thiamphenicol   Click here for help

GtoPdb Ligand ID: 12400

PDB Ligand
Compound class: Synthetic organic

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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 6
Hydrogen bond donors 3
Rotatable bonds 7
Topological polar surface area 112.08
Molecular weight 355
XLogP 0.31
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES OC[C@H]([C@@H](c1ccc(cc1)S(=O)(=O)C)O)NC(=O)C(Cl)Cl
Isomeric SMILES CS(=O)(=O)c1ccc(cc1)[C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O
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
InChI Key OTVAEFIXJLOWRX-NXEZZACHSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-methylsulfonylphenyl)propan-2-yl]acetamide
International Nonproprietary Names Click here for help
INN number INN
935 thiamphenicol
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Thiamphenicol
Other databases
CAS Registry No. 15318-45-3 (source: Scifinder)
ChEBI CHEBI:32215
ChEMBL Ligand CHEMBL1236282
DrugBank Ligand DB08621
DrugCentral Ligand 2624
GtoPdb PubChem SID 479821191
PubChem CID 27200
RCSB PDB Ligand TH8
Search Google for chemical match using the InChIKey OTVAEFIXJLOWRX-NXEZZACHSA-N
Search Google for chemicals with the same backbone OTVAEFIXJLOWRX
Search PubMed clinical trials thiamphenicol
Search PubMed titles thiamphenicol
Search PubMed titles/abstracts thiamphenicol
UniChem Compound Search for chemical match using the InChIKey OTVAEFIXJLOWRX-NXEZZACHSA-N
UniChem Connectivity Search for chemical match using the InChIKey OTVAEFIXJLOWRX-NXEZZACHSA-N

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MedChemExpress
Thiamphenicol (links to external site)
Cat. No. HY-B0479
Thiamphenicol (Standard) (links to external site)
Cat. No. HY-B0479R