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P9703

Pimaricin

from Streptomyces chattanoogensis, ≥95% (HPLC)

Synonym(s):

Natamycin

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About This Item

Empirical Formula (Hill Notation):
C33H47NO13
CAS Number:
7681-93-8
Molecular Weight:
665.73
NACRES:
NA.85
PubChem Substance ID:
24899055
UNSPSC Code:
51102829
EC Number:
231-683-5
MDL number:
MFCD00135085
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biological source

Streptomyces chattanoogensis

Quality Segment

300

assay

≥95% (HPLC)

form

lyophilized powder, powder

solubility

0.1% formic acid in methanol: soluble 1 mg/mL

antibiotic activity spectrum

fungi

application(s)

agriculture
environmental

mode of action

cell membrane | interferes

storage temp.

2-8°C

SMILES string

C[C@@H]1C\C=C\C=C\C=C\C=C\[C@@H](C[C@@H]2O[C@](O)(C[C@@H](O)C[C@H]3O[C@@H]3\C=C\C(=O)O1)C[C@H](O)[C@H]2C(O)=O)O[C@@H]4O[C@H](C)[C@@H](O)[C@H](N)[C@@H]4O

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

InChI key

NCXMLFZGDNKEPB-FFPOYIOWSA-N

General description

Chemical structure: macrolide

Application

Pimaricin is an amphoteric antibiotic from Streptomyces 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. Pimaricin is used as a fungicide in agar media. It is used to study the pleitropic regulator AdpAch and the gamma-butyrolactone regulatory system of Streptomyces chattanoogensis.

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

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Recommended storage temperature: 2 - 8 °C. Light sensitive.

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Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

Eyeshields, Gloves, type N95 (US)

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