Josamycin
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Basic Info
| Common Name | Josamycin(F06141) |
| 2D Structure | |
| FRCD ID | F06141 |
| CAS Number | |
| PubChem CID | 5282165 |
| Formula | C42H69NO15 |
| 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 Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic oxygen compounds |
| Class | Organooxygen compounds |
| Subclass | Carbohydrates and carbohydrate conjugates |
| Intermediate Tree Nodes | Aminosaccharides |
| Direct Parent | Aminoglycosides |
| Alternative Parents |
|
| Molecular Framework | Aliphatic heteromonocyclic compounds |
| Substituents | Aminoglycoside 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 |
| Description | This 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 Name | Property Value |
|---|---|
| Molecular Weight | 828.006 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 16 |
| Rotatable Bond Count | 14 |
| Complexity | 1390 |
| Monoisotopic Mass | 827.467 |
| Exact Mass | 827.467 |
| XLogP | 2.9 |
| Formal Charge | 0 |
| Heavy Atom Count | 58 |
| Defined Atom Stereocenter Count | 16 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 2 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB- | 0.9659 |
| Human Intestinal Absorption | HIA+ | 0.5235 |
| Caco-2 Permeability | Caco2- | 0.6872 |
| P-glycoprotein Substrate | Substrate | 0.5860 |
| P-glycoprotein Inhibitor | Inhibitor | 0.9010 |
| Inhibitor | 0.9010 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9274 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.5110 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7897 |
| CYP450 2D6 Substrate | Non-substrate | 0.9116 |
| CYP450 3A4 Substrate | Substrate | 0.5659 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9070 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9170 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9230 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9118 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8953 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9564 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9780 |
| Non-inhibitor | 0.9424 | |
| AMES Toxicity | Non AMES toxic | 0.8389 |
| Carcinogens | Non-carcinogens | 0.9287 |
| Fish Toxicity | High FHMT | 0.9331 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9822 |
| Honey Bee Toxicity | Low HBT | 0.5157 |
| Biodegradation | Not ready biodegradable | 1.0000 |
| Acute Oral Toxicity | IV | 0.7139 |
| Carcinogenicity (Three-class) | Non-required | 0.4879 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.3500 | LogS |
| Caco-2 Permeability | 0.4768 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.8513 | LD50, mol/kg |
| Fish Toxicity | 1.3582 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.6783 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Perciformes | Japan | 0.05ppm | |||
| Chicken,Edible Offal | Japan | 0.3ppm | |||
| Chicken,Kidney | Japan | 0.04ppm | |||
| Chicken,Liver | Japan | 0.04ppm | |||
| Chicken,Fat | Japan | 0.04ppm | |||
| Chicken,Muscle | Japan | 0.04ppm | |||
| Pig,Edible Offal | Japan | 0.3ppm | |||
| Pig,Kidney | Japan | 0.04ppm | |||
| Pig,Liver | Japan | 0.04ppm | |||
| Pig,Fat | Japan | 0.04ppm | |||
| Pig,Muscle | Japan | 0.04ppm |
References
| Title | Journal | Date | Pubmed 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 J | 2014 | 24976860 |