azidamfenicol   Click here for help

GtoPdb Ligand ID: 12397

Synonyms: azidamphenicol | azidoamfenicol | azidoamphenicol | Thilocof®
Approved drug
azidamfenicol is an approved drug
Compound class: Synthetic organic
Comment: Azidamfenicol is an analogue of chloramphenicol and classed as an amphenicol antibacterial compound [1].
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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Click here for structure editor
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 8
Topological polar surface area 125.06
Molecular weight 295.09
XLogP -0.51
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)[N+](=O)[O-])O)NC(=O)CN=[N+]=[N-]
Isomeric SMILES c1cc(ccc1[C@H]([C@@H](CO)NC(=O)CN=[N+]=[N-])O)[N+](=O)[O-]
InChI InChI=1S/C11H13N5O5/c12-15-13-5-10(18)14-9(6-17)11(19)7-1-3-8(4-2-7)16(20)21/h1-4,9,11,17,19H,5-6H2,(H,14,18)/t9-,11-/m1/s1
InChI Key SGRUZFCHLOFYHZ-MWLCHTKSSA-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
Approved drug? Yes.
IUPAC Name Click here for help
2-azido-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide
International Nonproprietary Names Click here for help
INN number INN
1703 azidamfenicol
Synonyms Click here for help
azidamphenicol | azidoamfenicol | azidoamphenicol | Thilocof®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Azidamfenicol
Other databases
CAS Registry No. 13838-08-9 (source: Scifinder)
ChEBI CHEBI:135238
ChEMBL Ligand CHEMBL3989525
DrugBank Ligand DB13294
DrugCentral Ligand 3011
GtoPdb PubChem SID 479821188
PubChem CID 62858
Search Google for chemical match using the InChIKey SGRUZFCHLOFYHZ-MWLCHTKSSA-N
Search Google for chemicals with the same backbone SGRUZFCHLOFYHZ
Search PubMed clinical trials azidamfenicol
Search PubMed titles azidamfenicol
Search PubMed titles/abstracts azidamfenicol
UniChem Compound Search for chemical match using the InChIKey SGRUZFCHLOFYHZ-MWLCHTKSSA-N
UniChem Connectivity Search for chemical match using the InChIKey SGRUZFCHLOFYHZ-MWLCHTKSSA-N