Record Information
Version1.0
Creation date2010-04-08 22:05:10 UTC
Update date2019-11-26 02:56:48 UTC
Primary IDFDB001946
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Leucine
Description(±)-Leucine, also known as DL-leucine or hleu, belongs to the class of organic compounds known as leucine and derivatives. Leucine and derivatives are compounds containing leucine or a derivative thereof resulting from reaction of leucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Thus, (±)-leucine is considered to be a fatty acid lipid molecule (±)-Leucine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (±)-Leucine is found, on average, in the highest concentration within a few different foods, such as red bell peppers, green zucchinis, and italian sweet red peppers and in a lower concentration in green bell peppers. This could make (±)-leucine a potential biomarker for the consumption of these foods.
CAS Number61-90-5
Structure
Thumb
Synonyms
SynonymSource
(+-)-LeucineChEBI
(RS)-LeucineChEBI
2-Amino-4-methylpentanoic acidChEBI
DL-LeucineChEBI
HleuChEBI
LChEBI
LeuChEBI
LeucinChEBI
LeuzinChEBI
2-Amino-4-methylpentanoateGenerator
PolyleucineMeSH
Poly(L-leucine)MeSH
Poly-L-leucineMeSH
(2S)-2-Amino-4-methylpentanoatebiospider
(2S)-2-amino-4-Methylpentanoic acidChEBI
(2S)-a-2-amino-4-MethylvalerateGenerator
(2S)-a-2-amino-4-Methylvaleric acidGenerator
(2S)-a-LeucineGenerator
(2S)-alpha-2-amino-4-MethylvalerateGenerator
(2S)-alpha-2-amino-4-Methylvaleric acidChEBI
(2S)-alpha-LeucineChEBI
(2S)-α-2-amino-4-methylvalerateGenerator
(2S)-α-2-amino-4-methylvaleric acidGenerator
(2S)-α-leucineGenerator
(S)-(+)-LeucineChEBI
(S)-2-Amino-4-methyl-pentanoic acidbiospider
(S)-2-Amino-4-methylpentanoatebiospider
(S)-2-amino-4-Methylpentanoic acidHMDB
(S)-2-Amino-4-methylvaleratebiospider
(S)-2-amino-4-Methylvaleric acidHMDB
(S)-LeucineChEBI
α-amino-α-aminoisocaproic acidbiospider
α-amino-«gamma»-methylvaleric acidbiospider
α-aminoisocaproic acidbiospider
2-Amino-4-methyl-valeric acidbiospider
2-amino-4-MethylvalerateGenerator
2-amino-4-Methylvaleric acidChEBI
4-methyl-L-Norvalinebiospider
FEMA 3297db_source
L-(+)-LeucineHMDB
L-2-Amino-4-methylpentanoic acidbiospider
L-2-Amino-4-methylvaleric acidbiospider
L-a-aminoisocaproatebiospider
L-a-Aminoisocaproic acidHMDB
L-alpha-aminoisocaproatebiospider
L-alpha-aminoisocaproic acidbiospider
L-LeucinChEBI
L-leucinebiospider
L-LeuzinChEBI
L-Norvaline, 4-methyl-biospider
LEUCINEChEBI
Leucine, 9CI, USAN; L-formdb_source
S-2-Amino-4-methylpentanoic acidbiospider
Predicted Properties
PropertyValueSource
Water Solubility69.8 g/LALOGPS
logP-1.8ALOGPS
logP-1.6ChemAxon
logS-0.27ALOGPS
pKa (Strongest Acidic)2.79ChemAxon
pKa (Strongest Basic)9.52ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity34.17 m³·mol⁻¹ChemAxon
Polarizability14.33 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC6H13NO2
IUPAC name2-amino-4-methylpentanoic acid
InChI IdentifierInChI=1S/C6H13NO2/c1-4(2)3-5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)
InChI KeyROHFNLRQFUQHCH-UHFFFAOYSA-N
Isomeric SMILESCC(C)CC(N)C(O)=O
Average Molecular Weight131.1729
Monoisotopic Molecular Weight131.094628665
Classification
Description belongs to the class of organic compounds known as leucine and derivatives. Leucine and derivatives are compounds containing leucine or a derivative thereof resulting from reaction of leucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentLeucine and derivatives
Alternative Parents
Substituents
  • Leucine or derivatives
  • Alpha-amino acid
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Fatty acid
  • Fatty acyl
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 54.94%; H 9.99%; N 10.68%; O 24.39%DFC
Melting PointMp 337 (293-295°)° dec.DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP-1.52HANSCH,C ET AL. (1995)
Experimental pKapKa2 9.74 (25°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]15D +17.3 (20% HCl)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-000i-9200000000-e6d3b36c12a4aec4abd2JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0a4i-1900000000-03b3ec429e0aedc946f6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-0900000000-f79f4d95d2df43505233JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-9e1901c72ddf2bca4bd8JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-000i-9100000000-991398731b9d8305622cJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-001i-0900000000-df557ff1e5f2eb62cf86JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-9100000000-5c9c34467c6dfc48536cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-9000000000-f34b46cb8fb87529bdf4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-9000000000-b3dd318079998826e948JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-000i-9000000000-18fba445b980b0e31f7eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-9000000000-eada8640560aac9a5800JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-9000000000-74bdf2f3d46a846bbebdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-4900000000-c727d81624633c25a855JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-9210000000-dad2c30020b4d935371fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-9000000000-1d904829702e07958a70JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-9000000000-d73af3689d7870fc55ccJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-9020000000-baee1e363027b359a5bfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-9100000000-d0d93ac13dda78e787fbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-9010000000-6102833218f4329e1e82JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-3900000000-065a2b56e0115c2fa6ecJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-9000000000-11c00b9c192007f304c8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0019-9700000000-9ca0528cb0f5d4c4e482JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9100000000-688e4e815455b96d48d3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-9a4bc07778f76172e1ecJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1900000000-d15c14abb456ab271111JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-7900000000-afc0316154ddc47ccadeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9000000000-b32e913349f93775ffb8JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-000l-9000000000-bf752e458f13eed8d7a2JSpectraViewer | MoNA
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID5880
ChEMBL IDCHEMBL291962
KEGG Compound IDC00123
Pubchem Compound ID6106
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB01746
HMDB IDHMDB00687
CRC / DFC (Dictionary of Food Compounds) IDBCS72-F:CBJ36-I
EAFUS ID2018
Dr. Duke IDLEUCINE
BIGG ID33942
KNApSAcK IDC00001377
HET IDLEU
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1030281
SuperScent IDNot Available
Wikipedia IDLeucine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti encephalopathic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
essentialDUKE
Enzymes
NameGene NameUniProt ID
Branched-chain-amino-acid aminotransferase, cytosolicBCAT1P54687
Branched-chain-amino-acid aminotransferase, mitochondrialBCAT2O15382
Probable leucine--tRNA ligase, mitochondrialLARS2Q15031
Leucine--tRNA ligase, cytoplasmicLARSQ9P2J5
Leucine carboxyl methyltransferase 1LCMT1Q9UIC8
Pathways
NameSMPDB LinkKEGG Link
Transcription/TranslationSMP00019 Not Available
Valine, Leucine and Isoleucine DegradationSMP00032 map00280
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
odorless
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).