(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[22.3.1.0^{5,7}]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid

• ChemBase ID: 705
• Molecular Formular: C33H47NO13
• Molecular Mass: 665.72518
• Monoisotopic Mass: 665.30474057
• SMILES: C\1=C/C=C/C=C/[C@@H](C[C@@H]2O[C@@](C[C@H](C[C@@H]3[C@@H](/C=C/C(=O)O[C@@H](C/C=C1)C)O3)O)(O)C[C@@H]([C@H]2C(=O)O)O)OC1O[C@@H]([C@H]([C@@H]([C@@H]1O)N)O)C
• Canonical SMILES: C[C@@H]1C/C=C/C=C/C=C/C=C/[C@H](OC2O[C@H](C)[C@H]([C@@H]([C@@H]2O)N)O)C[C@@H]2O[C@@](C[C@H](C[C@@H]3[C@@H](/C=C/C(=O)O1)O3)O)(O)C[C@@H]([C@H]2C(=O)O)O
• 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
• InChIKey: NCXMLFZGDNKEPB-BQGNJOPGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (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[22.3.1.0^{5,7}]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid
• IUPAC Traditional name: natamycin
• Brand Name: Natacyn; Pimaricin
• Synonyms: Natamycin

Database IDs

• CAS Number: 7681-93-8
• PubChem SID: 46509171; 160964168
• PubChem CID: 5281099

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.5797393
• H Acceptors: 13
• H Donor: 7
• LogD (pH = 5.5): -1.6976327
• LogD (pH = 7.4): -1.70116
• Log P: -1.6949131
• Molar Refractivity: 169.8826 cm^3
• Polarizability: 66.246475 Å^3
• Polar Surface Area: 230.99 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -3.46
• LOG S: -3.38
• Solubility (Water): 2.78e-01 g/l

PROPERTIES

Physical Property

• Solubility: 4100 mg/L
• Hydrophobicity(logP): 1.1

DETAILS

DrugBank - DB00826

• Drug Groups: approved
• Description: Amphoteric macrolide antifungal antibiotic from Streptomyces natalensis or S. chattanoogensis. It is used for a variety of fungal infections, mainly topically. [PubChem]
• Indication: For the treatment of fungal blepharitis, conjunctivitis, and keratitis caused by susceptible organisms including Fusarium solani keratitis.
• Pharmacology: 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.
• Affected Organisms: Various Fungus Species
• Absorption: Systemic absorption should not be expected following topical administration, and as with other polyene antibiotics, absorption from the gastrointestinal tract is very poor.
• External Links: Wikipedia; RxList; Drugs.com