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A-25822 A

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Category Antibiotics
Catalog number BBF-03132
CAS 50686-99-2
Molecular Weight 439.71
Molecular Formula C30H49NO

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Fermentation Lab

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Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

A-25822 A is an azasteroid antibiotic produced by Geotrichum flavobrienneum. It has anti-fungal activity, and the MIC for fungi such as Candida albicans, Cryptococcus neoformans, Trichophyton mentacea, Phytoplastria, Saccharomyces cerevisiae, Saccharomyces cerevisiae, Microsporum, etc. is 0.321-1.25 μg/mL. Antibacterial activity is weak.

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Synonyms A-25822A
IUPAC Name (1R,6aR,8S,10aS,12aR)-7,7,10a,12a-tetramethyl-1-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,5,6,6a,8,9,10,11,12-decahydro-1H-naphtho[1,2-h]quinolin-8-ol
Canonical SMILES CC(C)C(=C)CCC(C)C1CCN=C2C1(CCC3=C2CCC4C3(CCC(C4(C)C)O)C)C
InChI InChI=1S/C30H49NO/c1-19(2)20(3)9-10-21(4)23-15-18-31-27-22-11-12-25-28(5,6)26(32)14-17-29(25,7)24(22)13-16-30(23,27)8/h19,21,23,25-26,32H,3,9-18H2,1-2,4-8H3/t21-,23-,25+,26+,29-,30-/m1/s1
InChI Key YXYIUCIRNSZNRD-JALXZWLPSA-N
Appearance White Crystal
Antibiotic Activity Spectrum fungi
Melting Point 147°C
1. Antifungal antibiotics from Calcarisporium thermophilum: a new source of 15-azahomosterol derivatives
P Chrisp, P M Dewick, F T Boyle Z Naturforsch C J Biosci. 1990 Mar-Apr;45(3-4):179-86. doi: 10.1515/znc-1990-3-407.
Two antifungal metabolites isolated from Calcarisporium thermophilum were identified as 15-azahomosterols related to the compounds previously isolated from Geotrichum flavo-brunneum. By full spectral comparison with authentic 15-aza-24-methylene-D-homocholesta-8,14-dien-3 beta-ol (A 25822 B) from G. flavo-brunneum, the Calcarisporium metabolites were characterized as the 4 alpha-methyl- and 4,4-dimethyl-analogues of A 25822 B. Several minor members of the series were also detected, and tentatively identified by MS analysis. The 15-azahomosterols exhibited good antifungal activity towards Candida parapsiliosis, though the activities were somewhat lower than that of the 4-demethyl derivative A25822 B. Calcarisporium thermophilum is the second microorganism known to synthesize these unusual 15-azahomosterol derivatives.

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