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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:44:09 UTC
HMDB IDHMDB0000424
Secondary Accession Numbers
  • HMDB00424
Metabolite Identification
Common Name2-Hydroxydecanedioic acid
Description2-Hydroxydecanedioic acid appears in the urine of children affected with peroxisomal disorders such as urines of children with neonatal adrenoleukodystrophy and Zellweger syndrome and is a useful marker for these diseases. (PMID 2943344 ).
Structure
Data?1563860649
Synonyms
ValueSource
2-HydroxydecanedioateGenerator
2-Hydroxy-decandioateHMDB
2-Hydroxy-decandioic acidHMDB
2-HydroxysebacateHMDB
2-Hydroxysebacic acidHMDB
a-HydroxysebasateHMDB
a-Hydroxysebasic acidHMDB
alpha-HydroxysebasateHMDB
alpha-Hydroxysebasic acidHMDB
2-Hydroxy-decanedioateHMDB
Chemical FormulaC10H18O5
Average Molecular Weight218.2469
Monoisotopic Molecular Weight218.115423686
IUPAC Name2-hydroxydecanedioic acid
Traditional Name2-hydroxysebacic acid
CAS Registry Number103963-71-9
SMILES
OC(CCCCCCCC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C10H18O5/c11-8(10(14)15)6-4-2-1-3-5-7-9(12)13/h8,11H,1-7H2,(H,12,13)(H,14,15)
InChI KeyLPIOYESQKJFWPQ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassMedium-chain hydroxy acids and derivatives
Direct ParentMedium-chain hydroxy acids and derivatives
Alternative Parents
Substituents
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Hydroxy fatty acid
  • Alpha-hydroxy acid
  • Dicarboxylic acid or derivatives
  • Monosaccharide
  • Fatty acid
  • Fatty acyl
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point118 - 121 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.42 g/LALOGPS
logP0.87ALOGPS
logP1.4ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)4.16ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity52.64 m³·mol⁻¹ChemAxon
Polarizability23.38 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9710000000-5fe9b8e6d318d5edf2e9JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-016r-7649300000-ef73b5c677459a4e4032JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uyi-0890000000-b8439c284ac682367d51JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kh9-2920000000-3620dca641969f0dd8a2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a7m-9300000000-e8753077d260110272f2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1790000000-de7ab953c1ff73d7dc41JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-1910000000-80317878d8a89b878c50JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-9600000000-7364e1a98ebf40595428JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected and Quantified0.39-0.67 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
    UrineDetected and Quantified0.37-0.55 umol/mmol creatinineAdult (>18 years old)MaleNormal details
    Abnormal Concentrations
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    UrineDetected but not Quantified Not AvailableNot AvailablePeroxisomal diseases details
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB022037
    KNApSAcK IDNot Available
    Chemspider ID113866
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN ID5413
    PubChem Compound128458
    PDB IDNot Available
    ChEBI ID89312
    References
    Synthesis ReferenceChiruta, Chandramouli; Jachak, Santosh; Clive, Derrick L. J. A convenient general method for the synthesis of hydroxy diacids. Tetrahedron Letters (2007), 48(18), 3141-3143.
    Material Safety Data Sheet (MSDS)Not Available
    General References
    1. Rocchiccioli F, Cartier PH, Aubourg P, Bougneres PF: Mass spectrometric identification of 2-hydroxy-sebacic acid in the urines of patients with neonatal adrenoleukodystrophy and Zellweger syndrome. Biomed Environ Mass Spectrom. 1986 Jun;13(6):315-8. [PubMed:2943344 ]
    2. Kajita M, Iwase K, Matsumoto M, Kuhara T, Sinka T, Matsumoto I: [Clinical and biochemical studies in a case of acute encephalopathy associated with calcium hopanthenate administration]. No To Hattatsu. 1990 May;22(3):267-73. [PubMed:2194543 ]
    3. Muth A, Jung J, Bilke S, Scharrer A, Mosandl A, Sewell AC, Bohles H: Simultaneous enantioselective analysis of chiral urinary metabolites in patients with Zellweger syndrome. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 25;792(2):269-77. [PubMed:12860034 ]
    4. Muth A, Mosandl A, Wanders RJ, Nowaczyk MJ, Baric I, Bohles H, Sewell AC: Stereoselective analysis of 2-hydroxysebacic acid in urine of patients with Zellweger syndrome and of premature infants fed with medium-chain triglycerides. J Inherit Metab Dis. 2003;26(6):583-92. [PubMed:14605504 ]