Salinomycin
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Basic Info
Common Name | Salinomycin(F05891) |
2D Structure | |
FRCD ID | F05891 |
CAS Number | 53003-10-4 |
PubChem CID | 3085092 |
Formula | C42H70O11 |
IUPAC Name | (2R)-2-[(2R,5S,6R)-6-[(2S,3S,4S,6R)-6-[(3S,5S,7R,9S,10S,12R,15R)-3-[(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyloxan-2-yl]-15-hydroxy-3,10,12-trimethyl-4,6,8-trioxadispiro[4.1.5^{7}.3^{5}]pentadec-13-en-9-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-5-methyloxan-2-yl]butanoic acid |
InChI Key | KQXDHUJYNAXLNZ-XQSDOZFQSA-N |
InChI | InChI=1S/C42H70O11/c1-11-29(38(46)47)31-15-14-23(4)36(50-31)27(8)34(44)26(7)35(45)30(12-2)37-24(5)22-25(6)41(51-37)19-16-32(43)42(53-41)21-20-39(10,52-42)33-17-18-40(48,13-3)28(9)49-33/h16,19,23-34,36-37,43-44,48H,11-15,17-18,20-22H2,1-10H3,(H,46,47)/t23-,24-,25+,26-,27-,28-,29+,30-,31+,32+,33+,34+,36+,37-,39-,40+,41-,42-/m0/s1 |
Canonical SMILES | CCC(C1CCC(C(O1)C(C)C(C(C)C(=O)C(CC)C2C(CC(C3(O2)C=CC(C4(O3)CCC(O4)(C)C5CCC(C(O5)C)(CC)O)O)C)C)O)C)C(=O)O |
Isomeric SMILES | CC[C@H]([C@H]1CC[C@@H]([C@@H](O1)[C@@H](C)[C@@H]([C@H](C)C(=O)[C@H](CC)[C@@H]2[C@H](C[C@H]([C@]3(O2)C=C[C@H]([C@@]4(O3)CC[C@@](O4)(C)[C@H]5CC[C@@]([C@@H](O5)C)(CC)O)O)C)C)O)C)C(=O)O |
Synonyms | salinomycin Salinomycine [INN-French] Coxistac Bio-cox Procoxacin 53003-10-4 UNII-62UXS86T64 CHEBI:80025 62UXS86T64 Salinomycinum [INN-Latin] |
Classifies | Veterinary Drug |
Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
Kingdom | Organic compounds |
Superclass | Lipids and lipid-like molecules |
Class | Prenol lipids |
Subclass | Terpene glycosides |
Intermediate Tree Nodes | Not available |
Direct Parent | Diterpene glycosides |
Alternative Parents |
|
Molecular Framework | Aliphatic heteropolycyclic compounds |
Substituents | Diterpene glycoside - Diterpenoid - Fatty alcohol - Ketal - Branched fatty acid - Heterocyclic fatty acid - Hydroxy fatty acid - Beta-hydroxy ketone - Fatty acyl - Pyran - Oxane - Tetrahydrofuran - Tertiary alcohol - Secondary alcohol - Ketone - Acetal - Organoheterocyclic compound - Ether - Oxacycle - Dialkyl ether - Carboxylic acid - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Organooxygen compound - Hydrocarbon derivative - Carbonyl group - Organic oxide - Organic oxygen compound - Alcohol - Aliphatic heteropolycyclic compound |
Description | This compound belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. |
Properties
Property Name | Property Value |
---|---|
Molecular Weight | 751.011 |
Hydrogen Bond Donor Count | 4 |
Hydrogen Bond Acceptor Count | 11 |
Rotatable Bond Count | 12 |
Complexity | 1320 |
Monoisotopic Mass | 750.492 |
Exact Mass | 750.492 |
XLogP | 5.7 |
Formal Charge | 0 |
Heavy Atom Count | 53 |
Defined Atom Stereocenter Count | 18 |
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+ | 0.8288 |
Human Intestinal Absorption | HIA+ | 0.9739 |
Caco-2 Permeability | Caco2- | 0.7343 |
P-glycoprotein Substrate | Substrate | 0.7685 |
P-glycoprotein Inhibitor | Inhibitor | 0.5292 |
Inhibitor | 0.8616 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.8958 |
Distribution | ||
Subcellular localization | Mitochondria | 0.7936 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.8153 |
CYP450 2D6 Substrate | Non-substrate | 0.8928 |
CYP450 3A4 Substrate | Substrate | 0.6441 |
