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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 09:58:34 UTC
Update Date2021-09-14 14:57:37 UTC
HMDB IDHMDB0004051
Secondary Accession Numbers
  • HMDB04051
Metabolite Identification
Common NameAerobactin
DescriptionAerobactin 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 ).
Structure
Data?1601070029
Synonyms
ValueSource
(8S,16S)-3,12,21-Trihydroxy-2,10,14,22-tetraoxo-3,9,15,21-tetraazatricosane-8,12,16-tricarboxylic acidChEBI
(8S,16S)-3,12,21-Trihydroxy-2,10,14,22-tetraoxo-3,9,15,21-tetraazatricosane-8,12,16-tricarboxylateGenerator
AerobactinHMDB
Chemical FormulaC22H36N4O13
Average Molecular Weight564.5402
Monoisotopic Molecular Weight564.227887258
IUPAC Name(2S)-2-[3-carboxy-3-({[(1S)-1-carboxy-5-(N-hydroxyacetamido)pentyl]carbamoyl}methyl)-3-hydroxypropanamido]-6-(N-hydroxyacetamido)hexanoic acid
Traditional Nameaerobactin
CAS Registry Number26198-65-2
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
InChI Identifier
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
InChI KeyKDHHWXGBNUCREU-HOTGVXAUSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-alpha-amino acid
  • Tricarboxylic acid or derivatives
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Tertiary alcohol
  • Acetohydroxamic acid
  • Acetamide
  • Hydroxamic acid
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023292
KNApSAcK IDNot Available
Chemspider ID110318
KEGG Compound IDC05554
BioCyc IDAEROBACTIN
BiGG IDNot Available
Wikipedia LinkAerobactin
METLIN ID7008
PubChem Compound123762
PDB IDNot Available
ChEBI ID18157
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sharma S, Harjai K, Mittal R: Enhanced siderophore production and mouse kidney pathogenicity in Escherichia coli grown in urine. J Med Microbiol. 1991 Dec;35(6):325-9. [PubMed:1836502 ]
  2. Williams PH, Carbonetti NH: Iron, siderophores, and the pursuit of virulence: independence of the aerobactin and enterochelin iron uptake systems in Escherichia coli. Infect Immun. 1986 Mar;51(3):942-7. [PubMed:2936686 ]
  3. Vazquez F, Mendoza MC, Viejo G, Mendez FJ: Survey of Escherichia coli septicemia over a six-year period. Eur J Clin Microbiol Infect Dis. 1992 Feb;11(2):110-7. [PubMed:1396724 ]
  4. Schlager TA, Whittam TS, Hendley JO, Wilson RA, Bhang J, Grady R, Stapleton A: Expression of virulence factors among Escherichia coli isolated from the periurethra and urine of children with neurogenic bladder on intermittent catheterization. Pediatr Infect Dis J. 2000 Jan;19(1):37-41. [PubMed:10643848 ]
  5. Opal SM, Cross AS, Gemski P, Lyhte LW: Aerobactin and alpha-hemolysin as virulence determinants in Escherichia coli isolated from human blood, urine, and stool. J Infect Dis. 1990 Apr;161(4):794-6. [PubMed:2181035 ]
  6. Keller R, Pedroso MZ, Ritchmann R, Silva RM: Occurrence of virulence-associated properties in Enterobacter cloacae. Infect Immun. 1998 Feb;66(2):645-9. [PubMed:9453621 ]
  7. Yamamoto S, Shinoda S: [Iron uptake mechanisms of pathogenic bacteria]. Nihon Saikingaku Zasshi. 1996 Feb;51(2):523-47. [PubMed:8752377 ]