lincomycin   Click here for help

GtoPdb Ligand ID: 10941

Synonyms: Bactramycin® | L-Mycin® | LCM | Lincocin® | Lincorex® | U 10,149A | U-10149
Approved drug PDB Ligand
lincomycin is an approved drug (FDA (1964))
Compound class: Synthetic organic
Comment: Lincomycin is a lincosamide antibacterial that has activity against Gram-positive and anaerobic bacteria [2]. It was isolated from the actinomycete Streptomyces lincolnensis. Pathogenic species of bacteria that are sensitive to lincomycin include Streptococcus, Staphylococcus, and Mycoplasma.

lincomycin 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 8
Hydrogen bond donors 5
Rotatable bonds 8
Topological polar surface area 147.79
Molecular weight 406.21
XLogP 0.69
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 CCC[C@@H]1C[C@@H](C(=O)N[C@H]([C@@H](C)O)[C@@H]2[C@@H]([C@@H]([C@H]([C@H](O2)SC)O)O)O)N(C)C1
Isomeric SMILES CCC[C@H]1CN([C@@H](C1)C(=O)N[C@@H]([C@H]2O[C@H](SC)[C@@H]([C@H]([C@H]2O)O)O)[C@H](O)C)C
InChI InChI=1S/C18H34N2O6S/c1-5-6-10-7-11(20(3)8-10)17(25)19-12(9(2)21)16-14(23)13(22)15(24)18(26-16)27-4/h9-16,18,21-24H,5-8H2,1-4H3,(H,19,25)/t9-,10-,11+,12-,13+,14-,15-,16-,18-/m1/s1
InChI Key OJMMVQQUTAEWLP-KIDUDLJLSA-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 (FDA (1964))
Approved drug? Yes. FDA (1964)
IUPAC Name Click here for help
(2S,4R)-N-[(1R,2R)-2-hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide
International Nonproprietary Names Click here for help
INN number INN
1419 lincomycin
Synonyms Click here for help
Bactramycin® | L-Mycin® | LCM | Lincocin® | Lincorex® | U 10,149A | U-10149
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Lincomycin
Other databases
BindingDB Ligand 50335522
CAS Registry No. 154-21-2 (source: WHO INN record)
ChEMBL Ligand CHEMBL1447
DrugBank Ligand DB01627
DrugCentral Ligand 1582
GtoPdb PubChem SID 405560382
PubChem CID 3000540
RCSB PDB Ligand 3QB
Search Google for chemical match using the InChIKey OJMMVQQUTAEWLP-KIDUDLJLSA-N
Search Google for chemicals with the same backbone OJMMVQQUTAEWLP
Search PubMed clinical trials lincomycin
Search PubMed titles lincomycin
Search PubMed titles/abstracts lincomycin
UniChem Compound Search for chemical match using the InChIKey OJMMVQQUTAEWLP-KIDUDLJLSA-N
UniChem Connectivity Search for chemical match using the InChIKey OJMMVQQUTAEWLP-KIDUDLJLSA-N

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MedChemExpress
Lincomycin (links to external site)
Cat. No. HY-117660