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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-08-16 03:21:29 UTC
HMDB IDHMDB0000525
Secondary Accession Numbers
  • HMDB00525
Metabolite Identification
Common Name5-Hydroxyhexanoic acid
Description5-Hydroxyhexanoic acid is a normal dicarboxylic acid degradation product of fatty acids; however, it has been found in patients with non-ketotic dicarboxylic aciduria and one patient on a diet containing excessive amounts of medium-chain triglycerides. Increased amounts of dicarboxylic acids are excreted in human urine under conditions of medium-chain triglyceride (MCT) feeding, abnormal fatty acid oxidation (FAO) and fasting. Criteria to distinguish dicarboxylic aciduria originating from MCT feeding and other conditions are needed in urinary organic acid profiling for detecting inborn errors of metabolism. Medium-chain triglycerides (MCTs) are absorbed and metabolized differently from long-chain triglycerides (LCTs). MCTs may be useful as a dietary substitute in a variety of clinical disorders. Urinary excretion of 5-hydroxyhexanoic acid, the (omega-1) hydroxylation product, was increased during MCT feeding as compared with LCT feeding in patients with non-insulin-dependent diabetes mellitus. (PMID: 6897376 , 2239769 , 8596483 ).
Structure
Thumb
Synonyms
ValueSource
5-Hydroxy caproic acidChEBI
5-Hydroxy-hexanoic acidChEBI
5-Hydroxycaproic acidChEBI
5-OH-Caproic acidChEBI
5-Hydroxy caproateGenerator
5-HydroxyhexanoateGenerator
5-Hydroxy-hexanoateGenerator
5-HydroxycaproateGenerator
5-OH-CaproateGenerator
Chemical FormulaC6H12O3
Average Molecular Weight132.1577
Monoisotopic Molecular Weight132.07864425
IUPAC Name5-hydroxyhexanoic acid
Traditional Name5-hydroxyhexanoic acid
CAS Registry Number44843-89-2
SMILES
CC(O)CCCC(O)=O
InChI Identifier
InChI=1S/C6H12O3/c1-5(7)3-2-4-6(8)9/h5,7H,2-4H2,1H3,(H,8,9)
InChI KeyYDCRNMJQROAWFT-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Hydroxy fatty acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • 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
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 Solubility128.0 mg/mLALOGPS
logP0.32ALOGPS
logP0.35ChemAxon
logS-0.02ALOGPS
pKa (Strongest Acidic)4.71ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity32.82 m3·mol-1ChemAxon
Polarizability14.06 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Not SpecifiedNot Specified
    Normal
    details
    UrineDetected and Quantified1.1-2.9 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
    UrineDetected and Quantified0.7 (0.1-1.2) umol/mmol creatinineAdolescent (13-18 years old)Both
    Normal
    details
    UrineDetected and Quantified2.7 (0.8-5.7) umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified0.86-1.8 umol/mmol creatinineAdult (>18 years old)MaleNormal details
    UrineDetected and Quantified2.0 (0.1-11.2) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
    UrineDetected and Quantified4.0 (0.1-6.5) umol/mmol creatinineInfant (0-1 year old)BothNormal details
    UrineDetected and Quantified1.0 (0.1-1.6) umol/mmol creatinineChildren (1-13 years old)Both
    Normal
    details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
    UrineDetected and Quantified3.5 (0.0-7.0) umol/mmol creatinineAdult (>18 years old)BothMedium Chain Acyl-CoA Dehydrogenase Deficiency details
    UrineDetected and Quantified357.5 (15.00-700.00) umol/mmol creatinineChildren (1-13 years old)BothMedium chain acyl-CoA dehydrogenase deficiency (MCAD) details
    Associated Disorders and Diseases
    Disease References
    Medium Chain Acyl-CoA Dehydrogenase Deficiency
    1. MetaGene [Link]
    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 IDFDB022093
    KNApSAcK IDNot Available
    Chemspider ID149280
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    NuGOwiki LinkHMDB0000525
    METLIN ID5510
    PubChem Compound170748
    PDB IDNot Available
    ChEBI IDNot Available
    References
    Synthesis ReferenceValentin, H. E.; Schoenebaum, A.; Steinbuechel, A. Identification of 5-hydroxyhexanoic acid, 4-hydroxyheptanoic acid and 4-hydroxyoctanoic acid as new constituents of bacterial polyhydroxyalkanoic acids. Applied Microbiology and Biotechnology (1996), 46(3), 261-267.
    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. Kamerling JP, Duran M, Bruinvis L, Ketting D, Wadman SK, Vliegenthart JF: The absolute configuration of urinary 5-hydroxyhexanoic acid - a product of fatty acid (omega-1)-oxidation - in patients with non-ketotic dicarboxylic aciduria. Clin Chim Acta. 1982 Nov 10;125(3):247-54. [PubMed:6897376 ]
    4. Niwa T, Meada K, Ohki T, Saito A, Tsuchida I: Gas chromatographic-mass spectrometric profile of organic acids in urine and serum of diabetic ketotic patients. J Chromatogr. 1981 Sep 11;225(1):1-8. [PubMed:6795215 ]
    5. Loftus NJ, Laird WJ, Steel GT, Wilks MF, Woollen BH: Metabolism and pharmacokinetics of deuterium-labelled di-2-(ethylhexyl) adipate (DEHA) in humans. Food Chem Toxicol. 1993 Sep;31(9):609-14. [PubMed:8406236 ]
    6. Brass EP, Tserng KY, Eckel RH: Urinary organic acid excretion during feeding of medium-chain or long-chain triglyceride diets in patients with non-insulin-dependent diabetes mellitus. Am J Clin Nutr. 1990 Nov;52(5):923-6. [PubMed:2239769 ]
    7. Tserng KY, Griffin RL, Kerr DS: Distinction of dicarboxylic aciduria due to medium-chain triglyceride feeding from that due to abnormal fatty acid oxidation and fasting in children. Metabolism. 1996 Feb;45(2):162-7. [PubMed:8596483 ]