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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-07 01:16:09 UTC
HMDB IDHMDB0000350
Secondary Accession Numbers
  • HMDB00350
  • HMDB02534
Metabolite Identification
Common Name3-Hydroxysebacic acid
Description3-Hydroxysebacic acid is a normal urinary 3-hydroxydicarboxylic acid metabolite and can be elevated in patients with peroxisomal disorders such as Zellweger syndrome. Marked elevation of urinary 3- Hydroxysebacic acid has also been described in a malnourished infant with glycogen storage disease, mimicking long-chain L-3-hydroxyacyl-CoA dehydrogenase deficiency (OMIM 300438 ), a defect in the beta-oxidation of fatty acids characterized by massive excretion of 3-hydroxydicarboxylic acids in the urine and accumulation of 3-hydroxy fatty acids in serum (PMID 12860034 , 14708889 , 8295400 ). 3-Hydroxysebacic acid is also found to be associated with medium-chain Acyl-CoA dehydrogenase deficiency, which is an inborn error of metabolism.
Structure
Thumb
Synonyms
ValueSource
3-Hydroxy-decanedioic acidChEBI
3-Hydroxy-sebacic acidChEBI
3-Hydroxy-decanedioateGenerator
3-HydroxysebacateGenerator
3-Hydroxy-sebacateGenerator
3-HydroxydecanedioateHMDB
3-Hydroxydecanedioic acidHMDB
Chemical FormulaC10H18O5
Average Molecular Weight218.2469
Monoisotopic Molecular Weight218.115423686
IUPAC Name3-hydroxydecanedioic acid
Traditional Name3-hydroxysebacic acid
CAS Registry Number73141-46-5
SMILES
OC(CCCCCCC(O)=O)CC(O)=O
InChI Identifier
InChI=1S/C10H18O5/c11-8(7-10(14)15)5-3-1-2-4-6-9(12)13/h8,11H,1-7H2,(H,12,13)(H,14,15)
InChI KeyOQYZCCKCJQWHIE-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassHydroxy acids and derivatives
Direct ParentMedium-chain hydroxy acids and derivatives
Alternative Parents
Substituents
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Beta-hydroxy acid
  • Hydroxy fatty acid
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Fatty acid
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Biofluid and excreta:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.38 g/LALOGPS
logP0.63ALOGPS
logP1.04ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)4.45ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity52.66 m³·mol⁻¹ChemAxon
Polarizability23.36 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, Positivesplash10-052f-9710000000-84f7737e071eed92f742View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-01e9-7459200000-a1f5613b57112c5d2584View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0159-0940000000-f4f483b1636137e43945View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014m-9400000000-d0cc01c70aafa53f34abView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00mo-9000000000-316ddd132092b08d73b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0690000000-adfdd11672c699fbe0b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pc0-1920000000-04e756075b530fdc1c35View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9500000000-28ce1a7d162f222ab3daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014j-0960000000-dc3ec12cde243eb68c4aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aba-0910000000-50719a409f05424fe56dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9800000000-8f1d999d507005531c7dView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected and Quantified5.8 (5.8-5.8) umol/mmol creatinineInfant (0-1 year old)BothNormal details
    UrineDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified7.7 (1.5-24.1) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
    UrineDetected and Quantified1.9 (0.1-7.0) umol/mmol creatinineChildren (1-13 years old)Both
    Normal
    details
    UrineDetected and Quantified1.4 (1.0-1.7) umol/mmol creatinineChildren (1-13 years old)Both
    Normal
    details
    UrineDetected and Quantified2.7 (1.3-4.0) umol/mmol creatinineAdolescent (13-18 years old)Both
    Normal
    details
    UrineDetected and Quantified2.9(1.7-3.8) umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    UrineDetected and Quantified10.628-308.767 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedMedium Chain Acyl-CoA Dehydrogenase Deficiency details
    Associated Disorders and Diseases
    Disease References
    Medium Chain Acyl-CoA Dehydrogenase Deficiency
    1. Duran M, De Klerk JB, Wadman SK, Bruinvis L, Ketting D: The differential diagnosis of dicarboxylic aciduria. J Inherit Metab Dis. 1984;7 Suppl 1:48-51. [PubMed:6434845 ]
    Associated OMIM IDs
    • 201450 (Medium Chain Acyl-CoA Dehydrogenase Deficiency)
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB021973
    KNApSAcK IDNot Available
    Chemspider ID2285525
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN ID5339
    PubChem Compound3017884
    PDB IDNot Available
    ChEBI ID89182
    References
    Synthesis ReferenceHill, Frank Friedrich. Manufacture of 3-hydroxydicarboxylic acids. Ger. Offen. (1986), 14 pp.
    Material Safety Data Sheet (MSDS)Not Available
    General References
    1. Boulat O, Gradwohl M, Matos V, Guignard JP, Bachmann C: Organic acids in the second morning urine in a healthy Swiss paediatric population. Clin Chem Lab Med. 2003 Dec;41(12):1642-58. [PubMed:14708889 ]
    2. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
    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. Bergoffen J, Kaplan P, Hale DE, Bennett MJ, Berry GT: Marked elevation of urinary 3-hydroxydecanedioic acid in a malnourished infant with glycogen storage disease, mimicking long-chain L-3-hydroxyacyl-CoA dehydrogenase deficiency. J Inherit Metab Dis. 1993;16(5):851-6. [PubMed:8295400 ]