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CAS 54651-06-8

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Echinocandin B, 1-[(4R,5R)-4,5-dihydroxy-N2-(1-oxooctadecyl)-L-ornithine]-

Description:
Echinocandin B is a lipopeptide antifungal agent derived from the fungus Glarea lozoyensis. It is primarily used in the treatment of invasive fungal infections, particularly those caused by Candida and Aspergillus species. The compound features a cyclic hexapeptide structure linked to a long-chain fatty acid, which contributes to its mechanism of action by inhibiting the synthesis of β-(1,3)-D-glucan, an essential component of fungal cell walls. This disruption leads to cell lysis and death of the fungus. Echinocandin B is characterized by its solubility in water and organic solvents, making it suitable for various pharmaceutical formulations. Its stereochemistry, particularly the presence of specific chiral centers, is crucial for its biological activity. The compound is generally well-tolerated, with a favorable safety profile, although it may cause some side effects such as gastrointestinal disturbances. Overall, Echinocandin B represents a significant advancement in antifungal therapy, particularly for patients with compromised immune systems.
Formula:C52H85N7O16
InChI:InChI=1/C52H85N7O16/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-38(65)53-35-26-37(64)48(71)57-50(73)42-43(66)29(2)27-59(42)52(75)40(31(4)61)55-49(72)41(45(68)44(67)32-21-23-33(62)24-22-32)56-47(70)36-25-34(63)28-58(36)51(74)39(30(3)60)54-46(35)69/h21-24,29-31,34-37,39-45,48,60-64,66-68,71H,5-20,25-28H2,1-4H3,(H,53,65)(H,54,69)(H,55,72)(H,56,70)(H,57,73)
InChI key:InChIKey=CSFSSKWGOYOSPM-UHFFFAOYSA-N
SMILES:O=C1N2C(C(O)C(C)C2)C(=O)NC(O)C(O)CC(NC(CCCCCCCCCCCCCCCCC)=O)C(=O)NC(C(C)O)C(=O)N3C(C(=O)NC(C(C(O)C4=CC=C(O)C=C4)O)C(=O)NC1C(C)O)CC(O)C3
Synonyms:
  • Echinocandin B, 1-[(4R,5R)-4,5-dihydroxy-N2-(1-oxooctadecyl)-L-ornithine]-
  • 1H-Dipyrrolo[2,1-c:2′,1′-l][1,4,7,10,13,16]hexaazacycloheneicosine, cyclic peptide deriv.
  • Echinocandin B, tetrahydro-
  • Tetrahydro A-30912A
  • Tetrahydroechinocandin B
  • See more synonyms
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