TRYPTOPHAN

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Search structure


Synonyms	Gppe pdr sach L-tryptophan NSC-13119 Optimax Optimax wv Pacitron Tryptophan Tryptophan ((-),l,s) Tryptophan, l- Trytophan-
Status
Molecule Category	UNKNOWN
ATC	N06AX02
UNII	8DUH1N11BX
EPA CompTox	DTXSID5021419


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	QIVBCDIJIAJPQS-VIFPVBQESA-N
Smiles	N[C@@H](Cc1c[nH]c2ccccc12)C(=O)O
InChI	InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m0/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C11H12N2O2
Molecular Weight	204.23
AlogP	1.12
Hydrogen Bond Acceptor	2.0
Hydrogen Bond Donor	3.0
Number of Rotational Bond	3.0
Polar Surface Area	79.11
Molecular species	ZWITTERION
Aromatic Rings	2.0
Heavy Atoms	15.0

Assay Description	Organism	Bioactivity	Reference
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	93.19 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	97.09 %
Inhibition of ASCT2 mediated [3H]-D-serine uptake in rat hippocampal astrocytes at 1 mM after 5 mins by beta counting analysis	Rattus norvegicus	25.0 %
Antagonist activity at human GPR17 expressed in human 1321N1 cells assessed as inhibition of MDL 29,951-induced calcium mobilization at >30 nM after 1 hr by Oregon Green BAPTA-1/AM dye-based fluorescence assay relative to control	Homo sapiens	1.0 %
Cis-inhibition of human LAT1 expressed in TREx HEK293 cells at 200 uM assessed as inhibition of [3H]-gabapentin uptake at 200 uM preincubated for 3 mins at 37 degC followed by washing with choline buffer and measured after 3 hrs by scintillation counting analysis relative to BCH	Homo sapiens	79.0 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	-5.03 %
Cis-inhibition of human LAT1 expressed in TREx HEK293 cells at 200 uM assessed as inhibition of [3H]-gabapentin uptake preincubated for 3 mins at 37 degC followed by washing with choline buffer and measured after 3 hrs by scintillation counting analysis relative to BCH	Homo sapiens	79.0 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	-0.98 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	14.77 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.09 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.13 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.09 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.13 %
Inhibition of human LAT1 expressed in HEK293-T-Rex cells assessed as inhibition of [3H]-gabapentin uptake at 200 uM by scintillation counting cis-inhibition assay	Homo sapiens	79.0 %

Related Entries

Cross References

Resources	Reference
ChEBI	16828
ChEMBL	CHEMBL54976
DrugBank	DB00150
DrugCentral	2780
FDA SRS	8DUH1N11BX
Human Metabolome Database	HMDB0000929
Guide to Pharmacology	717
KEGG	C00078
PDB	TRP
PharmGKB	PA10323
PubChem	6305
SureChEMBL	SCHEMBL7328
ZINC	ZINC000000083315

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).