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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 03:17:48 UTC
Update Date2023-02-21 17:28:51 UTC
HMDB IDHMDB0041603
Secondary Accession Numbers
  • HMDB41603
Metabolite Identification
Common NameMethyl 3-hydroxybutyrate
DescriptionMethyl 3-hydroxybutyrate belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. Methyl 3-hydroxybutyrate is found, on average, in the highest concentration within pineapples (Ananas comosus). This could make methyl 3-hydroxybutyrate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Methyl 3-hydroxybutyrate.
Structure
Data?1677000531
Synonyms
ValueSource
Methyl 3-hydroxybutyric acidGenerator
Methyl-b-hydroxybutyrateGenerator
Methyl-b-hydroxybutyric acidGenerator
Methyl-beta-hydroxybutyric acidGenerator
Methyl-β-hydroxybutyrateGenerator
Methyl-β-hydroxybutyric acidGenerator
Chemical FormulaC5H10O3
Average Molecular Weight118.132
Monoisotopic Molecular Weight118.062994182
IUPAC Namemethyl 3-hydroxybutanoate
Traditional Namemethyl 3-hydroxybutyrate
CAS Registry Number1487-49-6
SMILES
COC(=O)CC(C)O
InChI Identifier
InChI=1S/C5H10O3/c1-4(6)3-5(7)8-2/h4,6H,3H2,1-2H3
InChI KeyLDLDJEAVRNAEBW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassBeta hydroxy acids and derivatives
Direct ParentBeta hydroxy acids and derivatives
Alternative Parents
Substituents
  • Beta-hydroxy acid
  • Fatty acid ester
  • Fatty acid methyl ester
  • Fatty acyl
  • Methyl ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point158.00 to 160.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility472800 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-0.412 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility500 g/LALOGPS
logP-0.08ALOGPS
logP-0.24ChemAxon
logS0.63ALOGPS
pKa (Strongest Acidic)15.41ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity28.23 m³·mol⁻¹ChemAxon
Polarizability12.07 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]+126.74731661259
DarkChem[M-H]-120.40731661259
DeepCCS[M+H]+128.28230932474
DeepCCS[M-H]-126.04930932474
DeepCCS[M-2H]-162.10830932474
DeepCCS[M+Na]+136.91930932474
AllCCS[M+H]+129.932859911
AllCCS[M+H-H2O]+125.732859911
AllCCS[M+NH4]+133.832859911
AllCCS[M+Na]+134.932859911
AllCCS[M-H]-127.032859911
AllCCS[M+Na-2H]-130.332859911
AllCCS[M+HCOO]-134.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Methyl 3-hydroxybutyrateCOC(=O)CC(C)O1449.4Standard polar33892256
Methyl 3-hydroxybutyrateCOC(=O)CC(C)O866.5Standard non polar33892256
Methyl 3-hydroxybutyrateCOC(=O)CC(C)O941.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Methyl 3-hydroxybutyrate,1TMS,isomer #1COC(=O)CC(C)O[Si](C)(C)C1031.1Semi standard non polar33892256
Methyl 3-hydroxybutyrate,1TBDMS,isomer #1COC(=O)CC(C)O[Si](C)(C)C(C)(C)C1242.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Methyl 3-hydroxybutyrate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4m-9100000000-2f53e310d610a36eff162017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl 3-hydroxybutyrate GC-MS (1 TMS) - 70eV, Positivesplash10-01dr-9700000000-e543ec98a0ab1fa589842017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl 3-hydroxybutyrate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl 3-hydroxybutyrate 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 - Methyl 3-hydroxybutyrate 10V, Positive-QTOFsplash10-0uxr-6900000000-df35618c412788fdc69d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 3-hydroxybutyrate 20V, Positive-QTOFsplash10-0uxr-9800000000-86c03303a8df11e0a2712016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 3-hydroxybutyrate 40V, Positive-QTOFsplash10-0006-9000000000-356911e4438c7dd9e4c42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 3-hydroxybutyrate 10V, Negative-QTOFsplash10-014i-8900000000-8a402c7e64d202f2270f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 3-hydroxybutyrate 20V, Negative-QTOFsplash10-014r-9300000000-baf775ea49882d9b2d922016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 3-hydroxybutyrate 40V, Negative-QTOFsplash10-0aou-9000000000-873dae99ae32c366c2002016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 3-hydroxybutyrate 10V, Negative-QTOFsplash10-01bc-9700000000-2c841182fb5aaaca7a2c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 3-hydroxybutyrate 20V, Negative-QTOFsplash10-0006-9000000000-ab3ea65814aa8c7caef92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 3-hydroxybutyrate 40V, Negative-QTOFsplash10-014l-9000000000-a5d5f906b7f123185fdb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 3-hydroxybutyrate 10V, Positive-QTOFsplash10-0v4j-9300000000-86207f8d43d38a3db0d72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 3-hydroxybutyrate 20V, Positive-QTOFsplash10-0002-9000000000-fdcff6401d1c8167512b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 3-hydroxybutyrate 40V, Positive-QTOFsplash10-0002-9000000000-541d7073aa951b0b2d422021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
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 IDFDB003804
KNApSAcK IDNot Available
Chemspider ID14417
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound15146
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1415671
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .