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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-10-23 18:27:21 UTC
HMDB IDHMDB0000888
Secondary Accession Numbers
  • HMDB00888
Metabolite Identification
Common NameUndecanedioic acid
DescriptionUndecanedioic acid has been found in parts of human aortas with advanced atherosclerotic lesions associated with intercellular matrix macromolecules and specifically with elastin, and may be the result of an increased hydrolysis of esters and (or) a decreased esterification. (PMID: 131675 ). Undecanedioic acid has been found (among other unusual dicarboxylic acids) in the urine from patients under hopantenate therapy during episodes of Reye's-like syndrome. (PMID: 2331533 ).
Structure
Thumb
Synonyms
ValueSource
1,11-Undecanedioic acidChEBI
1,9-Nonanedicarboxylic acidChEBI
Hendecanedioic acidChEBI
Undecanedionic acidChEBI
1,11-UndecanedioateGenerator
UndecanedioateGenerator
1,9-NonanedicarboxylateGenerator
HendecanedioateGenerator
UndecanedionateGenerator
Chemical FormulaC11H20O4
Average Molecular Weight216.2741
Monoisotopic Molecular Weight216.136159128
IUPAC Nameundecanedioic acid
Traditional Nameundecanedioic acid
CAS Registry Number1852-04-6
SMILES
OC(=O)CCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C11H20O4/c12-10(13)8-6-4-2-1-3-5-7-9-11(14)15/h1-9H2,(H,12,13)(H,14,15)
InChI KeyLWBHHRRTOZQPDM-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Chemical reaction:

    Biochemical process:

    Biochemical pathway:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point108 - 110 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.1 mg/mLYALKOWSKY,SH & DANNENFELSER,RM (1992)
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.45 g/LALOGPS
logP2.41ALOGPS
logP2.71ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)4.65ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity55.74 m³·mol⁻¹ChemAxon
Polarizability24.74 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9800000000-db85d280b172836331b1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dr-9770000000-a2d73ceb282e8a18157eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-014i-0290000000-7ae807700c28584d2e28View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0f6t-2900000000-3f0c97ba1c386d655464View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0fr2-9230000000-6e48936ad64fc2b1149bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0930000000-92c504d7493b68533709View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00r2-1910000000-84e296521dd0030ce164View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01td-9500000000-a014eaf3810192591c95View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0390000000-8d3496492a9c0c8977b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-1970000000-690951ba65eb6d7209eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9400000000-c06fbfff105dafce2635View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Feces
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Bothnon-inflamed (NI) control anaemic details
FecesDetected but not Quantified Adult (>18 years old)BothUlcerative colitis details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022300
KNApSAcK IDNot Available
Chemspider ID15037
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5846
PubChem Compound15816
PDB IDNot Available
ChEBI ID73713
References
Synthesis ReferenceDurham, Lois J.; McLeod, Donald J.; Cason, James. Hendecanedioic acid. Organic Syntheses (1958), 38 34-7.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Claire M, Jacotot B, Robert L: Characterization of lipids associated with macromolecules of the intercellular matrix of human aorta. Connect Tissue Res. 1976;4(2):61-71. [PubMed:131675 ]
  2. Matsumoto M, Kuhara T, Inoue Y, Shinka T, Matsumoto I, Kajita M: Mass spectrometric identification of 2-hydroxydodecanedioic acid and its homologues in urine from patients with hopantenate therapy during clinical episode. Biomed Environ Mass Spectrom. 1990 Mar;19(3):171-5. [PubMed:2331533 ]