1.0 2011-09-21 00:27:37 UTC 2015-07-21 06:57:37 UTC FDB023292 Aerobactin Aerobactin is a virulence factor for enteric bacteria found occasionally in humans, and is produced by bacteria such as Enterobacter cloacae. E. cloacae is part of the normal intestinal floras of many individuals and not a primary human pathogen but has been considered to be an important cause of nosocomial infections. Aerobactin secretion in vivo could be an important step in the stages of the infection cycle during which intestine-populating opportunistic bacteria effectively colonize the gut, penetrate the mucous layer covering the intestinal villi, translocate out of intestinal lumen through the epithelial cells, and finally spread to organs within which they may survive. (PMID: 9453621, 8752377) [HMDB] (8S,16S)-3,12,21-Trihydroxy-2,10,14,22-tetraoxo-3,9,15,21-tetraazatricosane-8,12,16-tricarboxylate (8S,16S)-3,12,21-Trihydroxy-2,10,14,22-tetraoxo-3,9,15,21-tetraazatricosane-8,12,16-tricarboxylic acid Ferric-aerobactin C22H36N4O13 564.5402 564.227887258 (2S)-2-[3-carboxy-3-({[(1S)-1-carboxy-5-(N-hydroxyacetamido)pentyl]carbamoyl}methyl)-3-hydroxypropanamido]-6-(N-hydroxyacetamido)hexanoic acid aerobactin 26198-65-2 CC(=O)N(O)CCCC[C@H](NC(=O)CC(O)(CC(=O)N[C@@H](CCCCN(O)C(C)=O)C(O)=O)C(O)=O)C(O)=O InChI=1S/C22H36N4O13/c1-13(27)25(38)9-5-3-7-15(19(31)32)23-17(29)11-22(37,21(35)36)12-18(30)24-16(20(33)34)8-4-6-10-26(39)14(2)28/h15-16,37-39H,3-12H2,1-2H3,(H,23,29)(H,24,30)(H,31,32)(H,33,34)(H,35,36)/t15-,16-/m0/s1 KDHHWXGBNUCREU-HOTGVXAUSA-N belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. N-acyl-alpha amino acids Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic acyclic compounds Acetamides Acetohydroxamic acids Alpha hydroxy acids and derivatives Carbonyl compounds Carboximidic acids Carboxylic acids Hydrocarbon derivatives Organic oxides Organonitrogen compounds Organopnictogen compounds Propargyl-type 1,3-dipolar organic compounds Tertiary alcohols Tricarboxylic acids and derivatives Acetamide Acetohydroxamic acid Alcohol Aliphatic acyclic compound Alpha-hydroxy acid Carbonyl group Carboximidic acid Carboximidic acid derivative Carboxylic acid Hydrocarbon derivative Hydroxamic acid Hydroxy acid N-acyl-alpha-amino acid Organic 1,3-dipolar compound Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Propargyl-type 1,3-dipolar organic compound Tertiary alcohol Tricarboxylic acid or derivatives L-lysine derivative Solid logp -0.98 ALOGPS logs -2.48 ALOGPS solubility 1.86e+00 g/l ALOGPS logp -3 ChemAxon pka_strongest_acidic 3.02 ChemAxon pka_strongest_basic -4.2 ChemAxon iupac (2S)-2-[3-carboxy-3-({[(1S)-1-carboxy-5-(N-hydroxyacetamido)pentyl]carbamoyl}methyl)-3-hydroxypropanamido]-6-(N-hydroxyacetamido)hexanoic acid ChemAxon average_mass 564.5402 ChemAxon mono_mass 564.227887258 ChemAxon smiles CC(=O)N(O)CCCC[C@H](NC(=O)CC(O)(CC(=O)N[C@@H](CCCCN(O)C(C)=O)C(O)=O)C(O)=O)C(O)=O ChemAxon formula C22H36N4O13 ChemAxon inchi InChI=1S/C22H36N4O13/c1-13(27)25(38)9-5-3-7-15(19(31)32)23-17(29)11-22(37,21(35)36)12-18(30)24-16(20(33)34)8-4-6-10-26(39)14(2)28/h15-16,37-39H,3-12H2,1-2H3,(H,23,29)(H,24,30)(H,31,32)(H,33,34)(H,35,36)/t15-,16-/m0/s1 ChemAxon inchikey KDHHWXGBNUCREU-HOTGVXAUSA-N ChemAxon polar_surface_area 271.41 ChemAxon refractivity 127.26 ChemAxon polarizability 54.02 ChemAxon rotatable_bond_count 19 ChemAxon acceptor_count 13 ChemAxon donor_count 8 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 26222 Specdb::MsMs 26223 Specdb::MsMs 26224 Specdb::MsMs 32780 Specdb::MsMs 32781 Specdb::MsMs 32782 Specdb::MsMs 2384534 Specdb::MsMs 2384535 Specdb::MsMs 2384536 Specdb::MsMs 2577180 Specdb::MsMs 2577181 Specdb::MsMs 2577182 Specdb::NmrOneD 41382 Specdb::NmrOneD 41383 Specdb::NmrOneD 41384 Specdb::NmrOneD 41385 Specdb::NmrOneD 41386 Specdb::NmrOneD 41387 Specdb::NmrOneD 41388 Specdb::NmrOneD 41389 Specdb::NmrOneD 41390 Specdb::NmrOneD 41391 Specdb::NmrOneD 41392 Specdb::NmrOneD 41393 Specdb::NmrOneD 41394 Specdb::NmrOneD 41395 Specdb::NmrOneD 41396 Specdb::NmrOneD 41397 Specdb::NmrOneD 41398 Specdb::NmrOneD 41399 Specdb::NmrOneD 41400 Specdb::NmrOneD 41401 Specdb::CMs 25942 Specdb::CMs 38696 Specdb::CMs 282092 Specdb::CMs 358498 Specdb::CMs 358499 Specdb::CMs 358500 Specdb::CMs 358501 Specdb::CMs 358502 Specdb::CMs 358503 Specdb::CMs 358504 Specdb::CMs 358505 Specdb::CMs 358506 Specdb::CMs 358507 Specdb::CMs 358508 Specdb::CMs 358509 Specdb::CMs 358510 Specdb::CMs 358511 Specdb::CMs 358512 Specdb::CMs 358513 Specdb::CMs 358514 Specdb::CMs 358515 Specdb::CMs 358516 Specdb::CMs 358517 Specdb::CMs 358518 Specdb::CMs 358519 HMDB04051 18157 #<Reference:0x000055ac40746098> #<Reference:0x000055ac40745ee0> #<Reference:0x000055ac40745d28> #<Reference:0x000055ac40745b70> #<Reference:0x000055ac407459b8> #<Reference:0x000055ac40745800> #<Reference:0x000055ac40745648> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823