Ageliferin

Ageliferin

IUPAC name N-[[(5S,6R,7R)-2-amino-7-(2-amino-1H-imidazol-5-yl)-5-[[[(4-bromo-1H-pyrrol-2-yl)carbonyl]amino]methyl]-4,5,6,7-tetrahydro-1H-benzimidazol-6-yl]methyl]-4-bromo-1H-pyrrole-2-carboxamide
Other names Ageliferine
Identifiers
CAS number	117417-64-8^Y
ChemSpider	10472083^Y
ChEMBL	CHEMBL502866^N
Jmol-3D images	Image 1
SMILES Brc1cc(nc1)C(=O)NC[C@H]3Cc5nc(N)nc5C([C@@H]3CNC(=O)c2cc(Br)cn2)c4cnc(N)n4
InChI InChI=1S/C22H24Br2N10O2/c23-10-2-14(27-5-10)19(35)29-4-9-1-13-18(34-22(26)32-13)17(16-8-31-21(25)33-16)12(9)7-30-20(36)15-3-11(24)6-28-15/h2-3,5-6,8-9,12,17,27-28H,1,4,7H2,(H,29,35)(H,30,36)(H3,25,31,33)(H3,26,32,34)/t9-,12-,17?/m1/s1^Y Key: DMMLTRAQSJWUHT-GQFUOHMQSA-N^Y InChI=1/C22H24Br2N10O2/c23-10-2-14(27-5-10)19(35)29-4-9-1-13-18(34-22(26)32-13)17(16-8-31-21(25)33-16)12(9)7-30-20(36)15-3-11(24)6-28-15/h2-3,5-6,8-9,12,17,27-28H,1,4,7H2,(H,29,35)(H,30,36)(H3,25,31,33)(H3,26,32,34)/t9-,12-,17?/m1/s1 Key: DMMLTRAQSJWUHT-GQFUOHMQBZ
Properties
Molecular formula	C₂₂H₂₄Br₂N₁₀O₂
Molar mass	620.3 g mol⁻¹
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Ageliferin is a chemical compound produced by some sponges. It was first isolated from Caribbean and then Okinawan marine sponges in the genus Agelas.^[1]^[2]^[3] It often co-exists with the related compound sceptrin and other similar compounds. (See also Agelas clathrodes and Agelas conifera.) It has antibacterial properties and can cause biofilms to dissolve.^[4]

References

^ Rinehart, Kenneth L; Holt, Tom G.; Fregeau, Nancy L.; Keifer, Paul A.; et al. (1990). "Bioactive Compounds from Aquatic and Terrestrial Sources". Journal of Natural Products 53 (4): 771–792. doi:10.1021/np50070a001.
^ Keifer, Paul A.; Schwartz, Robert E.; Koker, Moustapha E.S.; Hughes, Robert G., Jr.; Rittschoff, Dan; Rinehart, Kenneth L. (1991). "Bioactive Bromopyrrole Metabolites from the Caribbean Sponge Agelas conifera". J. Org. Chem. 56 (9): 2965–75. doi:10.1021/jo00009a008.
^ Kobayashi, Junichi; Tsuda, Masashi; Murayama, Tetsuya; Nakamura, Hideshi; Ohizumi, Yasushi; Ishibashi, Masami; Iwamura, Michiko; Ohta, Tomihisa; Nozoe, Shigeo (1990). "Ageliferins, potent actomyosin ATPase activators from the Okinawan marine sponge Agelas sp.". Tetrahedron 46 (16): 5579–86. doi:10.1016/S0040-4020(01)87756-5.
^ Laura Sanders (2009). "Sponge’s secret weapon restores antibiotics’ power: Bacteria treated with compound lose their resistance". Science News 175 (6): 16. http://www.sciencenews.org/view/generic/id/40894/title/Sponge%27s_secret_weapon_restores_antibiotics%27_power.