2.0 2012-07-30 14:54:58 -0600 2015-06-03 17:20:54 -0600 ECMDB21217 M2MDB001625 Ferrichrome minus Fe(III) Ferrichrome minus Fe(iii) 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. Ferrichrome is produced by several different fungi, but used by bacteria in iron transport. Ferrichrome Ferrichrome minus Fe(III) Iron-free ferrichrome C27H42N9O12 684.6755 684.295292853 N-(3-{3,6,9,12,15,18-hexahydroxy-5,17-bis[3-(N-oxidoacetamido)propyl]-1,4,7,10,13,16-hexaazacyclooctadeca-1(18),3,6,9,12,15-hexaen-2-yl}propyl)-N-oxidoacetamide N-(3-{3,6,9,12,15,18-hexahydroxy-5,17-bis[3-(N-oxidoacetamido)propyl]-1,4,7,10,13,16-hexaazacyclooctadeca-1(18),3,6,9,12,15-hexaen-2-yl}propyl)-N-oxidoacetamide CC(=O)N([O-])CCCC1N=C(O)C(CCCN([O-])C(C)=O)N=C(O)C(CCCN([O-])C(C)=O)N=C(O)CN=C(O)CN=C(O)CN=C1O InChI=1S/C27H42N9O12/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 GNGZPAKHDVFMFC-UHFFFAOYSA-N Cytosol Extra-organism Periplasm logp -0.06 ALOGPS logs -3.83 ALOGPS solubility 1.09e-01 g/l ALOGPS logp -2.3 ChemAxon pka_strongest_acidic 4.64 ChemAxon pka_strongest_basic -5.7 ChemAxon iupac N-(3-{3,6,9,12,15,18-hexahydroxy-5,17-bis[3-(N-oxidoacetamido)propyl]-1,4,7,10,13,16-hexaazacyclooctadeca-1(18),3,6,9,12,15-hexaen-2-yl}propyl)-N-oxidoacetamide ChemAxon average_mass 684.6755 ChemAxon mono_mass 684.295292853 ChemAxon smiles CC(=O)N([O-])CCCC1N=C(O)C(CCCN([O-])C(C)=O)N=C(O)C(CCCN([O-])C(C)=O)N=C(O)CN=C(O)CN=C(O)CN=C1O ChemAxon formula C27H42N9O12 ChemAxon inchi InChI=1S/C27H42N9O12/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 ChemAxon inchikey GNGZPAKHDVFMFC-UHFFFAOYSA-N ChemAxon polar_surface_area 325.65 ChemAxon refractivity 161.83 ChemAxon polarizability 66.89 ChemAxon rotatable_bond_count 12 ChemAxon acceptor_count 18 ChemAxon donor_count 6 ChemAxon physiological_charge 0 ChemAxon formal_charge -3 ChemAxon Specdb::MsMs 36974 Specdb::MsMs 36975 Specdb::MsMs 36976 Specdb::MsMs 39422 Specdb::MsMs 39423 Specdb::MsMs 39424 27425 25521 CPD0-2205 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 Iron(3+)-hydroxamate-binding protein fhuD P07822 FHUD_ECOLI fhuD http://ecmdb.ca/proteins/P07822.xml Fe3+ + Ferrichrome minus Fe(III) > Ferrichrome