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Compound Detail

CHEMBL504816

(L)-1-METHYLTRYPTOPHAN
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Cn1cc(C[C@H](N)C(=O)O)c2ccccc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL504816
Name (L)-1-METHYLTRYPTOPHAN
Phase Preclinical
Structure Type MOL
InChI Key ZADWXFSZEAPBJS-JTQLQIEISA-N
4
Targets
50
Activities
3
Assay Types
4
PK Parameters
20
Publications
0
Known Names

Molecular Properties

218.3
MW (Da)
1.13
ALogP
3
HBA
2
HBD
68.2
PSA (Ų)
0.81
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C12H14N2O2
MW 218.26
Aromatic Rings 2
Heavy Atoms 16
NP-Likeness 0.05

Activity Summary

IC50 30 meas. best 7.11
Ki 18 meas. best 5.18
EC50 2 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Indoleamine 2,3-dioxygenase 1
CHEMBL4685
 IC50 7.11 4.6193 78.0 15
Indoleamine 2,3-dioxygenase 1
CHEMBL4685
 Ki 5.18 4.5936 6600.0 11
Unchecked
CHEMBL612545
 IC50 4.47 4.47 34000.0 1
Unchecked
CHEMBL612545
 Ki 4.47 4.47 34000.0 3
Indoleamine 2,3-dioxygenase 2
CHEMBL3627587
 IC50 4.46 4.222 35000.0 5
Indoleamine 2,3-dioxygenase 1
CHEMBL1075294
 IC50 4.4 4.4 40000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1200.0 mg.hr Homo sapiens
Cmax 1200.0 mg Homo sapiens
T1/2 10.5 hr Homo sapiens
Tmax 2.9 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Indoleamine 2,3-dioxygenase 1 IC50 = 78.0 nM 7.11 Inhibition of N-terminus 6xHis-tagged human IDO1 expressed in Escherichia coli M... 27994758
Indoleamine 2,3-dioxygenase 1 Ki = 6600.0 nM 5.18 Inhibition of human indoleamine 2,3-dioxygenase expressed in Escherichia coli by... 17067170
Indoleamine 2,3-dioxygenase 1 Ki = 7000.0 nM 5.16 Competitive inhibition of histidine-tagged human recombinant IDO expressed in ba... 21419531
Indoleamine 2,3-dioxygenase 1 IC50 = 10000.0 nM 5.0 Inhibition of His-tagged recombinant human IDO1 expressed in Escherichia coli us... 22112538
Indoleamine 2,3-dioxygenase 1 IC50 = 14690.0 nM 4.83 Inhibition of IDO1 in IFN-gamma treated human HeLa cells incubated for 48 hrs by... 37060754
Indoleamine 2,3-dioxygenase 1 IC50 = 18400.0 nM 4.74 Inhibition of IDO1 in human U87MG cells in presence of L-tryptophan incubated fo... -
Indoleamine 2,3-dioxygenase 1 IC50 = 18400.0 nM 4.74 Inhibition of IDO1 in human HeLa cells 33215494
Indoleamine 2,3-dioxygenase 1 IC50 = 18400.0 nM 4.74 Inhibition of recombinant human IDO1 expressed in HEK293 cells assessed as reduc... 31580660
Indoleamine 2,3-dioxygenase 1 IC50 = 18400.0 nM 4.74 Inhibition of human IDO1 expressed in HEK293 cells assessed as kynurenine releas... 24099220
Indoleamine 2,3-dioxygenase 1 Ki = 19000.0 nM 4.72 Inhibition of IDO by cell-free assay 20055453
Indoleamine 2,3-dioxygenase 1 Ki = 30000.0 nM 4.52 Inhibition of IDO1 (unknown origin) 28667875
Unchecked Ki = 34000.0 nM 4.47 Inhibition of rabbit small intestine indoleamine 2,3-dioxygenase 18665584
Indoleamine 2,3-dioxygenase 1 Ki = 34000.0 nM 4.47 Competitive inhibition of human IDO1 in presence of tryptophan 24099220
Unchecked Ki = 34000.0 nM 4.47 Inhibition of IDO (unknown origin) -
Indoleamine 2,3-dioxygenase 1 Ki = 34000.0 nM 4.47 Inhibition of IDO1 (unknown origin) 32055299
Indoleamine 2,3-dioxygenase 1 Ki = 34000.0 nM 4.47 Competitive inhibition of recombinant human IDO1 expressed in Escherichia coli B... 31580660
Indoleamine 2,3-dioxygenase 1 Ki = 34000.0 nM 4.47 Competitive inhibition of IDO1 (unknown origin) using L-tryptophan as substrate ... -
Unchecked Ki = 34000.0 nM 4.47 Inhibition of rabbit IDO using L or D-tryptophan as substrate 33603967
Unchecked IC50 = 34000.0 nM 4.47 Inhibition of rabbit IDO using tryptophan as substrate 29456801
Indoleamine 2,3-dioxygenase 1 IC50 = 35000.0 nM 4.46 Inhibition of human IDO1 expressed in Escherichia coli BL21 Star assessed as kyn... 27469130

Literature References

PubMed DOI Target Context # Activities
39276584 10.1016/j.ejmech.2024.116852 ADMET 6
31580660 10.1021/acs.jmedchem.9b01079 Tryptophan 2,3-dioxygenase 6
31580660 10.1021/acs.jmedchem.9b01079 Indoleamine 2,3-dioxygenase 1 5
25815143 10.1021/ml500385d Indoleamine 2,3-dioxygenase 1 5
24099220 10.1021/jm401195n Indoleamine 2,3-dioxygenase 1 5
24099220 10.1021/jm401195n Mus musculus 5
31178268 10.1016/j.bmc.2019.05.048 Indoleamine 2,3-dioxygenase 1 4
32055299 10.1039/C9MD00208A ADMET 4
27475108 10.1016/j.ejmech.2016.07.013 Indoleamine 2,3-dioxygenase 2 4
30108875 10.1039/C7MD00226B Indoleamine 2,3-dioxygenase 1 3
27994758 10.1021/acsmedchemlett.6b00359 Indoleamine 2,3-dioxygenase 1 3
24099220 10.1021/jm401195n Lewis lung carcinoma cell line 3
20055453 10.1021/jm9014718 Indoleamine 2,3-dioxygenase 1 3
31999451 10.1021/acs.jmedchem.9b01386 B16-F10 3
21269836 10.1016/j.bmc.2010.12.032 Indoleamine 2,3-dioxygenase 1 2
30108875 10.1039/C7MD00226B MDA-MB-231 2
28667875 10.1016/j.ejmech.2017.06.039 Indoleamine 2,3-dioxygenase 1 2
20055453 10.1021/jm9014718 ADMET 2
23218716 10.1016/j.bmcl.2012.11.036 Indoleamine 2,3-dioxygenase 1 2
31580660 10.1021/acs.jmedchem.9b01079 Indoleamine 2,3-dioxygenase 2 2

Data from ChEMBL 36 via Core Engine