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name Structure Reference Source Properties Activities Metabolism

7-Hydroxy-1-methyl-β-carboline; 3,4-Dihydro, Me ether

AlkaPlorer ID: AK001169

Synonym: 4,9-Dihydro-7-methoxy-1-methyl-3H-pyrido[3,4-b]indole, 3,4-Dihydro-7-methoxy-1-methyl-β-carboline, Harmaline, Dihydroharmine, Harmidine 

IUPAC Name: 7-methoxy-1-methyl-4,9-dihydro-3H-pyrido[3,4-b]indole

Structure

SMILES: COC1=CC=C2C3=C(NC2=C1)C(C)=NCC3

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InChI: InChI=1S/C13H14N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-4,7,15H,5-6H2,1-2H3

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InChIKey: RERZNCLIYCABFS-UHFFFAOYSA-N

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Properties Information

Molecule Weight: 214.268

TPSA？: 37.38

MolLogP？: 2.5416000000000007

Number of H-Donors: 1

Number of H-Acceptors: 2

RingCount: 3

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bacillus anthracis Anthrax lethal factor Potency 25118.9 nM None
Candida albicans Candida albicans MIC 666.0 ug.mL-1 10.1016/j.ejmech.2021.114057
Cricetulus griseus CHO Activity 0.0 % 10.1021/np50028a027
Cricetulus griseus CHO Activity 2.3 % 10.1021/np50028a027
Cricetulus griseus CHO Activity 22.1 % 10.1021/np50028a027
Cricetulus griseus CHO Activity nan None 10.1021/np50028a027
Electrophorus electricus Acetylcholinesterase IC50 4900.0 nM 10.1016/j.bmcl.2012.02.057
Electrophorus electricus Acetylcholinesterase Inhibition 85.52 % 10.1016/j.bmcl.2012.02.057
Equus caballus Ferritin light chain Potency 35481.3 nM None
Escherichia coli K-12 Beta-lactamase AmpC Potency 316.2 nM None
Gallus gallus Tyrosine-protein kinase SRC Activity 94.0 % 10.1042/bj20070797
Homo sapiens 15-hydroxyprostaglandin dehydrogenase [NAD+] Potency 31622.8 nM None
Homo sapiens 15-hydroxyprostaglandin dehydrogenase [NAD+] Potency 35481.3 nM None
Homo sapiens 3-phosphoinositide dependent protein kinase-1 Activity 86.0 % 10.1042/bj20070797
Homo sapiens Acetylcholinesterase IC50 23700.0 nM 10.1016/j.bmcl.2012.02.057
Homo sapiens Acetylcholinesterase Inhibition 65.89 % 10.1016/j.bmcl.2012.02.057
Homo sapiens Aldehyde dehydrogenase 1A1 Potency 28183.8 nM None
Homo sapiens Aldehyde dehydrogenase 1A1 Potency 31622.8 nM None
Homo sapiens Aldehyde dehydrogenase 1A1 Potency 35481.3 nM None
Homo sapiens Alpha-galactosidase A Potency 35481.3 nM None
Homo sapiens Ataxin-2 Potency 8912.5 nM None
Homo sapiens ATPase family AAA domain-containing protein 5 Potency 9200.0 nM None
Homo sapiens ATP-dependent DNA helicase Q1 Potency 14125.4 nM None
Homo sapiens ATP-dependent DNA helicase Q1 Potency 35481.3 nM None
Homo sapiens ATP-dependent DNA helicase Q1 Potency 50118.7 nM None
Homo sapiens Bloom syndrome protein Potency 35481.3 nM None
Homo sapiens BR serine/threonine-protein kinase 2 Activity 103.0 % 10.1042/bj20070797
Homo sapiens CaM kinase I alpha Activity 103.0 % 10.1042/bj20070797
Homo sapiens CaM-kinase kinase alpha Activity 89.0 % 10.1042/bj20070797
Homo sapiens CaM-kinase kinase beta Activity 89.0 % 10.1042/bj20070797
Homo sapiens cAMP-dependent protein kinase alpha-catalytic subunit Activity 89.0 % 10.1042/bj20070797
Homo sapiens Casein kinase I delta Activity 65.0 % 10.1042/bj20070797
Homo sapiens Casein kinase II Activity 87.0 % 10.1042/bj20070797
Homo sapiens Caspase-1 Potency 12589.3 nM None
Homo sapiens Caspase-7 Potency 10000.0 nM None
Homo sapiens Caspase-7 Potency 12589.3 nM None
Homo sapiens c-Jun N-terminal kinase 1 Activity 96.0 % 10.1042/bj20070797
Homo sapiens c-Jun N-terminal kinase 2 Activity 86.0 % 10.1042/bj20070797
Homo sapiens c-Jun N-terminal kinase 3 Activity 89.0 % 10.1042/bj20070797
