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pirlimycin   Click here for help

GtoPdb Ligand ID: 13621

Synonyms: Pirsue® (veterinary) | U-57,930E | U-57930E
Compound class: Synthetic organic
Comment: Pirlimycin is a lincosamide antibacterial compound and analogue of clindamycin, with activity against Gram-positive bacteria [1-2]. It is used in veterinary medicine.

pirlimycin is commercially available from our sponsors

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 7
Hydrogen bond donors 5
Rotatable bonds 7
Topological polar surface area 136.35
Molecular weight 410.96
XLogP 1.76
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[C@@H]1CCN[C@@H](C1)C(=O)N[C@H]([C@H](C)Cl)[C@@H]2[C@@H]([C@@H]([C@H]([C@H](O2)SC)O)O)O
Isomeric SMILES CC[C@@H]1CCN[C@@H](C1)C(=O)N[C@@H]([C@@H]2[C@@H]([C@@H]([C@H]([C@H](O2)SC)O)O)O)[C@H](C)Cl
InChI InChI=1S/C17H31ClN2O5S/c1-4-9-5-6-19-10(7-9)16(24)20-11(8(2)18)15-13(22)12(21)14(23)17(25-15)26-3/h8-15,17,19,21-23H,4-7H2,1-3H3,(H,20,24)/t8-,9+,10-,11+,12-,13+,14+,15+,17+/m0/s1
InChI Key HBJOXQRURQPDEX-MHXMMLMNSA-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,4R)-N-[(1S,2S)-2-chloro-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]propyl]-4-ethylpiperidine-2-carboxamide
International Nonproprietary Names Click here for help
INN number INN
5195 pirlimycin
Synonyms Click here for help
Pirsue® (veterinary) | U-57,930E | U-57930E
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Pirlimycin
Other databases
CAS Registry No. 79548-73-5 (source: Scifinder)
ChEMBL Ligand CHEMBL1652611
DrugBank Ligand DB11537
DrugCentral Ligand 5600
GtoPdb PubChem SID 504705440
PubChem CID 157385
Search Google for chemical match using the InChIKey HBJOXQRURQPDEX-MHXMMLMNSA-N
Search Google for chemicals with the same backbone HBJOXQRURQPDEX
Search PubMed clinical trials pirlimycin
Search PubMed titles pirlimycin
Search PubMed titles/abstracts pirlimycin
UniChem Compound Search for chemical match using the InChIKey HBJOXQRURQPDEX-MHXMMLMNSA-N
UniChem Connectivity Search for chemical match using the InChIKey HBJOXQRURQPDEX-MHXMMLMNSA-N

Product suppliers

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Product supplier links are provided as a service to assist in identifying commercial suppliers of reagents that are mentioned on the IUPHAR/BPS Guide to PHARMACOLOGY database website, and do not imply their endorsement by NC-IUPHAR.

Links are provided in return for sponsorship, used to fund improvements to this database. The sponsorship account is managed and audited by the University of Edinburgh, a charitable body registered in Scotland, SC005336. If you are interested in sponsoring the database, please contact us.

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MedChemExpress
Pirlimycin (links to external site)
Cat. No. HY-106597