Neosordarin

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Category Antibiotics
Catalog number BBF-02118
CAS
Molecular Weight 658.77
Molecular Formula C36H50O11

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Description

Neosordarin is originally isolated from Sordaria araneosa Cain. Neosordarin has antifungal activity and inhibits S. Cerevisia with the IC50 of 0.2-0.3 μg/mL.

Specification

IUPAC Name (1R,2S,4R,5R,8R,9S,11R)-9-formyl-2-[[(2R,3S,4S,5R,6R)-3-hydroxy-4-[(2E,5E)-7-hydroxy-2-methyl-4-oxoocta-2,5-dienoyl]oxy-5-methoxy-6-methyloxan-2-yl]oxymethyl]-5-methyl-13-propan-2-yltetracyclo[7.4.0.02,11.04,8]tridec-12-ene-1-carboxylic acid
Canonical SMILES CC1CCC2C1CC3(C4CC2(C3(C(=C4)C(C)C)C(=O)O)C=O)COC5C(C(C(C(O5)C)OC)OC(=O)C(=CC(=O)C=CC(C)O)C)O
InChI InChI=1S/C36H50O11/c1-18(2)27-13-23-14-34(16-37)26-11-8-19(3)25(26)15-35(23,36(27,34)33(42)43)17-45-32-28(40)30(29(44-7)22(6)46-32)47-31(41)20(4)12-24(39)10-9-21(5)38/h9-10,12-13,16,18-19,21-23,25-26,28-30,32,38,40H,8,11,14-15,17H2,1-7H3,(H,42,43)/b10-9+,20-12+/t19-,21?,22-,23+,25-,26-,28+,29-,30+,32-,34+,35+,36+/m1/s1
InChI Key ZYLVYEPSNXRLDN-UPTYFVEISA-N

Properties

Appearance White Powder
Antibiotic Activity Spectrum fungi
Melting Point 53-57°C

Reference Reading

1. Neosordarin and hydroxysordarin, two new antifungal agents from Sordaria araneosa
Paolo Davoli, Günther Engel, Andreas Werle, Olov Sterner, Timm Anke J Antibiot (Tokyo). 2002 Apr;55(4):377-82. doi: 10.7164/antibiotics.55.377.
Two novel antifungal agents belonging to the sordarin family have been isolated from fermentations of Sordaria araneosa by bioassay-guided purification and their structures elucidated by NMR techniques. Neosordarin (1) is closely related to the recently discovered hypoxysordarin (2), with only small differences on the aliphatic side chain acylating the hydroxyl in the 3'-position of the sordarose moiety. Hydroxysordarin (3) closely resembles sordarin (4), the only slight difference being the replacement of sordarose with altrose as the sugar unit.

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