Homo sapiens Cyclin-dependent kinase 2 Inhibition 10.0 % 10.1016/s0960-894x(02)00094-x
Homo sapiens Cyclin-dependent kinase 2/cyclin A Activity 100.0 % 10.1042/bj20070797
Homo sapiens Cyclin-dependent kinase 5 Inhibition 7.0 % 10.1016/s0960-894x(02)00094-x
Homo sapiens Cytochrome P450 2D6 Potency 3981.1 nM None
Homo sapiens Cytochrome P450 3A4 Potency 19952.6 nM None
Homo sapiens DNA-(apurinic or apyrimidinic site) lyase Potency 25118.9 nM None
Homo sapiens DNA polymerase beta Potency 35481.3 nM None
Homo sapiens DNA polymerase kappa Potency 22387.2 nM None
Homo sapiens Dual specificity mitogen-activated protein kinase kinase 1 Activity 95.0 % 10.1042/bj20070797
Homo sapiens Dual-specificity tyrosine-phosphorylation regulated kinase 1A Activity 29.0 % 10.1042/bj20070797
Homo sapiens Dual-specificity tyrosine-phosphorylation regulated kinase 1A IC50 4600.0 nM 10.1021/acs.jmedchem.0c01887
Homo sapiens Dual-specificity tyrosine-phosphorylation regulated kinase 2 Activity 73.0 % 10.1042/bj20070797
Homo sapiens Dual-specificity tyrosine-phosphorylation regulated kinase 3 Activity 49.0 % 10.1042/bj20070797
Homo sapiens Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Potency 25118.9 nM None
Homo sapiens Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Potency 31622.8 nM None
Homo sapiens Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Potency 39810.7 nM None
Homo sapiens GABA-A receptor; anion channel IC50 100.0 microA 10.1021/acs.jmedchem.0c01887
Homo sapiens Geminin Potency 3264.3 nM None
Homo sapiens Glycogen synthase kinase-3 beta Activity 100.0 % 10.1042/bj20070797
Homo sapiens GTP-binding nuclear protein Ran/Importin subunit beta-1/Snurportin-1 Potency 1299.5 nM None
Homo sapiens Histone acetyltransferase GCN5 Potency 22387.2 nM None
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 89125.1 nM None
Homo sapiens HL-60 IC50 10000.0 nM 10.1021/acs.jnatprod.6b01146
Homo sapiens Homeodomain-interacting protein kinase 2 Activity 91.0 % 10.1042/bj20070797
Homo sapiens Homeodomain-interacting protein kinase 3 Activity 97.0 % 10.1042/bj20070797
Homo sapiens Huntingtin Potency 15848.9 nM None
Homo sapiens Inhibitor of nuclear factor kappa B kinase beta subunit Activity 94.0 % 10.1042/bj20070797
Homo sapiens Lysine-specific demethylase 4D-like Potency 25118.9 nM None
Homo sapiens Lysine-specific demethylase 4D-like Potency 28183.8 nM None
Homo sapiens Lysine-specific demethylase 4D-like Potency 31622.8 nM None
Homo sapiens Lysosomal alpha-glucosidase Potency 22387.2 nM None
Homo sapiens MAP kinase-activated protein kinase 2 Activity 89.0 % 10.1042/bj20070797
Homo sapiens MAP kinase-activated protein kinase 3 Activity 97.0 % 10.1042/bj20070797
Homo sapiens MAP kinase-activated protein kinase 5 Activity 74.0 % 10.1042/bj20070797
Homo sapiens MAP kinase ERK1 Activity 108.0 % 10.1042/bj20070797
Homo sapiens MAP kinase ERK2 Activity 87.0 % 10.1042/bj20070797
Homo sapiens MAP kinase-interacting serine/threonine-protein kinase MNK1 Activity 80.0 % 10.1042/bj20070797
Homo sapiens MAP kinase p38 alpha Activity 88.0 % 10.1042/bj20070797
Homo sapiens MAP kinase p38 beta Activity 92.0 % 10.1042/bj20070797
Homo sapiens MAP kinase p38 delta Activity 92.0 % 10.1042/bj20070797
Homo sapiens MAP kinase p38 gamma Activity 120.0 % 10.1042/bj20070797
Homo sapiens MAP kinase signal-integrating kinase 2 Activity 92.0 % 10.1042/bj20070797
Homo sapiens Maternal embryonic leucine zipper kinase Activity 95.0 % 10.1042/bj20070797
Homo sapiens Menin/Histone-lysine N-methyltransferase MLL Potency 15848.9 nM None
Homo sapiens Menin/Histone-lysine N-methyltransferase MLL Potency 39810.7 nM None
