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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:24 UTC
HMDB IDHMDB0000624
Secondary Accession Numbers
  • HMDB00624
Metabolite Identification
Common NameD-Leucic acid
DescriptionD-Leucic acid, also known as D-leucate or delta-leucic 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. D-Leucic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1582752144
Synonyms
ValueSource
(R)-2-Hydroxy-4-methylvaleric acidChEBI
(R)-2-Hydroxyisocaproic acidChEBI
(R)-Leucic acidChEBI
2-Hydroxy-4-methyl-D-valeric acidChEBI
alpha-Hydroxyisocaproic acidChEBI
D-2-Hydroxy-4-methylpentanoic acidChEBI
D-2-Hydroxy-4-methylvaleric acidChEBI
D-2-Hydroxyisocaproic acidChEBI
delta-Leucic acidChEBI
Leucic acidChEBI
D-2-HydroxyisocaproateKegg
(R)-2-Hydroxy-4-methylpentanoateKegg
D-LeucateKegg
(R)-2-Hydroxy-4-methylvalerateGenerator
(R)-2-HydroxyisocaproateGenerator
(R)-LeucateGenerator
2-Hydroxy-4-methyl-D-valerateGenerator
a-HydroxyisocaproateGenerator
a-Hydroxyisocaproic acidGenerator
alpha-HydroxyisocaproateGenerator
Α-hydroxyisocaproateGenerator
Α-hydroxyisocaproic acidGenerator
D-2-Hydroxy-4-methylpentanoateGenerator
D-2-Hydroxy-4-methylvalerateGenerator
delta-LeucateGenerator
Δ-leucateGenerator
Δ-leucic acidGenerator
LeucateGenerator
(R)-2-Hydroxy-4-methylpentanoic acidGenerator
(-)-2-HydroxyisocaproateHMDB
(-)-2-Hydroxyisocaproic acidHMDB
(-)-a-HydroxyisocaproateHMDB
(-)-a-Hydroxyisocaproic acidHMDB
(-)-alpha-HydroxyisocaproateHMDB
(-)-alpha-Hydroxyisocaproic acidHMDB
(R)-2-Hydroxy-4-methyl-pentanoateHMDB
(R)-2-Hydroxy-4-methyl-pentanoic acidHMDB
2-Hydroxy-4-methyl-delta-valerateHMDB
2-Hydroxy-4-methyl-delta-valeric acidHMDB
D-a-HydroxyisocaproateHMDB
D-a-Hydroxyisocaproic acidHMDB
delta-2-Hydroxy-4-methylpentanoateHMDB
delta-2-Hydroxy-4-methylpentanoic acidHMDB
delta-2-Hydroxy-4-methylvalerateHMDB
delta-2-Hydroxy-4-methylvaleric acidHMDB
delta-2-HydroxyisocaproateHMDB
delta-2-Hydroxyisocaproic acidHMDB
delta-alpha-HydroxyisocaproateHMDB
delta-alpha-Hydroxyisocaproic acidHMDB
Chemical FormulaC6H12O3
Average Molecular Weight132.1577
Monoisotopic Molecular Weight132.07864425
IUPAC Name(2R)-2-hydroxy-4-methylpentanoic acid
Traditional Name(-)-α-hydroxyisocaproate
CAS Registry Number20312-37-2
SMILES
CC(C)C[C@@H](O)C(O)=O
InChI Identifier
InChI=1S/C6H12O3/c1-4(2)3-5(7)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9)/t5-/m1/s1
InChI KeyLVRFTAZAXQPQHI-RXMQYKEDSA-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
  • Branched fatty acid
  • Hydroxy fatty acid
  • Methyl-branched fatty acid
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Secondary alcohol
  • 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 Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility124 g/LALOGPS
logP0.5ALOGPS
logP0.78ChemAxon
logS-0.03ALOGPS
pKa (Strongest Acidic)4.26ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity32.51 m³·mol⁻¹ChemAxon
Polarizability13.71 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-866999574fff80fabad1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-02gc-9440000000-7fffd162011678b17f4aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0900000000-74d5e5f39ea37f777acaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0019-9500000000-7c7c7dc2d6548a20789dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00kr-9000000000-226ab1053ca4714d6bc1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-9000000000-027f1c6ebbf703c13661Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-9000000000-6217c9555a8c971b5deeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-5900000000-01e9c211c49cea6fc5c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ap0-9300000000-a1f6fc289aa530d63fd8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-eb5a5d102c8e756f6834Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2900000000-1a66b9767516fbd45630Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06s9-9400000000-cf71f1c20e2a87bbb2b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-11e049c8df5b1a6268c9Spectrum
Biological Properties
Cellular Locations
  • 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 IDFDB022149
KNApSAcK IDNot Available
Chemspider ID388986
KEGG Compound IDC03264
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Hydroxyisocaproic acid
METLIN ID5597
PubChem Compound439960
PDB IDNot Available
ChEBI ID55534
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceKallwass, Helmut K. W. Potential of R-2-hydroxyisocaproate dehydrogenase from Lactobacillus casei for stereospecific reductions. Enzyme and Microbial Technology (1992), 14(1), 28-35.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Marschall HU, Roeb E, Yildiz Y, Busch N, Nguyen H, Purucker E, Thomas HG, Matern S: Study of human isoursodeoxycholic acid metabolism. J Hepatol. 1997 Apr;26(4):863-70. [PubMed:9126801 ]
  2. Heil M, Podebrad F, Beck T, Mosandl A, Sewell AC, Bohles H: Enantioselective multidimensional gas chromatography-mass spectrometry in the analysis of urinary organic acids. J Chromatogr B Biomed Sci Appl. 1998 Sep 4;714(2):119-26. [PubMed:9766851 ]