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penamecillin   Click here for help

GtoPdb Ligand ID: 12808

Synonyms: Havapen® | WY-20788
Approved drug
penamecillin is an approved drug
Compound class: Synthetic organic
Comment: Penamecillin is a β-lactam (penicillin) antibacterial compound and a prodrug (acetoxymethyl ester) of penicillin G [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 8
Hydrogen bond donors 1
Rotatable bonds 9
Topological polar surface area 127.31
Molecular weight 406.45
XLogP 1.78
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 CC(=O)OCOC(=O)[C@H]1C(C)(C)S[C@@H]2[C@@H](C(=O)N12)NC(=O)CC3=CC=CC=C3
Isomeric SMILES CC(=O)OCOC(=O)[C@H]1C(S[C@H]2N1C(=O)[C@H]2NC(=O)CC3=CC=CC=C3)(C)C
InChI InChI=1S/C19H22N2O6S/c1-11(22)26-10-27-18(25)15-19(2,3)28-17-14(16(24)21(15)17)20-13(23)9-12-7-5-4-6-8-12/h4-8,14-15,17H,9-10H2,1-3H3,(H,20,23)/t14-,15+,17-/m1/s1
InChI Key NLOOMWLTUVBWAW-HLLBOEOZSA-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.
Is prodrug? Yes
Active form penicillin G
IUPAC Name Click here for help
acetyloxymethyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
International Nonproprietary Names Click here for help
INN number INN
2057 penamecillin
Synonyms Click here for help
Havapen® | WY-20788
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Penamecillin
Other databases
CAS Registry No. 983-85-7 (source: Scifinder)
ChEBI CHEBI:131733
ChEMBL Ligand CHEMBL2106988
DrugBank Ligand DB13739
DrugCentral Ligand 2077
GtoPdb PubChem SID 483123356
PubChem CID 10250769
Search Google for chemical match using the InChIKey NLOOMWLTUVBWAW-HLLBOEOZSA-N
Search Google for chemicals with the same backbone NLOOMWLTUVBWAW
Search PubMed clinical trials penamecillin
Search PubMed titles penamecillin
Search PubMed titles/abstracts penamecillin
UniChem Compound Search for chemical match using the InChIKey NLOOMWLTUVBWAW-HLLBOEOZSA-N
UniChem Connectivity Search for chemical match using the InChIKey NLOOMWLTUVBWAW-HLLBOEOZSA-N