1.0 2010-04-08 22:05:20 UTC 2018-05-28 22:40:07 UTC FDB002337 Natamycin Primarily used as a surface treatment to prevent growth of yeasts and moulds, especies on cheese. Permitted agent in USA for surface treatment of cheeses as mould-inhibitor. No reported allergic reactions and it has GRAS status Natamycin (INN), also known as pimaricin, is a naturally occurring antifungal agent produced during fermentation by the bacterium Streptomyces natalensis, commonly found in soil. Natamycin has a very low solubility in water, due to the amphiphilic nature of the molecule. However, natamycin is effective at very low levels. Most Molds have an MIC (Minimum inhibitory concentration) of <10ppm. Natamycin is classified as a macrolide polyene antifungal and, as a drug, is used to treat fungal keratitis. It is especially effective against Aspergillus and Fusarium corneal infections. Other common members of the polyene macrolide antifungal family are Amphotericin B, Nystatin, and Filipin.; Natamycin is an antifungal drug for topical ophthalmic administration. It is a tetraene polyene antibiotic derived from Streptomyces natalensis. It possesses in vitro activity against a variety of yeast and filamentous fungi, including Candida, Aspergillus, Cephalosporium, Fusarium and Penicillium. Although the activity against fungi is dose-related, natamycin is predominantly fungicidal. Natamycin is not effective in vitro against gram-positive or gram-negative bacteria. Topical administration appears to produce effective concentrations of natamycin within the corneal stroma but not in intraocular fluid. A 5283 Antibiotic A 5283 Antibiotic A-5283 CL 12625 Delvocid Delvolan Delvopos E235 Mycophyt Myprozine Natacyn Natacyn (TN) Natafucin Natamycin (usp/inn) Natamycin [usan:inn:ban] Natamycin, BAN, INN, USAN Pimafucin Pimafugin Pimaricin (JP15) Pimaricine PMR Synogil Tennecetin Tymasil C33H47NO13 665.7252 665.304740595 (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-{[(3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.0⁵,⁷]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid natamycin 7681-93-8 C[C@H]1OC(O[C@@H]2C[C@@H]3O[C@@](O)(C[C@H](O)[C@H]3C(O)=O)C[C@@H](O)C[C@H]3O[C@@H]3\C=C\C(=O)O[C@H](C)C\C=C\C=C\C=C\C=C\2)[C@@H](O)[C@@H](N)[C@@H]1O InChI=1S/C33H47NO13/c1-18-10-8-6-4-3-5-7-9-11-21(45-32-30(39)28(34)29(38)19(2)44-32)15-25-27(31(40)41)22(36)17-33(42,47-25)16-20(35)14-24-23(46-24)12-13-26(37)43-18/h3-9,11-13,18-25,27-30,32,35-36,38-39,42H,10,14-17,34H2,1-2H3,(H,40,41)/b4-3+,7-5+,8-6+,11-9+,13-12+/t18-,19-,20+,21+,22+,23-,24-,25+,27-,28+,29-,30+,32?,33-/m1/s1 NCXMLFZGDNKEPB-BQGNJOPGSA-N belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars. Aminoglycosides Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic heteropolycyclic compounds 1,2-aminoalcohols Acetals Amino acids Beta hydroxy acids and derivatives Carbonyl compounds Carboxylic acids Dialkyl ethers Dicarboxylic acids and derivatives Enoate esters Epoxides Hemiacetals Hexoses Hydrocarbon derivatives Lactones Macrolides and analogues Monoalkylamines O-glycosyl compounds Organic oxides Organopnictogen compounds Oxacyclic compounds Oxanes Polyols Secondary alcohols 