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Compound Detail

CHEMBL275224

NORHARMANE
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c1ccc2c(c1)[nH]c1cnccc12

Basic Information

ChEMBL ID CHEMBL275224
Name NORHARMANE
Phase Preclinical
Structure Type MOL
InChI Key AIFRHYZBTHREPW-UHFFFAOYSA-N
15
Targets
29
Activities
3
Assay Types
1
PK Parameters
20
Publications
0
Known Names

Molecular Properties

168.2
MW (Da)
2.72
ALogP
1
HBA
1
HBD
28.7
PSA (Ų)
0.55
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C11H8N2
MW 168.20
Aromatic Rings 3
Heavy Atoms 13
NP-Likeness -0.13

Activity Summary

IC50 17 meas. best 5.92
Ki 9 meas. best 6.92
EC50 3 meas. best 5.06

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Indoleamine 2,3-dioxygenase 1
CHEMBL4685
Ki 6.92 6.92 120.0 1
Amine oxidase [flavin-containing] A
CHEMBL1951
Ki 6.58 6.58 260.0 1
Amine oxidase [flavin-containing] B
CHEMBL2039
Ki 5.95 5.935 1120.0 2
Tryptophan 2,3-dioxygenase
CHEMBL2140
IC50 5.92 5.92 1200.0 1
GABA-A receptor; anion channel
CHEMBL2093872
IC50 5.8 5.795 1600.0 2
Unchecked
CHEMBL612545
IC50 5.79 5.79 1620.0 4
GABA-A receptor; anion channel
CHEMBL1907607
IC50 5.79 5.79 1620.0 4
GABA-A receptor; anion channel
CHEMBL1907607
Ki 5.79 5.79 1620.0 1
Serine/threonine-protein kinase pim-1
CHEMBL2147
Ki 5.2 5.2 6309.6 1
Inhibitor of nuclear factor kappa-B kinase subunit beta
CHEMBL1991
Ki 5.1 5.1 7943.3 1
Chitinase
CHEMBL1795119
IC50 5.07 5.07 8460.0 1
Bovine viral diarrhea virus 1
CHEMBL612571
EC50 5.06 5.06 8800.0 2
Inhibitor of nuclear factor kappa-B kinase subunit alpha
CHEMBL3476
IC50 4.82 4.82 15000.0 1
Aurora kinase A
CHEMBL4722
Ki 4.8 4.8 15848.9 1
DNA topoisomerase 1
CHEMBL1781
IC50 4.51 4.51 31000.0 1
Human immunodeficiency virus 1
CHEMBL378
EC50 4.36 4.36 44100.0 1
Indoleamine 2,3-dioxygenase 1
CHEMBL4685
IC50 4.05 4.05 90000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 89.0 mL.min-1.g-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Indoleamine 2,3-dioxygenase 1 Ki = 120.0 nM 6.92 Inhibition of IDO 21269836
Amine oxidase [flavin-containing] A Ki = 260.0 nM 6.58 Competitive inhibition of recombinant human MAO-A using kynuramine as substrate ... 29925480
Amine oxidase [flavin-containing] B Ki = 1120.0 nM 5.95 Competitive inhibition of recombinant human MAO-B expressed in baculovirus syste... 27575476
Tryptophan 2,3-dioxygenase IC50 = 1200.0 nM 5.92 Inhibition of TDO (unknown origin) assessed as reduction in N-formylkynurenine f... 35938398
Amine oxidase [flavin-containing] B Ki = 1200.0 nM 5.92 Reversible inhibition of MAO-B 22071524
GABA-A receptor; anion channel IC50 = 1600.0 nM 5.8 Displacement of [3H]flunitrazepam from GABAA (unknown origin ) receptor by radio... 33528252
GABA-A receptor; anion channel IC50 = 1620.0 nM 5.79 In vitro inhibition of 3[H]Diazepam binding to Benzodiazepine receptor from rat ... 2167977
GABA-A receptor; anion channel Ki = 1620.0 nM 5.79 In vitro inhibition of [3H]diazepam binding to benzodiazepine receptor in rat ce... 6127411
Unchecked IC50 = 1621.81 nM 5.79 Binding affinity to GABA-A receptor benzodiazepine site (unknown origin) -
Unchecked IC50 = 1621.81 nM 5.79 Displacement of [3H]diazepam from benzodiazepine receptor in rat brain 18346822
Unchecked IC50 = 1621.81 nM 5.79 Displacement of [3H]diazepam from GABAA/BzR in rat brain membrane 17964693
GABA-A receptor; anion channel IC50 = 1621.81 nM 5.79 Inhibition on Benzodiazepine receptor 9435905
GABA-A receptor; anion channel IC50 = 1621.81 nM 5.79 Binding affinity towards benzodiazepine receptor inverse agonist site by the dis... 8411009
GABA-A receptor; anion channel IC50 = 1620.0 nM 5.79 In vitro inhibition of binding to the benzodiazepine receptor in rat cerebral co... 2842507
Unchecked IC50 = 1620.0 nM 5.79 In vitro displacement of [3H]-diazepam from GABA-A benzodiazepine receptor in ra... 3031296
GABA-A receptor; anion channel IC50 = 1621.81 nM 5.79 Binding affinity for rat benzodiazepine receptor inverse agonist site 8667357
Serine/threonine-protein kinase pim-1 Ki = 6309.57 nM 5.2 PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na... -
Inhibitor of nuclear factor kappa-B kinase subunit beta Ki = 7943.28 nM 5.1 PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na... -
Chitinase IC50 = 8460.0 nM 5.07 Inhibition of L3 larval stage of Onchocerca volvulus chitinase using 4-methylumb... 25815157
Bovine viral diarrhea virus 1 EC50 = 8800.0 nM 5.06 Antiviral activity against bovine viral diarrhea virus 1 infected in MDBK cells ... 30103193

Literature References

PubMed DOI Target Context # Activities
6195312 10.1021/np50028a027 CHO 6
27567367 10.1016/j.bmcl.2016.08.047 Calf thymus DNA 3
12828469 10.1021/np020592u Plasmodium falciparum 2
35938398 10.1021/acs.jmedchem.2c00677 Tryptophan 2,3-dioxygenase 2
30001916 10.1016/j.bmcl.2018.06.050 Staphylococcus aureus 2
12828469 10.1021/np020592u Leishmania donovani 2
30097370 10.1016/j.bmcl.2018.06.001 Staphylococcus aureus 2
25815157 10.1021/ml500516r Onchocerca volvulus 2
- 10.1039/C5MD00581G NON-PROTEIN TARGET 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
12824047 10.1016/s0960-894x(03)00408-6 Protein kinase C (PKC) 1
37866714 10.1016/j.bmcl.2023.129532 Indoleamine 2,3-dioxygenase 1 1
2167977 10.1021/jm00171a007 GABA-A receptor; anion channel 1
11909733 10.1016/s0960-894x(02)00094-x Cyclin-dependent kinase 2 1
11909733 10.1016/s0960-894x(02)00094-x Cyclin-dependent kinase 5 1
12824047 10.1016/s0960-894x(03)00408-6 Casein kinase II 1
12824047 10.1016/s0960-894x(03)00408-6 Inhibitor of nuclear factor kappa-B kinase subunit alpha 1
8411009 10.1021/jm00072a012 GABA-A receptor; anion channel 1
2842507 10.1021/jm00117a029 GABA-A receptor; anion channel 1
6708048 10.1021/jm00370a007 Nucleic Acid 1

Data from ChEMBL 36 via Core Engine