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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-05-18 14:35:54 UTC

Update Date

2021-09-14 15:45:46 UTC

HMDB ID

HMDB0013773

Secondary Accession Numbers

HMDB13773

Metabolite Identification

Common Name

D-Leucine

Description

An 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2R)-2-Amino-4-methylpentanoic acid	ChEBI
(R)-(-)-Leucine	ChEBI
(R)-Leucine	ChEBI
D-2-Amino-4-methylvaleric acid	ChEBI
D-Leucin	ChEBI
D-Leuzin	ChEBI
DLE	ChEBI
(2R)-2-Amino-4-methylpentanoate	Generator
D-2-Amino-4-methylvalerate	Generator
(R)-(−)-leucine	HMDB

Chemical Formula

C₆H₁₃NO₂

Average Molecular Weight

131.1729

Monoisotopic Molecular Weight

131.094628665

IUPAC Name

(2R)-2-amino-4-methylpentanoic acid

Traditional Name

L-(+)-leucine

CAS Registry Number

328-38-1

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 Key

ROHFNLRQFUQHCH-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Leucine 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 Framework

Aliphatic acyclic compounds

External Descriptors

D-alpha-amino acid (CHEBI:28225 )
leucine (CHEBI:28225 )
Other amino acids (C01570 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0013773)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	268 - 288 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	21.5 mg/mL	Not Available
LogP	-1.52	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Baker	135.759	30932474
[M-H]-	McLean	131.5	30932474
[M+H]+	McLean	135.0	30932474
[M-H]-	Not Available	135.759	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001746

