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name Structure Reference Source Properties Activities Metabolism

1-Methyl-β-carboline; 3,4-Dihydro

AlkaPlorer ID: AK019775

Synonym: 4,9-Dihydro-1-methyl-3H-pyrido[3,4-b]indole, 3,4-Dihydro-1-methyl-β-carboline, Harmalan, Dihydroharman 

IUPAC Name: 1-methyl-4,9-dihydro-3H-pyrido[3,4-b]indole

Structure

SMILES: CC1=NCCC2=C1NC1=CC=CC=C21

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InChI: InChI=1S/C12H12N2/c1-8-12-10(6-7-13-8)9-4-2-3-5-11(9)14-12/h2-5,14H,6-7H2,1H3

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InChIKey: CWOYLIJQLSNRRN-UHFFFAOYSA-N

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Properties Information

Molecule Weight: 184.242

TPSA？: 28.15

MolLogP？: 2.5330000000000004

Number of H-Donors: 1

Number of H-Acceptors: 1

RingCount: 3

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bacillus subtilis (strain 168) ATP-dependent Clp protease proteolytic subunit Potency 15848.9 nM None
Bos taurus Dopamine transporter Ki 10000.0 nM 10.1016/j.bmcl.2003.09.027
Escherichia coli K-12 Beta-lactamase AmpC Potency 6309.6 nM None
Homo sapiens Alpha-1a adrenergic receptor Ki nan nM 10.1016/j.bmcl.2003.09.027
Homo sapiens Alpha-1b adrenergic receptor Ki nan nM 10.1016/j.bmcl.2003.09.027
Homo sapiens Alpha-2a adrenergic receptor Ki nan nM 10.1016/j.bmcl.2003.09.027
Homo sapiens Alpha-2b adrenergic receptor Ki nan nM 10.1016/j.bmcl.2003.09.027
Homo sapiens Alpha-2c adrenergic receptor Ki nan nM 10.1016/j.bmcl.2003.09.027
Homo sapiens Beta-1 adrenergic receptor Ki nan nM 10.1016/j.bmcl.2003.09.027
Homo sapiens Beta-2 adrenergic receptor EC50 2770.0 nM None
Homo sapiens Beta-2 adrenergic receptor Ki nan nM 10.1016/j.bmcl.2003.09.027
Homo sapiens Bromodomain adjacent to zinc finger domain protein 2B Potency 35481.3 nM None
Homo sapiens DNA polymerase beta Potency 79432.8 nM None
Homo sapiens Dopamine receptor Ki 10000.0 nM 10.1016/j.bmcl.2003.09.027
Homo sapiens Flap endonuclease 1 Potency 28183.8 nM None
Homo sapiens GTP-binding nuclear protein Ran/Importin subunit beta-1/Snurportin-1 Potency 11582.1 nM None
Homo sapiens H9 IC50 110300.0 nM 10.1021/np0101189
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 44668.4 nM None
Homo sapiens Importin subunit beta-1/Snurportin-1 Potency 63095.7 nM None
Homo sapiens Lysine-specific demethylase 4A Potency 50118.7 nM None
Homo sapiens Lysine-specific demethylase 4D-like Potency 28183.8 nM None
Homo sapiens Menin/Histone-lysine N-methyltransferase MLL Potency 25118.9 nM None
Homo sapiens Microtubule-associated protein tau Potency 12589.3 nM None
Homo sapiens Microtubule-associated protein tau Potency 14125.4 nM None
Homo sapiens Muscarinic acetylcholine receptor Ki 10000.0 nM 10.1016/j.bmcl.2003.09.027
