apalcillin   Click here for help

GtoPdb Ligand ID: 10759

Synonyms: PC-904 | PC904 | WY-44,417 | WY-44417
Compound class: Synthetic organic
Comment: Apalcillin (PC-904) is a semisynthetic penicillin (β-lactam) derivative antibacterial [1-2]. It is highly active against Pseudomonas species. Toxicity issues meant that this compound did not progress beyond preclinical evaluation.
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 9
Hydrogen bond donors 4
Rotatable bonds 8
Topological polar surface area 186.86
Molecular weight 521.14
XLogP 0.66
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 O=C([C@@H](c1ccccc1)NC(=O)c1c[nH]c2c(c1=O)nccc2)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C
Isomeric SMILES O=C([C@@H](c1ccccc1)NC(=O)c1c[nH]c2c(c1=O)nccc2)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C
InChI InChI=1S/C25H23N5O6S/c1-25(2)19(24(35)36)30-22(34)17(23(30)37-25)29-21(33)15(12-7-4-3-5-8-12)28-20(32)13-11-27-14-9-6-10-26-16(14)18(13)31/h3-11,15,17,19,23H,1-2H3,(H,27,31)(H,28,32)(H,29,33)(H,35,36)/t15-,17-,19+,23-/m1/s1
InChI Key XMQVYNAURODYCQ-SLFBBCNNSA-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
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[[(2R)-2-[(4-oxo-1H-1,5-naphthyridine-3-carbonyl)amino]-2-phenylacetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
4422 apalcillin
Synonyms Click here for help
PC-904 | PC904 | WY-44,417 | WY-44417
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Apalcillin (PC-904)
Other databases
CAS Registry No. 63469-19-2 (source: WHO INN record)
ChEMBL Ligand CHEMBL3306902
DrugCentral Ligand 227
GtoPdb PubChem SID 405560200
PubChem CID 6602341
Search Google for chemical match using the InChIKey XMQVYNAURODYCQ-SLFBBCNNSA-N
Search Google for chemicals with the same backbone XMQVYNAURODYCQ
Search PubMed clinical trials apalcillin
Search PubMed titles apalcillin
Search PubMed titles/abstracts apalcillin
UniChem Compound Search for chemical match using the InChIKey XMQVYNAURODYCQ-SLFBBCNNSA-N
UniChem Connectivity Search for chemical match using the InChIKey XMQVYNAURODYCQ-SLFBBCNNSA-N