Navigation

name Structure Reference Source Properties Activities Metabolism

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

AlkaPlorer ID: AK001242

Synonym: 4,9-Dihydro-1-methyl-3H-pyrido[3,4-b]indol-7-ol, 3,4-Dihydro-7-hydroxy-1-methyl-β-carboline, Harmalol 

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

Structure

SMILES: CC1=NCCC2=C1NC1=CC(O)=CC=C21

copy

InChI: InChI=1S/C12H12N2O/c1-7-12-10(4-5-13-7)9-3-2-8(15)6-11(9)14-12/h2-3,6,14-15H,4-5H2,1H3

copy

InChIKey: RHVPEFQDYMMNSY-UHFFFAOYSA-N

copy

Reference

New alkaloids from Peganum harmala

PubChem CID: 3565

CAS: 6028-07-5

LOTUS: LTS0116566

NPASS: NPC72980

COCONUT: CNP0228337

data_source: manually

Properties Information

Molecule Weight: 200.241

TPSA？: 48.38

MolLogP？: 2.2386

Number of H-Donors: 2

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 31622.8 nM None
Bacillus subtilis 4'-phosphopantetheinyl transferase ffp Potency 79432.8 nM None
Candida albicans Candida albicans MIC 750.0 ug.mL-1 10.1016/j.ejmech.2021.114057
Electrophorus electricus Acetylcholinesterase IC50 11280.0 nM 10.1016/j.bmcl.2012.02.057
Electrophorus electricus Acetylcholinesterase Inhibition 88.61 % 10.1016/j.bmcl.2012.02.057
Escherichia coli GroEL/GroES IC50 16000.0 nM 10.1016/j.bmcl.2019.02.028
Escherichia coli GroEL/GroES IC50 100000.0 nM 10.1016/j.bmcl.2019.02.028
Escherichia coli GroEL/GroES Inhibition 82.0 % 10.1016/j.bmcl.2019.02.028
Escherichia coli GroEL/GroES Inhibition 87.0 % 10.1016/j.bmcl.2019.02.028
Escherichia coli (strain K12) 60 kDa chaperonin IC50 250000.0 nM 10.1016/j.bmcl.2019.02.028
Gallus gallus Tyrosine-protein kinase SRC Activity 85.0 % 10.1042/bj20070797
Homo sapiens 15-hydroxyprostaglandin dehydrogenase [NAD+] Potency 35481.3 nM None
Homo sapiens 3-phosphoinositide dependent protein kinase-1 Activity 93.0 % 10.1042/bj20070797
Homo sapiens Acetylcholinesterase IC50 nan None 10.1016/j.bmcl.2012.02.057
Homo sapiens Acetylcholinesterase Inhibition 49.66 % 10.1016/j.bmcl.2012.02.057
Homo sapiens Aldehyde dehydrogenase 1A1 Potency 35481.3 nM None
Homo sapiens Androgen Receptor Inhibition 162.0 % 10.1073/pnas.0708036104
Homo sapiens ATP-dependent DNA helicase Q1 Potency 31622.8 nM None
Homo sapiens Bloom syndrome protein Potency 39810.7 nM None
Homo sapiens Breast cancer type 1 susceptibility protein Potency 31622.8 nM None
Homo sapiens BR serine/threonine-protein kinase 2 Activity 98.0 % 10.1042/bj20070797
Homo sapiens CaM kinase I alpha Activity 101.0 % 10.1042/bj20070797
Homo sapiens CaM-kinase kinase alpha Activity 103.0 % 10.1042/bj20070797
Homo sapiens CaM-kinase kinase beta Activity 90.0 % 10.1042/bj20070797
Homo sapiens cAMP-dependent protein kinase alpha-catalytic subunit Activity 90.0 % 10.1042/bj20070797
Homo sapiens Casein kinase I delta Activity 94.0 % 10.1042/bj20070797
Homo sapiens Casein kinase II Activity 91.0 % 10.1042/bj20070797
Homo sapiens Caspase-1 Potency 15848.9 nM None
Homo sapiens Caspase-7 Potency 12589.3 nM None
Homo sapiens c-Jun N-terminal kinase 1 Activity 102.0 % 10.1042/bj20070797
Homo sapiens c-Jun N-terminal kinase 2 Activity 99.0 % 10.1042/bj20070797
Homo sapiens c-Jun N-terminal kinase 3 Activity 113.0 % 10.1042/bj20070797
Homo sapiens Cyclin-dependent kinase 2 Inhibition 13.0 % 10.1016/s0960-894x(02)00094-x
