Record Information
Version1.0
Creation date2011-09-21 00:27:37 UTC
Update date2015-07-21 06:57:37 UTC
Primary IDFDB023292
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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) [HMDB]
CAS Number26198-65-2
Structure
Thumb
Synonyms
SynonymSource
(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
Ferric-aerobactinhmdb
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC22H36N4O13
IUPAC name(2S)-2-[3-carboxy-3-({[(1S)-1-carboxy-5-(N-hydroxyacetamido)pentyl]carbamoyl}methyl)-3-hydroxypropanamido]-6-(N-hydroxyacetamido)hexanoic acid
InChI IdentifierInChI=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
Isomeric SMILESCC(=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
Average Molecular Weight564.5402
Monoisotopic Molecular Weight564.227887258
Classification
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
Disposition

Biological location:

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSAerobactin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00kf-9114360000-aae8c90dd540d7190ae4Spectrum
Predicted GC-MSAerobactin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-6004191000-a3d9063b76c1b9fcce3cSpectrum
Predicted GC-MSAerobactin, "Aerobactin,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAerobactin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAerobactin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAerobactin, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAerobactin, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAerobactin, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAerobactin, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAerobactin, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAerobactin, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAerobactin, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAerobactin, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAerobactin, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAerobactin, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAerobactin, TMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAerobactin, TMS_3_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAerobactin, TMS_3_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAerobactin, TMS_3_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAerobactin, TMS_3_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAerobactin, TMS_3_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAerobactin, TMS_3_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAerobactin, TMS_3_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAerobactin, TMS_3_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAerobactin, TMS_3_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0111190000-6cceaaf6740bbfb89d96Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052b-0791880000-fb56d3b8852220ec731aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2962330000-5df621761fc9c7904251Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-2024090000-7b805b2f239cf5b4ee97Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0v4j-2192280000-21815bd606980decb1a5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ufr-2291010000-4d44fb96363a2d143039Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-0000290000-4709b636547109837686Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0321390000-5cfd6c97627637f03efeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053u-2910300000-c2c77f243e63232cf5f2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fka-2000190000-14f7c8f7e438026bb6c8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1011290000-aee3ea2f25dfea9dc2d0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f89-2291100000-221052676a4a2ac8f391Spectrum
NMRNot Available
ChemSpider ID110318
ChEMBL IDNot Available
KEGG Compound IDC05554
Pubchem Compound ID123762
Pubchem Substance IDNot Available
ChEBI ID18157
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04051
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference