Lincomycin

Basic Info

Common NameLincomycin(F05688)
2D Structure
FRCD IDF05688
CAS Number154-21-2
PubChem CID3000540
FormulaC18H34N2O6S
IUPAC Name

(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

InChI Key

OJMMVQQUTAEWLP-KIDUDLJLSA-N

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

Canonical SMILES

CCCC1CC(N(C1)C)C(=O)NC(C2C(C(C(C(O2)SC)O)O)O)C(C)O

Isomeric SMILES

CCC[C@@H]1C[C@H](N(C1)C)C(=O)N[C@@H]([C@@H]2[C@@H]([C@@H]([C@H]([C@H](O2)SC)O)O)O)[C@@H](C)O

Synonyms
        
            Lincomycinum
        
            lincomycin
        
            154-21-2
        
            Cillimycin
        
            Lincomycin A
        
            Lincomycine
        
            UNII-BOD072YW0F
        
            CHEMBL1447
        
            Lincolnensin
        
            Lincomicina
Classifies
                

                  
                    Pollutant
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
SubclassAmino acids, peptides, and analogues
Intermediate Tree NodesAmino acids and derivatives - Alpha amino acids and derivatives
Direct ParentProline and derivatives
Alternative Parents
Molecular FrameworkAliphatic heteromonocyclic compounds
SubstituentsProline or derivatives - Alpha-amino acid amide - Glycosyl compound - S-glycosyl compound - Pyrrolidine carboxylic acid or derivatives - Pyrrolidine-2-carboxamide - Monosaccharide - Oxane - N-alkylpyrrolidine - Monothioacetal - Pyrrolidine - Tertiary aliphatic amine - Tertiary amine - Secondary carboxylic acid amide - Secondary alcohol - Carboxamide group - Azacycle - Organoheterocyclic compound - Oxacycle - Sulfenyl compound - Polyol - Hydrocarbon derivative - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Alcohol - Organopnictogen compound - Organic oxygen compound - Organic oxide - Carbonyl group - Amine - Organic nitrogen compound - Aliphatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as proline and derivatives. These are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Properties

Property NameProperty Value
Molecular Weight406.538
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count8
Rotatable Bond Count7
Complexity499
Monoisotopic Mass406.214
Exact Mass406.214
XLogP0.2
Formal Charge0
Heavy Atom Count27
Defined Atom Stereocenter Count9
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB-0.9659
Human Intestinal AbsorptionHIA+0.5937
Caco-2 PermeabilityCaco2-0.8957
P-glycoprotein SubstrateSubstrate0.7945
P-glycoprotein InhibitorNon-inhibitor0.6755
Non-inhibitor0.5633
Renal Organic Cation TransporterNon-inhibitor0.8868
Distribution
Subcellular localizationLysosome0.5026
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8417
CYP450 2D6 SubstrateNon-substrate0.8837
CYP450 3A4 SubstrateSubstrate0.6389
CYP450 1A2 InhibitorNon-inhibitor0.9222
CYP450 2C9 InhibitorNon-inhibitor0.9070
CYP450 2D6 InhibitorNon-inhibitor0.9269
CYP450 2C19 InhibitorNon-inhibitor0.9203
CYP450 3A4 InhibitorNon-inhibitor0.9342
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9563
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9847
Non-inhibitor0.7163
AMES ToxicityNon AMES toxic0.7696
CarcinogensNon-carcinogens0.9482
Fish ToxicityHigh FHMT0.5599
Tetrahymena Pyriformis ToxicityHigh TPT0.8981
Honey Bee ToxicityLow HBT0.6583
BiodegradationNot ready biodegradable0.9622
Acute Oral ToxicityIII0.7675
Carcinogenicity (Three-class)Non-required0.6495
Model Value Unit
Absorption
Aqueous solubility-1.8518LogS
Caco-2 Permeability-0.2337LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.5777LD50, mol/kg
Fish Toxicity1.8070pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.2901pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Muscle Of SwineUnited States0.1ppm
Liver Of SwineUnited States0.6ppm
ChickensUnited States0.t required
CrustaceansJapan0.1ppm
Shelled MolluscasJapan0.1ppm
Other FishJapan0.1ppm
PerciformesJapan0.05ppm
AnguilliformesJapan0.1ppm
SalmoniformesJapan0.1ppm
Other Poultry,EggsJapan0.1ppm
Chicken,EggsJapan0.1ppm
Other Poultry Animals,Edible OffalJapan0.1ppm
Chicken,Edible OffalJapan0.02ppm
Other Poultry Animals,KidneyJapan0.8ppm
Chicken,KidneyJapan0.5ppm
Other Poultry Animals,LiverJapan0.3ppm
Chicken,LiverJapan0.5ppm
Other Poultry Animals,FatJapan0.05ppm
Chicken,FatJapan0.3ppm
Other Poultry Animals,MuscleJapan0.1ppm

References

TitleJournalDatePubmed ID
Molecular genotyping, biofilm formation and antibiotic resistance of enterotoxigenic Clostridium perfringens isolated from meat supplied to school cafeterias in South Korea.Anaerobe2018 Aug29936108
Characterization of Bacillus cereus isolates from local dairy farms in China.FEMS Microbiol Lett2016 Jun27190168
Isolation and characterization of Salmonella enterica in day-old ducklings in Egypt.Pathog Glob Health2014 Jan24548159
DNA microarray based detection of genes involved in safety and technologically relevant properties of food associated coagulase-negative staphylococci.Int J Food Microbiol2011 Feb 2821329998
Identification of novel linear megaplasmids carrying a ß-lactamase gene in neurotoxigenic Clostridium butyricum type E strains.PLoS One201121738770
Toxic and genotoxic evaluation of six antibiotics on non-target organisms.Sci Total Environ2005 Jun 1515993685
Verotoxin-producing Escherichia coli--an environment-induced emerging zoonosis in and around Calcutta.Int J Environ Health Res2001 Mar11260792
Influence of the antibiotics lincomycin and tylosin on aflatoxicosis when added to aflatoxin-contaminated diets of growing swine.J Vet Diagn Invest1995 Jul7578454
Losses related to the ingestion of lincomycin-medicated feed in a range sheep flock.J Am Vet Med Assoc1988 Apr 153372336
Assay of the heat-labile enterotoxin of Escherichia coli in infant rabbits.J Med Microbiol1979 Aug381666
Survival and fertility of antibiotic-treated bovine spermatozoa.J Dairy Sci1976 Dec64480