Navigation

name Structure Reference Source Properties Activities Metabolism

Norharmane

AlkaPlorer ID: AK007935

Synonym: None

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

Structure

SMILES: C1=CC=C2C(=C1)NC1=CN=CC=C12

copy

InChI: InChI=1S/C11H8N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-7,13H

copy

InChIKey: AIFRHYZBTHREPW-UHFFFAOYSA-N

copy

Reference

Glucoindole Alkaloids from<i>Ophiorrhiza acuminata</i>

PubChem CID: 64961

CAS: 244-63-3

LOTUS: LTS0263207

COCONUT: CNP0135748

data_source: manually

Source

Species Genus Family Order Class Phylum Kingdom Domain
Eurycoma longifolia Eurycoma Simaroubaceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 168.19899999999998

TPSA？: 28.68

MolLogP？: 2.7161

Number of H-Donors: 1

Number of H-Acceptors: 1

RingCount: 3

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Amorphotheca resinae Amorphotheca resinae MIC 15.0 ug 10.1021/np50076a023
Bacillus cereus Bacillus cereus MIC 64.0 ug.mL-1 10.1016/j.bmcl.2018.06.001
Bacillus subtilis Bacillus subtilis MIC 7.5 ug 10.1021/np50076a023
Bacillus subtilis Bacillus subtilis MIC 64.0 ug.mL-1 10.1016/j.bmcl.2018.06.001
Bos taurus Calf thymus DNA Activity nan None 10.1016/j.bmcl.2016.08.047
Bovine viral diarrhea virus 1 Bovine viral diarrhea virus 1 EC50 8800.0 nM 10.1016/j.bmc.2008.01.052
Bovine viral diarrhea virus 1 Bovine viral diarrhea virus 1 EC50 8800.0 nM 10.1016/j.ejmech.2018.08.015
Candida albicans Candida albicans MIC 1.9 ug 10.1021/np50076a023
Candida albicans Candida albicans MIC 125000.0 nM 10.1016/j.bmcl.2018.06.050
[Candida] intermedia [Candida] intermedia MIC 125000.0 nM 10.1016/j.bmcl.2018.06.050
Chlorocebus sabaeus Vero Activity nan None 10.1021/np020592u
Cricetulus griseus CHO Activity 0.0 % 10.1021/np50028a027
Cricetulus griseus CHO Activity 6.7 % 10.1021/np50028a027
Cricetulus griseus CHO Activity nan None 10.1021/np50028a027
Electrophorus electricus Acetylcholinesterase Inhibition -1.66 % 10.1016/j.bmc.2012.09.040
Equus caballus Cholinesterase Inhibition 28.7 % 10.1016/j.bmc.2012.09.040
Equus caballus Ferritin light chain Potency 28183.8 nM None
Escherichia coli Escherichia coli MIC 3.7 ug 10.1021/np50076a023
Escherichia coli Escherichia coli MIC 250000.0 nM 10.1016/j.bmcl.2018.06.050
Homo sapiens 15-hydroxyprostaglandin dehydrogenase [NAD+] Potency 31622.8 nM None
Homo sapiens A549 IC50 100000.0 nM 10.1039/C5MD00581G
Homo sapiens Acetylcholinesterase IC50 40000.0 nM 10.1021/acs.jmedchem.0c01887
Homo sapiens Aldehyde dehydrogenase 1A1 Potency 31622.8 nM None
Homo sapiens Aldehyde dehydrogenase 1A1 Potency 35481.3 nM None
Homo sapiens ATPase family AAA domain-containing protein 5 Potency 4109.5 nM None
Homo sapiens Butyrylcholinesterase IC50 40000.0 nM 10.1021/acs.jmedchem.0c01887
Homo sapiens cAMP-dependent protein kinase (PKA) IC50 25000.0 nM 10.1016/s0960-894x(03)00408-6
Homo sapiens Casein kinase II IC50 25000.0 nM 10.1016/s0960-894x(03)00408-6
