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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL54976
CHEMBL54976
Compound Name TRYPTOPHAN
ChEMBL Synonyms OPTIMAX WV | L-TRYPTOPHAN | GPPE PDR SACH | TRYPTOPHAN | OPTIMAX | PACITRON
Max Phase 4 (Approved)
Withdrawn Yes
Trade Names GPPE PDR SACH | OPTIMAX WV | OPTIMAX | PACITRON
Molecular Formula C11H12N2O2

Additional synonyms for CHEMBL54976 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES N[C@@H](Cc1c[nH]c2ccccc12)C(=O)O
Standard InChI InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)1 ...
Download InChI
Standard InChI Key QIVBCDIJIAJPQS-VIFPVBQESA-N

Sources

  • AstraZeneca Deposited Data
  • BindingDB Database
  • British National Formulary
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification
  • Withdrawn Drugs

Alternate Forms of Compound in ChEMBL


CHEMBL54976

Molecule Features

CHEMBL54976 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:N Parenteral:N Topical:N Black Box:N Availability Type:Withdrawn

Withdrawal Information

Year 1989
Country United Kingdom; Germany
Reason Eosinophilic Myalgia Syndrome
Class Hematological toxicity

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
SchizophreniaD012559EFO:0000692schizophrenia2ClinicalTrials
ObesityD009765EFO:0001073obesity2ClinicalTrials
Cocaine-Related DisordersD019970EFO:0002610cocaine dependence2ClinicalTrials
Hernias, Diaphragmatic, CongenitalD065630EFO:0005207congenital heart disease2ClinicalTrials
Breast Neoplasms, MaleD018567EFO:0006861male breast carcinoma1ClinicalTrials
Depressive DisorderD003866EFO:0003761unipolar depression4ATC
NeoplasmsD009369EFO:0000616neoplasm1ClinicalTrials
Postoperative ComplicationsD011183EFO:0005323post-operative sign or symptom3ClinicalTrials

Clinical Data

ClinicalTrials.gov TRYPTOPHAN
The Cochrane Collaboration TRYPTOPHAN

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL54976. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL3768 Neprilysin Oryctolagus cuniculus 1.000
CHEMBL4791 Endothelin-converting enzyme 1 Homo sapiens 1.000
CHEMBL2625 Angiotensin-converting enzyme Rattus norvegicus 1.000
CHEMBL2854 Cholecystokinin B receptor Mus musculus 1.000
CHEMBL2871 Cholecystokinin A receptor Rattus norvegicus 0.987
CHEMBL4816 Serine/threonine-protein kinase AKT3 Homo sapiens 0.961
CHEMBL2439 Myeloperoxidase Homo sapiens 0.951
CHEMBL249 Neurokinin 1 receptor Homo sapiens 0.928
CHEMBL1293237 Bloom syndrome protein Homo sapiens 0.909
CHEMBL3636 Neuromedin B receptor Homo sapiens 0.906
CHEMBL1804 Somatostatin receptor 2 Homo sapiens 0.870
CHEMBL3278 Ghrelin receptor Rattus norvegicus 0.823
CHEMBL2693 Cystinyl aminopeptidase Homo sapiens 0.763
CHEMBL4581 Kinesin-like protein 1 Homo sapiens 0.721
CHEMBL333 Matrix metalloproteinase-2 Homo sapiens 0.689
CHEMBL4130 Endothelin receptor ET-A Sus scrofa 0.681
CHEMBL324 Serotonin 2c (5-HT2c) receptor Rattus norvegicus 0.664
CHEMBL2028 Somatostatin receptor 3 Homo sapiens 0.658
CHEMBL313 Serotonin transporter Rattus norvegicus 0.528
CHEMBL1983 Serotonin 1d (5-HT1d) receptor Homo sapiens 0.468



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL4077 Melanocortin receptor 1 Mus musculus 1.000
CHEMBL3768 Neprilysin Oryctolagus cuniculus 1.000
CHEMBL4791 Endothelin-converting enzyme 1 Homo sapiens 1.000
CHEMBL2625 Angiotensin-converting enzyme Rattus norvegicus 1.000
CHEMBL3636 Neuromedin B receptor Homo sapiens 1.000
CHEMBL2693 Cystinyl aminopeptidase Homo sapiens 1.000
CHEMBL5043 Endoplasmic reticulum aminopeptidase 2 Homo sapiens 1.000
CHEMBL2854 Cholecystokinin B receptor Mus musculus 1.000
CHEMBL1917 Somatostatin receptor 1 Homo sapiens 1.000
CHEMBL2871 Cholecystokinin A receptor Rattus norvegicus 0.998
CHEMBL2439 Myeloperoxidase Homo sapiens 0.997
CHEMBL1804 Somatostatin receptor 2 Homo sapiens 0.991
CHEMBL4581 Kinesin-like protein 1 Homo sapiens 0.990
CHEMBL2028 Somatostatin receptor 3 Homo sapiens 0.984
CHEMBL2919 Glutamate receptor ionotropic kainate 1 Rattus norvegicus 0.981
CHEMBL4130 Endothelin receptor ET-A Sus scrofa 0.977
CHEMBL5939 Endoplasmic reticulum aminopeptidase 1 Homo sapiens 0.977
CHEMBL249 Neurokinin 1 receptor Homo sapiens 0.974
CHEMBL2676 Endothelin-converting enzyme 1 Rattus norvegicus 0.962
CHEMBL259 Melanocortin receptor 4 Homo sapiens 0.936

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
204.2 204.0899 1.12 3 79.11 ZWITTERION


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
2 3 0 4 4 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
2.3 9.71 .7 -1.8 2 15 0.7

Structural Alerts

There are 1 structural alerts for CHEMBL54976. To view alerts please click here.

Compound Cross References

ATC N - NERVOUS SYSTEM
N06 - PSYCHOANALEPTICS
N06A - ANTIDEPRESSANTS
N06AX - Other antidepressants
N06AX02 - tryptophan

ChemSpider ChemSpider:QIVBCDIJIAJPQS-VIFPVBQESA-N
PubChem SID: 11111851 SID: 144208444 SID: 144210677 SID: 26732620 SID: 50107108 SID: 50107109 SID: 90341602
Wikipedia Tryptophan

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL54976



ACToR 6912-86-3
BindingDB 21974
Brenda 119 888 817 107453 420 107452
ChEBI 16828 57912
ChemicalBook CB3750054
DrugBank DB00150
DrugCentral 2780
eMolecules 533030 26755894
EPA CompTox Dashboard DTXSID5021419
FDA SRS 8DUH1N11BX
Guide to Pharmacology 717
Human Metabolome Database HMDB0000929
IBM Patent System 3037213DF67C696984F58EFB715AB997
KEGG Ligand C00078
Mcule MCULE-8004234494 MCULE-3721322622
Metabolights MTBLC57912 MTBLC16828
MolPort MolPort-001-794-499
Nikkaji J9.181B
PDBe TRP
PharmGKB PA10323
PubChem 6305 6923516
PubChem: Drugs of the Future 24714971
PubChem: Thomson Pharma 15195597 14916602
Recon trp_L
Rhea 57912
SureChEMBL SCHEMBL7328
ZINC ZINC000000083315

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/QIVBCDIJIAJPQS-VIFPVBQESA-N spacer
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