(1R,3S,5R,7R,8Z,12R,14Z,16Z,18Z,20Z,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: 134056
• 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)/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-UDMGDOCSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3S,5R,7R,8Z,12R,14Z,16Z,18Z,20Z,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,8Z,12R,14Z,16Z,18Z,20Z,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: Pimaricin; Pimaricin preparation; 那他霉素; 游霉素; 那他霉素 制备; 游霉素 制备

Database IDs

• CAS Number: 7681-93-8
• EC Number: 231-683-5
• MDL Number: MFCD00135085
• Beilstein Number: 1614878
• PubChem SID: 162228333; 24899055; 24898105
• PubChem CID: 71308755

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

• Apperance: aqueous suspension
• Density: 1.0 g/mL at 20 °C(lit.)

Safety Information

• RTECS: TK3325000
• German water hazard class: 2; 3
• Personal Protective Equipment: Eyeshields, Gloves; Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95% (HPLC)
• Concentration: ~2.5%
• Biological Source: from Streptomyces chattanoogensis
• Sterility: γ-irradiated
• Quality Level: PREMIUM

DETAILS

Sigma Aldrich - P0440

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.3
Application
Pimaricin is an amphoteric macrolide antifungal antibiotic from Streptomyces natalensis or S. chattanoogensis. It is used for a variety of fungal infections, mainly topically. It is used as an ergosterol and cholesterol binding agent to study lipid bilayer dynamics, especially in fungal cells. It is used to study pimaricin biosynthesis1 and as a fungicide in agar media2.

Sigma Aldrich - P9703

Biochem/physiol Actions
与麦角固醇特异性结合并阻止真菌生长的抗真菌多烯大环内脂。但不同于制霉菌素和菲律宾菌素不同，那他霉素不会改变细胞质膜的渗透性3
Application
Pimaricin is an amphoteric macrolide antifungal antibiotic from Streptomyces chattanoogensis. It is used for a variety of fungal infections, mainly topically. It is used as a ergosterol and cholesterol binding agent to study lipid bilayer dynamics, especially in fungal cells. Pimaricin is used as a fungicide in agar media. It is used to study the pleitropic regulator AdpAch 1 and the gamma-butyrolactone regulatory system of Streptomyces chattanoogensis2.