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Compound Detail

CHEMBL54976

TRYPTOPHAN
💊 Approved Drug
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💊 Approved Drug
N[C@@H](Cc1c[nH]c2ccccc12)C(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL54976
Name TRYPTOPHAN
Phase Approved
Structure Type MOL
InChI Key QIVBCDIJIAJPQS-VIFPVBQESA-N
Therapeutic ✓ Yes

Known Names

(-)-tryptophan Gppe pdr sach L-tryptophan NSC-13119 Optimax Optimax wv Pacitron Triptofano Tryptophan Tryptophan ((-),l,s) Tryptophan, l- Tryptophane +1 more
3
Targets
19
Activities
3
Assay Types
30
PK Parameters
20
Publications
13
Known Names
9
Indications

Molecular Properties

204.2
MW (Da)
1.12
ALogP
2
HBA
3
HBD
79.1
PSA (Ų)
0.70
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Withdrawn
Chirality Single Enantiomer

Flags

Withdrawn Natural Product
USAN Year 1979

Extended Properties

Molecular Formula C11H12N2O2
MW 204.23
Aromatic Rings 2
Heavy Atoms 15
NP-Likeness 0.39

Indications

Depressive Disorder Emergence Delirium Cocaine-Related Disorders Hernias, Diaphragmatic, Congenital Obesity Schizophrenia Breast Neoplasms, Male Neoplasms Social Behavior

ATC Classification

N06AX02
tryptophan
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOANALEPTICS

Drug Warnings

Withdrawn
musculoskeletal toxicity
eosinophilia-myalgia syndrome
Country: Germany; United Kingdom; Japan; Oman   Year: 1989
Withdrawn
hematological toxicity
eosinophilia-myalgia syndrome
Country: Germany; United Kingdom; Japan; Oman   Year: 1989
Withdrawn
hematological toxicity
Eosinophilic Myalgia Syndrome
Country: Germany; United Kingdom; Japan; Oman   Year: 1989
Withdrawn
musculoskeletal toxicity
Eosinophilic Myalgia Syndrome
Country: Germany; United Kingdom; Japan; Oman   Year: 1989

Activity Summary

IC50 15 meas. best 5.65
EC50 2 meas.
Ki 2 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Myeloperoxidase
CHEMBL2439
 IC50 5.65 5.65 2250.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.46 4.8933 3500.0 3
Plasmodium falciparum
CHEMBL364
 IC50 4.9 4.9 12589.2 4

Pharmacokinetic Data

Parameter Value Units Species
KA 16.0 uM Mus musculus
KA 44.0 uM Homo sapiens
KA 27.0 uM Homo sapiens
KA 44.0 uM Homo sapiens
KA 27.0 uM Homo sapiens
KA 57.5 uM Homo sapiens
KA 16.5 uM Homo sapiens
KA 1.13 uM Homo sapiens
KA 0.89 uM Homo sapiens
Ka 44.0 uM Homo sapiens
Ka 27.0 uM Homo sapiens
Ka 15.0 uM Homo sapiens
KA 44.0 uM Homo sapiens
KA 27.0 uM Homo sapiens
KA 37.5 uM Homo sapiens
KA 26.0 uM Homo sapiens
Ka 27.0 uM Homo sapiens
Ka 16.9 uM Methanothermobacter thermautotrophicus
Ka 91.0 uM Saccharomyces cerevisiae
Ka 27.0 uM Homo sapiens
Ka 44.0 uM Homo sapiens
Ka 1.13 uM Homo sapiens
Ka 20.0 uM Homo sapiens
Ka 37.0 uM Homo sapiens
Ka 1.13 uM Homo sapiens
Ka 0.89 uM Homo sapiens
Ka 15.0 uM Homo sapiens
Ka 57.0 uM Homo sapiens
Ka 37.0 uM Homo sapiens
Ka 26.0 uM Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Myeloperoxidase IC50 = 2250.0 nM 5.65 Inhibition of MPO (unknown origin) using H2O2 as substrate 30466896
NON-PROTEIN TARGET IC50 = 3500.0 nM 5.46 Antioxidant activity assessed as inhibition of HOCl-induced oxidation of DHR by ... 20727623
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910
NON-PROTEIN TARGET IC50 = 19200.0 nM 4.72 Antioxidant activity assessed as inhibition of peroxynitrite anion-induced oxida... 20727623
NON-PROTEIN TARGET IC50 = 31900.0 nM 4.5 Antioxidant activity assessed as inhibition of peroxynitrite anion-induced oxida... 20727623

Literature References

PubMed DOI Target Context # Activities
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
21493072 10.1016/j.bmc.2011.03.031 Rattus norvegicus 9
19442419 10.1016/j.ejmech.2009.04.018 Rattus norvegicus 8
20727623 10.1016/j.ejmech.2010.07.059 NON-PROTEIN TARGET 7
11278508 10.1074/jbc.m009462200 Monocarboxylate transporter 10 7
18472188 10.1016/j.ejmech.2008.03.035 Rattus norvegicus 6
7097726 10.1021/jm00348a022 Rattus norvegicus 5
19113967 10.1021/np800501m Unchecked 5
25815143 10.1021/ml500385d Indoleamine 2,3-dioxygenase 1 5
30108882 10.1039/C7MD00209B Aspergillus niger 4
30108882 10.1039/C7MD00209B Staphylococcus aureus 4
30108882 10.1039/C7MD00209B Escherichia coli 4
19734910 10.1038/nchembio.215 Plasmodium falciparum 4
30108882 10.1039/C7MD00209B Bacillus subtilis 4
30108882 10.1039/C7MD00209B Fusarium oxysporum 4
30108882 10.1039/C7MD00209B Candida albicans 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
20869876 10.1016/j.bmc.2010.08.052 Albumin 4
30108882 10.1039/C7MD00209B Klebsiella pneumoniae 4
20014752 10.1021/tx900326k Hepatotoxicity 3

Data from ChEMBL 36 via Core Engine