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Aerobactin (M2MDB001594)

Record Information
Version2.0
Creation Date2012-07-30 14:54:48 -0600
Update Date2015-06-03 17:20:50 -0600
Secondary Accession Numbers
  • ECMDB21185
Identification
Name:Aerobactin
DescriptionAerobactin is a iron chelating agent (siderophore) found in bacteria such as E. coli, allowing bacteria to transport and sequester iron. It is a virulence factor enabling E. coli to sequester iron in iron-poor environments such as host urinary tracts. (Wikipedia, ChEBI) Aerobactin can be made in E. coli through the degradation of lysine by the enzyme aerobactin synthase (EC 6.3.2.27). (Wikipedia, KEGG)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (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
  • Aerobactin
  • Ferric-aerobactin
  • N2,N2'-(3-carboxy-3-hydroxypentanedioyl)bis(N6-acetyl-N6-hydroxy-L-lysine)
Chemical Formula:C22H36N4O13
Weight:Average: 564.5402
Monoisotopic: 564.227887258
InChI Key:KDHHWXGBNUCREU-HOTGVXAUSA-N
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
CAS number:26198-65-2
IUPAC Name:(2S)-2-[3-carboxy-3-({[(1S)-1-carboxy-5-(N-hydroxyacetamido)pentyl]carbamoyl}methyl)-3-hydroxypropanamido]-6-(N-hydroxyacetamido)hexanoic acid
Traditional IUPAC Name:aerobactin
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
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
Physical Properties
State:Solid
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility1.86 g/LALOGPS
logP-0.98ALOGPS
logP-3ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)3.02ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area271.41 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity127.26 m³·mol⁻¹ChemAxon
Polarizability54.02 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Adenosine triphosphate + Water + Aerobactin > ADP + Aerobactin + Hydrogen ion + Phosphate
Adenosine triphosphate + Water + Aerobactin > ADP + Aerobactin + Hydrogen ion + Phosphate
Aerobactin + Fe3+ > Aerobactin
Aerobactin + Fe3+ > Aerobactin
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kf-9114360000-aae8c90dd540d7190ae4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-6004191000-a3d9063b76c1b9fcce3cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("Aerobactin,1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_6) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_7) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_8) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_9) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_10) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0111190000-6cceaaf6740bbfb89d96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052b-0791880000-fb56d3b8852220ec731aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2962330000-5df621761fc9c7904251View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-2024090000-7b805b2f239cf5b4ee97View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0v4j-2192280000-21815bd606980decb1a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ufr-2291010000-4d44fb96363a2d143039View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-0000290000-4709b636547109837686View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0321390000-5cfd6c97627637f03efeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053u-2910300000-c2c77f243e63232cf5f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fka-2000190000-14f7c8f7e438026bb6c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1011290000-aee3ea2f25dfea9dc2d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f89-2291100000-221052676a4a2ac8f391View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • Yamamoto S, Shinoda S: [Iron uptake mechanisms of pathogenic bacteria]. Nihon Saikingaku Zasshi. 1996 Feb;51(2):523-47. Pubmed: 8752377
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID18157
HMDB IDHMDB04051
Pubchem Compound ID123762
Kegg IDC05554
ChemSpider ID110318
WikipediaAerobactin
BioCyc IDCPD0-2234
EcoCyc IDCPD0-2234

Enzymes

Protein Details
1. Iron(3+)-hydroxamate import ATP-binding protein fhuC
General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex fhuCDB involved in iron(3+)-hydroxamate import. Responsible for energy coupling to the transport system
Gene Name:
fhuC
Uniprot ID:
P07821
Molecular weight:
28886
Reactions
ATP + H(2)O + iron chelate(Out) = ADP + phosphate + iron chelate(In).
Protein Details
2. Iron(3+)-hydroxamate import system permease protein fhuB
General function:
Involved in transporter activity
Specific function:
Part of the ABC transporter complex fhuCDB involved in iron(3+)-hydroxamate import. Responsible for the translocation of the substrate across the membrane
Gene Name:
fhuB
Uniprot ID:
P06972
Molecular weight:
70422
Protein Details
3. Iron(3+)-hydroxamate-binding protein fhuD
General function:
Involved in binding
Specific function:
Part of the ABC transporter complex fhuCDB involved in iron(3+)-hydroxamate import. Binds the iron(3+)-hydroxamate complex and transfers it to the membrane-bound permease. Required for the transport of all iron(3+)-hydroxamate siderophores such as ferrichrome, gallichrome, desferrioxamine, coprogen, aerobactin, shizokinen, rhodotorulic acid and the antibiotic albomycin
Gene Name:
fhuD
Uniprot ID:
P07822
Molecular weight:
32998

Transporters

Protein Details
1. Iron(3+)-hydroxamate import ATP-binding protein fhuC
General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex fhuCDB involved in iron(3+)-hydroxamate import. Responsible for energy coupling to the transport system
Gene Name:
fhuC
Uniprot ID:
P07821
Molecular weight:
28886
Reactions
ATP + H(2)O + iron chelate(Out) = ADP + phosphate + iron chelate(In).
Protein Details
2. Iron(3+)-hydroxamate import system permease protein fhuB
General function:
Involved in transporter activity
Specific function:
Part of the ABC transporter complex fhuCDB involved in iron(3+)-hydroxamate import. Responsible for the translocation of the substrate across the membrane
Gene Name:
fhuB
Uniprot ID:
P06972
Molecular weight:
70422
Protein Details
3. Iron(3+)-hydroxamate-binding protein fhuD
General function:
Involved in binding
Specific function:
Part of the ABC transporter complex fhuCDB involved in iron(3+)-hydroxamate import. Binds the iron(3+)-hydroxamate complex and transfers it to the membrane-bound permease. Required for the transport of all iron(3+)-hydroxamate siderophores such as ferrichrome, gallichrome, desferrioxamine, coprogen, aerobactin, shizokinen, rhodotorulic acid and the antibiotic albomycin
Gene Name:
fhuD
Uniprot ID:
P07822
Molecular weight:
32998