| Common Name |
5-Hydroxyhexanoic acid
| Description |
5-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 usefli 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-insliin-dependent diabetes mellitus. (PMID: 6897376 , 2239769 , 8596483 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
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 Formlia |
C6H12O3
| Average Molecliar Weight |
132.1577
| Monoisotopic Molecliar Weight |
132.07864425
| IUPAC Name |
5-hydroxyhexanoic acid
| Traditional Name |
5-hydroxyhexanoic acid
| CAS Registry Number |
44843-89-2
| 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 Key |
YDCRNMJQROAWFT-UHFFFAOYSA-N
| Chemical Taxonomy |
| Description |
This 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.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Lipids and lipid-like moleclies
| Sub Class |
Fatty Acyls
| Direct Parent |
Medium-chain fatty acids
| Alternative Parents |
Hydroxy fatty acids
Secondary alcohols
Monocarboxylic acids and derivatives
Carboxylic acids
Organic oxides
Hydrocarbon derivatives
Carbonyl compounds
| 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
| Molecliar Framework |
Aliphatic acyclic compounds
| External Descriptors |
Hydroxy fatty acids (LMFA01050014 )
| Ontology |
| Status |
Detected and Quantified
| Origin |
Endogenous
| Biofunction |
Not Available
| Application |
Not Available
| Cellliar locations |
Cytoplasm
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
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
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| Biological Properties |
| Cellliar Locations |
Cytoplasm
| Biofluid Locations |
Blood
Feces
Urine
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodExpected but not Quantified Not AvailableNot Available
Normal
details
FecesDetected but not Quantified Adlit (>18 years old)Both
Normal
24029555
details
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
20669995
details
UrineDetected and Quantified1.1-2.9 umol/mmol creatinineAdlit (>18 years old)FemaleNormal
27012787
details
UrineDetected and Quantified0.7 (0.1-1.2) umol/mmol creatinineAdolescent (13-18 years old)Both
Normal
8087979
details
UrineDetected and Quantified2.7 (0.8-5.7) umol/mmol creatinineAdlit (>18 years old)Both
Normal
24023812
details
UrineDetected and Quantified0.86-1.8 umol/mmol creatinineAdlit (>18 years old)MaleNormal
27012787
details
UrineDetected and Quantified2.0 (0.1-11.2) umol/mmol creatinineNewborn (0-30 days old)BothNormal
8087979
details
UrineDetected and Quantified4.0 (0.1-6.5) umol/mmol creatinineInfant (0-1 year old)BothNormal
8087979
details
UrineDetected and Quantified1.0 (0.1-1.6) umol/mmol creatinineChildren (1-13 years old)Both
Normal
8087979
details
|
| Abnormal Concentrations |
|
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
UrineDetected and Quantified3.5 (0.0-7.0) umol/mmol creatinineAdlit (>18 years old)BothMedium Chain Acyl-CoA Dehydrogenase Deficiency
MetaGene
details
UrineDetected and Quantified357.5 (15.00-700.00) umol/mmol creatinineChildren (1-13 years old)BothMedium chain acyl-CoA dehydrogenase deficiency (MCAD)
MetaGene
details
| Associated Disorders and Diseases |
| Disease References |
| Medium Chain Acyl-CoA Dehydrogenase Deficiency |
- MetaGene [Link]
| Associated OMIM IDs |
201450 (Medium Chain Acyl-CoA Dehydrogenase Deficiency)
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB022093
| KNApSAcK ID |
Not Available
| Chemspider ID |
149280
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00525
| Metagene Link |
HMDB00525
| METLIN ID |
5510
| PubChem Compound |
170748
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: SR12813
References |
| Synthesis Reference |
Valentin, 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 |
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
|
PMID: 25591864