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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:19:01 UTC
HMDB IDHMDB0000351
Secondary Accession Numbers
  • HMDB00351
Metabolite Identification
Common Name(2S,3R)-3-Hydroxy-2-methylbutanoic acid
Description(2S,3R)-3-Hydroxy-2-methylbutanoic acid, also known as 3-hydroxy-2-methyl-[R-(r*,s*)]-butanoate or (2S,3R)-nilic acid, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. Based on a literature review very few articles have been published on (2S,3R)-3-Hydroxy-2-methylbutanoic acid.
Structure
Data?1582752125
Synonyms
ValueSource
(2S,3R)-3-Hydroxy-2-methylbutanoateGenerator
3-Hydroxy-2-methyl-[R-(r*,s*)]-butanoateHMDB
3-Hydroxy-2-methyl-[R-(r*,s*)]-butanoic acidHMDB
3-Hydroxy-2-methyl-[R-(R,S)]-butanoateHMDB
(2S,3R)-3-Hydroxy-2-methylbutyric acidHMDB
(2S,3R)-Nilic acidHMDB
3-Hydroxy-2-methyl-[R-(R,S)]-butanoic acidHMDB
HMBAHMDB
(2S,3R)-3-Hydroxy-2-methylbutanoic acidHMDB
Chemical FormulaC5H10O3
Average Molecular Weight118.1311
Monoisotopic Molecular Weight118.062994186
IUPAC Name(2S,3R)-3-hydroxy-2-methylbutanoic acid
Traditional Name(2S,3R)-3-hydroxy-2-methylbutanoic acid
CAS Registry Number71526-30-2
SMILES
C[C@@H](O)[C@H](C)C(O)=O
InChI Identifier
InChI=1S/C5H10O3/c1-3(4(2)6)5(7)8/h3-4,6H,1-2H3,(H,7,8)/t3-,4+/m0/s1
InChI KeyVEXDRERIMPLZLU-IUYQGCFVSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Beta-hydroxy acid
  • Branched fatty acid
  • Hydroxy fatty acid
  • Short-chain hydroxy acid
  • Methyl-branched fatty acid
  • Hydroxy acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility336 g/LALOGPS
logP10(-0.13) g/LALOGPS
logP10(0.16) g/LChemAxon
logS10(0.45) g/LALOGPS
pKa (Strongest Acidic)4.51ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity28.04 m³·mol⁻¹ChemAxon
Polarizability11.76 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+127.31931661259
DarkChem[M+H]+127.31931661259
DarkChem[M-H]-122.08531661259
DarkChem[M-H]-122.08531661259
DarkChem[M+H]+127.31931661259
DarkChem[M+H]+127.31931661259
DarkChem[M-H]-122.08531661259
DarkChem[M-H]-122.08531661259
AllCCS[M+H]+129.86532859911
AllCCS[M-H]-125.83332859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(2S,3R)-3-Hydroxy-2-methylbutanoic acid,1TMS,#1C[C@H](C(=O)O)[C@@H](C)O[Si](C)(C)C1128.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
(2S,3R)-3-Hydroxy-2-methylbutanoic acid,1TMS,#2C[C@H](C(=O)O[Si](C)(C)C)[C@@H](C)O1061.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
(2S,3R)-3-Hydroxy-2-methylbutanoic acid,2TMS,#1C[C@H](C(=O)O[Si](C)(C)C)[C@@H](C)O[Si](C)(C)C1206.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
(2S,3R)-3-Hydroxy-2-methylbutanoic acid,1TBDMS,#1C[C@H](C(=O)O)[C@@H](C)O[Si](C)(C)C(C)(C)C1367.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
(2S,3R)-3-Hydroxy-2-methylbutanoic acid,1TBDMS,#2C[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](C)O1283.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
(2S,3R)-3-Hydroxy-2-methylbutanoic acid,2TBDMS,#1C[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](C)O[Si](C)(C)C(C)(C)C1646.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0097-9100000000-4296c67313a78a0150742017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00y1-9820000000-7256ed8afed29ebf4daa2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0r0r-9200000000-a7d6bf6e90c8c752f69c2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0a4j-9000000000-fe9a2716010ffb94cff82012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0a4l-9000000000-715b545170085466a6b22012-07-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid 10V, Positive-QTOFsplash10-0uxr-3900000000-d8f24d02712f429591a72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid 20V, Positive-QTOFsplash10-0zgi-9800000000-0821ba5748054e7de3692017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid 40V, Positive-QTOFsplash10-0a4i-9000000000-e5b2f743cb4dd5e99ec52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid 10V, Negative-QTOFsplash10-014i-5900000000-587bb9b1fdf10856b3a12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid 20V, Negative-QTOFsplash10-05fr-9100000000-a33491d8a46967cdd2d32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid 40V, Negative-QTOFsplash10-0a4i-9000000000-1ec2b5bb3af9f3c925ca2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid 10V, Negative-QTOFsplash10-01b9-8900000000-6e362f577b3d827a83872021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid 20V, Negative-QTOFsplash10-05fr-9100000000-6950ab2628a11bf6839a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid 40V, Negative-QTOFsplash10-052f-9000000000-5278bf25a974c9f303692021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid 10V, Positive-QTOFsplash10-0zgi-9400000000-aee3a280a6df1ae985b62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid 20V, Positive-QTOFsplash10-0002-9000000000-45e4e2c8c6ea7216859f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid 40V, Positive-QTOFsplash10-052b-9000000000-845222220a578798d8ce2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart 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 IDFDB021974
KNApSAcK IDNot Available
Chemspider ID13628066
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5340
PubChem Compound12313370
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNeri, Claudia; Williams, Jonathan M. J. Racemic auxiliaries: applications to asymmetric synthesis. Tetrahedron Letters (2002), 43(23), 4257-4260.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Heil M, Podebrad F, Prado E, Beck T, Mosand A, Sewell AC, Bohles H, Lehnert W: Enantioselective analysis of ketone bodies in patients with beta-ketothiolase deficiency, medium-chain acyl coenzyme A dehydrogenase deficiency and ketonemic vomiting. J Chromatogr B Biomed Sci Appl. 2000 Mar 10;739(2):313-24. [PubMed:10755375 ]