(±)-Leucine (CED0000558)

Record Information
Version1.0
Creation Date2016-05-25 21:00:42 UTC
Update Date2026-04-02 22:52:07 UTC
Accession NumberCHEM023371
Identification
Common Name(±)-Leucine
ClassSmall Molecule
Description
(±)-Leucine is an organic compound with the formula C6H13NO2 and an average molecular weight of 131.17 g/mol. (±)-Leucine belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. This compound is found in or released from 30 recorded sources across several categories. Within the realm of electrical and electronic equipment, it is associated with antennas, adjustable resistors, auxiliary devices, electric switches, and conductors or conductive bodies characterised by the conductive materials. In the category of food, food processing and cookware, it is linked to fermentation processes for beer, food preservation, and the preparation of malt, vinegar, wine, or sparkling wine, among four other sources. Additionally, it is found in household cleaning and consumer products, including bleaching agents, cigar cigarettes, non electric simulated smoking devices, other smoking requisites, and perfumes within detergents and soaps, as well as three further sources.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
(2S)-2-Amino-4-methylpentanoic acidChEBI
(2S)-alpha-2-Amino-4-methylvaleric acidChEBI
(2S)-alpha-LeucineChEBI
(S)-(+)-LeucineChEBI
(S)-LeucineChEBI
2-Amino-4-methylvaleric acidChEBI
LChEBI
L-LeucinChEBI
L-LeuzinChEBI
LeuChEBI
LEUCINEChEBI
(2S)-2-Amino-4-methylpentanoateGenerator
(2S)-a-2-Amino-4-methylvalerateGenerator
(2S)-a-2-Amino-4-methylvaleric acidGenerator
(2S)-alpha-2-Amino-4-methylvalerateGenerator
(2S)-Α-2-amino-4-methylvalerateGenerator
(2S)-Α-2-amino-4-methylvaleric acidGenerator
(2S)-a-LeucineGenerator
(2S)-Α-leucineGenerator
2-Amino-4-methylvalerateGenerator
(S)-2-Amino-4-methylpentanoateHMDB
(S)-2-Amino-4-methylpentanoic acidHMDB
(S)-2-Amino-4-methylvalerateHMDB
(S)-2-Amino-4-methylvaleric acidHMDB
4-Methyl-L-norvalineHMDB
L-(+)-LeucineHMDB
L-a-AminoisocaproateHMDB
L-a-Aminoisocaproic acidHMDB
L-alpha-AminoisocaproateHMDB
L-alpha-Aminoisocaproic acidHMDB
Leucine, L-isomerHMDB
L-Isomer leucineHMDB
Leucine, L isomerHMDB
Chemical FormulaC6H13NO2
Average Molecular Mass131.173 g/mol
Monoisotopic Mass131.095 g/mol
CAS Registry Number328-39-2
IUPAC Name(2S)-2-amino-4-methylpentanoic acid
Traditional NameL-leucine
SMILESCC(C)CC(N)C(O)=O
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
Chemical Taxonomy
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
  • L-alpha-amino acid
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Fatty acid
  • Fatty acyl
  • Amino acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Polarizability14.16 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-000i-9200000000-e6d3b36c12a4aec4abd2Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0a4i-1900000000-03b3ec429e0aedc946f6Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0a4i-0900000000-f79f4d95d2df43505233Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-9000000000-9e1901c72ddf2bca4bd8Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-000i-9100000000-991398731b9d8305622cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-df557ff1e5f2eb62cf86Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-9100000000-5c9c34467c6dfc48536cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-9000000000-f34b46cb8fb87529bdf4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9000000000-b3dd318079998826e948Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-9000000000-18fba445b980b0e31f7eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-9000000000-eada8640560aac9a5800Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-9000000000-74bdf2f3d46a846bbebdNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-4900000000-c727d81624633c25a855Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-9210000000-dad2c30020b4d935371fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-9000000000-1d904829702e07958a70Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-9000000000-d73af3689d7870fc55ccNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-9020000000-baee1e363027b359a5bfNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-9100000000-d0d93ac13dda78e787fbNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-9010000000-6102833218f4329e1e82Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-3900000000-065a2b56e0115c2fa6ecNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-9000000000-11c00b9c192007f304c8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0019-9700000000-9ca0528cb0f5d4c4e482Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-9100000000-688e4e815455b96d48d3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9000000000-9a4bc07778f76172e1ecNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-1900000000-d15c14abb456ab271111Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01q9-7900000000-afc0316154ddc47ccadeNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05fr-9000000000-b32e913349f93775ffb8Not AvailableView Spectrum
