| Record Information |
|---|
| Version | 1.0 |
|---|
| Creation Date | 2016-09-30 22:34:54 UTC |
|---|
| Update Date | 2020-06-04 22:32:44 UTC |
|---|
| BMDB ID | BMDB0000687 |
|---|
| Secondary Accession Numbers | |
|---|
| Metabolite Identification |
|---|
| Common Name | L-Leucine |
|---|
| Description | L-Leucine, also known as (S)-leucine or L-leucin, 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. L-Leucine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Leucine exists in all living species, ranging from bacteria to humans. L-Leucine can be converted into L-leucine through its interaction with the enzyme large neutral amino acids transporter small subunit 1. In cattle, L-leucine is involved in the metabolic pathway called the leucine stimulation ON insulin signaling pathway. L-Leucine is a potentially toxic compound. |
|---|
| Structure | |
|---|
| Synonyms | | Value | Source |
|---|
| (2S)-2-Amino-4-methylpentanoic acid | ChEBI | | (2S)-alpha-2-Amino-4-methylvaleric acid | ChEBI | | (2S)-alpha-Leucine | ChEBI | | (S)-(+)-Leucine | ChEBI | | (S)-Leucine | ChEBI | | 2-Amino-4-methylvaleric acid | ChEBI | | L | ChEBI | | L-Leucin | ChEBI | | L-Leuzin | ChEBI | | Leu | ChEBI | | LEUCINE | ChEBI | | (2S)-2-Amino-4-methylpentanoate | Generator | | (2S)-a-2-Amino-4-methylvalerate | Generator | | (2S)-a-2-Amino-4-methylvaleric acid | Generator | | (2S)-alpha-2-Amino-4-methylvalerate | Generator | | (2S)-Α-2-amino-4-methylvalerate | Generator | | (2S)-Α-2-amino-4-methylvaleric acid | Generator | | (2S)-a-Leucine | Generator | | (2S)-Α-leucine | Generator | | 2-Amino-4-methylvalerate | Generator | | (S)-2-Amino-4-methylpentanoate | HMDB | | (S)-2-Amino-4-methylpentanoic acid | HMDB | | (S)-2-Amino-4-methylvalerate | HMDB | | (S)-2-Amino-4-methylvaleric acid | HMDB | | 4-Methyl-L-norvaline | HMDB | | L-(+)-Leucine | HMDB | | L-a-Aminoisocaproate | HMDB | | L-a-Aminoisocaproic acid | HMDB | | L-alpha-Aminoisocaproate | HMDB | | L-alpha-Aminoisocaproic acid | HMDB | | Leucine, L-isomer | HMDB | | L-Isomer leucine | HMDB | | Leucine, L isomer | HMDB |
|
|---|
| Chemical Formula | C6H13NO2 |
|---|
| Average Molecular Weight | 131.1729 |
|---|
| Monoisotopic Molecular Weight | 131.094628665 |
|---|
| IUPAC Name | (2S)-2-amino-4-methylpentanoic acid |
|---|
| Traditional Name | L-leucine |
|---|
| CAS Registry Number | 61-90-5 |
|---|
| 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 Key | ROHFNLRQFUQHCH-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. |
|---|
| 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
- 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 Framework | Aliphatic acyclic compounds |
|---|
| External Descriptors | |
|---|
| Ontology |
|---|
| Status | Detected and Quantified |
|---|
| Origin | |
|---|
| Biofunction | Not Available |
|---|
| Application | Not Available |
|---|
| Cellular locations | |
|---|
| Physical Properties |
|---|
| State | Solid |
|---|
| Experimental 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) |
|
|---|
| Predicted Properties | |
|---|
| Spectra |
|---|
| Spectra | |
|---|
| Biological Properties |
|---|
| Cellular Locations | |
|---|
| Biospecimen Locations | - Adipose Tissue
- Adrenal Medulla
- Bladder
- Blood
- Colostrum
- Epidermis
- Fibroblasts
- Intestine
- Kidney
- Liver
- Longissimus Thoracis Muscle
- Mammary Gland
- Milk
- Muscle
- Neuron
- Placenta
- Platelet
- Prostate Tissue
- Ruminal Fluid
- Semen
- Semimembranosus Muscle
- Testis
|
|---|
| Pathways | |
|---|
| Normal Concentrations |
|---|
| |
| Adipose Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Adrenal Medulla | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Bladder | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 107.2 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 205-264 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 132.6 uM | Not Specified | Both | Normal | | details | | Blood | Detected and Quantified | 90-117 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 212 +/- 24 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 67-1877 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 152-162 uM | Not Specified | Not Specified | Normal | | details | | Colostrum | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Colostrum | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Epidermis | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Fibroblasts | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Intestine | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Kidney | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected and Quantified | 426 +/- 117 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Longissimus Thoracis Muscle | Detected and Quantified | 154 +/- 37 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 4.64 +/- 1.55 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 2 - 22 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 25919.988 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 25919.988 