Dactylfungin A

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Dactylfungin A
Category Antibiotics
Catalog number BBF-00778
CAS 146935-35-5
Molecular Weight 700.94
Molecular Formula C41H64O9

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Description

Dactylfungin is an antifungal antibiotic produced by Dactylaria parvispora D500 and separates the two components A and B. A and B have no antibacterial activity.

Specification

Synonyms 2H-Pyran-2-one, 3-(4-deoxy-beta-xylo-hexopyranosyl)-4-hydroxy-6-(2-hydroxy-7-(hydroxymethyl)-1,1,5,9,11,13,17,19-octamethyl-3,5,13,15,17-heneicosapentaenyl)-
Storage Store at -20°C
IUPAC Name 3-[(2S,3R,4S,6S)-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-4-hydroxy-6-[(4E,6E,14E,16E,18E)-3-hydroxy-8-(hydroxymethyl)-2,6,10,12,14,18,20-heptamethyldocosa-4,6,14,16,18-pentaen-2-yl]pyran-2-one
Canonical SMILES CCC(C)C=C(C)C=CC=C(C)CC(C)CC(C)CC(CO)C=C(C)C=CC(C(C)(C)C1=CC(=C(C(=O)O1)C2C(C(CC(O2)CO)O)O)O)O
InChI InChI=1S/C41H64O9/c1-10-25(2)16-26(3)12-11-13-27(4)17-29(6)18-30(7)20-31(23-42)19-28(5)14-15-35(46)41(8,9)36-22-33(44)37(40(48)50-36)39-38(47)34(45)21-32(24-43)49-39/h11-16,19,22,25,29-32,34-35,38-39,42-47H,10,17-18,20-21,23-24H2,1-9H3/b12-11+,15-14+,26-16+,27-13+,28-19+/t25?,29?,30?,31?,32-,34-,35?,38+,39-/m0/s1
InChI Key RFFNWAQLYUMOFF-CKGFFVAASA-N

Properties

Boiling Point 859.6°C at 760 mmHg
Melting Point 120-122°C(dec.)
Density 1.139 g/cm3
Solubility Soluble in Methanol, Butanol, Pyridine, Chloroform, DMSO

Reference Reading

1. Dactylfungins, novel antifungal antibiotics produced by Dactylaria parvispora
J Xaio, S Kumazawa, N Yoshikawa, T Mikawa, Y Sato J Antibiot (Tokyo). 1993 Jan;46(1):48-55. doi: 10.7164/antibiotics.46.48.
Novel antifungal antibiotics, designated as dactylfungins A (1) and B (3), were isolated from the culture broth of Dactylaria parvispora D500. Dactylfungins A and B were found to be new substances containing an alpha-pyrone and a gamma-pyrone ring, respectively, which conjoined with a polyalcohol moiety and a long side chain, based on NMR spectral analyses. The antibiotics were active against Candida pseudotropicalis and other fungi, with an MIC value at less than 10 micrograms/ml.

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