olamufloxacin   Click here for help

GtoPdb Ligand ID: 10838

Synonyms: HSR-903 | HSR903
Compound class: Synthetic organic
Comment: Olamufloxacin (HSR-903) is a low toxicity synthetic fluoroquinolone antibacterial agent [1-3]. It inhibits supercoiling by Escherichia coli DNA gyrase, but it is much less active against human topoisomerase II [3].
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 5
Hydrogen bond donors 3
Rotatable bonds 3
Topological polar surface area 114.58
Molecular weight 386.18
XLogP 3.61
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 N[C@@H]1CN(CC21CC2)c1c(F)c(N)c2c(c1C)n(cc(c2=O)C(=O)O)C1CC1
Isomeric SMILES N[C@@H]1CN(CC21CC2)c1c(F)c(N)c2c(c1C)n(cc(c2=O)C(=O)O)C1CC1
InChI InChI=1S/C20H23FN4O3/c1-9-16-13(18(26)11(19(27)28)6-25(16)10-2-3-10)15(23)14(21)17(9)24-7-12(22)20(8-24)4-5-20/h6,10,12H,2-5,7-8,22-23H2,1H3,(H,27,28)/t12-/m1/s1
InChI Key LEILBPMISZFZQK-GFCCVEGCSA-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
5-amino-7-[(7S)-7-amino-5-azaspiro[2.4]heptan-5-yl]-1-cyclopropyl-6-fluoro-8-methyl-4-oxoquinoline-3-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
7740 olamufloxacin
Synonyms Click here for help
HSR-903 | HSR903
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Olamufloxacin (HSR-903)
Other databases
CAS Registry No. 167887-97-0 (source: WHO INN record)
ChEMBL Ligand CHEMBL2078925
GtoPdb PubChem SID 405560279
PubChem CID 477670
Search Google for chemical match using the InChIKey LEILBPMISZFZQK-GFCCVEGCSA-N
Search Google for chemicals with the same backbone LEILBPMISZFZQK
Search PubMed clinical trials olamufloxacin
Search PubMed titles olamufloxacin
Search PubMed titles/abstracts olamufloxacin
UniChem Compound Search for chemical match using the InChIKey LEILBPMISZFZQK-GFCCVEGCSA-N
UniChem Connectivity Search for chemical match using the InChIKey LEILBPMISZFZQK-GFCCVEGCSA-N