Homo sapiens Cyclin-dependent kinase 2/cyclin A Activity 101.0 % 10.1042/bj20070797
Homo sapiens Cyclin-dependent kinase 5 Inhibition 15.0 % 10.1016/s0960-894x(02)00094-x
Homo sapiens Cytochrome P450 2D6 Potency 31622.8 nM None
Homo sapiens Cytochrome P450 3A4 Potency 19952.6 nM None
Homo sapiens DNA-(apurinic or apyrimidinic site) lyase Potency 31622.8 nM None
Homo sapiens DNA dC->dU-editing enzyme APOBEC-3G Potency 21136.0 nM None
Homo sapiens DNA polymerase kappa Potency 12589.3 nM None
Homo sapiens Dual specificity mitogen-activated protein kinase kinase 1 Activity 86.0 % 10.1042/bj20070797
Homo sapiens Dual-specificity tyrosine-phosphorylation regulated kinase 1A Activity 67.0 % 10.1042/bj20070797
Homo sapiens Dual-specificity tyrosine-phosphorylation regulated kinase 2 Activity 86.0 % 10.1042/bj20070797
Homo sapiens Dual-specificity tyrosine-phosphorylation regulated kinase 3 Activity 71.0 % 10.1042/bj20070797
Homo sapiens Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Potency 31622.8 nM None
Homo sapiens Glycogen synthase kinase-3 beta Activity 88.0 % 10.1042/bj20070797
Homo sapiens Homeodomain-interacting protein kinase 2 Activity 101.0 % 10.1042/bj20070797
Homo sapiens Homeodomain-interacting protein kinase 3 Activity 93.0 % 10.1042/bj20070797
Homo sapiens HSP60/HSP10 IC50 100000.0 nM 10.1016/j.bmcl.2019.02.028
Homo sapiens Inhibitor of nuclear factor kappa B kinase beta subunit Activity 74.0 % 10.1042/bj20070797
Homo sapiens Lysine-specific demethylase 4D-like Potency 31622.8 nM None
Homo sapiens MAP kinase-activated protein kinase 2 Activity 88.0 % 10.1042/bj20070797
Homo sapiens MAP kinase-activated protein kinase 3 Activity 99.0 % 10.1042/bj20070797
Homo sapiens MAP kinase-activated protein kinase 5 Activity 85.0 % 10.1042/bj20070797
Homo sapiens MAP kinase ERK1 Activity 107.0 % 10.1042/bj20070797
Homo sapiens MAP kinase ERK2 Activity 95.0 % 10.1042/bj20070797
Homo sapiens MAP kinase-interacting serine/threonine-protein kinase MNK1 Activity 97.0 % 10.1042/bj20070797
Homo sapiens MAP kinase p38 alpha Activity 96.0 % 10.1042/bj20070797
Homo sapiens MAP kinase p38 beta Activity 95.0 % 10.1042/bj20070797
Homo sapiens MAP kinase p38 delta Activity 89.0 % 10.1042/bj20070797
Homo sapiens MAP kinase p38 gamma Activity 104.0 % 10.1042/bj20070797
Homo sapiens MAP kinase signal-integrating kinase 2 Activity 106.0 % 10.1042/bj20070797
Homo sapiens Maternal embryonic leucine zipper kinase Activity 77.0 % 10.1042/bj20070797
Homo sapiens Menin/Histone-lysine N-methyltransferase MLL Potency 7943.3 nM None
Homo sapiens Microtubule-associated protein tau Potency 1412.5 nM None
Homo sapiens Microtubule-associated protein tau Potency 17782.8 nM None
Homo sapiens Mitogen-activated protein kinase 15 Activity 62.0 % 10.1042/bj20070797
Homo sapiens Myosin light chain kinase, smooth muscle Activity 107.0 % 10.1042/bj20070797
Homo sapiens Protein kinase C alpha Activity 92.0 % 10.1042/bj20070797
Homo sapiens Protein kinase C mu Activity 111.0 % 10.1042/bj20070797
Homo sapiens Protein kinase C zeta Activity 88.0 % 10.1042/bj20070797
Homo sapiens Protein kinase N2 Activity 86.0 % 10.1042/bj20070797
Homo sapiens Rho-associated protein kinase 2 Activity 91.0 % 10.1042/bj20070797
