A25822B

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 571086

CAS#: 50686-98-1

Description: A25822B is an antifungal agent. It is an azasterol that may decrease the ratio of unsaturated to saturated fatty acids.


Price and Availability

Size
Price

Size
Price

Size
Price

A25822B is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

img

Theoretical Analysis

MedKoo Cat#: 571086
Name: A25822B
CAS#: 50686-98-1
Chemical Formula: C28H45NO
Exact Mass: 411.3501
Molecular Weight: 411.67
Elemental Analysis: C, 81.69; H, 11.02; N, 3.40; O, 3.89


Synonym: A25822B

IUPAC/Chemical Name: (1R,6aS,8S,10aR,12aS)-10a,12a-dimethyl-1-((R)-6-methyl-5-methyleneheptan-2-yl)-1,2,3,5,6,6a,7,8,9,10,10a,11,12,12a-tetradecahydronaphtho[1,2-h]quinolin-8-ol

InChi Key: JZFNKAMRJSGWIF-QXQLARFDSA-N

InChi Code: InChI=1S/C28H45NO/c1-18(2)19(3)7-8-20(4)24-13-16-29-26-23-10-9-21-17-22(30)11-14-27(21,5)25(23)12-15-28(24,26)6/h18,20-22,24,30H,3,7-17H2,1-2,4-6H3/t20-,21+,22+,24-,27-,28+/m1/s1

SMILES Code: C[C@@]12CC[C@H](O)C[C@@H]1CCC3=C2CC[C@@]4(C)[C@@H]([C@H](C)CCC(C(C)C)=C)CCN=C34


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Georgopapadakou NH, Dix BA, Smith SA, Freudenberger J, Funke PT. Effect of antifungal agents on lipid biosynthesis and membrane integrity in Candida albicans. Antimicrob Agents Chemother. 1987 Jan;31(1):46-51. PubMed PMID: 3551826; PubMed Central PMCID: PMC174649.

2: Jančič S, Frisvad JC, Kocev D, Gostinčar C, Džeroski S, Gunde-Cimerman N. Production of Secondary Metabolites in Extreme Environments: Food- and Airborne Wallemia spp. Produce Toxic Metabolites at Hypersaline Conditions. PLoS One. 2016 Dec 30;11(12):e0169116. doi: 10.1371/journal.pone.0169116. eCollection 2016. PubMed PMID: 28036382; PubMed Central PMCID: PMC5201246.

3: Michel KH, Hamill RL, Larsen SH, Williams RH. New azasteroidal antifungal antibiotics from Geotrichum flavo-brunneum. II. Isolation and characterization. J Antibiot (Tokyo). 1975 Feb;28(2):102-11. PubMed PMID: 1167541.

4: Gordee RS, Butler TF. New azasteroidal antifungal antibiotics from Geotrichum flavo-brunneum. III. Biological activity. J Antibiot (Tokyo). 1975 Feb;28(2):112-7. PubMed PMID: 1089623.

5: Kasbekar DP, Papavinasasundaram KG. An inducible, nondegradative phytoalexin resistance mechanism in Dictyostelium discoideum is suppressed by mutations that alter membrane sterol composition. Appl Environ Microbiol. 1992 Jun;58(6):2071-4. PubMed PMID: 1622285; PubMed Central PMCID: PMC195728.

6: Schrick K, Mayer U, Martin G, Bellini C, Kuhnt C, Schmidt J, Jürgens G. Interactions between sterol biosynthesis genes in embryonic development of Arabidopsis. Plant J. 2002 Jul;31(1):61-73. PubMed PMID: 12100483.

7: Parks LW, Rodríguez RJ. The biochemical action of the azasteroid antibiotics. Biochem Soc Trans. 1983 Dec;11(6):656. PubMed PMID: 6667771.

8: Rodriguez RJ, Parks LW. Physiological response of Saccharomyces cerevisiae to 15-azasterol-mediated growth inhibition. Antimicrob Agents Chemother. 1981 Aug;20(2):184-9. PubMed PMID: 7025753; PubMed Central PMCID: PMC181661.

9: Taylor FR, Rodriguez RJ, Parks LW. Relationship between antifungal activity and inhibition of sterol biosynthesis in miconazole, clotrimazole, and 15-azasterol. Antimicrob Agents Chemother. 1983 Apr;23(4):515-21. PubMed PMID: 6344784; PubMed Central PMCID: PMC184691.

10: Takahashi I, Maruta R, Ando K, Yoshida M, Iwasaki T, Kanazawa J, Okabe M, Tamaoki T. UCA1064-B, a new antitumor antibiotic isolated from Wallemia sebi: production, isolation and structural determination. J Antibiot (Tokyo). 1993 Aug;46(8):1312-4. PubMed PMID: 8407596.

11: Haughan PA, Chance ML, Goad LJ. Effects of an azasterol inhibitor of sterol 24-transmethylation on sterol biosynthesis and growth of Leishmania donovani promastigotes. Biochem J. 1995 May 15;308 ( Pt 1):31-8. PubMed PMID: 7755579; PubMed Central PMCID: PMC1136839.

12: Rodriguez RJ, Parks LW. Growth and antifungal homoazasterol production in Geotrichum flavo-brunneum. Antimicrob Agents Chemother. 1980 Nov;18(5):822-8. PubMed PMID: 7192535; PubMed Central PMCID: PMC284097.