2.0 2012-07-30 14:54:59 -0600 2015-06-03 17:20:55 -0600 ECMDB21218 M2MDB001626 Ferrichrome Ferrichrome is a cyclic hexa-peptide that forms a complex with iron atoms. It is a siderophore composed of three glycine and three modified ornithine residues with hydroxamate groups [-N(OH)C(=O)C-]. The 6 oxygen atoms from the three hydroxamate groups bind Fe(III) in near perfect octahedral coordination. (cyclo{glycyl-N5-(hydroxy-kappaO)-N5-[1-(oxo-kappaO)ethyl]-L-ornithyl-N5-(hydroxy-kappaO)-N5-[1-(oxo-kappaO)ethyl]-L-ornithyl-N5-(hydroxy-kappaO)-N5-[1-(oxo-kappaO)ethyl]-L-ornithylglycylglycyl})iron Ferrichrome C27H42FeN9O12 740.52 740.230234986 1-{3,29-diacetyl-9,12,15,18,21,34-hexahydroxy-2,27,28-trioxa-3,8,11,14,17,20,26,29,33-nonaaza-1-ferratricyclo[17.8.5.2⁷,²²]tetratriaconta-8,11,14,17,20,33-hexaen-26-yl}ethan-1-one 1-{3,29-diacetyl-9,12,15,18,21,34-hexahydroxy-2,27,28-trioxa-3,8,11,14,17,20,26,29,33-nonaaza-1-ferratricyclo[17.8.5.2⁷,²²]tetratriaconta-8,11,14,17,20,33-hexaen-26-yl}ethanone 15630-64-5 CC(=O)N1CCCC2N=C(O)CN=C(O)CN=C(O)CN=C(O)C3CCCN(O[Fe](O1)ON(CCCC(N=C2O)C(O)=N3)C(C)=O)C(C)=O InChI=1S/C27H42N9O12.Fe/c1-16(37)34(46)10-4-7-19-25(43)30-14-23(41)28-13-22(40)29-15-24(42)31-20(8-5-11-35(47)17(2)38)26(44)33-21(27(45)32-19)9-6-12-36(48)18(3)39;/h19-21H,4-15H2,1-3H3,(H,28,41)(H,29,40)(H,30,43)(H,31,42)(H,32,45)(H,33,44);/q-3;+3 GGUNGDGGXMHBMJ-UHFFFAOYSA-N Cytosol Extra-organism Periplasm logp 0.04 ALOGPS logs -3.71 ALOGPS solubility 1.45e-01 g/l ALOGPS logp 0.34 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic 4.67 ChemAxon iupac 1-{3,29-diacetyl-9,12,15,18,21,34-hexahydroxy-2,27,28-trioxa-3,8,11,14,17,20,26,29,33-nonaaza-1-ferratricyclo[17.8.5.2⁷,²²]tetratriaconta-8,11,14,17,20,33-hexaen-26-yl}ethan-1-one ChemAxon average_mass 740.52 ChemAxon mono_mass 740.230234986 ChemAxon smiles CC(=O)N1CCCC2N=C(O)CN=C(O)CN=C(O)CN=C(O)C3CCCN(O[Fe](O1)ON(CCCC(N=C2O)C(O)=N3)C(C)=O)C(C)=O ChemAxon formula C27H42FeN9O12 ChemAxon inchi InChI=1S/C27H42N9O12.Fe/c1-16(37)34(46)10-4-7-19-25(43)30-14-23(41)28-13-22(40)29-15-24(42)31-20(8-5-11-35(47)17(2)38)26(44)33-21(27(45)32-19)9-6-12-36(48)18(3)39;/h19-21H,4-15H2,1-3H3,(H,28,41)(H,29,40)(H,30,43)(H,31,42)(H,32,45)(H,33,44);/q-3;+3 ChemAxon inchikey GGUNGDGGXMHBMJ-UHFFFAOYSA-N ChemAxon polar_surface_area 284.16 ChemAxon refractivity 161.55 ChemAxon polarizability 68.22 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 18 ChemAxon donor_count 6 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 36638 Specdb::MsMs 36639 Specdb::MsMs 36640 Specdb::MsMs 39086 Specdb::MsMs 39087 Specdb::MsMs 39088 644251 25520 C06228 5019 CPD0-2241 Ferrichrome Iron(3+)-hydroxamate import ATP-binding protein fhuC P07821 FHUC_ECOLI fhuC http://ecmdb.ca/proteins/P07821.xml Iron(3+)-hydroxamate import system permease protein fhuB P06972 FHUB_ECOLI fhuB http://ecmdb.ca/proteins/P06972.xml Iron(3+)-hydroxamate-binding protein fhuD P07822 FHUD_ECOLI fhuD http://ecmdb.ca/proteins/P07822.xml Iron(3+)-hydroxamate import ATP-binding protein fhuC P07821 FHUC_ECOLI fhuC http://ecmdb.ca/proteins/P07821.xml Iron(3+)-hydroxamate import system permease protein fhuB P06972 FHUB_ECOLI fhuB http://ecmdb.ca/proteins/P06972.xml Ferrichrome-iron receptor P06971 FHUA_ECOLI fhuA http://ecmdb.ca/proteins/P06971.xml Biopolymer transport protein exbB P0ABU7 EXBB_ECOLI exbB http://ecmdb.ca/proteins/P0ABU7.xml Biopolymer transport protein exbD P0ABV2 EXBD_ECOLI exbD http://ecmdb.ca/proteins/P0ABV2.xml Protein tonB P02929 TONB_ECOLI tonB http://ecmdb.ca/proteins/P02929.xml Iron(3+)-hydroxamate-binding protein fhuD P07822 FHUD_ECOLI fhuD http://ecmdb.ca/proteins/P07822.xml Adenosine triphosphate + Water + Ferrichrome > ADP + Ferrichrome + Hydrogen ion + Phosphate Adenosine triphosphate + Water + Ferrichrome > ADP + Ferrichrome + Hydrogen ion + Phosphate Fe3+ + Ferrichrome minus Fe(III) > Ferrichrome