Rosaramicin
Rosaramicin
Names
IUPAC name
{(1S ,2R ,3R ,7R ,8S ,9S ,10R ,12R ,14E ,16S )-3-Ethyl-7-hydroxy-2,8,12,16-tetramethyl-5,13-dioxo-9-[3,4,6-trideoxy-3-(dimethylamino)-β-D -xylo -hexopyranosyloxy]-4,17-dioxabicyclo[14.1.0]heptadec-14-en-10-yl}acetaldehyde
Systematic IUPAC name
[(1S ,2R ,3R ,7R ,8S ,9S ,10R ,12R ,14E ,16S )-9-{[(2S ,3R ,4S ,6R )-4-(Dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-3-ethyl-7-hydroxy-2,8,12,16-tetramethyl-5,13-dioxo-4,17-dioxabicyclo[14.1.0]heptadec-14-en-10-yl]acetaldehyde
Other names
Rosamicin; Juvenimicin A3
Identifiers
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
100.047.933
EC Number
KEGG
UNII
InChI=1S/C31H51NO9/c1-9-25-20(5)29-31(6,41-29)12-10-23(34)17(2)14-21(11-13-33)28(19(4)24(35)16-26(36)39-25)40-30-27(37)22(32(7)8)15-18(3)38-30/h10,12-13,17-22,24-25,27-30,35,37H,9,11,14-16H2,1-8H3/b12-10+/t17-,18-,19+,20-,21+,22+,24-,25-,27-,28-,29+,30+,31+/m1/s1
Key: IUPCWCLVECYZRV-JZMZINANSA-N
InChI=1/C31H51NO9/c1-9-25-20(5)29-31(6,41-29)12-10-23(34)17(2)14-21(11-13-33)28(19(4)24(35)16-26(36)39-25)40-30-27(37)22(32(7)8)15-18(3)38-30/h10,12-13,17-22,24-25,27-30,35,37H,9,11,14-16H2,1-8H3/b12-10+/t17-,18-,19+,20-,21+,22+,24-,25-,27-,28-,29+,30+,31+/m1/s1
Key: IUPCWCLVECYZRV-JZMZINANBR
O=CC[C@@H]2[C@H](O[C@@H]1O[C@@H](C[C@H](N(C)C)[C@H]1O)C)[C@@H](C)[C@H](O)CC(=O)O[C@H](CC)[C@@H](C)[C@@H]3O[C@]3(\C=C\C(=O)[C@H](C)C2)C
Properties
C 31 H 51 N O 9
Molar mass
581.747 g·mol−1
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Rosaramicin (rosamicin ) is an antibacterial substance that is chemically a lipid-soluble basic macrolide similar to erythromycin but with a better activity against Gram-negative bacteria.[citation needed ]
Experiments in dogs have shown that it is more concentrated in the prostate than erythromycin is, and thus may be better for treating infections of that organ.[ 1]
References
^ Baumueller A, Kjaer TB, Madsen PO (September 1977). "Prostatic tissue and secretion concentrations of rosamicin and erythromycin. Experimental studies in the dog". Invest Urol . 15 (2): 158– 60. PMID 903212 .