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bacampicillin   Click here for help

GtoPdb Ligand ID: 12292

Synonyms: Penglobe® | Spectrobid®
Approved drug
bacampicillin is an approved drug (FDA (1980))
Compound class: Synthetic organic
Comment: Bacampicillin is a semisynthetic penicillin belonging to the β-lactam group of antibacterial compounds. It is a prodrug that is hydrolysed to ampicillin following absorption from the gastrointestinal tract [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 10
Hydrogen bond donors 2
Rotatable bonds 11
Topological polar surface area 162.56
Molecular weight 465.16
XLogP 1.98
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 CCOC(=O)OC(OC(=O)[C@@H]1N2C(=O)[C@H]([C@H]2SC1(C)C)NC(=O)[C@@H](c1ccccc1)N)C
Isomeric SMILES CCOC(=O)OC(C)OC(=O)[C@H]1C(S[C@H]2N1C(=O)[C@H]2NC(=O)[C@@H](c1ccccc1)N)(C)C
InChI InChI=1S/C21H27N3O7S/c1-5-29-20(28)31-11(2)30-19(27)15-21(3,4)32-18-14(17(26)24(15)18)23-16(25)13(22)12-9-7-6-8-10-12/h6-11,13-15,18H,5,22H2,1-4H3,(H,23,25)/t11?,13-,14-,15+,18-/m1/s1
InChI Key PFOLLRNADZZWEX-FFGRCDKISA-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. US FDA (1980)
Is prodrug? Yes
Active form ampicillin
IUPAC Name Click here for help
1-ethoxycarbonyloxyethyl (2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
International Nonproprietary Names Click here for help
INN number INN
3630 bacampicillin
Synonyms Click here for help
Penglobe® | Spectrobid®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Bacampicillin
Other databases
CAS Registry No. 50972-17-3 (source: Scifinder)
ChEBI CHEBI:2968
ChEMBL Ligand CHEMBL1583
DrugBank Ligand DB01602
DrugCentral Ligand 280
GtoPdb PubChem SID 479821083
PubChem CID 441397
Search Google for chemical match using the InChIKey PFOLLRNADZZWEX-FFGRCDKISA-N
Search Google for chemicals with the same backbone PFOLLRNADZZWEX
Search PubMed clinical trials bacampicillin
Search PubMed titles bacampicillin
Search PubMed titles/abstracts bacampicillin
UniChem Compound Search for chemical match using the InChIKey PFOLLRNADZZWEX-FFGRCDKISA-N
UniChem Connectivity Search for chemical match using the InChIKey PFOLLRNADZZWEX-FFGRCDKISA-N