Ageliferin

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. It has antibacterial properties and can cause biofilms to dissolve.[4]

Ageliferin

Names
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^N
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL502866^N
ChemSpider	9344613^N
PubChem CID	11169518
CompTox Dashboard (EPA)	DTXSID40457473
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^N Key: DMMLTRAQSJWUHT-OGTWGDGJSA-N^N 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-OGTWGDGJBG
SMILES C1[C@@H]([C@H]([C@@H](C2=C1NC(=N2)N)C3=CN=C(N3)N)CNC(=O)C4=CC(=CN4)Br)CNC(=O)C5=CC(=CN5)Br
Properties
Chemical formula	C22H24Br2N10O2
Molar mass	620.310 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

See also

• Agelas clathrodes
• Agelas conifera

References

1. Rinehart, Kenneth L; et al. (1990). "Bioactive Compounds from Aquatic and Terrestrial Sources". Journal of Natural Products. 53 (4): 771–792. doi:10.1021/np50070a001.
2. Keifer, Paul A.; et al. (1991). "Bioactive Bromopyrrole Metabolites from the Caribbean Sponge Agelas conifera". J. Org. Chem. 56 (9): 2965–75. doi:10.1021/jo00009a008.
3. Kobayashi, Junichi; et al. (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.
4. Laura Sanders (2009). "Sponge's secret weapon restores antibiotics' power: Bacteria treated with compound lose their resistance". Science News. 175 (6): 16. doi:10.1002/scin.2009.5591750616.