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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:00 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?1676999700
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
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point251.31 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility165500 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.522 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+129.12831661259
DarkChem[M-H]-125.30231661259
AllCCS[M+H]+131.97632859911
AllCCS[M-H]-129.50532859911
DeepCCS[M+H]+128.87330932474
DeepCCS[M-H]-125.23930932474
DeepCCS[M-2H]-162.50430932474
DeepCCS[M+Na]+137.61630932474
AllCCS[M+H]+132.032859911
AllCCS[M+H-H2O]+127.932859911
AllCCS[M+NH4]+135.832859911
AllCCS[M+Na]+136.932859911
AllCCS[M-H]-129.532859911
AllCCS[M+Na-2H]-132.332859911
AllCCS[M+HCOO]-135.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
D-Leucic acidCC(C)C[C@@H](O)C(O)=O1935.3Standard polar33892256
D-Leucic acidCC(C)C[C@@H](O)C(O)=O1027.3Standard non polar33892256
D-Leucic acidCC(C)C[C@@H](O)C(O)=O1108.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
D-Leucic acid,1TMS,isomer #1CC(C)C[C@@H](O[Si](C)(C)C)C(=O)O1189.3Semi standard non polar33892256
D-Leucic acid,1TMS,isomer #2CC(C)C[C@@H](O)C(=O)O[Si](C)(C)C1121.8Semi standard non polar33892256
D-Leucic acid,2TMS,isomer #1CC(C)C[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C1237.3Semi standard non polar33892256
D-Leucic acid,1TBDMS,isomer #1CC(C)C[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O1404.6Semi standard non polar33892256
D-Leucic acid,1TBDMS,isomer #2CC(C)C[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C1356.0Semi standard non polar33892256
D-Leucic acid,2TBDMS,isomer #1CC(C)C[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1676.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - D-Leucic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-866999574fff80fabad12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Leucic acid GC-MS (2 TMS) - 70eV, Positivesplash10-02gc-9440000000-7fffd162011678b17f4a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Leucic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Leucic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Leucic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Leucic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Leucic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Leucic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Leucic acid LC-ESI-QQ , negative-QTOFsplash10-001i-0900000000-74d5e5f39ea37f777aca2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Leucic acid LC-ESI-QQ , negative-QTOFsplash10-0019-9500000000-7c7c7dc2d6548a20789d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Leucic acid LC-ESI-QQ , negative-QTOFsplash10-00kr-9000000000-226ab1053ca4714d6bc12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Leucic acid LC-ESI-QQ , negative-QTOFsplash10-014i-9000000000-027f1c6ebbf703c136612017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Leucic acid LC-ESI-QQ , negative-QTOFsplash10-014i-9000000000-6217c9555a8c971b5dee2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Leucic acid 10V, Positive-QTOFsplash10-0159-5900000000-01e9c211c49cea6fc5c62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Leucic acid 20V, Positive-QTOFsplash10-0ap0-9300000000-a1f6fc289aa530d63fd82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Leucic acid 40V, Positive-QTOFsplash10-0a4i-9000000000-eb5a5d102c8e756f68342017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Leucic acid 10V, Negative-QTOFsplash10-001i-2900000000-1a66b9767516fbd456302017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Leucic acid 20V, Negative-QTOFsplash10-06s9-9400000000-cf71f1c20e2a87bbb2b02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Leucic acid 40V, Negative-QTOFsplash10-0a4i-9000000000-11e049c8df5b1a6268c92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Leucic acid 10V, Negative-QTOFsplash10-0019-9700000000-a7d0b1ce1c211b31bc0d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Leucic acid 20V, Negative-QTOFsplash10-00kr-9100000000-504826b66e199a65ef092021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Leucic acid 40V, Negative-QTOFsplash10-014l-9000000000-ccecb4a470c359949fec2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Leucic acid 10V, Positive-QTOFsplash10-014i-9000000000-3019a9d0620e7da019632021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Leucic acid 20V, Positive-QTOFsplash10-00kf-9000000000-e587d44396e53f2409fa2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Leucic acid 40V, Positive-QTOFsplash10-0006-9000000000-457ece1d510dad645c892021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 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
MarkerDB IDNot Available
Good Scents IDrw1118401
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 ]