Erythromycin

Basic Info

Common NameErythromycin(F05928)
2D Structure
FRCD IDF05928
CAS Number114-07-8
PubChem CID12560
FormulaC37H67NO13
IUPAC Name

(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione

InChI Key

ULGZDMOVFRHVEP-RWJQBGPGSA-N

InChI

InChI=1S/C37H67NO13/c1-14-25-37(10,45)30(41)20(4)27(39)18(2)16-35(8,44)32(51-34-28(40)24(38(11)12)15-19(3)47-34)21(5)29(22(6)33(43)49-25)50-26-17-36(9,46-13)31(42)23(7)48-26/h18-26,28-32,34,40-42,44-45H,14-17H2,1-13H3/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30-,31+,32-,34+,35-,36-,37-/m1/s1

Canonical SMILES

CCC1C(C(C(C(=O)C(CC(C(C(C(C(C(=O)O1)C)OC2CC(C(C(O2)C)O)(C)OC)C)OC3C(C(CC(O3)C)N(C)C)O)(C)O)C)C)O)(C)O

Isomeric SMILES

CC[C@@H]1[C@@]([C@@H]([C@H](C(=O)[C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)O)C)C)O)(C)O

Synonyms
        
            erythromycin
        
            Erythromycin A
        
            114-07-8
        
            E-Mycin
        
            Abomacetin
        
            Erythrocin
        
            Erythromycinum
        
            Erymax
        
            Erythromycine
        
            Eritromicina
Classifies
                

                  
                    Veterinary Drug
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds
SubclassCarbohydrates and carbohydrate conjugates
Intermediate Tree NodesAminosaccharides
Direct ParentAminoglycosides
Alternative Parents
Molecular FrameworkAliphatic heteromonocyclic compounds
SubstituentsAminoglycoside core - Macrolide - Glycosyl compound - O-glycosyl compound - Oxane - Monosaccharide - Tertiary alcohol - 1,2-aminoalcohol - Amino acid or derivatives - Carboxylic acid ester - Ketone - Cyclic ketone - Tertiary aliphatic amine - Tertiary amine - Secondary alcohol - Lactone - Acetal - Carboxylic acid derivative - Dialkyl ether - Ether - Oxacycle - Organoheterocyclic compound - Polyol - Monocarboxylic acid or derivatives - Organic nitrogen compound - Hydrocarbon derivative - Alcohol - Amine - Organopnictogen compound - Organic oxide - Organonitrogen compound - Carbonyl group - Aliphatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.

Properties

Property NameProperty Value
Molecular Weight733.937
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count14
Rotatable Bond Count7
Complexity1180
Monoisotopic Mass733.461
Exact Mass733.461
XLogP2.7
Formal Charge0
Heavy Atom Count51
Defined Atom Stereocenter Count18
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-0.9889
Human Intestinal AbsorptionHIA+0.5114
Caco-2 PermeabilityCaco2-0.8957
P-glycoprotein SubstrateSubstrate0.8098
P-glycoprotein InhibitorInhibitor0.8564
Non-inhibitor0.5963
Renal Organic Cation TransporterNon-inhibitor0.9222
Distribution
Subcellular localizationLysosome0.6348
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7898
CYP450 2D6 SubstrateNon-substrate0.9225
CYP450 3A4 SubstrateSubstrate0.6528
CYP450 1A2 InhibitorNon-inhibitor0.9045
CYP450 2C9 InhibitorNon-inhibitor0.9070
CYP450 2D6 InhibitorNon-inhibitor0.9230
CYP450 2C19 InhibitorNon-inhibitor0.9074
CYP450 3A4 InhibitorNon-inhibitor0.5744
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9391
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9902
Non-inhibitor0.8956
AMES ToxicityNon AMES toxic0.9133
CarcinogensNon-carcinogens0.9335
Fish ToxicityHigh FHMT0.9618
Tetrahymena Pyriformis ToxicityHigh TPT0.9673
Honey Bee ToxicityLow HBT0.5399
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityIII0.7984
Carcinogenicity (Three-class)Non-required0.5441
Model Value Unit
Absorption
Aqueous solubility-2.3634LogS
Caco-2 Permeability0.0949LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.2296LD50, mol/kg
Fish Toxicity1.4288pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.4549pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Edible Tissues Of TurkeysUnited States0.125ppm
Edible Tissues Of ChickensUnited States0.125ppm
EggsUnited States0.025ppm
Edible Tissues Of SwineUnited States0.1ppm
Other Aquatic AnimalJapan0.2ppm
CrustaceansJapan0.2ppm
Shelled MolluscasJapan0.2ppm
Other FishJapan0.2ppm
PerciformesJapan0.06ppm
AnguilliformesJapan0.2ppm
SalmoniformesJapan0.2ppm
Other Poultry,EggsJapan0.09ppm
Chicken,EggsJapan0.09ppm
Other Poultry Animals,Edible OffalJapan0.2ppm
Chicken,Edible OffalJapan0.05ppm
Chicken,KidneyJapan0.05ppm
Other Poultry Animals,KidneyJapan0.2ppm
Other Poultry Animals,LiverJapan0.2ppm
Chicken,LiverJapan0.05ppm
Other Poultry Animals,FatJapan0.2ppm

