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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-08 14:58:34 UTC
Update Date2022-03-07 03:17:33 UTC
HMDB IDHMDB0029166
Secondary Accession Numbers
  • HMDB29166
Metabolite Identification
Common Name2-Methyl-3-hydroxyvaleric acid
Description2-Methyl-3-hydroxyvaleric acid, also known as 3-hydroxy-2-methylvalerate, 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 significant number of articles have been published on 2-Methyl-3-hydroxyvaleric acid.
Structure
Data?1582753383
Synonyms
ValueSource
2-Methyl-3-hydroxyvalerateGenerator
3-Hydroxy-2-methylvalerateHMDB
3-Hydroxy-2-methylpentanoateHMDB
3-Hydroxy-2-methylvaleric acidHMDB
Chemical FormulaC6H12O3
Average Molecular Weight132.1577
Monoisotopic Molecular Weight132.07864425
IUPAC Name3-hydroxy-2-methylpentanoic acid
Traditional Name3-hydroxy-2-methylpentanoic acid
CAS Registry Number28892-73-1
SMILES
CCC(O)C(C)C(O)=O
InChI Identifier
InChI=1S/C6H12O3/c1-3-5(7)4(2)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9)
InChI KeyNVIHALDXJWGLFD-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
  • 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
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point250.45 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility305300 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.099 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility184 g/LALOGPS
logP0.4ALOGPS
logP0.68ChemAxon
logS0.14ALOGPS
pKa (Strongest Acidic)4.63ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity32.56 m³·mol⁻¹ChemAxon
Polarizability13.77 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]+128.72431661259
DarkChem[M-H]-125.72331661259
DeepCCS[M+H]+127.63530932474
DeepCCS[M-H]-124.76530932474
DeepCCS[M-2H]-161.35630932474
DeepCCS[M+Na]+136.22530932474
AllCCS[M+H]+132.732859911
AllCCS[M+H-H2O]+128.632859911
AllCCS[M+NH4]+136.632859911
AllCCS[M+Na]+137.732859911
AllCCS[M-H]-129.332859911
AllCCS[M+Na-2H]-132.132859911
AllCCS[M+HCOO]-135.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Methyl-3-hydroxyvaleric acidCCC(O)C(C)C(O)=O2399.0Standard polar33892256
2-Methyl-3-hydroxyvaleric acidCCC(O)C(C)C(O)=O1066.4Standard non polar33892256
2-Methyl-3-hydroxyvaleric acidCCC(O)C(C)C(O)=O1125.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Methyl-3-hydroxyvaleric acid,1TMS,isomer #1CCC(O[Si](C)(C)C)C(C)C(=O)O1222.2Semi standard non polar33892256
2-Methyl-3-hydroxyvaleric acid,1TMS,isomer #2CCC(O)C(C)C(=O)O[Si](C)(C)C1137.0Semi standard non polar33892256
2-Methyl-3-hydroxyvaleric acid,2TMS,isomer #1CCC(O[Si](C)(C)C)C(C)C(=O)O[Si](C)(C)C1273.6Semi standard non polar33892256
2-Methyl-3-hydroxyvaleric acid,1TBDMS,isomer #1CCC(O[Si](C)(C)C(C)(C)C)C(C)C(=O)O1441.1Semi standard non polar33892256
2-Methyl-3-hydroxyvaleric acid,1TBDMS,isomer #2CCC(O)C(C)C(=O)O[Si](C)(C)C(C)(C)C1371.2Semi standard non polar33892256
2-Methyl-3-hydroxyvaleric acid,2TBDMS,isomer #1CCC(O[Si](C)(C)C(C)(C)C)C(C)C(=O)O[Si](C)(C)C(C)(C)C1694.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methyl-3-hydroxyvaleric acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9100000000-c77e714fa25ca86c7f092017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methyl-3-hydroxyvaleric acid GC-MS (2 TMS) - 70eV, Positivesplash10-00ar-9730000000-2090be8a55197cd841742017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methyl-3-hydroxyvaleric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methyl-3-hydroxyvaleric 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-Methyl-3-hydroxyvaleric acid 10V, Positive-QTOFsplash10-0159-3900000000-b7479e4ae46ce765a84b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-3-hydroxyvaleric acid 20V, Positive-QTOFsplash10-014i-9600000000-499dc986196a7e19f15b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-3-hydroxyvaleric acid 40V, Positive-QTOFsplash10-066r-9000000000-820417ce16de045a909f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-3-hydroxyvaleric acid 10V, Negative-QTOFsplash10-001i-2900000000-7bb52492419e78ad823b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-3-hydroxyvaleric acid 20V, Negative-QTOFsplash10-05tr-9200000000-c111c9e17baa4a6a63302017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-3-hydroxyvaleric acid 40V, Negative-QTOFsplash10-0a4r-9000000000-60e73d535852d3356b652017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-3-hydroxyvaleric acid 10V, Positive-QTOFsplash10-014i-9300000000-6d71a8572110a28cf9a92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-3-hydroxyvaleric acid 20V, Positive-QTOFsplash10-0a4i-9000000000-0842f6b29e29b826b3cd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-3-hydroxyvaleric acid 40V, Positive-QTOFsplash10-052f-9000000000-8b1630673f977a944f692021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-3-hydroxyvaleric acid 10V, Negative-QTOFsplash10-001i-5900000000-10e04cd8c4a8c3804d472021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-3-hydroxyvaleric acid 20V, Negative-QTOFsplash10-0a4i-9000000000-1c87173d2679b8be04632021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-3-hydroxyvaleric acid 40V, Negative-QTOFsplash10-0a4i-9000000000-46c7ef1ed9bbc3f1e6852021-09-22Wishart 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 IDNot Available
KNApSAcK IDNot Available
Chemspider ID134822
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound152968
PDB IDNot Available
ChEBI ID173537
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1477151
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. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.