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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-20 22:13:12 UTC
Update Date2017-10-23 19:03:53 UTC
HMDB IDHMDB0001624
Secondary Accession Numbers
  • HMDB01624
Metabolite Identification
Common Name2-Hydroxycaproic acid
Description2-Hydroxycaproic acid is a branched-chain alpha-keto acid that have been reported in normal human blood (PMID: 7130306 ) and in normal amniotic fluid. (PMID: 7076774 ). It has been found that 2-Hydroxycaproic acid is the most significant metabolite found in the CSF of patients infected with Nocardia. Nocardia sp. is an uncommon cause of meningitis, and Nocardia meningitis has a clinical picture similar to that of tuberculous meningitis (PMID: 3818936 ).
Structure
Thumb
Synonyms
ValueSource
2-HydroxycaproateHMDB
2-HydroxyhexanoateHMDB
2-Hydroxyhexanoic acidHMDB
DL-2-HydroxycaproateHMDB
DL-2-Hydroxycaproic acidHMDB
DL-2-HydroxyhexanoateHMDB
DL-2-Hydroxyhexanoic acidHMDB
DL-2-Hydroxyhexanoic acidhydroxyhexanoateHMDB
DL-2-Hydroxyhexanoic acidhydroxyhexanoic acidHMDB
DL-HydroxycaproateHMDB
DL-Hydroxycaproic acidHMDB
Hydroxy-N-caproateHMDB
Hydroxy-N-caproic acidHMDB
HydroxycaproateHMDB
Hydroxycaproic acidHMDB
HydroxyhexanoateHMDB
Hydroxyhexanoic acidHMDB
Chemical FormulaC6H12O3
Average Molecular Weight132.1577
Monoisotopic Molecular Weight132.07864425
IUPAC Name2-hydroxyhexanoic acid
Traditional Namehydroxyhexanoate
CAS Registry Number6064-63-7
SMILES
CCCCC(O)C(O)=O
InChI Identifier
InChI=1S/C6H12O3/c1-2-3-4-5(7)6(8)9/h5,7H,2-4H2,1H3,(H,8,9)
InChI KeyNYHNVHGFPZAZGA-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
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Monosaccharide
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Biofluid and excreta:

  Subcellular:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Chemical reaction:

    Biochemical process:

    Biochemical pathway:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point55 - 58 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility88.5 g/LALOGPS
logP0.86ALOGPS
logP0.94ChemAxon
logS-0.17ALOGPS
pKa (Strongest Acidic)4.26ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity32.57 m³·mol⁻¹ChemAxon
Polarizability14.04 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, Positivesplash10-002f-9000000000-8a7d8360cf90ac0786f6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-009i-9430000000-1998df84d5020aa101f4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0019-9600000000-10146667ecdae4cce5b2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-000b-9000000000-c862568de48398a07c5aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0002-9200000000-f1ecc474a71b65c8401bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-001i-0900000000-e7e9ac132b84240918a7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9400000000-acfd79e3f78eb9bbdde9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9000000000-174fc428947a51fb1c48View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-001r-9000000000-3c2f2415c8308cc882bfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-001i-9000000000-c1e754811538f745822eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0900000000-e7e9ac132b84240918a7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9400000000-acfd79e3f78eb9bbdde9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-174fc428947a51fb1c48View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001r-9000000000-3c2f2415c8308cc882bfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-9000000000-c1e754811538f745822eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-4900000000-6aef6b562dd04c12e7b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ap0-9300000000-f45f59d1359081efdc5dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-a3e49c43493abd03741aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-3900000000-e83a45b173d15048668bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01p9-9500000000-b23fa478546cbc48f849View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-9000000000-3753a08be3115affee2aView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
details
UrineDetected and Quantified0.0 umol/mmol creatinineChildren (1 - 18 years old)Both
Normal
    • BC Children's Hos...
details
Abnormal Concentrations
Not Available
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 IDFDB022697
KNApSAcK IDNot Available
Chemspider ID90191
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6332
PubChem Compound99824
PDB IDNot Available
ChEBI ID86542
References
Synthesis ReferenceAbderhalden, Emil; Weil, Arthur. A New Amino Acid of the Composition C6H13NO3, Obtained by the Total Hydrolysis of Nerve Proteins. Z. physiol. Chem. (1913), 84 39-59.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Woolf LI, Hasinoff C, Perry A: Estimation of branched-chain alpha-keto acids in blood by gas chromatography. J Chromatogr. 1982 Sep 10;231(2):237-45. [PubMed:7130306 ]
  2. Ng KJ, Andresen BD, Bianchine JR, Iams JD, O'Shaugnessy RW, Stempel LE, Zuspan FP: Capillary gas chromatographic-mass spectrometric profiles of trimethylsilyl derivatives of organic acids from amniotic fluids of different gestational age. J Chromatogr. 1982 Mar 12;228:43-50. [PubMed:7076774 ]
  3. Brooks JB, Kasin JV, Fast DM, Daneshvar MI: Detection of metabolites by frequency-pulsed electron capture gas-liquid chromatography in serum and cerebrospinal fluid of a patient with Nocardia infection. J Clin Microbiol. 1987 Feb;25(2):445-8. [PubMed:3818936 ]