enmetazobactam   Click here for help

GtoPdb Ligand ID: 12188

Synonyms: AAI101 | OCID-5090
Compound class: Synthetic organic
Comment: Enmetazobactam is an extended-spectrum β-lactamase inhibitor. It is an N-methylated tazobactam derivative, under clinical development for use alongside β-lactam-containing antibacterial compounds to reduce their lactamase-induced degradation.
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 CDK toolkit. 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 7
Hydrogen bond donors 0
Rotatable bonds 3
Topological polar surface area 124.66
Molecular weight 314.07
XLogP -1.75
No. Lipinski's rules broken 0
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.

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Canonical SMILES [O-]C(=O)[C@@H]1N2C(=O)C[C@H]2S(=O)(=O)[C@@]1(C)Cn1cc[n+](n1)C
Isomeric SMILES C[C@@]1([C@@H](N2[C@H](S1(=O)=O)CC2=O)C(=O)[O-])Cn1cc[n+](n1)C
InChI InChI=1S/C11H14N4O5S/c1-11(6-14-4-3-13(2)12-14)9(10(17)18)15-7(16)5-8(15)21(11,19)20/h3-4,8-9H,5-6H2,1-2H3/t8-,9+,11+/m1/s1
InChI Key HFZITXBUTWITPT-YWVKMMECSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(2S,3S,5R)-3-methyl-3-[(3-methyltriazol-3-ium-1-yl)methyl]-4,4,7-trioxo-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
International Nonproprietary Names Click here for help
INN number INN
10913 enmetazobactam
Synonyms Click here for help
AAI101 | OCID-5090
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Enmetazobactam, AAI101, OCID 5090
Other databases
CAS Registry No. 1001404-83-6 (source: Scifinder)
ChEMBL Ligand CHEMBL4458276
GtoPdb PubChem SID 472319310
PubChem CID 23653540
Search Google for chemical match using the InChIKey HFZITXBUTWITPT-YWVKMMECSA-N
Search Google for chemicals with the same backbone HFZITXBUTWITPT
Search PubMed clinical trials enmetazobactam
Search PubMed titles enmetazobactam
Search PubMed titles/abstracts enmetazobactam
UniChem Compound Search for chemical match using the InChIKey HFZITXBUTWITPT-YWVKMMECSA-N
UniChem Connectivity Search for chemical match using the InChIKey HFZITXBUTWITPT-YWVKMMECSA-N