(1R,3S,5R,7R,12R,22R,24S,25R,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: 156224
• Molecular Formular: C33H47NO13
• Molecular Mass: 665.72518
• Monoisotopic Mass: 665.30474057
• SMILES: C[C@@H]1C/C=C/C=C\C=C\C=C\[C@@H](C[C@H]2[C@@H]([C@H](C[C@](O2)(C[C@H](C[C@@H]2[C@H](O2)/C=C/C(=O)O1)O)O)O)C(=O)O)O[C@H]1[C@H]([C@H]([C@@H]([C@H](O1)C)O)N)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@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)/t18-,19-,20+,21+,22+,23-,24-,25+,27-,28+,29-,30+,32+,33-/m1/s1
• InChIKey: NCXMLFZGDNKEPB-YWDKRKKXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3S,5R,7R,12R,22R,24S,25R,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,12R,22R,24S,25R,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: Natamycin preparation; Pimaricin preparation; Natamycin; Pimaricin; Natamycin; 那他霉素 制备; 游霉素 制备; 游霉素; 那他霉素; 那他霉素

Database IDs

• CAS Number: 7681-93-8
• EC Number: 231-683-5
• MDL Number: MFCD00135085
• Beilstein Number: 1614878
• PubChem SID: 24887548; 162250362
• PubChem CID: 57417192
• E Number: E235

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

Physical Property

• Density: 1.0 g/mL at 20 °C(lit.)

Safety Information

• RTECS: TK3325000
• German water hazard class: 2; 3
• Personal Protective Equipment: Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ~90% (N)
• Grade: VETRANAL™, analytical standard
• Quality: aqueous suspension 2.5%; sterile
• Empirical Formula (Hill Notation): C33H47NO13

DETAILS

Sigma Aldrich - 80482

Biochem/physiol Actions
An antifungal polyene macrolide that binds specifically to ergosterol and blocks fungal growth. However, unlike nysatin and filipin, pimaricin does not change the permeability of the plasma membrane.1
Other Notes
Polyene antibiotic, review2

Sigma Aldrich - 32417

Biochem/physiol Actions
An antifungal polyene macrolide that binds specifically to ergosterol and blocks fungal growth. However, unlike nysatin and filipin, pimaricin does not change the permeability of the plasma membrane1
Legal Information
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