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 |