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

• ChemBase ID: 175024
• Molecular Formular: C33H47NO13
• Molecular Mass: 665.72518
• Monoisotopic Mass: 665.30474057
• SMILES: [C@H]1(C/C=C/C=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)O1)O3)O)(C[C@@H]([C@@H]2C(=O)O)O)O)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C)O)N)O)C
• Canonical SMILES: C[C@@H]1C/C=C/C=C/C=C/C=C/[C@H](O[C@@H]2O[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-FXFORKDQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25S,26S)-22-{[(2R,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: (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25S,26S)-22-{[(2R,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
• Synonyms: Pimaricin; Antibiotic A 5283; Tennecetin; Cl-12625; Mycophyt; Myprozine; Natacyn; Synogil; Natamycin

Database IDs

• CAS Number: 7681-93-8
• PubChem SID: 164230934
• PubChem CID: 71750954

CALCULATED PROPERTIES

• Polarizability: 66.246475 Å^3
• Polar Surface Area: 230.99 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false
• 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

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 200°C (dec)

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer
• Storage Warning: Light sensitive

DETAILS

Toronto Research Chemicals - N379100

Polyene antifungal antibiotic.

REFERENCES

• Levinskas, G.J., et al.: Toxicol. Appl. Pharmacol., 8, 97 (1966)
• Pandey, R.C., et al.: J. Antibiot., 29, 1035 (1966)
• Brik, H., et al.: Anal. Profiles Drug Subs. Excip., 23, 399 (1966)