Homo sapiens Microtubule-associated protein tau Potency 8912.5 nM None
Homo sapiens Microtubule-associated protein tau Potency 17782.8 nM None
Homo sapiens Microtubule-associated protein tau Potency 22387.2 nM None
Homo sapiens Mitogen-activated protein kinase 15 Activity 44.0 % 10.1042/bj20070797
Homo sapiens Monoamine oxidase A IC50 2.5 nM 10.1021/acs.jmedchem.0c01887
Homo sapiens Monoamine oxidase A IC50 32.9 nM 10.1016/j.ejmech.2020.112911
Homo sapiens Monoamine oxidase B IC50 100000.0 nM 10.1016/j.ejmech.2020.112911
Homo sapiens Muscleblind-like protein 1 Potency 28183.8 nM None
Homo sapiens Myosin light chain kinase, smooth muscle Activity 112.0 % 10.1042/bj20070797
Homo sapiens PC-3 IC50 10000.0 nM 10.1021/acs.jnatprod.6b01146
Homo sapiens Prelamin-A/C Potency 7079.5 nM None
Homo sapiens Protein kinase C alpha Activity 90.0 % 10.1042/bj20070797
Homo sapiens Protein kinase C mu Activity 108.0 % 10.1042/bj20070797
Homo sapiens Protein kinase C zeta Activity 108.0 % 10.1042/bj20070797
Homo sapiens Protein kinase N2 Activity 85.0 % 10.1042/bj20070797
Homo sapiens Rho-associated protein kinase 2 Activity 79.0 % 10.1042/bj20070797
Homo sapiens Ribosomal protein S6 kinase 1 Activity 93.0 % 10.1042/bj20070797
Homo sapiens Ribosomal protein S6 kinase alpha 1 Activity 110.0 % 10.1042/bj20070797
Homo sapiens Ribosomal protein S6 kinase alpha 3 Activity 112.0 % 10.1042/bj20070797
Homo sapiens Ribosomal protein S6 kinase alpha 5 Activity 94.0 % 10.1042/bj20070797
Homo sapiens Serine-protein kinase ATM Potency 35481.3 nM None
Homo sapiens Serine/threonine-protein kinase AKT Activity 95.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase AKT2 Activity 105.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase Aurora-B Activity 90.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase Aurora-C Activity 99.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase Chk1 Activity 94.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase Chk2 Activity 117.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase c-TAK1 Activity 110.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase EEF2K Activity 107.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase MST2 Activity 101.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase NEK2 Activity 96.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase NEK6 Activity 94.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase NEK7 Activity 107.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase PAK 4 Activity 90.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase PAK6 Activity 106.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase PAK7 Activity 84.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase PIM1 Activity 104.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase PIM2 Activity 117.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase PIM3 Activity 90.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase PLK1 Activity 80.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase Sgk1 Activity 85.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase SRPK1 Activity 89.0 % 10.1042/bj20070797
Homo sapiens Serotonin 1a (5-HT1a) receptor Ki 10000.0 nM 10.1021/acs.jmedchem.0c01887
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 10.1021/acs.jmedchem.0c01887
Homo sapiens Serotonin 2a (5-HT2a) receptor Ki 5000.0 nM 10.1021/acs.jmedchem.0c01887
Homo sapiens Serotonin 2c (5-HT2c) receptor Ki 9400.0 nM 10.1021/acs.jmedchem.0c01887
Homo sapiens Serotonin 3a (5-HT3a) receptor Ki 10000.0 nM 10.1021/acs.jmedchem.0c01887
Homo sapiens Serotonin 5a (5-HT5a) receptor Ki 10000.0 nM 10.1021/acs.jmedchem.0c01887
