Semduramicin
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Basic Info
Common Name | Semduramicin(F05854) |
2D Structure | |
FRCD ID | F05854 |
CAS Number | 113378-31-7 |
PubChem CID | 71327 |
Formula | C45H76O16 |
IUPAC Name | 2-[(2R,3S,4S,5R,6S)-2,4-dihydroxy-6-[(1R)-1-[(2S,5R,7S,8R,9S)-7-hydroxy-2-[(2R,5S)-5-[(2R,3S,5R)-5-[(2S,3S,5R,6S)-6-hydroxy-3,5,6-trimethyloxan-2-yl]-3-[(2S,5S,6R)-5-methoxy-6-methyloxan-2-yl]oxyoxolan-2-yl]-5-methyloxolan-2-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]ethyl]-5-methoxy-3-methyloxan-2-yl]acetic acid |
InChI Key | WINSLRIENGBHSH-ASZYJFLUSA-N |
InChI | InChI=1S/C45H76O16/c1-22-18-23(2)43(9,50)58-36(22)30-19-31(55-34-13-12-29(52-10)27(6)54-34)40(56-30)42(8)15-14-32(57-42)41(7)16-17-44(61-41)20-28(46)24(3)37(59-44)25(4)38-39(53-11)35(49)26(5)45(51,60-38)21-33(47)48/h22-32,34-40,46,49-51H,12-21H2,1-11H3,(H,47,48)/t22-,23+,24+,25+,26-,27+,28-,29-,30+,31-,32+,34-,35-,36-,37-,38-,39+,40+,41-,42-,43-,44+,45+/m0/s1 |
Canonical SMILES | CC1CC(C(OC1C2CC(C(O2)C3(CCC(O3)C4(CCC5(O4)CC(C(C(O5)C(C)C6C(C(C(C(O6)(CC(=O)O)O)C)O)OC)C)O)C)C)OC7CCC(C(O7)C)OC)(C)O)C |
Isomeric SMILES | C[C@H]1C[C@H]([C@@](O[C@@H]1[C@H]2C[C@@H]([C@@H](O2)[C@@]3(CC[C@@H](O3)[C@@]4(CC[C@@]5(O4)C[C@@H]([C@H]([C@H](O5)[C@@H](C)[C@H]6[C@@H]([C@H]([C@@H]([C@](O6)(CC(=O)O)O)C)O)OC)C)O)C)C)O[C@H]7CC[C@@H]([C@H](O7)C)OC)(C)O)C |
Synonyms | Semduramicine Aviax Semduramicinum [INN-Latin] Semduramicin UNII-P6VXL377WL P6VXL377WL 113378-31-7 Semduramicina Semduramicinum Semduramicine [INN-French] |
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 | Glycosyl compounds |
Direct Parent | C-glycosyl compounds |
Alternative Parents | |
Molecular Framework | Aliphatic heteropolycyclic compounds |
Substituents | C-glycosyl compound - Ketal - Monosaccharide - Oxane - Tetrahydrofuran - Hemiacetal - Secondary alcohol - Acetal - Carboxylic acid derivative - Carboxylic acid - Dialkyl ether - Ether - Organoheterocyclic compound - Oxacycle - Monocarboxylic acid or derivatives - Carbonyl group - Hydrocarbon derivative - Alcohol - Organic oxide - Aliphatic heteropolycyclic compound |
Description | This compound belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond. |
Properties
Property Name | Property Value |
---|---|
Molecular Weight | 873.087 |
Hydrogen Bond Donor Count | 5 |
Hydrogen Bond Acceptor Count | 16 |
Rotatable Bond Count | 11 |
Complexity | 1540 |
Monoisotopic Mass | 872.513 |
Exact Mass | 872.513 |
XLogP | 3.8 |
Formal Charge | 0 |
Heavy Atom Count | 61 |
Defined Atom Stereocenter Count | 23 |
Undefined Atom Stereocenter Count | 0 |
Defined Bond Stereocenter Count | 0 |
Undefined Bond Stereocenter Count | 0 |
Isotope Atom Count | 0 |
Covalently-Bonded Unit Count | 1 |
ADMET
Model | Result | Probability |
---|---|---|
Absorption | ||
Blood-Brain Barrier | BBB- | 0.5062 |
Human Intestinal Absorption | HIA+ | 0.7051 |
Caco-2 Permeability | Caco2- | 0.7441 |
P-glycoprotein Substrate | Substrate | 0.7465 |
P-glycoprotein Inhibitor | Inhibitor | 0.5569 |
Inhibitor | 0.9479 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.8545 |
Distribution | ||
Subcellular localization | Mitochondria | 0.7334 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.8051 |
CYP450 2D6 Substrate | Non-substrate | 0.8689 |
CYP450 3A4 Substrate | Substrate | 0.6747 |
CYP450 1A2 Inhibitor | Non-inhibitor | 0.9383 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.8561 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.9443 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.8986 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.8595 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9304 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9839 |
Non-inhibitor | 0.6163 | |
AMES Toxicity | Non AMES toxic | 0.7690 |
