Showing Compound Card for L-Leucine (CDB000133)

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Record Information
Version1.0
Created at2020-03-18 23:26:00 UTC
Updated at2020-12-07 19:07:09 UTC
CannabisDB IDCDB000133
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameL-Leucine
DescriptionLeucine, abbreviated as Leu or L, l-leucine, is an essential amino acid (meaning the body cannot synthesize it and it must be obtained from the diet) that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated −NH3+ form under biological conditions), an α-carboxylic acid group (which is in the deprotonated −COO− form under biological conditions), and a side chain isobutyl group, making it a non-polar aliphatic amino acid. Human dietary sources are foods that contain protein, such as meats, dairy products, soy products, beans and legumes. L-Leucine is a branched-chain amino acid (BCAA). BCAAs are essential amino acids whose carbon structure is marked by a branch point. These three amino acids are critical to human life and are particularly involved in stress, energy, and muscle metabolism. BCAA supplementation as therapy, both oral and intravenous, in human health and disease holds great promise. Despite their structural similarities, the branched amino acids have different metabolic routes, with valine going solely to carbohydrates, leucine solely to fats, and isoleucine to both. The different metabolism accounts for different requirements for these essential amino acids in humans: 12 mg/kg, 14 mg/kg, and 16 mg/kg of valine, leucine, and isoleucine, respectively. Furthermore, these amino acids have different deficiency symptoms. Valine deficiency is marked by neurological defects in the brain, while isoleucine deficiency is marked by muscle tremors. Many types of inborn errors of BCAA metabolism exist and are marked by various abnormalities. The most common form is the maple syrup urine disease (PMID: 10234605 ), marked by a characteristic sweet smell of urine. Other abnormalities are associated with a wide range of symptoms, such as mental retardation, ataxia, hypoglycemia, spinal muscle atrophy, rash, vomiting, and excessive muscle movement. Most forms of BCAA metabolism errors are corrected by dietary restriction of BCAA and at least one form is correctable by supplementation with 10 mg of biotin daily. BCAA are useful because they are metabolized primarily by muscle and particularly leucine, are most essential for muscle health. BCAA and other amino acids are frequently fed intravenously (TPN) to malnourished surgical patients and, in some cases, those with severe trauma. BCAA, particularly leucine, stimulate protein synthesis, increase reutilization of amino acids in many organs and reduce protein breakdown. Furthermore, leucine can be an important source of calories, and is superior as fuel to the ubiquitous intravenous glucose (dextrose). Leucine also stimulates insulin release, which in turn stimulates protein synthesis and inhibits protein breakdown. These effects are particularly useful in athletic training. BCAA should also replace the use of steroids by weightlifters. Huntington's chorea and anorexic disorders both are characterized by low serum BCAA. These diseases, as well as forms of Parkinson's, may respond to BCAA therapy. L-Leucine can be found in most biofluids, including blood, cerebrospinal fluid (CSF), feces, and sweat, as well as throughout most human tissues. L-Leucine exists in all living species, ranging from bacteria to humans. L-leucine is also found in Cannabis plants (PMID: 6991645 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
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 Weight131.17
Monoisotopic Molecular Weight131.0946
IUPAC Name(2S)-2-amino-4-methylpentanoic acid
Traditional NameL-leucine
CAS Registry Number71000-80-1
SMILES
CC(C)C[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C6H13NO2/c1-4(2)3-5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t5-/m0/s1
InChI KeyROHFNLRQFUQHCH-YFKPBYRVSA-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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point268 - 288 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility21.5 mg/mLNot Available
logP-1.52HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-000l-9000000000-bf752e458f13eed8d7a2Spectrum
GC-MSL-Leucine, 2 TMS, GC-MS Spectrumsplash10-0pb9-0900000000-c0176b3cef05fc597576Spectrum
GC-MSL-Leucine, 2 TMS, GC-MS Spectrumsplash10-0a4i-0900000000-eb7cee37b9d78694010cSpectrum
GC-MSL-Leucine, 2 TMS, GC-MS Spectrumsplash10-0a4i-0900000000-7033b5fdcd4216168462Spectrum
GC-MSL-Leucine, non-derivatized, GC-MS Spectrumsplash10-0a4i-0900000000-cd1de48a6db61eb4455eSpectrum
GC-MSL-Leucine, 2 TMS, GC-MS Spectrumsplash10-05fr-7900000000-e3b993b282ec2115b484Spectrum
GC-MSL-Leucine, non-derivatized, GC-MS Spectrumsplash10-0019-9000000000-6e468213b3429cf627bcSpectrum