Homo sapiens Serotonin 5a (5-HT5a) receptor Ki 10000.0 nM 10.1021/jm030080s
Homo sapiens Serotonin 6 (5-HT6) receptor Ki 1500.0 nM 10.1021/acs.jmedchem.0c01887
Homo sapiens Serotonin 7 (5-HT7) receptor Ki 5500.0 nM 10.1021/acs.jmedchem.0c01887
Homo sapiens SGC-7901 IC50 10000.0 nM 10.1021/acs.jnatprod.6b01146
Homo sapiens Solute carrier organic anion transporter family member 1B1 Inhibition 92.56 % 10.1124/mol.112.084152
Homo sapiens Solute carrier organic anion transporter family member 1B3 Inhibition 115.89 % 10.1124/mol.112.084152
Homo sapiens Thyroid stimulating hormone receptor Potency 31622.8 nM None
Homo sapiens Tyrosine-protein kinase CSK Activity 82.0 % 10.1042/bj20070797
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 6309.6 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 9200.0 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 11885.6 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 13335.9 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 18356.4 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 29092.9 nM None
Leishmania amazonensis Leishmania amazonensis IC50 99000.0 nM 10.1016/j.bmc.2008.05.074
Leishmania donovani Leishmania donovani IC50 1160.0 nM 10.1016/j.bmcl.2014.06.030
Leishmania donovani Leishmania donovani IC50 116800.0 nM 10.1016/j.bmcl.2014.06.030
Leishmania infantum Leishmania infantum IC50 1160.0 nM 10.1016/j.bmcl.2014.06.030
Leishmania infantum Leishmania infantum IC50 116800.0 nM 10.1016/j.bmcl.2014.06.030
Leishmania infantum Leishmania infantum IC50 116800.0 nM 10.1016/j.ejmech.2016.08.014
Leishmania infantum Leishmania infantum IC50 119000.0 nM 10.1016/j.bmc.2008.05.074
Mus musculus Nuclear receptor ROR-gamma Potency 12589.3 nM None
Mus musculus Tyrosine-protein kinase LCK Activity 81.0 % 10.1042/bj20070797
Plasmodium falciparum Plasmodium falciparum Potency 18526.0 nM None
Rattus norvegicus Dual specificity tyrosine-phosphorylation-regulated kinase 1A AC50 1236.0 nM None
Rattus norvegicus Inositol monophosphatase 1 Potency 10000.0 nM None
Rattus norvegicus Monoamine oxidase A IC50 12.0 nM 10.1021/jm00024a006
Rattus norvegicus Monoamine oxidase B IC50 150000.0 nM 10.1021/jm00024a006
Saccharomyces cerevisiae S288c CAAX prenyl protease 1 AC50 2766.0 nM None
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
Trypanosoma cruzi Cruzipain Potency 10000.0 nM None
Trypanosoma cruzi Trypanothione reductase Inhibition 19.0 % 10.1016/j.bmc.2008.05.074
None NON-PROTEIN TARGET IC50 130000.0 nM 10.1016/j.ejmech.2011.09.027
None NON-PROTEIN TARGET IC50 130000.0 nM 10.1021/jm901816j
None Unchecked Activity 84.0 % 10.1042/bj20070797
None Unchecked Activity 106.0 % 10.1042/bj20070797
None Unchecked Potency 10000.0 nM None
None Unchecked Potency 12589.3 nM None
None Unchecked Potency 17782.8 nM None
None Unchecked Potency 18356.4 nM None
None Unchecked Potency 19952.6 nM None
None Unchecked Potency 22387.2 nM None
None Unchecked Potency 25118.9 nM None
None Unchecked Potency 35481.3 nM None
None Unchecked Ratio IC50 0.0003 None 10.1016/j.ejmech.2020.112911
None Unchecked Selectivity 5.0 None 10.1021/jm00024a006

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT000486 *C.CC1=NCCc2c1[nH]c1cc(O)ccc21>>COc1ccc2c3c([nH]c2c1)C(C)=NCC3 RXN-9317
AKRT011900 COc1ccc2c3c([nH]c2c1)C(C)=NCC3>>*C MNXR177461
AKRT011901 COc1ccc2c3c([nH]c2c1)C(C)=NCC3>>CC1=NCCc2c1[nH]c1cc(O)ccc21 MNXR177461
AKRT011902 COc1ccc2c3c([nH]c2c1)C(C)=NCC3>>COc1ccc2c(c1)[nH]c1c(C)nccc12 RXN-9318
AKRT011903 COc1ccc2c3c([nH]c2c1)C(C)=NCC3>>COc1ccc2c3c([nH]c2c1)[C@@H](C)NCC3 R08486
AKRT011904 COc1ccc2c3c([nH]c2c1)C(C)=NCC3>>COc1ccc2c3c([nH]c2c1)[C@H](C)NCC3 retrobiocat_279