmcl.2016.10.004
Bacillus subtilis Bacillus subtilis MIC 60.8 ug.mL-1 10.1016/j.bmcl.2016.10.004
Candida albicans Candida albicans Inhibition 3.97 % 10.6019/CHEMBL4513141
Cryptococcus neoformans Cryptococcus neoformans Inhibition -39.41 % 10.6019/CHEMBL4513141
Electrophorus electricus Acetylcholinesterase Inhibition 7.19 % 10.1016/j.bmcl.2012.02.057
Escherichia coli Escherichia coli Inhibition -0.18 % 10.6019/CHEMBL4513141
Escherichia coli Escherichia coli MIC 60.8 ug.mL-1 10.1016/j.bmcl.2016.10.004
Homo sapiens Acetylcholinesterase IC50 nan None 10.1016/j.bmcl.2012.02.057
Homo sapiens Acetylcholinesterase Inhibition 14.68 % 10.1016/j.bmcl.2012.02.057
Homo sapiens Bromodomain adjacent to zinc finger domain protein 2B Potency 70794.6 nM None
Homo sapiens Cytochrome P450 1A2 AC50 1584.89 nM None
Homo sapiens Cytochrome P450 2C19 AC50 nan None None
Homo sapiens Cytochrome P450 2C9 AC50 nan None None
Homo sapiens Cytochrome P450 2D6 AC50 nan None None
Homo sapiens Cytochrome P450 3A4 AC50 nan None None
Homo sapiens DNA polymerase iota Potency 89125.1 nM None
Homo sapiens Dopamine D1 receptor Potency 18356.4 nM None
Homo sapiens HEK293 Potency 1457.5 nM None
Homo sapiens Lysine-specific demethylase 4A Potency 50118.7 nM None
Homo sapiens Microtubule-associated protein tau Potency 14125.4 nM None
Homo sapiens Nuclear factor NF-kappa-B p105 subunit Potency 5011.9 nM None
Homo sapiens POU domain, class 2, transcription factor 1 Ratio 3.8 None 10.1021/acs.jmedchem.2c01075
Homo sapiens POU domain, class 2, transcription factor 2 Ratio 7.1 None 10.1021/acs.jmedchem.2c01075
Homo sapiens Serotonin 1a (5-HT1a) receptor Ki 3.2 nM 10.1021/jm950498t
Homo sapiens Serotonin 1b (5-HT1b) receptor Ki 3.5 nM 10.1021/jm950498t
Homo sapiens Serotonin 1d (5-HT1d) receptor Ki 4.1 nM 10.1021/jm950498t
Homo sapiens Serotonin 1d (5-HT1d) receptor Ki 5.4 nM 10.1021/jm950498t
Homo sapiens Serotonin 1d (5-HT1d) receptor Selectivity 1.5 None 10.1021/jm950498t
Homo sapiens Serotonin 2a (5-HT2a) receptor EC50 0.503 nM 10.1016/j.bmcl.2014.07.062
Homo sapiens Serotonin 2a (5-HT2a) receptor Emax 119.0 % 10.1016/j.bmcl.2014.07.062
Homo sapiens Serotonin 2a (5-HT2a) receptor Ki 4.8 nM 10.1021/jm00039a004
Homo sapiens Serotonin 2a (5-HT2a) receptor Ki 300.0 nM 10.1021/jm00039a004
Homo sapiens Serotonin 2c (5-HT2c) receptor Ki 45.0 nM 10.1021/jm00384a001
Homo sapiens Serotonin 2c (5-HT2c) receptor Ratio 104.0 None 10.1021/jm00039a004
Homo sapiens Serotonin 4 (5-HT4) receptor Activity 100.0 % 10.1016/j.ejmech.2009.01.015
Homo sapiens Serotonin 4 (5-HT4) receptor Ki 26.92 nM 10.1016/j.ejmech.2009.01.015
Homo sapiens Serotonin 4 (5-HT4) receptor Ki 245.47 nM 10.1016/j.ejmech.2009.01.015
Homo sapiens Serotonin 6 (5-HT6) receptor Ki 50.0 nM 10.1021/jm049615n
Homo sapiens Serotonin 6 (5-HT6) receptor Ki 88.0 nM 10.1021/jm990550b
Homo sapiens Serotonin 7 (5-HT7) receptor Ki 2.0 nM 10.1021/jm030030n
Homo sapiens Serotonin 7 (5-HT7) receptor Ki 5.012 nM 10.1016/j.ejmech.2019.111705
Homo sapiens Solute carrier family 22 member 3 Ratio 2.2 None 10.1021/acs.jmedchem.2c01075
Homo sapiens Solute carrier organic anion transporter family member 1B1 Inhibition 59.83 % 10.1124/mol.112.084152
Homo sapiens Solute carrier organic anion transporter family member 1B3 Inhibition 73.24 % 10.1124/mol.112.084152
Homo sapiens Thyroid stimulating hormone receptor Potency 39810.7 nM None
Homo sapiens Transient receptor potential cation channel subfamily M member 8 IC50 11600.0 nM 10.1016/j.bmcl.2010.09.099
Homo sapiens Transient receptor potential cation channel subfamily M member 8 IC50 12400.0 nM 10.1016/j.bmcl.2010.09.099
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 16360.1 nM None