MSMS Spectrumsplash10-000l-9000000000-bf752e458f13eed8d7a2Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2402.0Log mg/kg[1400:4300]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
490Personal care & cosmeticsNot Available
504Adjustable ResistorsElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
551Processing FishFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
553Treatment Of HopsFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
634BucklesTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Excitatory amino acid transporter 3 structureClick to view 3D structureExcitatory amino acid transporter 3P43005HumansPredicted (SEA)0.544945
Glutamate receptor ionotropic, kainate 1 structureClick to view 3D structureGlutamate receptor ionotropic, kainate 1P39086HumansPredicted (SEA)0.311397
Click to view 3D structureAsc-type amino acid transporter 1P63116RatPredicted (SEA)0.155698
Click to view 3D structureGlutamate receptor ionotropic, kainate 1P22756Rattus norvegicusPredicted (SEA)1.16774
Click to view 3D structureGlutamate receptor ionotropic, kainate 3P42264Rattus norvegicusPredicted (SEA)0.934191
Click to view 3D structureGlutamate receptor ionotropic, kainate 2P42260Rattus norvegicusPredicted (SEA)0.700643
Metabotropic glutamate receptor 2 structureClick to view 3D structureMetabotropic glutamate receptor 2Q14416HumansPredicted (SEA)2.33548
Glutamate receptor ionotropic, kainate 2 structureClick to view 3D structureGlutamate receptor ionotropic, kainate 2Q13002HumansPredicted (SEA)0.544945
Click to view 3D structureGlutamate transporter homologO59010Pyrococcus horikoshii (strain ATCC 700860 / DSM 12428 / JCM 9974 /NBRC 100139 / OT-3)Predicted (SEA)0.155698
Click to view 3D structureMetabotropic glutamate receptor 6O15303HumansPredicted (SEA)1.24559
Metabotropic glutamate receptor 1 structureClick to view 3D structureMetabotropic glutamate receptor 1Q13255HumansPredicted (SEA)2.88042
Click to view 3D structureGlutamate receptor 1P19490Rattus norvegicusPredicted (SEA)1.32344
Click to view 3D structureMetabotropic glutamate receptor 2P31421Rattus norvegicusPredicted (SEA)3.19182
Click to view 3D structureGlutamine synthetaseP0A9C5Escherichia coli K-12Predicted (SEA)0.311397
Click to view 3D structureS-methylmethionine--homocysteine S-methyltransferase BHMT2Q9H2M3HumansPredicted (SEA)0.389246
Click to view 3D structureMetabotropic glutamate receptor 8P47743Mus musculusPredicted (SEA)0.467095
Click to view 3D structureGlutamate receptor 4P48058HumansPredicted (SEA)0.155698
Click to view 3D structureMetabotropic glutamate receptor 6P35349Rattus norvegicusPredicted (SEA)1.08989
Glutamate receptor 1 structureClick to view 3D structureGlutamate receptor 1P42261HumansPredicted (SEA)2.56902
Glutamate receptor 2 structureClick to view 3D structureGlutamate receptor 2P42262HumansPredicted (SEA)0.856341
Click to view 3D structureGlutamate receptor ionotropic, kainate 5Q16478HumansPredicted (SEA)0.700643
Click to view 3D structureIntestinal-type alkaline phosphataseP09923HumansPredicted (SEA)0.311397
Alkaline phosphatase, tissue-nonspecific isozyme structureClick to view 3D structureAlkaline phosphatase, tissue-nonspecific isozymeP05186HumansPredicted (SEA)1.16774
Click to view 3D structureGlutamate receptor ionotropic, kainate 3Q13003HumansPredicted (SEA)0.467095
Click to view 3D structureAminopeptidase NP15145Sus scrofaPredicted (SEA)11.7552
Concentrations
Not Available
External Links
DrugBank IDDB00149
HMDB IDHMDB0000687
FooDB IDFDB000899
Phenol Explorer IDNot Available
KNApSAcK IDC00001377
BiGG ID33942
BioCyc IDLEU
METLIN ID24
PDB IDNot Available
Wikipedia LinkLeucine
Chemspider ID5880
ChEBI ID15603
PubChem Compound ID6106
Kegg Compound IDC00123
YMDB IDYMDB00387
ECMDB IDECMDB00687
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Leuchtenberger, Wolfgang; Karrenbauer, Michael; Ploecker, Ulf. Scale-up of an enzyme membrane reactor process for the manufacture of L-enantiomeric compounds. Annals of the New York Academy of Sciences (1984), 434(Enzyme Eng.), 78-86.
