Basic Info

Common NameTylosin(F05882)
2D Structure
FRCD IDF05882
CAS Number
PubChem CID5280440
FormulaC46H77NO17
IUPAC Name

2-[(4R,5S,6S,7R,9R,11E,13E,15R,16R)-6-[(2R,3R,4R,5S,6R)-5-[(2S,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-16-ethyl-4-hydroxy-15-[[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-5,9,13-trimethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde

InChI Key

WBPYTXDJUQJLPQ-VMXQISHHSA-N

InChI

InChI=1S/C46H77NO17/c1-13-33-30(22-58-45-42(57-12)41(56-11)37(52)26(5)60-45)18-23(2)14-15-31(49)24(3)19-29(16-17-48)39(25(4)32(50)20-34(51)62-33)64-44-38(53)36(47(9)10)40(27(6)61-44)63-35-21-46(8,55)43(54)28(7)59-35/h14-15,17-18,24-30,32-33,35-45,50,52-55H,13,16,19-22H2,1-12H3/b15-14+,23-18+/t24-,25+,26-,27-,28+,29+,30-,32-,33-,35+,36-,37-,38-,39-,40-,41-,42-,43+,44+,45-,46-/m1/s1

Canonical SMILES

CCC1C(C=C(C=CC(=O)C(CC(C(C(C(CC(=O)O1)O)C)OC2C(C(C(C(O2)C)OC3CC(C(C(O3)C)O)(C)O)N(C)C)O)CC=O)C)C)COC4C(C(C(C(O4)C)O)OC)OC

Isomeric SMILES

CC[C@@H]1[C@H](/C=C(/C=C/C(=O)[C@@H](C[C@@H]([C@@H]([C@H]([C@@H](CC(=O)O1)O)C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C)O[C@H]3C[C@@]([C@H]([C@@H](O3)C)O)(C)O)N(C)C)O)CC=O)C)\C)CO[C@H]4[C@@H]([C@@H]([C@@H]([C@H](O4)C)O)OC)OC

Synonyms
        
            Tylan
        
            Fradizine
        
            Tylosin
        
            Tilosina
        
            Tylosinum
        
            UNII-YEF4JXN031
        
            Tylocine
        
            Tylosine
        
            Tylosin A
        
            YEF4JXN031
        
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 - Disaccharide - Glycosyl compound - O-glycosyl compound - Oxane - Alpha-hydrogen aldehyde - Tertiary alcohol - 1,2-aminoalcohol - Amino acid or derivatives - Carboxylic acid ester - Ketone - Lactone - Cyclic ketone - Secondary alcohol - Tertiary aliphatic amine - Tertiary amine - Acetal - Organoheterocyclic compound - Ether - Monocarboxylic acid or derivatives - Dialkyl ether - Oxacycle - Carboxylic acid derivative - Organopnictogen compound - Carbonyl group - Alcohol - Organic oxide - Hydrocarbon derivative - Organonitrogen compound - Organic nitrogen compound - Amine - Aldehyde - 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 Weight916.112
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count18
Rotatable Bond Count13
Complexity1560
Monoisotopic Mass915.519
Exact Mass915.519
XLogP1
Formal Charge0
Heavy Atom Count64
Defined Atom Stereocenter Count21
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB-0.9910
Human Intestinal AbsorptionHIA+0.5414
Caco-2 PermeabilityCaco2-0.7275
P-glycoprotein SubstrateSubstrate0.8267
P-glycoprotein InhibitorInhibitor0.9174
Non-inhibitor0.5836
Renal Organic Cation TransporterNon-inhibitor0.9209
Distribution
Subcellular localizationMitochondria0.6271
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8680
CYP450 2D6 SubstrateNon-substrate0.9027
CYP450 3A4 SubstrateSubstrate0.6348
CYP450 1A2 InhibitorNon-inhibitor0.8952
CYP450 2C9 InhibitorNon-inhibitor0.9055
CYP450 2D6 InhibitorNon-inhibitor0.9240
CYP450 2C19 InhibitorNon-inhibitor0.8891
CYP450 3A4 InhibitorNon-inhibitor0.8309
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9643
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9743
Non-inhibitor0.7947
AMES ToxicityNon AMES toxic0.7971
CarcinogensNon-carcinogens0.9286
Fish ToxicityHigh FHMT0.9852
Tetrahymena Pyriformis ToxicityHigh TPT0.9966
Honey Bee ToxicityHigh HBT0.5817
BiodegradationNot ready biodegradable0.9675
Acute Oral ToxicityIII0.7906
Carcinogenicity (Three-class)Non-required0.5168

Model Value Unit
Absorption
Aqueous solubility-2.8665LogS
Caco-2 Permeability0.3985LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.2943LD50, mol/kg
Fish Toxicity1.1082pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.6462pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Other Poultry Animals,KidneyJapan0.2ppm
Other Terrestrial Mammals,Edible OffalJapan0.1ppm
Chicken,KidneyJapan0.05ppm
Other Poultry Animals,LiverJapan0.2ppm
Chicken,LiverJapan0.05ppm
Other Poultry Animals,FatJapan0.2ppm
Chicken,FatJapan0.05ppm
Other Poultry Animals,MuscleJapan0.2ppm
Chicken,MuscleJapan0.05ppm
MilkJapan0.05ppm
Pig,Edible OffalJapan0.05ppm
Cattle,Edible OffalJapan0.05ppm
Other Terrestrial Mammals,KidneyJapan0.1ppm
Pig,KidneyJapan0.05ppm
Cattle,KidneyJapan0.05ppm
Other Terrestrial Mammals,LiverJapan0.1ppm
Pig,LiverJapan0.05ppm
Cattle,LiverJapan0.05ppm
Other Terrestrial Mammals,FatJapan0.1ppm
Pig,FatJapan0.05ppm

References

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