Homo sapiens Nischarin Ki 46.0 nM 10.1016/j.bmcl.2003.09.027
Homo sapiens Nischarin Ki 148.0 nM 10.1016/j.bmcl.2003.09.027
Homo sapiens Norepinephrine transporter Ki 10000.0 nM 10.1016/j.bmcl.2003.09.027
Homo sapiens Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 Potency 19952.6 nM None
Homo sapiens Serotonin 1a (5-HT1a) receptor Ki 1670.0 nM 10.1016/j.bmcl.2003.09.027
Homo sapiens Serotonin 1a (5-HT1a) receptor Ki 1700.0 nM 10.1021/acs.jmedchem.0c01887
Homo sapiens Serotonin 1b (5-HT1b) receptor Ki 10000.0 nM 10.1016/j.bmcl.2003.09.027
Homo sapiens Serotonin 1b (5-HT1b) receptor Ki 10000.0 nM 10.1021/acs.jmedchem.0c01887
Homo sapiens Serotonin 1d (5-HT1d) receptor Ki 10000.0 nM 10.1016/j.bmcl.2003.09.027
Homo sapiens Serotonin 1d (5-HT1d) receptor Ki 10000.0 nM 10.1021/acs.jmedchem.0c01887
Homo sapiens Serotonin 2a (5-HT2a) receptor Ki 990.0 nM 10.1021/acs.jmedchem.0c01887
Homo sapiens Serotonin 2c (5-HT2c) receptor Ki 1860.0 nM 10.1016/j.bmcl.2003.09.027
Homo sapiens Serotonin 2c (5-HT2c) receptor Ki 1900.0 nM 10.1021/acs.jmedchem.0c01887
Homo sapiens Serotonin 3 (5-HT3) receptor Ki 10000.0 nM 10.1016/j.bmcl.2003.09.027
Homo sapiens Serotonin 3a (5-HT3a) receptor Ki 10000.0 nM 10.1021/acs.jmedchem.0c01887
Homo sapiens Serotonin 5a (5-HT5a) receptor Ki 845.0 nM 10.1016/j.bmcl.2003.09.027
Homo sapiens Serotonin 5a (5-HT5a) receptor Ki 850.0 nM 10.1021/acs.jmedchem.0c01887
Homo sapiens Serotonin 6 (5-HT6) receptor Ki 1450.0 nM 10.1016/j.bmcl.2003.09.027
Homo sapiens Serotonin 6 (5-HT6) receptor Ki 1500.0 nM 10.1021/acs.jmedchem.0c01887
Homo sapiens Serotonin 7 (5-HT7) receptor Ki 280.0 nM 10.1016/j.bmcl.2003.09.027
Homo sapiens Serotonin 7 (5-HT7) receptor Ki 280.0 nM 10.1021/acs.jmedchem.0c01887
Homo sapiens Serotonin transporter Ki 10000.0 nM 10.1016/j.bmcl.2003.09.027
Homo sapiens TAR DNA-binding protein 43 Potency 501.2 nM None
Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 32000.0 nM 10.1021/np0101189
Mus musculus FM3A EC50 45000.0 nM 10.1016/j.bmcl.2004.01.055
Mus musculus FM3A Selective toxicity 2.1 None 10.1016/j.bmcl.2004.01.055
Plasmodium falciparum Plasmodium falciparum EC50 18000.0 nM 10.1016/j.bmcl.2004.01.055
Plasmodium falciparum Plasmodium falciparum Potency 2078.7 nM None
Rattus norvegicus GABA-A receptor; anion channel Ki 10000.0 nM 10.1016/j.bmcl.2003.09.027
Rattus norvegicus Metabotropic glutamate receptor Ki 10000.0 nM 10.1016/j.bmcl.2003.09.027
Rattus norvegicus Serotonin 2a (5-HT2a) receptor Ki 1150.0 nM 10.1016/j.bmcl.2003.09.027
None ADMET Ratio IC50/EC50 3.4 uM 10.1021/np0101189
None Unchecked Potency 8912.5 nM None
None Unchecked Potency 25929.0 nM None

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT007019 CC1=NCCc2c1[nH]c1ccccc21>>C[C@@H]1NCCc2c1[nH]c1ccccc21 retrobiocat_275