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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-10-15 12:12:16 UTC
Update Date2021-09-14 15:00:41 UTC
HMDB IDHMDB0010722
Secondary Accession Numbers
  • HMDB10722
Metabolite Identification
Common Name(R)-3-Hydroxyoctanoic acid
Description(R)-3-Hydroxyoctanoic acid, also known as (R)-3-OH-caprylic acid or (3R)-3-hydroxy-octanoate, 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-Hydroxyoctanoic acid exists in all eukaryotes, ranging from yeast to plants to humans. In humans, (R)-3-hydroxyoctanoic acid is involved in the fatty acid biosynthesis pathway (R)-3-Hydroxyoctanoic acid has been detected, but not quantified in, several different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), domestic pigs (Sus scrofa domestica), fruits, and milk and milk products. This could make (R)-3-hydroxyoctanoic acid a potential biomarker for the consumption of these foods (R)-3-Hydroxyoctanoic 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-Hydroxyoctanoic acid.
Structure
Data?1582752866
Synonyms
ValueSource
(3R)-3-Hydroxy-octanoic acidChEBI
(R)-3-Hydroxycaprylic acidChEBI
(R)-3-OH Octanoic acidChEBI
(R)-3-OH-Caprylic acidChEBI
(R)-beta-Hydroxycaprylic acidChEBI
(R)-beta-Hydroxyoctanoic acidChEBI
(R)-beta-OH-Caprylic acidChEBI
(R)-beta-OH-Octanoic acidChEBI
(3R)-3-Hydroxy-octanoateGenerator
(R)-3-HydroxycaprylateGenerator
(R)-3-OH OctanoateGenerator
(R)-3-OH-CaprylateGenerator
(R)-b-HydroxycaprylateGenerator
(R)-b-Hydroxycaprylic acidGenerator
(R)-beta-HydroxycaprylateGenerator
(R)-Β-hydroxycaprylateGenerator
(R)-Β-hydroxycaprylic acidGenerator
(R)-b-HydroxyoctanoateGenerator
(R)-b-Hydroxyoctanoic acidGenerator
(R)-beta-HydroxyoctanoateGenerator
(R)-Β-hydroxyoctanoateGenerator
(R)-Β-hydroxyoctanoic acidGenerator
(R)-b-OH-CaprylateGenerator
(R)-b-OH-Caprylic acidGenerator
(R)-beta-OH-CaprylateGenerator
(R)-Β-OH-caprylateGenerator
(R)-Β-OH-caprylic acidGenerator
(R)-b-OH-OctanoateGenerator
(R)-b-OH-Octanoic acidGenerator
(R)-beta-OH-OctanoateGenerator
(R)-Β-OH-octanoateGenerator
(R)-Β-OH-octanoic acidGenerator
(R)-3-HydroxyoctanoateGenerator
Chemical FormulaC8H16O3
Average Molecular Weight160.2108
Monoisotopic Molecular Weight160.109944378
IUPAC Name(3R)-3-hydroxyoctanoic acid
Traditional Name(R)-3-hydroxyoctanoic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(CCCCC)CC(O)=O
InChI Identifier
InChI=1S/C8H16O3/c1-2-3-4-5-7(9)6-8(10)11/h7,9H,2-6H2,1H3,(H,10,11)/t7-/m1/s1
InChI KeyNDPLAKGOSZHTPH-SSDOTTSWSA-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 Solubility13.6 g/LALOGPS
logP10(1.44) g/LALOGPS
logP10(1.47) g/LChemAxon
logS10(-1.1) g/LALOGPS
pKa (Strongest Acidic)4.84ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity41.79 m³·mol⁻¹ChemAxon
Polarizability18.14 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+138.19331661259
DarkChem[M-H]-136.81731661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(R)-3-Hydroxyoctanoic acid[H][C@@](O)(CCCCC)CC(O)=O2430.0Standard polar33892256
(R)-3-Hydroxyoctanoic acid[H][C@@](O)(CCCCC)CC(O)=O1296.0Standard non polar33892256
(R)-3-Hydroxyoctanoic acid[H][C@@](O)(CCCCC)CC(O)=O1367.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(R)-3-Hydroxyoctanoic acid,1TMS,isomer #1CCCCC[C@H](CC(=O)O)O[Si](C)(C)C1378.0Semi standard non polar33892256
(R)-3-Hydroxyoctanoic acid,1TMS,isomer #2CCCCC[C@@H](O)CC(=O)O[Si](C)(C)C1382.0Semi standard non polar33892256
(R)-3-Hydroxyoctanoic acid,2TMS,isomer #1CCCCC[C@H](CC(=O)O[Si](C)(C)C)O[Si](C)(C)C1471.9Semi standard non polar33892256
(R)-3-Hydroxyoctanoic acid,1TBDMS,isomer #1CCCCC[C@H](CC(=O)O)O[Si](C)(C)C(C)(C)C1601.6Semi standard non polar33892256
(R)-3-Hydroxyoctanoic acid,1TBDMS,isomer #2CCCCC[C@@H](O)CC(=O)O[Si](C)(C)C(C)(C)C1616.6Semi standard non polar33892256
(R)-3-Hydroxyoctanoic acid,2TBDMS,isomer #1CCCCC[C@H](CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1923.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (R)-3-Hydroxyoctanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-052o-9200000000-43d57763d2a30e89979b2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-3-Hydroxyoctanoic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00ri-9350000000-f1efc144e4aa8ba19a722017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-3-Hydroxyoctanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-3-Hydroxyoctanoic 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-Hydroxyoctanoic acid 10V, Positive-QTOFsplash10-01ox-1900000000-e5cda5e57d0fb350dc6e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxyoctanoic acid 20V, Positive-QTOFsplash10-002g-8900000000-206c3ff570d17b537e392016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxyoctanoic acid 40V, Positive-QTOFsplash10-052f-9000000000-c32a98aa8083b6459b4a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxyoctanoic acid 10V, Negative-QTOFsplash10-0a4i-2900000000-9112efe71e9f56f43bab2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxyoctanoic acid 20V, Negative-QTOFsplash10-0aos-8900000000-f482349594658282b6e52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxyoctanoic acid 40V, Negative-QTOFsplash10-0a4m-9100000000-b0b3f7b33ed057654f962016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxyoctanoic acid 10V, Positive-QTOFsplash10-0zna-9400000000-ba19979661ce66d42c472021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxyoctanoic acid 20V, Positive-QTOFsplash10-05fr-9000000000-7a423069bad50c00a0fd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxyoctanoic acid 40V, Positive-QTOFsplash10-05mo-9000000000-7c89cf68b731953f37972021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxyoctanoic acid 10V, Negative-QTOFsplash10-0a4l-3900000000-ef763a7f3b584b7714122021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxyoctanoic acid 20V, Negative-QTOFsplash10-052b-9100000000-9b510a15a343a9e2d3652021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxyoctanoic acid 40V, Negative-QTOFsplash10-0006-9000000000-05f3a26a1fda3e795cba2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart 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 IDFDB010907
KNApSAcK IDNot Available
Chemspider ID4472286
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5312861
PDB IDNot Available
ChEBI ID37099
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

Enzymes

General function:
Involved in transferase activity
Specific function:
Fatty acid synthetase catalyzes the formation of long-chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. This multifunctional protein has 7 catalytic activities and an acyl carrier protein.
Gene Name:
FASN
Uniprot ID:
P49327
Molecular weight:
273424.06