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 25919.988 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 25919.988 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 25157.635 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 25157.635 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 25157.635 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 3.80 +/- 1.31 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 6.8 +/- 0.5 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 4.9 +/- 0.4 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 5.5 +/- 0.5 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 6.3 +/- 1.4 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 3.81 +/- 0.83 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 138.21 +/- 19.52 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 150.85 +/- 24.51 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 80-424 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 390.39 +/- 33.32 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 770 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 7100 +/- 1140 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 8630 +/- 1800 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 1860 +/- 400 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 4030 +/- 990 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 86.05 +/- 6.13 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 180-256 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 238-960 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Neuron | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Platelet | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Prostate Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 119.2 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 182.8 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 191.3 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 125.8 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 125.79 +/- 5.98 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 76-571 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 70-159 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 119 +/- 17 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 183 +/- 76 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 191 +/- 44 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 146 +/- 46 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 145 +/- 46 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 603 +/- 119 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 99.2 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 164 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 155 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 109 uM | Not Specified | Not Specified | Normal | | details | | Semen | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Semen | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Semimembranosus Muscle | Detected and Quantified | 158 +/- 33 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Testis | Detected and Quantified | 40 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Testis | Detected and Quantified | 138 +/- 23 nmol/g of tissue | Not Specified | Not Specified | Normal | | details |
|
|---|
| Abnormal Concentrations |
|---|
| |
| Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Treated with growth-promoting hormones | | details | | Blood | Detected and Quantified | 102.2 uM | Not Specified | Not Specified | Bovine spongiform encephalopathy negative | | details | | Blood | Detected and Quantified | 120.7 uM | Not Specified | Not Specified | Bovine spongiform encephalopathy positive | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Sub/clinical ketosis | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | All Mycobacterium avium subsp. paratuberculosis-infected | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | High dose Mycobacterium avium subsp. paratuberculosis-infected | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Low dose Mycobacterium avium subsp. paratuberculosis-infected | | details | | Ruminal Fluid | Detected and Quantified | 191.29 +/- 42.3 uM | Not Specified | Not Specified | Rumen acidosis | | details |
|
|---|
| External Links |
|---|
| HMDB ID | HMDB0000687 |
|---|
| DrugBank ID | DB00149 |
|---|
| Phenol Explorer Compound ID | Not Available |
|---|
| FooDB ID | FDB000899 |
|---|
| KNApSAcK ID | C00001377 |
|---|
| Chemspider ID | 5880 |
|---|
| KEGG Compound ID | C00123 |
|---|
| BioCyc ID | LEU |
|---|
| BiGG ID | 33942 |
|---|
| Wikipedia Link | Leucine |
|---|
| METLIN ID | 24 |
|---|
| PubChem Compound | 6106 |
|---|
| PDB ID | Not Available |
|---|
| ChEBI ID | 15603 |
|---|
| References |
|---|
| Synthesis Reference | 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. |
|---|
| Material Safety Data Sheet (MSDS) | Not Available |
|---|
| General References | - A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
- Fooddata+, The Technical University of Denmark (DTU) [Link]
|
|---|