CAS 116249-65-1

Benanomicin A

Description:

Benanomicin A is a naturally occurring compound classified as a macrolide antibiotic, primarily derived from the fermentation of certain Streptomyces species. It exhibits a complex molecular structure characterized by a large lactone ring, which is typical of macrolides, and contains multiple functional groups that contribute to its biological activity. Benanomicin A is known for its potent antibacterial properties, particularly against Gram-positive bacteria, making it of interest in pharmaceutical research. Its mechanism of action involves inhibition of protein synthesis, which disrupts bacterial growth and replication. Additionally, Benanomicin A has shown potential in antitumor activity, further expanding its relevance in medicinal chemistry. The compound's stability, solubility, and bioavailability are critical factors that influence its therapeutic efficacy and application. As with many antibiotics, the development of resistance is a concern, prompting ongoing studies to optimize its use and explore its derivatives for enhanced activity and reduced side effects. Overall, Benanomicin A represents a significant area of study in the search for effective antimicrobial agents.

Formula: C₃₉H₄₁NO₁₉

InChI: InChI=1S/C39H41NO19/c1-10-5-17-23(30(48)20(10)36(52)40-11(2)37(53)54)22-15(8-16-24(31(22)49)27(45)14-6-13(55-4)7-18(41)21(14)26(16)44)28(46)34(17)58-39-33(51)35(25(43)12(3)57-39)59-38-32(50)29(47)19(42)9-56-38/h5-8,11-12,19,25,28-29,32-35,38-39,41-43,46-51H,9H2,1-4H3,(H,40,52)(H,53,54)/t11-,12-,19-,25+,28+,29+,32-,33-,34+,35+,38+,39+/m1/s1

InChI key: InChIKey=GOYUMGXIFMGKFN-NUVDETJMSA-N

SMILES: OC1=C2C=3C(=CC4=C(C3O)C(=O)C=5C(C4=O)=C(O)C=C(OC)C5)[C@H](O)[C@@H](O[C@H]6[C@H](O)[C@@H](O[C@H]7[C@H](O)[C@@H](O)[C@H](O)CO7)[C@@H](O)[C@@H](C)O6)C2=CC(C)=C1C(N[C@@H](C(O)=O)C)=O

Synonyms:

• Benzo[a]naphthacene, D-alanine deriv.
• Benanomicin A
• N-[[(5S,6S)-5-[(6-Deoxy-3-O-β-D-xylopyranosyl-β-D-galactopyranosyl)oxy]-5,6,8,13-tetrahydro-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxobenzo[a]naphthacen-2-yl]carbonyl]-D-alanine
• D-Alanine, N-[[5-[(6-deoxy-3-O-β-D-xylopyranosyl-β-D-galactopyranosyl)oxy]-5,6,8,13-tetrahydro-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxobenzo[a]naphthacen-2-yl]carbonyl]-, (5S-trans)-
• D-Alanine, N-[[(5S,6S)-5-[(6-deoxy-3-O-β-D-xylopyranosyl-β-D-galactopyranosyl)oxy]-5,6,8,13-tetrahydro-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxobenzo[a]naphthacen-2-yl]carbonyl]-

Benanomicin A

CAS: 116249-65-1

"Benanomicin A, from Actinomycetes, is antifungal and antiviral, effective against pathogens like C. albicans and HIV-1 (MICs 3.13-50 μg/ml)."

Formula: C₃₉H₄₁NO₁₉

Color and Shape: Solid

Molecular weight: 827.745

Ref: TM-T37749