Influenza A virus Nonstructural protein 1 Potency 316.2 nM None
Klebsiella pneumoniae Klebsiella pneumoniae Inhibition 5.41 % 10.6019/CHEMBL4513141
Plasmodium falciparum Plasmodium falciparum Activity 14.1 % 10.1016/j.ejmech.2014.03.055
Plasmodium falciparum Plasmodium falciparum Activity 19.7 % 10.1016/j.ejmech.2014.03.055
Plasmodium falciparum Plasmodium falciparum Potency 14715.7 nM None
Pseudomonas aeruginosa Pseudomonas aeruginosa Inhibition -13.25 % 10.6019/CHEMBL4513141
Rattus norvegicus Dopamine transporter EC50 11031.0 nM 10.1016/j.bmcl.2014.07.062
Rattus norvegicus Norepinephrine transporter EC50 10000.0 nM 10.1016/j.bmcl.2014.07.062
Rattus norvegicus Serotonin 1 (5-HT1) receptor Ki 2.0 nM 10.1021/jm00384a001
Rattus norvegicus Serotonin 1a (5-HT1a) receptor Ki 3.2 nM 10.1021/jm00128a039
Rattus norvegicus Serotonin 1a (5-HT1a) receptor Ki 3.2 nM 10.1021/jm00399a031
Rattus norvegicus Serotonin 1a (5-HT1a) receptor Ki 5.0 nM 10.1021/jm00172a016
Rattus norvegicus Serotonin 1a (5-HT1a) receptor Ki 9.0 nM 10.1021/jm00384a001
Rattus norvegicus Serotonin 1a (5-HT1a) receptor Ki 10.72 nM 10.1021/jm950410b
Rattus norvegicus Serotonin 1b (5-HT1b) receptor Ki 4.0 nM 10.1021/jm00399a031
Rattus norvegicus Serotonin 1b (5-HT1b) receptor Ki 6.457 nM 10.1021/jm00402a026
Rattus norvegicus Serotonin 1b (5-HT1b) receptor Ki 400.0 nM 10.1021/jm00384a001
Rattus norvegicus Serotonin 2 (5-HT2) receptor Ki 4.8 nM 10.1021/jm00399a031
Rattus norvegicus Serotonin 2 (5-HT2) receptor Ki 14.0 nM 10.1021/jm00384a001
Rattus norvegicus Serotonin 2 (5-HT2) receptor Ki 302.0 nM 10.1021/jm00172a016
Rattus norvegicus Serotonin 2 (5-HT2) receptor Ki 305.0 nM 10.1021/jm00399a031
Rattus norvegicus Serotonin 2 (5-HT2) receptor Ki 690.0 nM 10.1021/jm00384a001
Rattus norvegicus Serotonin 2 (5-HT2) receptor Ki 1023.29 nM 10.1021/jm00402a026
Rattus norvegicus Serotonin 2 (5-HT2) receptor Ki 2570.0 nM 10.1021/jm00384a001
Rattus norvegicus Serotonin 2c (5-HT2c) receptor Ki 500.0 nM 10.1021/jm00039a004
Rattus norvegicus Serotonin 7 (5-HT7) receptor Increase nan None 10.1021/jm030826m
Rattus norvegicus Serotonin 7 (5-HT7) receptor Ki 0.9333 nM 10.1021/jm030826m
Rattus norvegicus Serotonin transporter EC50 2169.0 nM 10.1016/j.bmcl.2014.07.062
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 12.01 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -0.05 % 10.6019/CHEMBL4495565
Staphylococcus aureus Staphylococcus aureus Inhibition 3.43 % 10.6019/CHEMBL4513141
Staphylococcus aureus Staphylococcus aureus MIC 60.8 ug.mL-1 10.1016/j.bmcl.2016.10.004
Trypanosoma brucei 6-phospho-1-fructokinase Potency 10.7 nM None
None Unchecked Inhibition -1.9 % 10.1016/j.ejmech.2018.10.027
None Unchecked Ki 45.8 nM 10.1021/np50094a001
None Unchecked Ki 500.0 nM 10.1021/np50094a001
None Unchecked Potency 18356.4 nM None
None Unchecked Potency 25118.9 nM None
None Unchecked Potency 31622.8 nM None
None Unchecked Potency 35481.3 nM None
None Unchecked Ratio 63.0 None 10.1021/jm00039a004
None Unchecked Selectivity 1.0 None 10.1021/jm950498t

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT004387 CC(=O)[32S].COc1ccc2[nH]cc(CCN)c2c1>>COc1ccc2[nH]cc(CCNC(C)=O)c2c1 None
AKRT004562 CC(=O)[CoA].COc1ccc2[nH]cc(CCN)c2c1>>COc1ccc2[nH]cc(CCNC(C)=O)c2c1 66144
AKRT010635 CN1c2c(nc(N)[nH]c2=O)NC[C@@H]1CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1.NCCc1c[nH]c2ccc(O)cc12>>COc1ccc2[nH]cc(CCN)c2c1 R02912
AKRT011855 COc1ccc2[nH]cc(CCN)c2c1>>COc1ccc2[nH]cc(CC=O)c2c1 RXN-11067
AKRT011862 COc1ccc2[nH]cc(CCNC(C)=O)c2c1>>COc1ccc2[nH]cc(CCN)c2c1 RXN-11066
AKRT012647 C[33S].NCCc1c[nH]c2ccc(O)cc12>>COc1ccc2[nH]cc(CCN)c2c1 None
AKRT014654 C[SAH].NCCc1c[nH]c2ccc(O)cc12>>COc1ccc2[nH]cc(CCN)c2c1 enzymemap_27364