CAS 20283-48-1

Chalcomycin

Description:

Chalcomycin is a naturally occurring antibiotic that belongs to the class of compounds known as macrolides. It is produced by certain strains of the bacterium Streptomyces. This compound exhibits antibacterial properties, particularly against a range of Gram-positive bacteria, making it of interest in the field of medicinal chemistry. Chalcomycin's structure features a large lactone ring, which is characteristic of macrolide antibiotics, contributing to its mechanism of action by inhibiting bacterial protein synthesis. The compound is typically characterized by its solubility in organic solvents and limited solubility in water, which can influence its bioavailability and therapeutic applications. Additionally, chalcomycin may possess antifungal and antitumor activities, although its primary use remains in combating bacterial infections. As with many antibiotics, the potential for resistance development is a concern, necessitating careful consideration in clinical applications. Overall, chalcomycin represents an important compound in the study of antibiotic development and the ongoing search for effective treatments against resistant bacterial strains.

Formula: C₃₅H₅₆O₁₄

InChI: InChI=1/C35H56O14/c1-17-10-13-26(37)46-20(4)22(16-44-34-32(43-9)31(42-8)27(38)21(5)47-34)30-23(48-30)11-12-25(36)35(6,40)15-18(2)29(17)49-33-28(39)24(41-7)14-19(3)45-33/h10-13,17-24,27-34,38-40H,14-16H2,1-9H3/b12-11+,13-10+/t17-,18-,19+,20+,21+,22+,23-,24-,27+,28+,29-,30-,31+,32+,33-,34+,35-/m0/s1

InChI key: InChIKey=KLGADJPDTCIJLO-RVMREVNESA-N

SMILES: C(O[C@H]1[C@H](OC)[C@H](OC)[C@H](O)[C@@H](C)O1)[C@H]2[C@]3([C@@](O3)(/C=C/C(=O)[C@@](C)(O)C[C@H](C)[C@H](O[C@H]4[C@H](O)[C@@H](OC)C[C@@H](C)O4)[C@@H](C)\C=C\C(=O)O[C@@H]2C)[H])[H]

Synonyms:

• 4,17-Dioxabicyclo[14.1.0]heptadecane, chalcomycin deriv.
• (1S,2R,3R,6E,8S,9S,10S,12S,14E,16S)-2-[[(6-Deoxy-2,3-di-O-methyl-β-D-allopyranosyl)oxy]methyl]-9-[(4,6-dideoxy-3-O-methyl-β-D-xylo-hexopyranosyl)oxy]-12-hydroxy-3,8,10,12-tetramethyl-4,17-dioxabicyclo[14.1.0]heptadeca-6,14-diene-5,13-dione
• 4,17-Dioxabicyclo[14.1.0]heptadeca-6,14-diene-5,13-dione, 2-[[(6-deoxy-2,3-di-O-methyl-β-D-allopyranosyl)oxy]methyl]-9-[(4,6-dideoxy-3-O-methyl-β-D-xylo-hexopyranosyl)oxy]-12-hydroxy-3,8,10,12-tetramethyl-, (1S,2R,3R,6E,8S,9S,10S,12S,14E,16S)-
• Chalcomycin
• Stereoisomer of 2-[[(6-deoxy-2,3-di-O-methyl-β-D-allopyranosyl)oxy]methyl]-9-[(4,6-dideoxy-3-O-methyl-β-D-xylo-hexopyranosyl)oxy]-12-hydroxy-3,8,10,12-tetramethyl-4,17-dioxabicyclo[14.1.0]heptadeca-6,14-diene-5,13-dione

Chalcomycin

CAS: 20283-48-1

Chalcomycin is a macrolide antibiotic effective against Gram-positive Staphylococcus aureus and Streptococcus pyogenes. It protects mice from infections caused by various Staphylococcus and Streptococcus strains and exhibits no significant toxicity (LD50>2500 mg/kg).

Formula: C₃₅H₅₆O₁₄

Molecular weight: 700.36701

Ref: TM-TN11198

Chalcomycin

CAS: 20283-48-1

Formula: C₃₅H₅₆O₁₄

Molecular weight: 700.8

Ref: 7W-GL8173