Hmdb loader
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:31:14 UTC
Update Date2022-09-22 18:34:23 UTC
HMDB IDHMDB0029576
Secondary Accession Numbers
  • HMDB29576
Metabolite Identification
Common Name2,3-Dihydroxy-2-methylbutanoic acid
Description2,3-Dihydroxy-2-methylbutanoic acid, also known as 2,3-dimethylglyceric 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 a small amount of articles have been published on 2,3-Dihydroxy-2-methylbutanoic acid.
Structure
Data?1582753437
Synonyms
ValueSource
2,3-Dihydroxy-2-methylbutanoateGenerator
2,3-Dimethylglyceric acidHMDB
Chemical FormulaC5H10O4
Average Molecular Weight134.1305
Monoisotopic Molecular Weight134.057908808
IUPAC Name2,3-dihydroxy-2-methylbutanoic acid
Traditional Name2,3-dihydroxy-2-methylbutanoic acid
CAS Registry Number14868-24-7
SMILES
CC(O)C(C)(O)C(O)=O
InChI Identifier
InChI=1S/C5H10O4/c1-3(6)5(2,9)4(7)8/h3,6,9H,1-2H3,(H,7,8)
InChI KeyAOWPAWLEXIYETE-UHFFFAOYSA-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
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Tertiary alcohol
  • Secondary alcohol
  • 1,2-diol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateNot Available
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 Solubility441 g/LALOGPS
logP-0.89ALOGPS
logP-0.67ChemAxon
logS0.52ALOGPS
pKa (Strongest Acidic)3.76ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity29.52 m³·mol⁻¹ChemAxon
Polarizability12.51 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]+128.58131661259
DarkChem[M-H]-123.51931661259
DeepCCS[M+H]+123.70830932474
DeepCCS[M-H]-120.53130932474
DeepCCS[M-2H]-157.37930932474
DeepCCS[M+Na]+132.3230932474
AllCCS[M+H]+132.332859911
AllCCS[M+H-H2O]+128.232859911
AllCCS[M+NH4]+136.132859911
AllCCS[M+Na]+137.232859911
AllCCS[M-H]-125.532859911
AllCCS[M+Na-2H]-128.332859911
AllCCS[M+HCOO]-131.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2,3-Dihydroxy-2-methylbutanoic acidCC(O)C(C)(O)C(O)=O2519.1Standard polar33892256
2,3-Dihydroxy-2-methylbutanoic acidCC(O)C(C)(O)C(O)=O1094.1Standard non polar33892256
2,3-Dihydroxy-2-methylbutanoic acidCC(O)C(C)(O)C(O)=O1134.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2,3-Dihydroxy-2-methylbutanoic acid,1TMS,isomer #1CC(O[Si](C)(C)C)C(C)(O)C(=O)O1233.7Semi standard non polar33892256
2,3-Dihydroxy-2-methylbutanoic acid,1TMS,isomer #2CC(O)C(C)(O[Si](C)(C)C)C(=O)O1259.3Semi standard non polar33892256
2,3-Dihydroxy-2-methylbutanoic acid,1TMS,isomer #3CC(O)C(C)(O)C(=O)O[Si](C)(C)C1147.2Semi standard non polar33892256
2,3-Dihydroxy-2-methylbutanoic acid,2TMS,isomer #1CC(O[Si](C)(C)C)C(C)(O[Si](C)(C)C)C(=O)O1330.6Semi standard non polar33892256
2,3-Dihydroxy-2-methylbutanoic acid,2TMS,isomer #2CC(O[Si](C)(C)C)C(C)(O)C(=O)O[Si](C)(C)C1261.9Semi standard non polar33892256
2,3-Dihydroxy-2-methylbutanoic acid,2TMS,isomer #3CC(O)C(C)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1255.8Semi standard non polar33892256
2,3-Dihydroxy-2-methylbutanoic acid,3TMS,isomer #1CC(O[Si](C)(C)C)C(C)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1364.1Semi standard non polar33892256
2,3-Dihydroxy-2-methylbutanoic acid,1TBDMS,isomer #1CC(O[Si](C)(C)C(C)(C)C)C(C)(O)C(=O)O1487.2Semi standard non polar33892256
2,3-Dihydroxy-2-methylbutanoic acid,1TBDMS,isomer #2CC(O)C(C)(O[Si](C)(C)C(C)(C)C)C(=O)O1501.3Semi standard non polar33892256
2,3-Dihydroxy-2-methylbutanoic acid,1TBDMS,isomer #3CC(O)C(C)(O)C(=O)O[Si](C)(C)C(C)(C)C1385.8Semi standard non polar33892256
2,3-Dihydroxy-2-methylbutanoic acid,2TBDMS,isomer #1CC(O[Si](C)(C)C(C)(C)C)C(C)(O[Si](C)(C)C(C)(C)C)C(=O)O1761.4Semi standard non polar33892256
2,3-Dihydroxy-2-methylbutanoic acid,2TBDMS,isomer #2CC(O[Si](C)(C)C(C)(C)C)C(C)(O)C(=O)O[Si](C)(C)C(C)(C)C1717.6Semi standard non polar33892256
2,3-Dihydroxy-2-methylbutanoic acid,2TBDMS,isomer #3CC(O)C(C)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1717.8Semi standard non polar33892256
2,3-Dihydroxy-2-methylbutanoic acid,3TBDMS,isomer #1CC(O[Si](C)(C)C(C)(C)C)C(C)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1993.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2,3-Dihydroxy-2-methylbutanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-000l-9000000000-8060c77c70d1401c62962017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,3-Dihydroxy-2-methylbutanoic acid GC-MS (3 TMS) - 70eV, Positivesplash10-0159-5693000000-e6114a40a3e178e75a6f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,3-Dihydroxy-2-methylbutanoic 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 - 2,3-Dihydroxy-2-methylbutanoic acid 10V, Positive-QTOFsplash10-000i-5900000000-23e969df406e88f971612016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Dihydroxy-2-methylbutanoic acid 20V, Positive-QTOFsplash10-00rj-9500000000-98a61ebd4254fd477f612016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Dihydroxy-2-methylbutanoic acid 40V, Positive-QTOFsplash10-00di-9000000000-14933eec5b98adfb43f92016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Dihydroxy-2-methylbutanoic acid 10V, Negative-QTOFsplash10-0019-9600000000-5973372858938417b6f22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Dihydroxy-2-methylbutanoic acid 20V, Negative-QTOFsplash10-000i-9000000000-f760aedb6486baf6aecf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Dihydroxy-2-methylbutanoic acid 40V, Negative-QTOFsplash10-00di-9000000000-9e34d48afdfc64e229e12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Dihydroxy-2-methylbutanoic acid 10V, Negative-QTOFsplash10-0019-9500000000-7bb83293cba61b428e562021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Dihydroxy-2-methylbutanoic acid 20V, Negative-QTOFsplash10-00du-9100000000-21f6885e812b3d4e8ced2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Dihydroxy-2-methylbutanoic acid 40V, Negative-QTOFsplash10-0006-9000000000-80c26ba46da018f73c4f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Dihydroxy-2-methylbutanoic acid 10V, Positive-QTOFsplash10-006t-9100000000-ff8bec7e4f1070dbff422021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Dihydroxy-2-methylbutanoic acid 20V, Positive-QTOFsplash10-0002-9000000000-5569a336b1ae620ba37a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Dihydroxy-2-methylbutanoic acid 40V, Positive-QTOFsplash10-0002-9000000000-192d9f73cc356b2b25c22021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000732
KNApSAcK IDC00012985
Chemspider ID266858
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound301941
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 References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.