CYP450 1A2 Inhibitor | Non-inhibitor | 0.9336 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.9195 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.9624 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.8875 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.5747 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9527 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9780 |
Non-inhibitor | 0.7271 | |
AMES Toxicity | Non AMES toxic | 0.7878 |
Carcinogens | Non-carcinogens | 0.9403 |
Fish Toxicity | High FHMT | 0.9940 |
Tetrahymena Pyriformis Toxicity | High TPT | 0.9998 |
Honey Bee Toxicity | High HBT | 0.6948 |
Biodegradation | Not ready biodegradable | 0.9928 |
Acute Oral Toxicity | I | 0.7721 |
Carcinogenicity (Three-class) | Non-required | 0.5187 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -3.7676 | LogS |
Caco-2 Permeability | 0.5114 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 4.5855 | LD50, mol/kg |
Fish Toxicity | 1.1716 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | 1.0958 | pIGC50, ug/L |
MRLs
Food | Product Code | Country | MRLs | Application Date | Notes |
---|---|---|---|---|---|
Chicken,Edible Offal | Japan | 0.5ppm | |||
Other Poultry,Eggs | Japan | 0.02ppm | |||
Chicken,Eggs | Japan | 0.02ppm | |||
Other Poultry Animals,Edible Offal | Japan | 0.5ppm | |||
Other Poultry Animals,Kidney | Japan | 0.5ppm | |||
Chicken,Kidney | Japan | 0.5ppm | |||
Other Poultry Animals,Liver | Japan | 0.5ppm | |||
Chicken,Liver | Japan | 0.5ppm | |||
Other Poultry Animals,Fat | Japan | 0.1ppm | |||
Chicken,Fat | Japan | 0.4ppm | |||
Other Poultry Animals,Muscle | Japan | 0.1ppm | |||
Chicken,Muscle | Japan | 0.1ppm | |||
Pig,Edible Offal | Japan | 0.1ppm | |||
Cattle,Edible Offal | Japan | 0.5ppm | |||
Pig,Kidney | Japan | 0.1ppm | |||
Cattle,Kidney | Japan | 0.5ppm | |||
Pig,Liver | Japan | 0.2ppm | |||
Cattle,Liver | Japan | 0.4ppm | |||
Pig,Fat | Japan | 0.1ppm | |||
Cattle,Fat | Japan | 0.02ppm |
References
Title | Journal | Date | Pubmed ID |
---|---|---|---|
Evaluation of PCR and DNA sequencing for direct detection of Clostridium perfringens in the intestinal tract of broilers. | Avian Dis | 2009 Sep | 19848086 |
Pathotype and antibiotic resistance gene distributions of Escherichia coli isolates from broiler chickens raised on antimicrobial-supplemented diets. | Appl Environ Microbiol | 2009 Nov | 19749070 |
An integrated sample preparation to determine coccidiostats and emerging Fusarium-mycotoxins in various poultry tissues with LC-MS/MS. | Mol Nutr Food Res | 2007 May | 17440994 |
A new method for in vitro detection of microbially produced mitochondrial toxins. | Toxicol In Vitro | 2003 Oct-Dec | 14599472 |
Effects of dietary fat source and subtherapeutic levels of antibiotic on the bacterial community in the ileum of broiler chickens at various ages. | Appl Environ Microbiol | 2002 Dec | 12450811 |
Salinomycin-induced polyneuropathy in cats: morphologic and epidemiologic data. | Vet Pathol | 1999 Mar | 10098644 |
A chronic cardiomyopathy in feedlot cattle attributed to toxic levels of salinomycin in the feed. | J S Afr Vet Assoc | 1996 Mar | 8786618 |
Lipolysis and biohydrogenation of soybean oil in the rumen in vitro: inhibition by antimicrobials. | J Dairy Sci | 1995 Dec | 8675762 |