FCE 24366

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Category Antibiotics
Catalog number BBF-02835
CAS
Molecular Weight 809.81
Molecular Formula C40H47N3O15

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Description

FCE 24366 is produced by the strain of Streptomyces peucetius. Its IC50 inhibitory effect on HeLa and P388 cells was less than that of dunomycin, and its anti-P388 effect was stronger than that of dunomycin in vivo.

Specification

Synonyms 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-[(2R,4R,5S,6aS,8S,10R,10aS)-8-[[(1R,3S)-3-acetyl-1,2,3,4,6,11-hexahydro-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1-naphthacenyl]oxy]octahydro-2-[(2S)-2-hydroxypropyl]-4,10-dimethylpyrano[3,4-d]-1,3,6-dioxazocin-5-yl]-1,3-dimethyl-
IUPAC Name 5-[(2R,4R,5S,6aS,8S,10R,10aS)-8-[[(1R,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy]-2-[(2S)-2-hydroxypropyl]-4,10-dimethyl-4,5,6,6a,7,8,10,10a-octahydropyrano[3,4-d][1,3,6]dioxazocin-5-yl]-1,3-dimethyl-1,3-diazinane-2,4,6-trione
Canonical SMILES CC1C(NC2CC(OC(C2OC(O1)CC(C)O)C)OC3CC(CC4=C3C(=C5C(=C4O)C(=O)C6=C(C5=O)C(=CC=C6)OC)O)(C(=O)C)O)C7C(=O)N(C(=O)N(C7=O)C)C
InChI InChI=1S/C40H47N3O15/c1-15(44)11-24-55-16(2)31(30-37(50)42(5)39(52)43(6)38(30)51)41-21-12-25(56-17(3)36(21)58-24)57-23-14-40(53,18(4)45)13-20-27(23)35(49)29-28(33(20)47)32(46)19-9-8-10-22(54-7)26(19)34(29)48/h8-10,15-17,21,23-25,30-31,36,41,44,47,49,53H,11-14H2,1-7H3/t15-,16+,17+,21-,23+,24+,25+,31+,36+,40-/m0/s1
InChI Key BJEGYFWQNFXTQG-ODUMSTJCSA-N

Properties

Antibiotic Activity Spectrum neoplastics (Tumor)
Boiling Point 932.9±75.0°C at 760 mmHg
Melting Point 195-196°C
Density 1.5±0.1 g/cm3

Reference Reading

1. New biosynthetic anthracyclines related to barminomycins incorporating barbiturates in their moiety
G Cassinelli, E Arlandini, M Ballabio, T Bordoni, C Geroni, F Giuliani, A Grein, S Merli, G Rivola J Antibiot (Tokyo). 1990 Jan;43(1):19-28. doi: 10.7164/antibiotics.43.19.
Three new anthracyclines, FCE 21424 (2), FCE 24366 (3) and FCE 24367 (4), were isolated from culture broths of Streptomyces peucetius and its mutant strains after addition of sodium barbiturates during the fermentation. Structural assignment, achieved through spectroscopic and degradative studies, that the new anthracyclines had a common barminomycin-like structure incorporating different barbiturate moieties. The new anthracyclines were found to display outstanding cytotoxicity and remarkable potency "in vivo" against P388 ascitic leukemia.

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