2. A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)
3. Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en
4. Leuchtenberger, Wolfgang; Karrenbauer, Michael; Ploecker, Ulf. Scale-up of an enzyme membrane reactor process for the manufacture of L-enantiomeric compounds. Annals of the New York Academy of Sciences (1984), 434(Enzyme Eng.), 78-86.
5. Deng C, Shang C, Hu Y, Zhang X: Rapid diagnosis of phenylketonuria and other aminoacidemias by quantitative analysis of amino acids in neonatal blood spots by gas chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Jul 25;775(1):115-20.
6. Peng CT, Wu KH, Lan SJ, Tsai JJ, Tsai FJ, Tsai CH: Amino acid concentrations in cerebrospinal fluid in children with acute lymphoblastic leukemia undergoing chemotherapy. Eur J Cancer. 2005 May;41(8):1158-63. Epub 2005 Apr 14.
7. Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6.
8. Yoshimasa T, Nakao K, Ohtsuki H, Li S, Imura H: Methionine-enkephalin and leucine-enkephalin in human sympathoadrenal system and pheochromocytoma. J Clin Invest. 1982 Mar;69(3):643-50.
9. Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24.
10. Jansson T, Scholtbach V, Powell TL: Placental transport of leucine and lysine is reduced in intrauterine growth restriction. Pediatr Res. 1998 Oct;44(4):532-7.
11. Nicholson JK, O'Flynn MP, Sadler PJ, Macleod AF, Juul SM, Sonksen PH: Proton-nuclear-magnetic-resonance studies of serum, plasma and urine from fasting normal and diabetic subjects. Biochem J. 1984 Jan 15;217(2):365-75.
12. Lichtenstein AH, Hachey DL, Millar JS, Jenner JL, Booth L, Ordovas J, Schaefer EJ: Measurement of human apolipoprotein B-48 and B-100 kinetics in triglyceride-rich lipoproteins using [5,5,5-2H3]leucine. J Lipid Res. 1992 Jun;33(6):907-14.
13. Mero A: Leucine supplementation and intensive training. Sports Med. 1999 Jun;27(6):347-58.
14. Sakamoto M, Nakao K, Yoshimasa T, Ikeda Y, Suda M, Takasu K, Shimbo S, Yanaihara N, Imura H: Occurrence of methionine-enkephalin-Arg6-Gly7-Leu8 with methionine-enkephalin, leucine-enkephalin and methionine-enkephalin-Arg6-Phe7 in human gastric antrum. J Clin Endocrinol Metab. 1983 Jan;56(1):202-4.
15. Yudkoff M, Daikhin Y, Nissim I, Horyn O, Luhovyy B, Lazarow A, Nissim I: Brain amino acid requirements and toxicity: the example of leucine. J Nutr. 2005 Jun;135(6 Suppl):1531S-8S.
16. Iannoli P, Miller JH, Wang HT, Bode B, Souba WW, Avissar NE, Sax HC: Characterization of L-leucine transport system in brush border membranes from human and rabbit small intestine. Metabolism. 1999 Nov;48(11):1432-6.
17. Hagenfeldt L, Bjerkenstedt L, Edman G, Sedvall G, Wiesel FA: Amino acids in plasma and CSF and monoamine metabolites in CSF: interrelationship in healthy subjects. J Neurochem. 1984 Mar;42(3):833-7.
18. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762.
19. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=17609475
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=22735334
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=24206068
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=24333966
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=8798704