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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-27 07:39:36 UTC
HMDB IDHMDB0000394
Secondary Accession Numbers
  • HMDB00394
Metabolite Identification
Common Name3-Hydroxytetradecanedioic acid
Description3-Hydroxytetradecanedioic acid is an unusual 3-hydroxydicarboxylic acid human metabolite found occasionally in urine. (PMID 2925825 ) High levels of 3-Hydroxytetradecanedioic acid (and other 3-hydroxydicarboxylic acids) were detected in the urine of a patient with 3-hydroxydicarboxylic aciduria (PMID 1507493 ), due to acute intoxication associated with hopantenate occurs owing to pantothenic acid deficiency or the inhibition of CoA-requiring reactions during stress, i.e., infection, prolonged fasting, or malnutrition (PMID 2026687 ), and in a patient with thanatophoric dysplasia due to enhanced but incomplete oxidation of fatty acid, a consequence of a heterozygous point mutation, S249C in the fibroblast growth factor receptor 3 gene. (PMID 11879084 ).
Structure
Thumb
Synonyms
ValueSource
3-HydroxytetradecanedioateHMDB
Chemical FormulaC14H26O5
Average Molecular Weight274.3532
Monoisotopic Molecular Weight274.178023942
IUPAC Name3-hydroxytetradecanedioic acid
Traditional Name3-hydroxytetradecanedioic acid
CAS Registry Number73179-89-2
SMILES
OC(CCCCCCCCCCC(O)=O)CC(O)=O
InChI Identifier
InChI=1S/C14H26O5/c15-12(11-14(18)19)9-7-5-3-1-2-4-6-8-10-13(16)17/h12,15H,1-11H2,(H,16,17)(H,18,19)
InChI KeyCEDZIURHISELSQ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Beta-hydroxy acid
  • Hydroxy 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 Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Chemical reaction:

    Biochemical process:

    Biochemical pathway:

Role

Industrial application:

Biological role:

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 Solubility0.29 g/LALOGPS
logP2.03ALOGPS
logP2.82ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)4.49ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity71.06 m³·mol⁻¹ChemAxon
Polarizability31.84 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, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a70-0090000000-d1bf3dd36ae3dbdb5185View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08i9-0490000000-31021daf233368701f5cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-040d-4910000000-e13f32a9e5177e2e956fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-a11f84f48743557a02abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0729-1190000000-d4f10462ec57b05c5171View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9330000000-d55db446d3aebb26fa93View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    UrineDetected but not Quantified Not AvailableNot AvailableKetosis details
    UrineDetected but not Quantified Not AvailableNot AvailableCHAD/TFP deficiency details
    UrineDetected but not Quantified Not AvailableNot AvailableHepatocellular disease 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 IDFDB022012
    KNApSAcK IDNot Available
    Chemspider ID13628077
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN ID5383
    PubChem Compound20848956
    PDB IDNot Available
    ChEBI 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. Lefevere MF, Verhaeghe BJ, Declerck DH, Van Bocxlaer JF, De Leenheer AP, De Sagher RM: Metabolic profiling of urinary organic acids by single and multicolumn capillary gas chromatography. J Chromatogr Sci. 1989 Jan;27(1):23-9. [PubMed:2925825 ]
    2. Matsumoto M, Kuhara T, Inoue Y, Shinka T, Matsumoto I: Abnormal fatty acid metabolism in patients in hopantenate therapy during clinical episodes. J Chromatogr. 1991 Jan 2;562(1-2):139-45. [PubMed:2026687 ]
    3. Okajima K, Asai K, Niwa T, Ohki S, Sobajima H, Tyson J, Malcolm S, Wada Y: Clinical and biochemical findings of a patient with thanatophoric dysplasia type I: additional finding of dicarboxylic aciduria. Cleft Palate Craniofac J. 2002 Mar;39(2):246-8. [PubMed:11879084 ]
    4. Shimizu A, Nakanishi T: [Quantitative analysis of urinary organic acid]. Rinsho Byori. 1992 Jul;40(7):743-50. [PubMed:1507493 ]