Basic Info

Common NameJosamycin(F06141)
2D Structure
FRCD IDF06141
CAS Number
PubChem CID5282165
FormulaC42H69NO15
IUPAC Name

[(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-6-[[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-4-acetyloxy-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2,4-dimethyloxan-3-yl] 3-methylbutanoate

InChI Key

XJSFLOJWULLJQS-NGVXBBESSA-N

InChI

InChI=1S/C42H69NO15/c1-23(2)19-32(47)56-40-27(6)53-34(22-42(40,8)50)57-37-26(5)54-41(36(49)35(37)43(9)10)58-38-29(17-18-44)20-24(3)30(46)16-14-12-13-15-25(4)52-33(48)21-31(39(38)51-11)55-28(7)45/h12-14,16,18,23-27,29-31,34-41,46,49-50H,15,17,19-22H2,1-11H3/b13-12+,16-14+/t24-,25-,26-,27+,29+,30+,31-,34+,35-,36-,37-,38+,39+,40+,41+,42-/m1/s1

Canonical SMILES

CC1CC=CC=CC(C(CC(C(C(C(CC(=O)O1)OC(=O)C)OC)OC2C(C(C(C(O2)C)OC3CC(C(C(O3)C)OC(=O)CC(C)C)(C)O)N(C)C)O)CC=O)C)O

Isomeric SMILES

C[C@@H]1C/C=C/C=C/[C@@H]([C@@H](C[C@@H]([C@@H]([C@H]([C@@H](CC(=O)O1)OC(=O)C)OC)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)OC(=O)CC(C)C)(C)O)N(C)C)O)CC=O)C)O

Synonyms
        
            Antibiotic yl-704 A3
        
            josamycin
        
            Leucomycin A3
        
            Turimycin A5
        
            Kitasamycin A3
        
            Josamycine
        
            Josamicina
        
            Josamycinum
        
            Josamycine [INN-French]
        
            Josamycinum [INN-Latin]
        
Classifies
                

                  
                    Predicted: 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 - Tricarboxylic acid or derivatives - Fatty acid ester - Fatty acyl - Oxane - Alpha-hydrogen aldehyde - Tertiary alcohol - 1,2-aminoalcohol - Amino acid or derivatives - Carboxylic acid ester - Lactone - Tertiary aliphatic amine - Tertiary amine - Secondary alcohol - Ether - Dialkyl ether - Carboxylic acid derivative - Acetal - Oxacycle - Organoheterocyclic compound - Hydrocarbon derivative - Organic oxide - Alcohol - Carbonyl group - Organopnictogen compound - Aldehyde - Organonitrogen compound - Organic nitrogen compound - Amine - 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 Weight828.006
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count16
Rotatable Bond Count14
Complexity1390
Monoisotopic Mass827.467
Exact Mass827.467
XLogP2.9
Formal Charge0
Heavy Atom Count58
Defined Atom Stereocenter Count16
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-0.9659
Human Intestinal AbsorptionHIA+0.5235
Caco-2 PermeabilityCaco2-0.6872
P-glycoprotein SubstrateSubstrate0.5860
P-glycoprotein InhibitorInhibitor0.9010
Inhibitor0.9010
Renal Organic Cation TransporterNon-inhibitor0.9274
Distribution
Subcellular localizationMitochondria0.5110
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7897
CYP450 2D6 SubstrateNon-substrate0.9116
CYP450 3A4 SubstrateSubstrate0.5659
CYP450 1A2 InhibitorNon-inhibitor0.9070
CYP450 2C9 InhibitorNon-inhibitor0.9170
CYP450 2D6 InhibitorNon-inhibitor0.9230
CYP450 2C19 InhibitorNon-inhibitor0.9118
CYP450 3A4 InhibitorNon-inhibitor0.8953
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9564
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9780
Non-inhibitor0.9424
AMES ToxicityNon AMES toxic0.8389
CarcinogensNon-carcinogens0.9287
Fish ToxicityHigh FHMT0.9331
Tetrahymena Pyriformis ToxicityHigh TPT0.9822
Honey Bee ToxicityLow HBT0.5157
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityIV0.7139
Carcinogenicity (Three-class)Non-required0.4879

Model Value Unit
Absorption
Aqueous solubility-2.3500LogS
Caco-2 Permeability0.4768LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.8513LD50, mol/kg
Fish Toxicity1.3582pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.6783pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
PerciformesJapan0.05ppm
Chicken,Edible OffalJapan0.3ppm
Chicken,KidneyJapan0.04ppm
Chicken,LiverJapan0.04ppm
Chicken,FatJapan0.04ppm
Chicken,MuscleJapan0.04ppm
Pig,Edible OffalJapan0.3ppm
Pig,KidneyJapan0.04ppm
Pig,LiverJapan0.04ppm
Pig,FatJapan0.04ppm
Pig,MuscleJapan0.04ppm

References

TitleJournalDatePubmed ID
Simultaneous determination of tylosin and josamycin residues in muscles, liver, eggs and milk by MLC with a monolithic column and time-programmed UV detection: application to baby food and formulae.Chem Cent J201424976860