Narasin
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Basic Info
Common Name | Narasin(F05946) |
2D Structure | |
FRCD ID | F05946 |
CAS Number | |
PubChem CID | 65452 |
Formula | C43H72O11 |
IUPAC Name | (2R)-2-[(2R,3S,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]-3,5-dimethyloxan-2-yl]butanoic acid |
InChI Key | VHKXXVVRRDYCIK-CWCPJSEDSA-N |
InChI | InChI=1S/C43H72O11/c1-12-30(35(46)27(8)34(45)28(9)36-23(4)21-24(5)37(51-36)31(13-2)39(47)48)38-25(6)22-26(7)42(52-38)18-15-32(44)43(54-42)20-19-40(11,53-43)33-16-17-41(49,14-3)29(10)50-33/h15,18,23-34,36-38,44-45,49H,12-14,16-17,19-22H2,1-11H3,(H,47,48)/t23-,24-,25-,26+,27-,28-,29-,30-,31+,32+,33+,34+,36+,37+,38-,40-,41+,42-,43-/m0/s1 |
Canonical SMILES | CCC(C1C(CC(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)C(=O)O |
Isomeric SMILES | CC[C@H]([C@H]1[C@H](C[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)C(=O)O |
Synonyms | Narasin A Narasine [INN-French] narasin Monteban Compound 79891 Antibiotic C 7819B Antibiotic A 28086A Narasinum [INN-Latin] Narasino [INN-Spanish] UNII-DZY9VU539P |
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 | 765.038 |
Hydrogen Bond Donor Count | 4 |
Hydrogen Bond Acceptor Count | 11 |
Rotatable Bond Count | 12 |
Complexity | 1360 |
Monoisotopic Mass | 764.507 |
Exact Mass | 764.507 |
XLogP | 6.2 |
Formal Charge | 0 |
Heavy Atom Count | 54 |
Defined Atom Stereocenter Count | 19 |
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 |
---|---|---|---|---|---|
Other Poultry Animals,Edible Offal | Japan | 0.3ppm | |||
Chicken,Edible Offal | Japan | 0.3ppm | |||
Other Poultry Animals,Kidney | Japan | 0.3ppm | |||
Chicken,Kidney | Japan | 0.3ppm | |||
Other Poultry Animals,Liver | Japan | 0.3ppm | |||
Chicken,Liver | Japan | 0.3ppm | |||
Other Poultry Animals,Fat | Japan | 0.1ppm | |||
Chicken,Fat | Japan | 0.5ppm | |||
Other Poultry Animals,Muscle | Japan | 0.1ppm | |||
Chicken,Muscle | Japan | 0.1ppm | |||
Cattle,Edible Offal | Japan | 0.05ppm | |||
Cattle,Kidney | Japan | 0.05ppm | |||
Cattle,Liver | Japan | 0.05ppm | |||
Cattle,Fat | Japan | 0.05ppm | |||
Cattle,Muscle | Japan | 0.05ppm |
References
Title | Journal | Date | Pubmed ID |
---|---|---|---|
Magnetic solid-phase extraction based on carbon nanotubes for the determinationof polyether antibiotic and s-triazine drug residues in animal food withLC-MS/MS. | J Sep Sci | 2017 Jun | 28402029 |
Determination of the residue levels of nicarbazin and combinationnicarbazin-narasin in broiler chickens after oral administration. | PLoS One | 2017 Jul 27 | 28750013 |
A multi-residue method for 17 anticoccidial drugs and ractopamine in animaltissues by liquid chromatography-tandem mass spectrometry and time-of-flight massspectrometry. | Drug Test Anal | 2016 May | 27443201 |
Transformation of ionophore antimicrobials in poultry litter during pilot-scalecomposting. | Environ Pollut | 2016 May | 26874321 |
Determination of Narasin in Chicken Fat: A Bridging Study Comparing theBioautographic Method (FSIS CLG Method R22) to a Liquid Chromatography withTandem Mass Spectrometry Method (AOAC Method 2011.24). | J AOAC Int | 2016 Mar-Apr | 26961063 |
Evaluation of ionophore sensitivity of Eimeria acervulina and Eimeria maximaisolated from the Algerian to Jijel province poultry farms. | Vet Parasitol | 2016 Jul 15 | 27270394 |
Determination of six polyether antibiotic residues in foods of animal origin bysolid phase extraction combined with liquid chromatography-tandem massspectrometry. | J Chromatogr B Analyt Technol Biomed Life Sci | 2016 Apr 1 | 26990733 |
Comparison of fatty acid profile in the chicken meat after feeding with narasin, nicarbazin and salinomycin sodium and phyto-additive substances. | J Environ Sci Health B | 2016 | 26950416 |
Quantification of four ionophores in soil, sediment and manure using pressurised liquid extraction. | J Chromatogr A | 2013 Sep 13 | 23890553 |
The determination of six ionophore coccidiostats in feed by liquid chromatographywith postcolumn derivatisation and spectrofotometric/fluorescence detection. | ScientificWorldJournal | 2013 Oct 29 | 24288505 |
Detection and quantification of ionophore antibiotics in runoff, soil and poultrylitter. | J Chromatogr A | 2013 Oct 18 | 24028934 |
Single-laboratory validation of a multiplex flow cytometric immunoassay for thesimultaneous detection of coccidiostats in eggs and feed. | Anal Bioanal Chem | 2013 Nov | 24081566 |
Determination and confirmation of narasin and monensin in chicken, swine, andbovine tissues by LC/MS/MS: Final Action 2011.24. | J AOAC Int | 2013 Jul-Aug | 24000767 |
Risk assessment of coccidostatics during feed cross-contamination: animal andhuman health aspects. | Toxicol Appl Pharmacol | 2013 Aug 1 | 21215766 |
Development of a five-plex flow cytometric immunoassay for the simultaneousdetection of six coccidiostats in feed and eggs. | Anal Bioanal Chem | 2012 Sep | 22850895 |
Detection and quantitative analysis of 21 veterinary drugs in river water usinghigh-pressure liquid chromatography coupled to tandem mass spectrometry. | Environ Sci Pollut Res Int | 2012 Sep | 22392691 |
Rapid method for the simultaneous determination of six ionophores in feed byliquid chromatography/mass spectrometry. | J AOAC Int | 2012 Jul-Aug | 22970566 |
Determination of narasin and monensin in bovine, swine, and chicken tissues byliquid chromatography with tandem mass spectrometry: first action 2011.24. | J AOAC Int | 2012 Jul-Aug | 22970563 |
Quantification of ionophores in aged poultry litter using liquid chromatographytandem mass spectrometry. | J Environ Sci Health B | 2012 | 22938580 |
Non-soluble fibres and narasin reduce spontaneous gizzard erosion and ulceration in broiler chickens. | Avian Pathol | 2012 | 22515541 |