GC-MSL-Leucine, non-derivatized, GC-MS Spectrumsplash10-0a4i-0900000000-ef06e48ca82519977a37Spectrum
GC-MSL-Leucine, non-derivatized, GC-MS Spectrumsplash10-0pb9-0900000000-c0176b3cef05fc597576Spectrum
GC-MSL-Leucine, non-derivatized, GC-MS Spectrumsplash10-0a4i-0900000000-eb7cee37b9d78694010cSpectrum
GC-MSL-Leucine, non-derivatized, GC-MS Spectrumsplash10-0a4i-0900000000-7033b5fdcd4216168462Spectrum
GC-MSL-Leucine, non-derivatized, GC-MS Spectrumsplash10-0a4i-0900000000-cd1de48a6db61eb4455eSpectrum
GC-MSL-Leucine, non-derivatized, GC-MS Spectrumsplash10-0udi-1391000000-5183562a14017e557e33Spectrum
GC-MSL-Leucine, non-derivatized, GC-MS Spectrumsplash10-05fr-7900000000-e3b993b282ec2115b484Spectrum
Predicted GC-MSL-Leucine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9000000000-70cdb961a0819be4318aSpectrum
Predicted GC-MSL-Leucine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-9100000000-991398731b9d8305622cSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9100000000-05b5a7a191a32803595eSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-5302e9c96e75e06e9705Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-9e70778b46864cd22996Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0019-9000000000-6e468213b3429cf627bcSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-4f403c61aaa8a103c049Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-d85fcc558423654f45fdSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-931937d3bdd49b3ae623Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-0930000000-aa1256c9224fecacf025Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-0a72425a86f804d3a16bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-4ed8cafebf4ee4e82e6aSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-3ac62b780abd90dd28b1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-eb75eb03a58512ea36dfSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-001i-0900000000-c0f28e4ebdef67c5b509Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-001i-0900000000-0751a9e803a2e7715d1aSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-001i-5900000000-8040fc883917239630a7Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-016s-9000000000-a7f9e8d43e66dbd02b6fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-001r-7900000000-da119558c426d9c9d3a1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-9000000000-ae8365105ae2a18e0c10Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-000f-9000000000-228ee614be6648b37433Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0006-9000000000-d1f3e047af455e156a1eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0006-9000000000-409dfbdb20719c3afda5Spectrum
MS/MSLC-MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positivesplash10-001i-0900000000-720554d58264a9cfdb67Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-001i-0900000000-90fab591d1f6d6318002Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0900000000-ed843252a559d532dc5eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0019-9500000000-b9f1203176ce0ca7c11cSpectrum
NMR
TypeDescriptionView
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Branched-chain-amino-acid aminotransferase, cytosolicBCAT112p12.1P54687 details
Branched-chain-amino-acid aminotransferase, mitochondrialBCAT219q13O15382 details
Probable leucine--tRNA ligase, mitochondrialLARS23p21.3Q15031 details
Leucine--tRNA ligase, cytoplasmicLARS5q32Q9P2J5 details
Leucine carboxyl methyltransferase 2LCMT215q15.3O60294 details
Leucine carboxyl methyltransferase 1LCMT116p12.1Q9UIC8 details
Transporters
Protein NameGene NameLocusUniprot IDDetails
Large neutral amino acids transporter small subunit 2SLC7A814q11.2Q9UHI5 details
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified2.31 mg/g dry wt
    • Jiamin Zheng, Yil...
 details
GabriolaDetected and Quantified1.21 mg/g dry wt
    • Jiamin Zheng, Yil...
 details
Island HoneyDetected and Quantified1.58 mg/g dry wt
    • Jiamin Zheng, Yil...
 details
QuadraDetected and Quantified1.4 mg/g dry wt
    • Jiamin Zheng, Yil...
 details
Sensi StarDetected and Quantified0.438 mg/g dry wt
    • Jiamin Zheng, Yil...
 details
Tangerine DreamDetected and Quantified1.26 mg/g dry wt
    • Jiamin Zheng, Yil...
 details
HMDB IDHMDB0000687
DrugBank IDDB00149
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000899
KNApSAcK IDC00001377
Chemspider ID5880
KEGG Compound IDC00123
BioCyc IDLEU
BiGG ID33942
Wikipedia LinkLeucine
METLIN ID24
PubChem Compound6106
PDB IDNot Available
ChEBI ID15603
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. Podebrad F, Heil M, Reichert S, Mosandl A, Sewell AC, Bohles H: 4,5-dimethyl-3-hydroxy-2[5H]-furanone (sotolone)--the odour of maple syrup urine disease. J Inherit Metab Dis. 1999 Apr;22(2):107-14. doi: 10.1023/a:1005433516026. [PubMed:10234605 ]

Enzymes

Enzyme Details
1. Branched-chain-amino-acid aminotransferase, cytosolic
General function:
Involved in catalytic activity
Specific function:
Catalyzes the first reaction in the catabolism of the essential branched chain amino acids leucine, isoleucine, and valine.
Gene Name:
BCAT1
Uniprot ID:
P54687
Molecular weight:
38644.77
Enzyme Details
2. Branched-chain-amino-acid aminotransferase, mitochondrial
General function:
Involved in catalytic activity
Specific function:
Catalyzes the first reaction in the catabolism of the essential branched chain amino acids leucine, isoleucine, and valine. May also function as a transporter of branched chain alpha-keto acids.
Gene Name:
BCAT2
Uniprot ID:
O15382
Molecular weight:
33776.315
Enzyme Details
3. Probable leucine--tRNA ligase, mitochondrial
General function:
Involved in nucleotide binding
Specific function:
Not Available
Gene Name:
LARS2
Uniprot ID:
Q15031
Molecular weight:
101975.43
Enzyme Details
4. Leucine--tRNA ligase, cytoplasmic
General function:
Involved in nucleotide binding
Specific function:
Catalyzes the specific attachment of an amino acid to its cognate tRNA in a two step reaction: the amino acid (AA) is first activated by ATP to form AA-AMP and then transferred to the acceptor end of the tRNA. Exhibits a post-transfer editing activity to hydrolyze mischarged tRNAs.
Gene Name:
LARS
Uniprot ID:
Q9P2J5
Molecular weight:
134465.155
Enzyme Details
5. Leucine carboxyl methyltransferase 2
General function:
Involved in methyltransferase activity
Specific function:
Probable S-adenosyl-L-methionine-dependent methyltransferase that acts as a component of the wybutosine biosynthesis pathway. Wybutosine is a hyper modified guanosine with a tricyclic base found at the 3'-position adjacent to the anticodon of eukaryotic phenylalanine tRNA. May methylate the carboxyl group of leucine residues to form alpha- leucine ester residues
Gene Name:
LCMT2
Uniprot ID:
O60294
Molecular weight:
75601.1
Enzyme Details
6. Leucine carboxyl methyltransferase 1
General function:
Involved in methyltransferase activity
Specific function:
Methylates the carboxyl group of the C-terminal leucine residue of protein phosphatase 2A catalytic subunits to form alpha-leucine ester residues.
Gene Name:
LCMT1
Uniprot ID:
Q9UIC8
Molecular weight:
32171.66

Transporters

Enzyme Details
1. Large neutral amino acids transporter small subunit 2
General function:
Involved in transport
Specific function:
Sodium-independent, high-affinity transport of small and large neutral amino acids such as alanine, serine, threonine, cysteine, phenylalanine, tyrosine, leucine, arginine and tryptophan, when associated with SLC3A2/4F2hc. Acts as an amino acid exchanger. Has higher affinity for L-phenylalanine than LAT1 but lower affinity for glutamine and serine. L-alanine is transported at physiological concentrations. Plays a role in basolateral (re)absorption of neutral amino acids. Involved in the uptake of methylmercury (MeHg) when administered as the L-cysteine or D,L-homocysteine complexes, and hence plays a role in metal ion homeostasis and toxicity. Involved in the cellular activity of small molecular weight nitrosothiols, via the stereoselective transport of L-nitrosocysteine (L-CNSO) across the transmembrane. Plays an essential role in the reabsorption of neutral amino acids from the epithelial cells to the bloodstream in the kidney
Gene Name:
SLC7A8
Uniprot ID:
Q9UHI5
Molecular weight:
58381.1