CAS 104542-46-3

urdamycin B

Description:

Urdamycin B is a natural antibiotic compound belonging to the class of anthracycline antibiotics, which are known for their potent antibacterial properties. It is produced by the fermentation of certain strains of Streptomyces bacteria. Urdamycin B exhibits a complex molecular structure characterized by a polycyclic ring system, which contributes to its biological activity. The compound has shown effectiveness against a range of Gram-positive bacteria, making it of interest in the field of medicinal chemistry and antibiotic development. Its mechanism of action typically involves interference with bacterial DNA synthesis, leading to cell death. Additionally, urdamycin B may possess antitumor properties, although its primary application remains in combating bacterial infections. As with many antibiotics, the potential for resistance development is a concern, necessitating ongoing research into its efficacy and safety profile. Overall, urdamycin B represents a significant compound in the study of natural products and their applications in pharmacology.

Formula: C₃₇H₄₄O₁₃

InChI: InChI=1/C37H44O13/c1-15-24(49-28-11-22(38)32(40)16(2)48-28)9-10-27(47-15)50-26-12-25(46-17(3)33(26)41)19-7-8-21-31(34(19)42)36(44)20-6-5-18-13-37(4,45)14-23(39)29(18)30(20)35(21)43/h5-8,15-17,22,24-28,32-33,38,40-42,45H,9-14H2,1-4H3/t15-,16+,17+,22+,24-,25+,26+,27-,28-,32+,33+,37+/m0/s1

InChI key: InChIKey=RVYIFZVNJLDNAV-VSYBRGMMSA-N

SMILES: O=C1C=2C3=C(C=CC2C(=O)C=4C1=CC=C(C4O)[C@H]5C[C@@H](O[C@@H]6O[C@@H](C)[C@@H](O[C@H]7C[C@@H](O)[C@H](O)[C@@H](C)O7)CC6)[C@H](O)[C@@H](C)O5)C[C@@](C)(O)CC3=O

Synonyms:

• (1R)-1,5-anhydro-2,6-dideoxy-3-O-{(2S,5S,6S)-5-[(2,6-dideoxy-beta-D-arabino-hexopyranosyl)oxy]-6-methyltetrahydro-2H-pyran-2-yl}-1-[(3R)-3,8-dihydroxy-3-methyl-1,7,12-trioxo-1,2,3,4,7,12-hexahydrotetraphen-9-yl]-D-arabino-hexitol
• (3R)-9-[2,6-Dideoxy-3-O-[(2S,5S,6S)-5-[(2,6-dideoxy-β-<span class="text-smallcaps">D</smallcap>-arabino-hexopyranosyl)oxy]tetrahydro-6-methyl-2H-pyran-2-yl]-β-<smallcap>D</span>-arabino-hexopyranosyl]-3,4-dihydro-3,8-dihydroxy-3-methylbenz[a]anthracene-1,7,12(2H)-trione
• (R)-9-(2,6-Dideoxy-3-O-((2S-(2alpha,5beta,6beta))-5-((2,6-dideoxy-beta-D-arabino-hexopyranosyl)oxy)tetrahydro-6-methyl-2H-pyran-2-yl)-beta-D-arabino-hexopyranosyl)-3,4-dihydro-3,8-dihydroxy-3-methylbenz(a)anthracene-1,7,12(2H)-trione
• Benz(a)anthracene-1,7,12(2H)-trione, 9-(2,6-dideoxy-3-O-((2S-(2alpha,5beta,6beta))-5-((2,6-dideoxy-beta-D-arabino-hexopyranosyl)oxy)tetrahydro-6-methyl-2H-pyran-2-yl)-beta-D-arabino-hexopyranosyl)-3,4-dihydro-3,8-dihydroxy-3-methyl-, (R)-
• Benz[a]anthracene-1,7,12(2H)-trione, 9-[2,6-dideoxy-3-O-[(2S,5S,6S)-5-[(2,6-dideoxy-β-<span class="text-smallcaps">D</smallcap>-arabino-hexopyranosyl)oxy]tetrahydro-6-methyl-2H-pyran-2-yl]-β-<smallcap>D</span>-arabino-hexopyranosyl]-3,4-dihydro-3,8-dihydroxy-3-methyl-, (3R)-
• Benz[a]anthracene-1,7,12(2H)-trione, 9-[2,6-dideoxy-3-O-[[2S-(2α,5β,6β)]-5-[(2,6-dideoxy-β-<span class="text-smallcaps">D</smallcap>-arabino-hexopyranosyl)oxy]tetrahydro-6-methyl-2H-pyran-2-yl]-β-<smallcap>D</span>-arabino-hexopyranosyl]-3,4-dihydro-3,8-dihydroxy-3-methyl-, (R)-
• Urdamycin B
• (3R)-9-[2,6-Dideoxy-3-O-[(2S,5S,6S)-5-[(2,6-dideoxy-β-D-arabino-hexopyranosyl)oxy]tetrahydro-6-methyl-2H-pyran-2-yl]-β-D-arabino-hexopyranosyl]-3,4-dihydro-3,8-dihydroxy-3-methylbenz[a]anthracene-1,7,12(2H)-trione
• Benz[a]anthracene-1,7,12(2H)-trione, 9-[2,6-dideoxy-3-O-[(2S,5S,6S)-5-[(2,6-dideoxy-β-D-arabino-hexopyranosyl)oxy]tetrahydro-6-methyl-2H-pyran-2-yl]-β-D-arabino-hexopyranosyl]-3,4-dihydro-3,8-dihydroxy-3-methyl-, (3R)-
• Benz[a]anthracene-1,7,12(2H)-trione, 9-[2,6-dideoxy-3-O-[[2S-(2α,5β,6β)]-5-[(2,6-dideoxy-β-D-arabino-hexopyranosyl)oxy]tetrahydro-6-methyl-2H-pyran-2-yl]-β-D-arabino-hexopyranosyl]-3,4-dihydro-3,8-dihydroxy-3-methyl-, (R)-
• C12406

Urdamycin B

CAS: 104542-46-3

Formula: C₃₇H₄₄O₁₃

Purity: 88.18%

Color and Shape: Purple amorphous solid

Molecular weight: 697.0

Ref: 8R-JU0097

Urdamycin B

CAS: 104542-46-3

Urdamycin B, an antibiotic derived from the metabolic products of Streptomyces fradiae, effectively inhibits fungi and bacteria, and exhibits anti-proliferative activity against mouse leukemia cells L1210. Its potential uses include research on cancer, bacterial, and fungal infections [1] [2].

Formula: C₃₇H₄₄O₁₃

Color and Shape: Solid

Molecular weight: 696.74

Ref: TM-TN7537

Urdamycin B

CAS: 104542-46-3

Urdamycin B is an anthracycline antibiotic, which is derived from the bacterium *Streptomyces fradiae*. This compound acts by intercalating into DNA, disrupting the replication and transcription processes, leading to cell death. Its mode of action involves inhibiting topoisomerase II, an enzyme critical for DNA replication and cell cycle progression. This mechanism impairs cellular proliferation, making it effective against rapidly dividing cells.

Formula: C₃₇H₄₄O₁₃

Purity: Min. 95%

Molecular weight: 696.70 g/mol

Ref: 3D-EEA54246