Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-10-15 12:12:16 UTC
Update Date2021-09-14 15:45:11 UTC
HMDB IDHMDB0010718
Secondary Accession Numbers
  • HMDB10718
Metabolite Identification
Common Name(R)-3-Hydroxyhexanoic acid
Description(R)-3-Hydroxyhexanoic acid, also known as D-beta-hydroxycaproate or D-β-hydroxycaproic acid, belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain (R)-3-Hydroxyhexanoic acid exists in all eukaryotes, ranging from yeast to plants to humans. In humans, (R)-3-hydroxyhexanoic acid is involved in the fatty acid biosynthesis pathway (R)-3-Hydroxyhexanoic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make (R)-3-hydroxyhexanoic acid a potential biomarker for the consumption of these foods (R)-3-Hydroxyhexanoic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on (R)-3-Hydroxyhexanoic acid.
Structure
Data?1582752865
Synonyms
ValueSource
(R)-3-HydroxyhexanoateGenerator
(3R)-3-HydroxyhexanoateHMDB
(3R)-3-Hydroxyhexanoic acidHMDB
(±)-3-hydroxyhexanoateHMDB
(±)-3-hydroxyhexanoic acidHMDB
3-HydroxycaproateHMDB
3-Hydroxycaproic acidHMDB
3-HydroxyhexanoateHMDB
3-Hydroxyhexanoic acidHMDB
D-beta-HydroxycaproateHMDB
D-beta-Hydroxycaproic acidHMDB
D-Β-hydroxycaproateHMDB
D-Β-hydroxycaproic acidHMDB
FA(6:0(3-OH))HMDB
FA(6:0(3R-OH))HMDB
beta-Hydroxy-N-caproateHMDB
beta-Hydroxy-N-caproic acidHMDB
beta-HydroxycaproateHMDB
beta-Hydroxycaproic acidHMDB
beta-HydroxyhexanoateHMDB
beta-Hydroxyhexanoic acidHMDB
Β-hydroxy-N-caproateHMDB
Β-hydroxy-N-caproic acidHMDB
Β-hydroxycaproateHMDB
Β-hydroxycaproic acidHMDB
Β-hydroxyhexanoateHMDB
Β-hydroxyhexanoic acidHMDB
(R)-3-Hydroxyhexanoic acidHMDB
Chemical FormulaC6H12O3
Average Molecular Weight132.1577
Monoisotopic Molecular Weight132.07864425
IUPAC Name(3R)-3-hydroxyhexanoic acid
Traditional Name3R-hydroxy-hexanoic acid
CAS Registry Number77877-35-1
SMILES
CCC[C@@H](O)CC(O)=O
InChI Identifier
InChI=1S/C6H12O3/c1-2-3-5(7)4-6(8)9/h5,7H,2-4H2,1H3,(H,8,9)/t5-/m1/s1
InChI KeyHPMGFDVTYHWBAG-RXMQYKEDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassMedium-chain hydroxy acids and derivatives
Direct ParentMedium-chain hydroxy acids and derivatives
Alternative Parents
Substituents
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Beta-hydroxy acid
  • Hydroxy fatty acid
  • Fatty acyl
  • Fatty acid
  • 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

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility133 g/LALOGPS
logP10(0.57) g/LALOGPS
logP10(0.58) g/LChemAxon
logS10(0) g/LALOGPS
pKa (Strongest Acidic)4.67ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity32.59 m³·mol⁻¹ChemAxon
Polarizability13.87 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+129.03931661259
DarkChem[M-H]-126.47431661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(R)-3-Hydroxyhexanoic acidCCC[C@@H](O)CC(O)=O2255.3Standard polar33892256
(R)-3-Hydroxyhexanoic acidCCC[C@@H](O)CC(O)=O1119.4Standard non polar33892256
(R)-3-Hydroxyhexanoic acidCCC[C@@H](O)CC(O)=O1177.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(R)-3-Hydroxyhexanoic acid,1TMS,isomer #1CCC[C@H](CC(=O)O)O[Si](C)(C)C1221.0Semi standard non polar33892256
(R)-3-Hydroxyhexanoic acid,1TMS,isomer #2CCC[C@@H](O)CC(=O)O[Si](C)(C)C1196.6Semi standard non polar33892256
(R)-3-Hydroxyhexanoic acid,2TMS,isomer #1CCC[C@H](CC(=O)O[Si](C)(C)C)O[Si](C)(C)C1311.2Semi standard non polar33892256
(R)-3-Hydroxyhexanoic acid,1TBDMS,isomer #1CCC[C@H](CC(=O)O)O[Si](C)(C)C(C)(C)C1445.4Semi standard non polar33892256
(R)-3-Hydroxyhexanoic acid,1TBDMS,isomer #2CCC[C@@H](O)CC(=O)O[Si](C)(C)C(C)(C)C1426.2Semi standard non polar33892256
(R)-3-Hydroxyhexanoic acid,2TBDMS,isomer #1CCC[C@H](CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1751.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (R)-3-Hydroxyhexanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-5263808e33ccb6565b3c2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-3-Hydroxyhexanoic acid GC-MS (2 TMS) - 70eV, Positivesplash10-009i-9330000000-5a1f5b24235b7a70faba2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-3-Hydroxyhexanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxyhexanoic acid 10V, Positive-QTOFsplash10-0159-5900000000-16b15ce70244c2b64d0c2016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxyhexanoic acid 20V, Positive-QTOFsplash10-014j-9300000000-3cfe9ed23a846d781f372016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxyhexanoic acid 40V, Positive-QTOFsplash10-0006-9000000000-b3878b3c92a65ddc51fd2016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxyhexanoic acid 10V, Negative-QTOFsplash10-001i-5900000000-ae1b58fe367907c50ffe2016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxyhexanoic acid 20V, Negative-QTOFsplash10-05nr-9300000000-f5a6c18cc1d3fca5f1092016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxyhexanoic acid 40V, Negative-QTOFsplash10-05mo-9000000000-7911aea05314b944272c2016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxyhexanoic acid 10V, Positive-QTOFsplash10-0avi-9100000000-82b86020a271d61ba1b52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxyhexanoic acid 20V, Positive-QTOFsplash10-052f-9000000000-5b86d65468321ff154262021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxyhexanoic acid 40V, Positive-QTOFsplash10-0006-9000000000-ab813e477e382c5c6c082021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxyhexanoic acid 10V, Negative-QTOFsplash10-053r-6900000000-605bc451889b03fcac772021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxyhexanoic acid 20V, Negative-QTOFsplash10-0a4l-9100000000-e58c13d9ebd5ab0dbbbf2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxyhexanoic acid 40V, Negative-QTOFsplash10-0006-9000000000-191e4c2a7ad7ea5541dd2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027868
KNApSAcK IDNot Available
Chemspider ID8373213
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10197713
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available