Homo sapiens Ribosomal protein S6 kinase 1 Activity 94.0 % 10.1042/bj20070797
Homo sapiens Ribosomal protein S6 kinase alpha 1 Activity 100.0 % 10.1042/bj20070797
Homo sapiens Ribosomal protein S6 kinase alpha 3 Activity 83.0 % 10.1042/bj20070797
Homo sapiens Ribosomal protein S6 kinase alpha 5 Activity 96.0 % 10.1042/bj20070797
Homo sapiens Runt-related transcription factor 1/Core-binding factor subunit beta Potency 11220.2 nM None
Homo sapiens Serine/threonine-protein kinase AKT Activity 89.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase AKT2 Activity 81.0 % 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 91.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase Chk1 Activity 84.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase Chk2 Activity 122.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase c-TAK1 Activity 131.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase EEF2K Activity 102.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase MST2 Activity 90.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase NEK2 Activity 82.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase NEK6 Activity 93.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase NEK7 Activity 109.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase PAK 4 Activity 105.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase PAK6 Activity 92.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase PAK7 Activity 95.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase PIM1 Activity 92.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase PIM2 Activity 101.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase PIM3 Activity 71.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase PLK1 Activity 83.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase Sgk1 Activity 86.0 % 10.1042/bj20070797
Homo sapiens Serine/threonine-protein kinase SRPK1 Activity 88.0 % 10.1042/bj20070797
Homo sapiens Serotonin 5a (5-HT5a) receptor Ki 10000.0 nM 10.1021/jm030080s
Homo sapiens Thiosulfate sulfurtransferase IC50 9700.0 nM 10.1016/j.bmcl.2019.02.028
Homo sapiens Tyrosine-protein kinase CSK Activity 84.0 % 10.1042/bj20070797
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 12589.3 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 26608.6 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 33498.3 nM None
Human herpesvirus 8 ORF 73 AC50 350000.0 nM None
Mus musculus Tyrosine-protein kinase LCK Activity 93.0 % 10.1042/bj20070797
Rattus norvegicus Inositol monophosphatase 1 Potency 14125.4 nM None
Rattus norvegicus Inositol monophosphatase 1 Potency 31622.8 nM None
Trypanosoma cruzi Cruzipain Potency 12589.3 nM None
Trypanosoma cruzi Cruzipain Potency 28183.8 nM None
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 87.0 % 10.1042/bj20070797
None Unchecked Activity 110.0 % 10.1042/bj20070797
None Unchecked IC50 63000.0 nM 10.1016/j.bmcl.2019.02.028
None Unchecked Potency 10000.0 nM None
None Unchecked Potency 15848.9 nM None

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT000486 *C.CC1=NCCc2c1[nH]c1cc(O)ccc21>>COc1ccc2c3c([nH]c2c1)C(C)=NCC3 RXN-9317
AKRT007018 CC1=NCCc2c1[nH]c1cc(O)ccc21>>Cc1nccc2c1[nH]c1cc(O)ccc12 RXN-9319
AKRT011901 COc1ccc2c3c([nH]c2c1)C(C)=NCC3>>CC1=NCCc2c1[nH]c1cc(O)ccc21 MNXR177461