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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-01-27 04:26:46 UTC
HMDB IDHMDB0000413
Secondary Accession Numbers
  • HMDB00413
Metabolite Identification
Common Name3-Hydroxydodecanedioic acid
Description3-Hydroxydecanedioic acid appears in the urine of children affected with peroxisomal disorders. Peroxisomal biogenesis disorders (PBDs) are characterized by generalized peroxisomal dysfunction due to defective assembly of the organelle and include the Zellweger, neonatal adrenoleukodystrophy and infantile Refsum phenotypes (PMID 10896310).
Structure
Thumb
Synonyms
ValueSource
3-HydroxydodecanedioateHMDB
Chemical FormulaC12H22O5
Average Molecular Weight246.3001
Monoisotopic Molecular Weight246.146723814
IUPAC Name3-hydroxydodecanedioic acid
Traditional Name3-hydroxydodecanedioic acid
CAS Registry Number34574-69-1
SMILES
OC(CCCCCCCCC(O)=O)CC(O)=O
InChI Identifier
InChI=1S/C12H22O5/c13-10(9-12(16)17)7-5-3-1-2-4-6-8-11(14)15/h10,13H,1-9H2,(H,14,15)(H,16,17)
InChI KeyFYVQCLGZFXHEGL-UHFFFAOYSA-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
  • 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:

  Subcellular:

  Cell and elements:

  Biofluid and excreta:

Source:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

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 Solubility0.83 g/LALOGPS
logP1.49ALOGPS
logP1.93ChemAxon
logS-2.5ALOGPS
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 Count11ChemAxon
Refractivity61.86 m³·mol⁻¹ChemAxon
Polarizability27.58 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, Positivesplash10-0006-9840000000-ba1d51f5769b6001dfc1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-009t-6339200000-6b8f2d46e5131baa2bf8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0190000000-56a5ca0692bd052ae94fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02e9-1960000000-e2b23bf3215485b28bbaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-029y-9800000000-cdbf0382e047c2655d99View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002b-0190000000-659140900506a85c6c83View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kea-0590000000-30d125dca29237080fb2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9610000000-9f27770ca089c740fe35View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0 umol/mmol creatinineChildren (1-13 years old)Not Specified
Normal
details
UrineDetected and Quantified0.918 +/- 1.836 umol/mmol creatinineChildren (1-13 years old)Not Specified
Normal
details
UrineDetected and Quantified3.672 +/- 3.213 umol/mmol creatinineChildren (1-13 years old)Not Specified
Normal
details
UrineDetected and Quantified9.181 +/- 3.672 umol/mmol creatinineChildren (1-13 years old)Not Specified
Normal
details
UrineDetected and Quantified20.657 +/- 15.148 umol/mmol creatinineChildren (1-13 years old)Not Specified
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)Femaleovarian cancer details
UrineDetected and Quantified37.182-550.840 umol/mmol creatinineInfant (0-1 year old)Not Specified3-Hydroxydicarboxylic aciduria details
Associated Disorders and Diseases
Disease References
3-Hydroxydicarboxylic aciduria
  1. Tserng KY, Jin SJ, Kerr DS, Hoppel CL: Urinary 3-hydroxydicarboxylic acids in pathophysiology of metabolic disorders with dicarboxylic aciduria. Metabolism. 1991 Jul;40(7):676-82. [PubMed:1870421 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022029
KNApSAcK IDNot Available
Chemspider ID13628081
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5402
PubChem Compound16663321
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceSchreurs, P. H. M.; Montijn, P. P.; Hoff, S. New synthesis of trans-2-dodecene-1,12-dioic acid (traumatic acid). Recueil des Travaux Chimiques des Pays-Bas (1971), 90(12), 1331-2.
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. Korman SH, Mandel H, Gutman A: Characteristic urine organic acid profile in peroxisomal biogenesis disorders. J Inherit Metab Dis. 2000 Jun;23(4):425-8. [PubMed:10896310 ]