Epelmycin B

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Category Antibiotics
Catalog number BBF-01237
CAS 107807-24-9
Molecular Weight 825.85
Molecular Formula C42H51NO16

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Description

It is produced by the strain of Streptomyces violaceus A262. It has anti-gram positive, negative bacteria and candida albicans activity, and has anti-leukemic L1210 activity, which is stronger than Aclacinomycin.

Specification

Synonyms 11-Hydroxyauramycin B
IUPAC Name methyl (1R,2R,4R)-4-[(2R,4R,5R,6S)-4-(dimethylamino)-5-[[(1R,3S,5S,8S,10S,12R,14S)-5,14-dimethyl-6-oxo-2,4,9,13-tetraoxatricyclo[8.4.0.03,8]tetradecan-12-yl]oxy]-6-methyloxan-2-yl]oxy-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate
Canonical SMILES CCC1(CC(C2=C(C1C(=O)OC)C(=C3C(=C2O)C(=O)C4=C(C3=O)C=CC=C4O)O)OC5CC(C(C(O5)C)OC6CC7C(C(O6)C)OC8C(O7)CC(=O)C(O8)C)N(C)C)O
InChI InChI=1S/C42H51NO16/c1-8-42(51)15-25(29-30(33(42)40(50)52-7)37(49)31-32(36(29)48)35(47)28-19(34(31)46)10-9-11-21(28)44)57-26-12-20(43(5)6)38(17(3)53-26)58-27-14-23-39(18(4)54-27)59-41-24(56-23)13-22(45)16(2)55-41/h9-11,16-18,20,23-27,33,38-39,41,44,48-49,51H,8,12-15H2,1-7H3/t16-,17-,18-,20+,23-,24-,25+,26-,27+,33-,38-,39+,41+,42+/m0/s1
InChI Key DKXGZTHFCJJLIP-PGFBMTGHSA-N

Properties

Appearance Red Powder
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria; Neoplastics (Tumor); Yeast
Boiling Point 860.2 °C at 760 mmHg
Melting Point 175-178 °C
Density 1.48 g/cm3
Solubility Soluble in Methanol, Chloroform

Reference Reading

1. Anthracycline metabolites from Streptomyces violaceus A262. II. New anthracycline epelmycins produced by a blocked mutant strain SU2-730
O Johdo, Y Watanabe, T Ishikura, A Yoshimoto, H Naganawa, T Sawa, T Takeuchi J Antibiot (Tokyo). 1991 Oct;44(10):1121-9. doi: 10.7164/antibiotics.44.1121.
New anthracycline antibiotics, identified as epsilon-rhodomycinone glycosides, were isolated from the culture broth of a blocked mutant of beta-rhodomycin-producing Streptomyces violaceus A262. They were designated as epelmycins A, B, C, D and E, and assayed for their in vitro cytotoxicities against murine leukemic L1210 cell culture and the antimicrobial activities in comparison with known anthracycline antibiotics.

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