References

TitleJournalDatePubmed ID
Determination of antibiotic resistance of lactic acid bacteria isolated fromtraditional Turkish fermented dairy products.Iran J Vet Res2018 Winter29805464
Cellular metabolism network of Bacillus thuringiensis related to erythromycinstress and degradation.Ecotoxicol Environ Saf2018 Sep 3029857237
The occurrence, transmission, virulence and antibiotic resistance of Listeriamonocytogenes in fish processing plant.Int J Food Microbiol2018 Oct 329929178
Prevalence, Enterotoxin Genes, and Antibiotic Resistance of Bacillus cereus Isolated from Raw Vegetables in Korea.J Food Prot2018 Oct30169119
Biotransformation of macrolide antibiotics using enriched activated sludgeculture: Kinetics, transformation routes and ecotoxicological evaluation.J Hazard Mater2018 May 529414746
Effect of electron beam and gamma radiation on drug-susceptible anddrug-resistant Listeria monocytogenes strains in salmon under differenttemperature.J Appl Microbiol2018 May 429727511
Genetic Basis and Clonal Population Structure of Antibiotic Resistance inCampylobacter jejuni Isolated From Broiler Carcasses in Belgium.Front Microbiol2018 May 1729867900
Systemic Contact Dermatitis.Clin Rev Allergy Immunol2018 May 1529766368
Selection and characterization of probiotic lactic acid bacteria and its impacton growth, nutrient digestibility, health and antioxidant status in weanedpiglets.PLoS One2018 Mar 829518093
In Vitro and in Vivo Selection of Potentially Probiotic Lactobacilli FromNocellara del Belice Table Olives.Front Microbiol2018 Mar 2829643848
Diversity and Antibiotic Susceptibility of Acinetobacter Strains From Milk PowderProduced in Germany.Front Microbiol2018 Mar 2729636733
Most commensally bacterial strains in human milk of healthy mothers displaymultiple antibiotic resistance.Microbiologyopen2018 Mar 25:e0061829577668
Characterization of multiple antibiotic resistance of culturable microorganismsand metagenomic analysis of total microbial diversity of marine fish sold inretail shops in Mumbai, India.Environ Sci Pollut Res Int2018 Mar29243150
Antimicrobial susceptibility of enterococci recovered from healthy cattle, pigsand chickens in nine EU countries (EASSA Study) to critically importantantibiotics.Vet Microbiol2018 Mar29519512
LAB Bacteriocins Controlling the Food Isolated (Drug-Resistant) Staphylococci.Front Microbiol2018 Jun 1229946300
Water supply and feed as sources of antimicrobial-resistant Enterococcus spp. in aquacultures of rainbow trout (Oncorhyncus mykiss), Portugal.Sci Total Environ2018 Jun 129996407
Molecular characterization and drug susceptibility of non-O1/O139 V. cholerae strains of seafood, environmental and clinical origin, Italy.Food Microbiol2018 Jun29407408
Antibiotic-Resistant Genes and Pathogens Shed by Wild Deer Correlate with Land Application of Residuals.Ecohealth2018 Jun29524057
Assessment of Antibiotic Susceptibility within Lactic Acid Bacteria andCoagulase-Negative Staphylococci Isolated from Hunan Smoked Pork, a NaturallyFermented Meat Product in China.J Food Sci2018 Jun29786847
Explaining the accelerated degradation of ciprofloxacin, sulfamethazine, anderythromycin in different soil exposure scenarios by their aqueousextractability.Environ Sci Pollut Res Int2018 Jun29594886