Carcinogens | Non-carcinogens | 0.9553 |
Fish Toxicity | High FHMT | 0.9036 |
Tetrahymena Pyriformis Toxicity | High TPT | 0.9984 |
Honey Bee Toxicity | High HBT | 0.7362 |
Biodegradation | Not ready biodegradable | 0.9842 |
Acute Oral Toxicity | I | 0.6882 |
Carcinogenicity (Three-class) | Non-required | 0.6269 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -3.0320 | LogS |
Caco-2 Permeability | 0.3455 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 4.9596 | LD50, mol/kg |
Fish Toxicity | 1.4577 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | 1.1784 | pIGC50, ug/L |
MRLs
Food | Product Code | Country | MRLs | Application Date | Notes |
---|---|---|---|---|---|
Muscle Of Broiler Chickens | United States | 130ppb | |||
Liver Of Broiler Chickens | United States | 400ppb | |||
Other Poultry Animals,Edible Offal | Japan | 0.5ppm | |||
Chicken,Edible Offal | Japan | 0.03ppm | |||
Other Poultry Animals,Kidney | Japan | 0.5ppm | |||
Chicken,Kidney | Japan | 0.2ppm | |||
Other Poultry Animals,Liver | Japan | 0.5ppm | |||
Chicken,Liver | Japan | 0.5ppm | |||
Other Poultry Animals,Fat | Japan | 0.5ppm | |||
Chicken,Fat | Japan | 0.5ppm | |||
Other Poultry Animals,Muscle | Japan | 0.09ppm | |||
Chicken,Muscle | Japan | 0.09ppm |
References
Title | Journal | Date | Pubmed ID |
---|---|---|---|
Validation of a liquid chromatography-electrospray ionization tandem massspectrometric method to determine six polyether ionophores in raw, UHT,pasteurized and powdered milk. | Food Chem | 2016 Apr 1 | 26593474 |
Semduramicin in eggs--the incompatibility of feed and food maximum levels. | Food Chem | 2014 Apr 15 | 24295692 |
Distribution of semduramicin in hen eggs and tissues after administration ofcross-contaminated feed. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2014 | 24856255 |
The determination of six ionophore coccidiostats in feed by liquid chromatographywith postcolumn derivatisation and spectrofotometric/fluorescence detection. | ScientificWorldJournal | 2013 Oct 29 | 24288505 |
Determination of semduramicin in poultry feed additive, premixture and compoundfeed by liquid chromatography and UV spectrophotometric detection afterpost-column derivatisation. | J Pharm Biomed Anal | 2012 Mar 5 | 22169468 |
Inter-laboratory comparison of an analytical method for the determination of the feed additive semduramicin in poultry feed at authorised level by liquidchromatography single quadrupole mass spectrometry. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2011Jan | 21240826 |
The efficacy of anticoccidial products against Eimeria spp. in northernbobwhites. | Avian Dis | 2011 Mar | 21500637 |
Simultaneous determination of polyether ionophores, macrolides and lincosamidesin hen eggs by liquid chromatography-electrospray ionization tandem massspectrometry using a simple solvent extraction. | Anal Chim Acta | 2010 Dec 3 | 21056719 |
Determination of semduramicin in poultry feed at authorized level by liquidchromatography single quadrupole mass spectrometry. | J Pharm Biomed Anal | 2010 Dec 1 | 20619995 |
The activity and compatibility of the antibiotic tiamulin with other drugs inpoultry medicine--A review. | Poult Sci | 2009 Nov | 19834086 |
[Development of monoclonal-based enzyme-linked immunosorbent assay andimmunochromatographic assay for lasalocid and semduramicin]. | Shokuhin Eiseigaku Zasshi | 2004 Jun | 15468928 |
Phenotypic and genotypic changes in Salmonella enterica subsp. enterica serotype typhimurium during passage in intestines of broiler chickens fed on diets thatincluded ionophore anticoccidial supplements. | J Clin Microbiol | 2004 Aug | 15297474 |
Effects of the ionophore anticoccidial semduramicin on broiler breeders. | Poult Sci | 2001 Mar | 11261553 |