1,2-aminoalcohol Acetal Alcohol Aliphatic heteropolycyclic compound Alpha,beta-unsaturated carboxylic ester Amine Amino acid Amino acid or derivatives Aminoglycoside core Beta-hydroxy acid Carbonyl group Carboxylic acid Carboxylic acid derivative Carboxylic acid ester Dialkyl ether Dicarboxylic acid or derivatives Enoate ester Ether Glycosyl compound Hemiacetal Hexose monosaccharide Hydrocarbon derivative Hydroxy acid Lactone Macrolide Monosaccharide O-glycosyl compound Organic nitrogen compound Organic oxide Organoheterocyclic compound Organonitrogen compound Organopnictogen compound Oxacycle Oxane Oxirane Polyol Primary aliphatic amine Primary amine Secondary alcohol Antibiotic fungicides antibiotic antifungal drug macrolide Solid logp -3.46 ALOGPS logs -3.38 ALOGPS solubility 2.78e-01 g/l ALOGPS melting_point Mp 200° logp -1.7 ChemAxon pka_strongest_acidic 3.58 ChemAxon pka_strongest_basic 9.11 ChemAxon iupac (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-{[(3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.0⁵,⁷]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid ChemAxon average_mass 665.7252 ChemAxon mono_mass 665.304740595 ChemAxon smiles C[C@H]1OC(O[C@@H]2C[C@@H]3O[C@@](O)(C[C@H](O)[C@H]3C(O)=O)C[C@@H](O)C[C@H]3O[C@@H]3\C=C\C(=O)O[C@H](C)C\C=C\C=C\C=C\C=C\2)[C@@H](O)[C@@H](N)[C@@H]1O ChemAxon formula C33H47NO13 ChemAxon inchi InChI=1S/C33H47NO13/c1-18-10-8-6-4-3-5-7-9-11-21(45-32-30(39)28(34)29(38)19(2)44-32)15-25-27(31(40)41)22(36)17-33(42,47-25)16-20(35)14-24-23(46-24)12-13-26(37)43-18/h3-9,11-13,18-25,27-30,32,35-36,38-39,42H,10,14-17,34H2,1-2H3,(H,40,41)/b4-3+,7-5+,8-6+,11-9+,13-12+/t18-,19-,20+,21+,22+,23-,24-,25+,27-,28+,29-,30+,32?,33-/m1/s1 ChemAxon inchikey NCXMLFZGDNKEPB-BQGNJOPGSA-N ChemAxon polar_surface_area 230.99 ChemAxon refractivity 169.88 ChemAxon polarizability 68.19 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 13 ChemAxon donor_count 7 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::NmrOneD 153310 Specdb::NmrOneD 153311 Specdb::NmrOneD 153312 Specdb::NmrOneD 153313 Specdb::NmrOneD 153314 Specdb::NmrOneD 153315 Specdb::NmrOneD 153316 Specdb::NmrOneD 153317 Specdb::NmrOneD 153318 Specdb::NmrOneD 153319 Specdb::NmrOneD 153320 Specdb::NmrOneD 153321 Specdb::NmrOneD 153322 Specdb::NmrOneD 153323 Specdb::NmrOneD 153324 Specdb::NmrOneD 153325 Specdb::NmrOneD 153326 Specdb::NmrOneD 153327 Specdb::NmrOneD 153328 Specdb::NmrOneD 153329 Specdb::MsMs 49356 Specdb::MsMs 49357 Specdb::MsMs 49358 Specdb::MsMs 136698 Specdb::MsMs 136699 Specdb::MsMs 136700 Specdb::MsMs 3219157 Specdb::MsMs 3219158 Specdb::MsMs 3219159 Specdb::MsMs 3219160 Specdb::MsMs 3219161 Specdb::MsMs 3219162 Specdb::CMs 12544 Specdb::CMs 676806 Specdb::CMs 676807 Specdb::CMs 676808 Specdb::CMs 676809 Specdb::CMs 676810 Specdb::CMs 676811 Specdb::CMs 676812 Specdb::CMs 676813 Specdb::CMs 676814 Specdb::CMs 676815 Specdb::CMs 676816 Specdb::CMs 676817 Specdb::CMs 676818 Specdb::CMs 676819 Specdb::CMs 676820 Specdb::CMs 676821 Specdb::CMs 676822 Specdb::CMs 676823 Specdb::CMs 676824 Specdb::CMs 676825 Specdb::CMs 676826 Specdb::CMs 676827 Specdb::CMs 676828 Specdb::CMs 676829 HMDB14964 #<Reference:0x000055ce33618468>