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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-05-11 20:54:31 UTC
HMDB IDHMDB0000350
Secondary Accession Numbers
  • HMDB0002534
  • HMDB00350
  • HMDB02534
Metabolite Identification
Common Name3-Hydroxysebacic acid
Description3-Hydroxysebacic acid (CAS: 73141-46-5) is a normal urinary 3-hydroxydicarboxylic acid metabolite that 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
Data?1582752125
Synonyms
ValueSource
(R)-3-Hydroxydecanedioic acidHMDB
(R)-3-Hydroxysebacic acidHMDB
3-Hydroxydecanedioic acidHMDB
3-Hydroxysebacic acidHMDB
3-Hydroxy-decanedioic acidChEBI
3-Hydroxy-sebacic acidChEBI
3-Hydroxy-decanedioateGenerator
3-HydroxysebacateGenerator
3-Hydroxy-sebacateGenerator
3-HydroxydecanedioateHMDB
Chemical FormulaC10H18O5
Average Molecular Weight218.249
Monoisotopic Molecular Weight218.11542368
IUPAC Name(3R)-3-hydroxydecanedioic acid
Traditional Name(3R)-3-hydroxydecanedioic acid
CAS Registry Number446881-43-2
SMILES
O[C@H](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)/t8-/m1/s1
InChI KeyOQYZCCKCJQWHIE-MRVPVSSYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Beta-hydroxy acid
  • Fatty acyl
  • Fatty acid
  • Dicarboxylic acid or derivatives
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0159-0940000000-f4f483b1636137e43945Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014m-9400000000-d0cc01c70aafa53f34abSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00mo-9000000000-316ddd132092b08d73b4Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    BloodDetected and Quantified0.65(0.32-1.2) uMInfant (0-1 year old)Not SpecifiedNormal details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified5.8 umol/mmol creatinineInfant (0-1 year old)BothNormal details
    UrineDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified0-0.6 umol/mmol creatinineInfant (0-1 year old)Male
    Normal
    details
    UrineDetected and Quantified0.0-0.4 umol/mmol creatinineInfant (0-1 year old)Female
    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
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    BloodDetected and Quantified0.95-33.5 uMInfant (0-1 year old)Female3-Hydroxydicarboxylic aciduria details
    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
    Phenol Explorer Compound IDNot Available
    FooDB IDFDB021973
    KNApSAcK IDNot Available
    Chemspider IDNot Available
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN IDNot Available
    PubChem Compound124350389
    PDB IDNot Available
    ChEBI IDNot Available
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    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. 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 ]
    2. 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 ]
    3. 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 ]
    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 ]