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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-06-10 21:22:19 UTC
HMDB IDHMDB00525
Secondary Accession NumbersNone
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-hexanoateHMDB
5-Hydroxy-hexanoic acidHMDB
5-HydroxycaproateHMDB
5-Hydroxycaproic acidHMDB
5-HydroxyhexanoateHMDB
5-OH-CaproateHMDB
5-OH-Caproic acidHMDB
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 KeyInChIKey=YDCRNMJQROAWFT-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Hydroxy fatty acid
  • Medium-chain fatty acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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 QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot 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
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 LinkHMDB00525
Metagene LinkHMDB00525
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. [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. [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. [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. [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. [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. [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. [8596483 ]