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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:44:20 UTC
HMDB IDHMDB0000624
Secondary Accession Numbers
  • HMDB00624
Metabolite Identification
Common NameD-Leucic acid
DescriptionD-Leucic acid is an alpha-hydroxycarboxylic acid present in patients affected with Short-bowel syndrome (an Inborn errors of metabolism, OMIM 175200 ) (PMID 9766851 ), and in Maple Syrup Urine Disease (MSUD, an autosomal recessive inherited metabolic disorder of branched-chain amino acid) (PMID 9766851 ).
Structure
Data?1563860660
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-866999574fff80fabad1JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-02gc-9440000000-7fffd162011678b17f4aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0900000000-74d5e5f39ea37f777acaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0019-9500000000-7c7c7dc2d6548a20789dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00kr-9000000000-226ab1053ca4714d6bc1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-9000000000-027f1c6ebbf703c13661JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-9000000000-6217c9555a8c971b5deeJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-5900000000-01e9c211c49cea6fc5c6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ap0-9300000000-a1f6fc289aa530d63fd8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-eb5a5d102c8e756f6834JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2900000000-1a66b9767516fbd45630JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06s9-9400000000-cf71f1c20e2a87bbb2b0JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-11e049c8df5b1a6268c9JSpectraViewer | MoNA
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
FoodDB 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
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 ]