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.
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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