THIAMPHENICOL

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Search structure


Synonyms	Armai Dextrosulphenidol NSC-522822 Thiamphenicol Thiamphenicol aminoacetate hydrochloride Thiocymetin Thiophenicol WIN 5063-2 WIN-5063-2
Status
Molecule Category	UNKNOWN
ATC	J01BA02
UNII	FLQ7571NPM
EPA CompTox	DTXSID5021338


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

Structure


InChI Key	OTVAEFIXJLOWRX-NXEZZACHSA-N
Smiles	CS(=O)(=O)c1ccc([C@@H](O)[C@@H](CO)NC(=O)C(Cl)Cl)cc1
InChI	InChI=1S/C12H15Cl2NO5S/c1-21(19,20)8-4-2-7(3-5-8)10(17)9(6-16)15-12(18)11(13)14/h2-5,9-11,16-17H,6H2,1H3,(H,15,18)/t9-,10-/m1/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C12H15Cl2NO5S
Molecular Weight	356.23
AlogP	0.4
Hydrogen Bond Acceptor	5.0
Hydrogen Bond Donor	3.0
Number of Rotational Bond	6.0
Polar Surface Area	103.7
Molecular species	NEUTRAL
Aromatic Rings	1.0
Heavy Atoms	21.0

Assay Description	Organism	Bioactivity	Reference
Tested for inhibition of puromycin reaction and reported as equilibrium constant derived from primary and secondary kinetic plots for the inhibition of peptide bond formation	Escherichia coli	400.0 nM
PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Identify Inhibitors of Streptokinase Promotor Activity. (Class of assay: confirmatory) [Related pubchem assays: 1677 (Project Summary), 1662 (Primary HTS)]	Streptococcus pyogenes M1 GAS	740.0 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	102.12 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	103.48 %
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	0.64 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	16.32 %
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	-0.08 %		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	-0.08 %

Cross References

Resources	Reference
ChEBI	32215
ChEMBL	CHEMBL1236282
DrugBank	DB08621
DrugCentral	2624
FDA SRS	FLQ7571NPM
KEGG	C12853
PDB	TH8
PubChem	27200
SureChEMBL	SCHEMBL34635
ZINC	ZINC000000538440

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).