Homo sapiens Chromobox protein homolog 1 Potency 63095.7 nM None
Homo sapiens Cyclin-dependent kinase 2 Inhibition 37.0 % 10.1016/s0960-894x(02)00094-x
Homo sapiens Cyclin-dependent kinase 5 Inhibition 35.0 % 10.1016/s0960-894x(02)00094-x
Homo sapiens DNA-(apurinic or apyrimidinic site) lyase Potency 15.8 nM None
Homo sapiens DNA-(apurinic or apyrimidinic site) lyase Potency 25118.9 nM None
Homo sapiens DNA topoisomerase I ED50 34.4 ug ml-1 10.1016/j.ejmech.2021.113321
Homo sapiens DNA topoisomerase I IC50 31000.0 nM 10.1016/j.ejmech.2021.113688
Homo sapiens Dual-specificity tyrosine-phosphorylation regulated kinase 1A IC50 1800.0 nM 10.1021/acs.jmedchem.0c01887
Homo sapiens GABA-A receptor; anion channel IC50 1600.0 nM 10.1021/acs.jmedchem.0c01887
Homo sapiens GABA-A receptor; anion channel IC50 1621.81 nM 10.1021/jm970488n
Homo sapiens Geminin Potency 92.0 nM None
Homo sapiens H9 IC50 141700.0 nM 10.1021/np0101189
Homo sapiens HEK-293T Activity nan None 10.1021/ml500516r
Homo sapiens HeLa IC50 100000.0 nM 10.1039/C5MD00581G
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 446.7 nM None
Homo sapiens Indoleamine 2,3-dioxygenase IC50 90000.0 nM 10.1016/j.bmc.2011.10.068
Homo sapiens Indoleamine 2,3-dioxygenase Inhibition 48.0 % 10.1021/acs.jmedchem.2c00677
Homo sapiens Indoleamine 2,3-dioxygenase Ki 120.0 nM 10.1016/j.bmc.2010.12.032
Homo sapiens Indoleamine 2,3-dioxygenase Ki 180000.0 nM 10.1021/acs.jmedchem.0c00925
Homo sapiens Inhibitor of nuclear factor kappa B kinase alpha subunit IC50 15000.0 nM 10.1016/s0960-894x(03)00408-6
Homo sapiens Inhibitor of nuclear factor kappa B kinase beta subunit Ki 7943.28 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 MCF7 IC50 100000.0 nM 10.1039/C5MD00581G
Homo sapiens Monoamine oxidase A Ki 260.0 nM 10.1016/j.bmcl.2018.06.023
Homo sapiens Monoamine oxidase B Ki 1120.0 nM 10.1016/j.bmcl.2016.08.044
Homo sapiens Monoamine oxidase B Ki 1200.0 nM 10.1016/j.bmc.2011.10.049
Homo sapiens Protein kinase C (PKC) IC50 25000.0 nM 10.1016/s0960-894x(03)00408-6
Homo sapiens Serine/threonine-protein kinase Aurora-A Ki 15848.93 nM None
Homo sapiens Serine/threonine-protein kinase PIM1 Ki 6309.57 nM None
Homo sapiens Solute carrier organic anion transporter family member 1B1 Inhibition 95.1 % 10.1124/mol.112.084152
Homo sapiens Solute carrier organic anion transporter family member 1B3 Inhibition 87.66 % 10.1124/mol.112.084152
Homo sapiens Survival motor neuron protein Potency 1412.5 nM None
Homo sapiens Tryptophan 2,3-dioxygenase IC50 1200.0 nM 10.1021/acs.jmedchem.2c00677
Homo sapiens Tryptophan 2,3-dioxygenase Inhibition 86.0 % 10.1021/acs.jmedchem.2c00677
Human alphaherpesvirus 1 Human alphaherpesvirus 1 IZ nan None 10.1021/np50076a023
Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 44100.0 nM 10.1021/np0101189
Leishmania donovani Leishmania donovani Activity nan None 10.1021/np020592u
Metarhizium anisopliae Metarhizium anisopliae Activity 11.9 % 10.1016/j.ejmech.2021.114057
