Record Information
Version1.0
Creation Date2016-05-26 05:16:27 UTC
Update Date2016-11-09 01:21:12 UTC
Accession NumberCHEM034849
Identification
Common Name(5R)-5-Hydroxyhexanoic acid
ClassSmall Molecule
DescriptionAn (omega-1)-hydroxy fatty acid that is caproic acid in which the 5-pro-R hydrogen is replaced by a hydroxy group.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
Synonyms
ValueSource
(-)-5-Hydroxycaproic acidChEBI
(-)-5-Hydroxyhexanoic acidChEBI
(5R)-5-Hydroxycaproic acidChEBI
(R)-(-)-5-Hydroxyhexanoic acidChEBI
(-)-5-HydroxycaproateGenerator
(-)-5-HydroxyhexanoateGenerator
(5R)-5-HydroxycaproateGenerator
(R)-(-)-5-HydroxyhexanoateGenerator
(5R)-5-HydroxyhexanoateGenerator
(5R)-5-Hydroxy-hexanoateHMDB
(5R)-5-Hydroxy-hexanoic acidHMDB
HMBAHMDB
5R-Hydroxy-hexanoateHMDB
Chemical FormulaC6H12O3
Average Molecular Mass132.158 g/mol
Monoisotopic Mass132.079 g/mol
CAS Registry Number83972-61-6
IUPAC Name(5R)-5-hydroxyhexanoic acid
Traditional NameHMBA
SMILESC[C@@H](O)CCCC(O)=O
InChI IdentifierInChI=1S/C6H12O3/c1-5(7)3-2-4-6(8)9/h5,7H,2-4H2,1H3,(H,8,9)/t5-/m1/s1
InChI KeyYDCRNMJQROAWFT-RXMQYKEDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility128 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity32.82 m³·mol⁻¹ChemAxon
Polarizability14.02 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0077-9100000000-13a584fc9ff05431f359Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-007c-9420000000-7b0146069089183f6082Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-5900000000-3bf905a3ced857b422b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9400000000-b18891bb2981129af001Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066r-9000000000-3510777085e9e83a6561Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2900000000-3b9f578bc70674738913Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03e9-4900000000-9944af827f01e265b301Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-9f3f80d6749af1cc6dbbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03ei-3900000000-49a5b195fc6d1869f127Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bta-9400000000-9da83e480e59bbc1ade7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052g-9000000000-e9748f05fe518d153135Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-9400000000-744ecd7d7e40b1357594Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05tk-9000000000-086484b097d1ba55d5d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-db58a877cf5945d523f9Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000409
FooDB IDFDB022025
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5398
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID5474600
ChEBI ID78842
PubChem Compound ID7131043
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Fazio, Fabio; Schneider, Manfred P. FA-catalyzed trimerization of R-(+)-6-methyltetrahydro-2-pyranone. FB 9-Bergische Universitat-GH-Wuppertal, Wuppertal, Germany. Tetrahedron Letters (2002), 43(5), 811-814.
2. 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.