Predicted Molecular Properties

Property	Value	Source
Water Solubility	69.8 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-1.6	ChemAxon
logS	-0.27	ALOGPS
pKa (Strongest Acidic)	2.79	ChemAxon
pKa (Strongest Basic)	9.52	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	34.17 m³·mol⁻¹	ChemAxon
Polarizability	14.25 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	128.887	31661259
DarkChem	[M-H]-	125.281	31661259
DeepCCS	[M+H]+	130.407	30932474
DeepCCS	[M-H]-	126.723	30932474
DeepCCS	[M-2H]-	164.035	30932474
DeepCCS	[M+Na]+	139.2	30932474
AllCCS	[M+H]+	132.0	32859911
AllCCS	[M+H-H2O]+	127.9	32859911
AllCCS	[M+NH4]+	135.8	32859911
AllCCS	[M+Na]+	136.9	32859911
AllCCS	[M-H]-	130.0	32859911
AllCCS	[M+Na-2H]-	132.9	32859911
AllCCS	[M+HCOO]-	136.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
D-Leucine	CC(C)C[C@@H](N)C(O)=O	1933.5	Standard polar	33892256
D-Leucine	CC(C)C[C@@H](N)C(O)=O	1111.9	Standard non polar	33892256
D-Leucine	CC(C)C[C@@H](N)C(O)=O	1204.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
D-Leucine,1TMS,isomer #1	CC(C)C[C@@H](N)C(=O)O[Si](C)(C)C	1170.2	Semi standard non polar	33892256
D-Leucine,1TMS,isomer #2	CC(C)C[C@@H](N[Si](C)(C)C)C(=O)O	1254.8	Semi standard non polar	33892256
D-Leucine,2TMS,isomer #1	CC(C)C[C@@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1291.2	Semi standard non polar	33892256
D-Leucine,2TMS,isomer #1	CC(C)C[C@@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1309.8	Standard non polar	33892256
D-Leucine,2TMS,isomer #1	CC(C)C[C@@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1399.1	Standard polar	33892256
D-Leucine,2TMS,isomer #2	CC(C)C[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1455.3	Semi standard non polar	33892256
D-Leucine,2TMS,isomer #2	CC(C)C[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1364.0	Standard non polar	33892256
D-Leucine,2TMS,isomer #2	CC(C)C[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1562.8	Standard polar	33892256
D-Leucine,3TMS,isomer #1	CC(C)C[C@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1493.4	Semi standard non polar	33892256
D-Leucine,3TMS,isomer #1	CC(C)C[C@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1445.1	Standard non polar	33892256
D-Leucine,3TMS,isomer #1	CC(C)C[C@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1394.1	Standard polar	33892256
D-Leucine,1TBDMS,isomer #1	CC(C)C[C@@H](N)C(=O)O[Si](C)(C)C(C)(C)C	1398.1	Semi standard non polar	33892256
D-Leucine,1TBDMS,isomer #2	CC(C)C[C@@H](N[Si](C)(C)C(C)(C)C)C(=O)O	1488.3	Semi standard non polar	33892256
D-Leucine,2TBDMS,isomer #1	CC(C)C[C@@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1716.4	Semi standard non polar	33892256
D-Leucine,2TBDMS,isomer #1	CC(C)C[C@@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1724.8	Standard non polar	33892256
D-Leucine,2TBDMS,isomer #1	CC(C)C[C@@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1705.1	Standard polar	33892256
D-Leucine,2TBDMS,isomer #2	CC(C)C[C@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1852.9	Semi standard non polar	33892256
D-Leucine,2TBDMS,isomer #2	CC(C)C[C@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1787.1	Standard non polar	33892256
D-Leucine,2TBDMS,isomer #2	CC(C)C[C@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1780.4	Standard polar	33892256
D-Leucine,3TBDMS,isomer #1	CC(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)C	2117.0	Semi standard non polar	33892256
D-Leucine,3TBDMS,isomer #1	CC(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)C	2059.0	Standard non polar	33892256
D-Leucine,3TBDMS,isomer #1	CC(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)C	1820.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - D-Leucine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-70cdb961a0819be4318a	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Leucine GC-MS (1 TMS) - 70eV, Positive	splash10-006x-9400000000-7ab4fbb59fba95725d96	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Leucine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Leucine 10V, Positive-QTOF	splash10-0019-9500000000-b9f1203176ce0ca7c11c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Leucine 20V, Positive-QTOF	splash10-000i-9000000000-67a158ab1e4ae695adc0	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Leucine 40V, Positive-QTOF	splash10-0a4i-9000000000-26a6ce4e691e4a2e9a2e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Leucine 10V, Negative-QTOF	splash10-001i-1900000000-09bf92d358bbbf126e1b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Leucine 20V, Negative-QTOF	splash10-001i-8900000000-22b88c9f4eb6879081b5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Leucine 40V, Negative-QTOF	splash10-00di-9000000000-b95540fcafb248239e0b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Leucine 10V, Positive-QTOF	splash10-000i-9000000000-5b4d8d22ada5e6162a78	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Leucine 20V, Positive-QTOF	splash10-014i-9000000000-14b265a605e9048488ab	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Leucine 40V, Positive-QTOF	splash10-0006-9000000000-3c0a6fc73f829886989f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Leucine 10V, Negative-QTOF	splash10-001i-0900000000-39ea95bd23a0a91c505e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Leucine 20V, Negative-QTOF	splash10-001i-0900000000-9ce542c94acb97cb068f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Leucine 40V, Negative-QTOF	splash10-0006-9000000000-5cb04fd3e04c46a6e8a5	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01746

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB111645

KNApSAcK ID

Not Available

Chemspider ID

388617

KEGG Compound ID

C01570

BioCyc ID

CPD-12150

BiGG ID

Not Available

Wikipedia Link

Leucine

METLIN ID

Not Available

PubChem Compound

439524

PDB ID

DLE

ChEBI ID

28225

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for D-Leucine (HMDB0013773)

MOL for HMDB0013773 (D-Leucine)

3D MOL for HMDB0013773 (D-Leucine)

3D SDF for HMDB0013773 (D-Leucine)

3D-SDF for HMDB0013773 (D-Leucine)

PDB for HMDB0013773 (D-Leucine)

3D PDB for HMDB0013773 (D-Leucine)

SMILES for HMDB0013773 (D-Leucine)

INCHI for HMDB0013773 (D-Leucine)

Structure for HMDB0013773 (D-Leucine)

3D Structure for HMDB0013773 (D-Leucine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra