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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-05-18 14:35:54 UTC
Update Date2021-09-14 15:45:46 UTC
HMDB IDHMDB0013773
Secondary Accession Numbers
  • HMDB13773
Metabolite Identification
Common NameD-Leucine
DescriptionAn essential branched-chain amino acid important for hemoglobin formation. [PubChem]; Branched chain amino acids (BCAA) 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. 'BCAA' denotes valine, isoleucine and leucine which are branched chain essential amino acids. 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, marked by a characteristic urinary odor. 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. Stress state- e.g surgery, trauma, cirrhosis, infections, fever and starvation--require proportionately more BCAA than other amino acids and probably proportionately more leucine than either valine or isoleucine. BCAA and other amino acids are frequently fed intravenously (TPN) to malnourished surgical patients and in some cases of 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 as commonly used 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. BCAA, and particularly leucine, are among the amino acids most essential for muscle health. (http://www.dcnutrition.com); Leucine (abbreviated as Leu or L) is a branched-chain amino acid with the chemical formula HO2CCH(NH2)CH2CH(CH3)2. Leucine is classified as a hydrophobic amino acid due to its aliphatic isobutyl side chain. It is encoded by six codons (UUA, UUG, CUU, CUC, CUA, and CUG) and is a major component of the subunits in ferritin, astacin and other 'buffer' proteins. Leucine is an essential amino acid. Leucine is a branched-chain amino acid (BCAA) since it possesses an aliphatic side-chain that is non-linear.
Structure
Data?1582753145
Synonyms
ValueSource
(2R)-2-Amino-4-methylpentanoic acidChEBI
(R)-(-)-LeucineChEBI
(R)-LeucineChEBI
D-2-Amino-4-methylvaleric acidChEBI
D-LeucinChEBI
D-LeuzinChEBI
DLEChEBI
(2R)-2-Amino-4-methylpentanoateGenerator
D-2-Amino-4-methylvalerateGenerator
(R)-(−)-leucineHMDB
Chemical FormulaC6H13NO2
Average Molecular Weight131.1729
Monoisotopic Molecular Weight131.094628665
IUPAC Name(2R)-2-amino-4-methylpentanoic acid
Traditional NameL-(+)-leucine
CAS Registry Number328-38-1
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-/m1/s1
InChI KeyROHFNLRQFUQHCH-RXMQYKEDSA-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
  • D-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 effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point268 - 288 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility21.5 mg/mLNot Available
LogP-1.52HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker135.75930932474
[M-H]-McLean131.530932474
[M+H]+McLean135.030932474
[M-H]-Not Available135.759http://allccs.zhulab.cn/database/detail?ID=AllCCS00001746
Predicted Molecular 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
Polarizability14.25 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]+128.88731661259
DarkChem[M-H]-125.28131661259
DeepCCS[M+H]+130.40730932474
DeepCCS[M-H]-126.72330932474
DeepCCS[M-2H]-164.03530932474
DeepCCS[M+Na]+139.230932474
AllCCS[M+H]+132.032859911
AllCCS[M+H-H2O]+127.932859911
AllCCS[M+NH4]+135.832859911
AllCCS[M+Na]+136.932859911
AllCCS[M-H]-130.032859911
AllCCS[M+Na-2H]-132.932859911
AllCCS[M+HCOO]-136.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
D-LeucineCC(C)C[C@@H](N)C(O)=O1933.5Standard polar33892256
D-LeucineCC(C)C[C@@H](N)C(O)=O1111.9Standard non polar33892256
D-LeucineCC(C)C[C@@H](N)C(O)=O1204.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
D-Leucine,1TMS,isomer #1CC(C)C[C@@H](N)C(=O)O[Si](C)(C)C1170.2Semi standard non polar33892256
D-Leucine,1TMS,isomer #2CC(C)C[C@@H](N[Si](C)(C)C)C(=O)O1254.8Semi standard non polar33892256
D-Leucine,2TMS,isomer #1CC(C)C[C@@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C1291.2Semi standard non polar33892256
D-Leucine,2TMS,isomer #1CC(C)C[C@@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C1309.8Standard non polar33892256
D-Leucine,2TMS,isomer #1CC(C)C[C@@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C1399.1Standard polar33892256
D-Leucine,2TMS,isomer #2CC(C)C[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1455.3Semi standard non polar33892256
D-Leucine,2TMS,isomer #2CC(C)C[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1364.0Standard non polar33892256
D-Leucine,2TMS,isomer #2CC(C)C[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1562.8Standard polar33892256
D-Leucine,3TMS,isomer #1CC(C)C[C@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1493.4Semi standard non polar33892256
D-Leucine,3TMS,isomer #1CC(C)C[C@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1445.1Standard non polar33892256
D-Leucine,3TMS,isomer #1CC(C)C[C@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1394.1Standard polar33892256
D-Leucine,1TBDMS,isomer #1CC(C)C[C@@H](N)C(=O)O[Si](C)(C)C(C)(C)C1398.1Semi standard non polar33892256
D-Leucine,1TBDMS,isomer #2CC(C)C[C@@H](N[Si](C)(C)C(C)(C)C)C(=O)O1488.3Semi standard non polar33892256
D-Leucine,2TBDMS,isomer #1CC(C)C[C@@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1716.4Semi standard non polar33892256
D-Leucine,2TBDMS,isomer #1CC(C)C[C@@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1724.8Standard non polar33892256
D-Leucine,2TBDMS,isomer #1CC(C)C[C@@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1705.1Standard polar33892256
D-Leucine,2TBDMS,isomer #2CC(C)C[C@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1852.9Semi standard non polar33892256
D-Leucine,2TBDMS,isomer #2CC(C)C[C@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1787.1Standard non polar33892256
D-Leucine,2TBDMS,isomer #2CC(C)C[C@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1780.4Standard polar33892256
D-Leucine,3TBDMS,isomer #1CC(C)C[C@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2117.0Semi standard non polar33892256
D-Leucine,3TBDMS,isomer #1CC(C)C[C@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2059.0Standard non polar33892256
D-Leucine,3TBDMS,isomer #1CC(C)C[C@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1820.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - D-Leucine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-70cdb961a0819be4318a2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Leucine GC-MS (1 TMS) - 70eV, Positivesplash10-006x-9400000000-7ab4fbb59fba95725d962017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Leucine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Leucine 10V, Positive-QTOFsplash10-0019-9500000000-b9f1203176ce0ca7c11c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Leucine 20V, Positive-QTOFsplash10-000i-9000000000-67a158ab1e4ae695adc02016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Leucine 40V, Positive-QTOFsplash10-0a4i-9000000000-26a6ce4e691e4a2e9a2e2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Leucine 10V, Negative-QTOFsplash10-001i-1900000000-09bf92d358bbbf126e1b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Leucine 20V, Negative-QTOFsplash10-001i-8900000000-22b88c9f4eb6879081b52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Leucine 40V, Negative-QTOFsplash10-00di-9000000000-b95540fcafb248239e0b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Leucine 10V, Positive-QTOFsplash10-000i-9000000000-5b4d8d22ada5e6162a782021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Leucine 20V, Positive-QTOFsplash10-014i-9000000000-14b265a605e9048488ab2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Leucine 40V, Positive-QTOFsplash10-0006-9000000000-3c0a6fc73f829886989f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Leucine 10V, Negative-QTOFsplash10-001i-0900000000-39ea95bd23a0a91c505e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Leucine 20V, Negative-QTOFsplash10-001i-0900000000-9ce542c94acb97cb068f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Leucine 40V, Negative-QTOFsplash10-0006-9000000000-5cb04fd3e04c46a6e8a52021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01746
Phenol Explorer Compound IDNot Available
FooDB IDFDB111645
KNApSAcK IDNot Available
Chemspider ID388617
KEGG Compound IDC01570
BioCyc IDCPD-12150
BiGG IDNot Available
Wikipedia LinkLeucine
METLIN IDNot Available
PubChem Compound439524
PDB IDDLE
ChEBI ID28225
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available