aspoxicillin   Click here for help

GtoPdb Ligand ID: 12293

Synonyms: Doyle® | TA-058
Approved drug
aspoxicillin is an approved drug (Japan)
Compound class: Synthetic organic
Comment: Aspoxicillin is penicillin derivative belonging to the β-lactam class of antibacterial compounds [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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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 11
Hydrogen bond donors 6
Rotatable bonds 11
Topological polar surface area 216.46
Molecular weight 493.16
XLogP -3.53
No. Lipinski's rules broken 2

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 CNC(=O)C[C@H](C(=O)N[C@H](c1ccc(cc1)O)C(=O)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C)N
Isomeric SMILES CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](c1ccc(cc1)O)NC(=O)[C@@H](CC(=O)NC)N)C(=O)O)C
InChI InChI=1S/C21H27N5O7S/c1-21(2)15(20(32)33)26-18(31)14(19(26)34-21)25-17(30)13(9-4-6-10(27)7-5-9)24-16(29)11(22)8-12(28)23-3/h4-7,11,13-15,19,27H,8,22H2,1-3H3,(H,23,28)(H,24,29)(H,25,30)(H,32,33)/t11-,13-,14-,15+,19-/m1/s1
InChI Key BHELIUBJHYAEDK-OAIUPTLZSA-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 (Japan)
IUPAC Name Click here for help
(2S,5R,6R)-6-[[(2R)-2-[[(2R)-2-amino-4-methylamino-4-oxobutanoyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
5350 aspoxicillin
Synonyms Click here for help
Doyle® | TA-058
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Aspoxicillin
Other databases
CAS Registry No. 63358-49-6 (source: Scifinder)
ChEBI CHEBI:31240
ChEMBL Ligand CHEMBL1318150
DrugBank Ligand DB13816
DrugCentral Ligand 248
GtoPdb PubChem SID 479821084
PubChem CID 71961
Search Google for chemical match using the InChIKey BHELIUBJHYAEDK-OAIUPTLZSA-N
Search Google for chemicals with the same backbone BHELIUBJHYAEDK
Search PubMed clinical trials aspoxicillin
Search PubMed titles aspoxicillin
Search PubMed titles/abstracts aspoxicillin
UniChem Compound Search for chemical match using the InChIKey BHELIUBJHYAEDK-OAIUPTLZSA-N
UniChem Connectivity Search for chemical match using the InChIKey BHELIUBJHYAEDK-OAIUPTLZSA-N