Record Information
Version1.0
Creation date2010-04-08 22:05:10 UTC
Update date2018-01-23 18:49:49 UTC
Primary IDFDB001946
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Leucine
DescriptionFlavouring ingredient; dietary supplement, nutrient. L-Leucine is found in many foods, some of which are lettuce, common bean, pacific herring, and kefir.
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
Bioavailability1ChemAxon
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
DescriptionThis compound belongs to the class of organic compounds known as leucine and derivatives. These 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
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 Key
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
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).