Mus musculus P388 IC50 25.0 ug.mL-1 10.1021/np50076a023
Mycobacterium tuberculosis Mycobacterium tuberculosis MIC nan None 10.1021/np020592u
Onchocerca volvulus Chitinase IC50 8460.0 nM 10.1021/ml500516r
Onchocerca volvulus Onchocerca volvulus Activity nan None 10.1021/ml500516r
Onchocerca volvulus Onchocerca volvulus Inhibition nan % 10.1021/ml500516r
Pichia kudriavzevii Pichia kudriavzevii MIC 125000.0 nM 10.1016/j.bmcl.2018.06.050
Plasmodium falciparum Plasmodium falciparum Activity nan None 10.1021/np020592u
Poliovirus 1 Poliovirus 1 IZ nan None 10.1021/np50076a023
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 60.0 ug 10.1021/np50076a023
Ralstonia solanacearum Ralstonia solanacearum MIC 64.0 ug.mL-1 10.1016/j.bmcl.2018.06.001
Rattus norvegicus Dual specificity tyrosine-phosphorylation-regulated kinase 1A AC50 8746.0 nM None
Rattus norvegicus GABA-A receptor; anion channel IC50 1620.0 nM 10.1021/jm00117a029
Rattus norvegicus GABA-A receptor; anion channel IC50 1620.0 nM 10.1021/jm00171a007
Rattus norvegicus GABA-A receptor; anion channel IC50 1621.81 nM 10.1021/jm00072a012
Rattus norvegicus GABA-A receptor; anion channel IC50 1621.81 nM 10.1021/jm950589q
Rattus norvegicus GABA-A receptor; anion channel Ki 1620.0 nM 10.1021/jm00351a015
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 79432.8 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
Staphylococcus aureus Staphylococcus aureus MIC 64.0 ug.mL-1 10.1016/j.bmcl.2018.06.001
Staphylococcus aureus Staphylococcus aureus MIC 250000.0 nM 10.1016/j.bmcl.2018.06.050
Staphylococcus aureus Staphylococcus aureus MIC 1000000.0 nM 10.1016/j.bmcl.2018.06.050
Trichophyton interdigitale Trichophyton interdigitale MIC 100.0 ug.mL-1 10.1016/j.ejmech.2021.114057
Trichophyton mentagrophytes Trichophyton mentagrophytes MIC 0.9 ug 10.1021/np50076a023
Trypanosoma cruzi Trypanothione reductase Inhibition 10.0 % 10.1016/j.bmc.2008.05.074
None ADMET CC50 78000.0 nM 10.1016/j.bmc.2008.01.052
None ADMET CL 89.0 mL.min-1.g-1 10.6019/CHEMBL3301361
None ADMET IZ nan None 10.1021/np50076a023
None ADMET Ratio IC50/EC50 3.2 uM 10.1021/np0101189
None NON-PROTEIN TARGET IC50 100000.0 nM 10.1016/j.ejmech.2010.11.044
None NON-PROTEIN TARGET IC50 100000.0 nM 10.1039/C5MD00581G
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 NON-PROTEIN TARGET Inhibition nan % 10.1016/j.bmc.2013.04.025
None No relevant target Solubility 338800.0 nM 10.6019/CHEMBL3301361
None Nucleic Acid Log Kd 5.34 None 10.1021/jm00370a007
None Unchecked IC50 1620.0 nM 10.1021/jm00387a033
None Unchecked IC50 1621.81 nM 10.1007/s00044-008-9111-6
None Unchecked IC50 1621.81 nM 10.1016/j.ejmech.2007.09.004
None Unchecked IC50 1621.81 nM 10.1016/j.ejmech.2008.01.030
None Unchecked Potency 12589.3 nM None
None Unchecked Potency 22387.2 nM None

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT014768 C[SAH].c1ccc2c(c1)[nH]c1cnccc12>>Cc1nccc2c1[nH]c1ccccc12 MNXR103685