(1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-{[(2R,3S,4S,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

• ChemBase ID: 120139
• Molecular Formular: C33H47NO13
• Molecular Mass: 665.72518
• Monoisotopic Mass: 665.30474057
• SMILES: [C@@]12(O[C@H]([C@@H]([C@H](C1)O)C(=O)O)C[C@@H](O[C@H]1[C@H]([C@H](C([C@H](O1)C)O)N)O)/C=C/C=C/C=C/C=C/C[C@H](OC(=O)/C=C/[C@@H]1O[C@@H]1C[C@@H](C2)O)C)O
• Canonical SMILES: C[C@@H]1C/C=C/C=C/C=C/C=C/[C@H](O[C@@H]2O[C@H](C)C([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-WFAGHZHHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-{[(2R,3S,4S,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: (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-{[(2R,3S,4S,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
• Synonyms: (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-(((2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyltetrahydro-2H-pyran-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 ac id; Mycophyt; Myprozine; Natacyn; Natafucin; Pimafucin; Pimafugin; Synogil; Tennecetin; Tymasil; Natamycin

Database IDs

• CAS Number: 7681-93-8
• PubChem SID: 162214492
• PubChem CID: 17571562

CALCULATED PROPERTIES

• 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

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Binds to ergosterol in the plasma membrane, preventing ergosterol-dependent fusion of vacuoles, as well as membrane fusion and fission.

Product Information

• Application(s): Macrolide polyene antifungal antibiotic.; Used to treat fungal keratitis.

REFERENCES

• 1. te Welscher YM, Jones L, van Leeuwen MR, Dijksterhuis J, de Kruijff B, Eitzen G, Breukink E: Natamycin inhibits vacuole fusion at the priming phase via a specific interaction with ergosterol.
• Antimicrob Agents Chemother. 2010 Jun;54(6):2618-25. Epub 2010 Apr 12.
• 2. te Welscher YM, ten Napel HH, Balague MM, Souza CM, Riezman H, de Kruijff B, Breukink E: Natamycin blocks fungal growth by binding specifically to ergosterol without permeabilizing the membrane.
• J Biol Chem. 2008 Mar 7;283(10):6393-401. Epub 2007 Dec 29.