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Showing NP-Card for L-Leucine (NP0001387)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2022-02-14 17:24:25 UTC
NP-MRD IDNP0001387
Secondary Accession NumbersNone
Natural Product Identification
Common NameL-Leucine
DescriptionLeucine (Leu) or L-leucine is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-leucine is one of 20 proteinogenic amino acids, i.E., The amino acids used in the biosynthesis of proteins. Leucine is found in all organisms ranging from bacteria to plants to animals. It is classified as a non-polar, uncharged (at physiological pH) aliphatic amino acid. Leucine is essential in humans, meaning the body cannot synthesize it, and it must be obtained from the diet. 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). The BCAAs consist of leucine, valine and isoleucine (and occasionally threonine). BCAAs are essential amino acids whose carbon structure is marked by a branch point at the beta-carbon position. BCAAs 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. BCAAs have different metabolic routes, with valine going solely to carbohydrates (glucogenic), leucine solely to fats (ketogenic) and isoleucine being both a glucogenic and a ketogenic amino acid. 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. The primary metabolic end products of leucine metabolism are acetyl-CoA and acetoacetate; consequently, it is one of the two exclusively ketogenic amino acids, with lysine being the other. Leucine is the most important ketogenic amino acid in humans. The vast majority of l-leucine metabolism is initially catalyzed by the branched-chain amino acid aminotransferase enzyme, producing alpha-ketoisocaproate (alpha-KIC). Alpha-KIC is metabolized by the mitochondrial enzyme branched-chain alpha-ketoacid dehydrogenase, which converts it to isovaleryl-CoA. Isovaleryl-CoA is subsequently metabolized by the enzyme isovaleryl-CoA dehydrogenase and converted to beta-methylcrotonyl-CoA (MC-CoA), which is used in the synthesis of acetyl-CoA and other compounds. During biotin deficiency, HMB can be synthesized from MC-CoA via enoyl-CoA hydratase and an unknown thioesterase enzyme, which convert MC-CoA into HMB-CoA and HMB-CoA into HMB respectively. Leucine has the capacity to directly stimulate myofibrillar muscle protein synthesis (PMID 15051860 ). This effect of leucine arises results from its role as an activator of the mechanistic target of rapamycin (mTOR) (PMID 23551944 ) a serine-threonine protein kinase that regulates protein biosynthesis and cell growth. The activation of mTOR by leucine is mediated through Rag GTPases. Leucine, like other BCAAs, is associated with insulin resistance. In particular, higher levels of leucine are observed in the blood of diabetic mice, rats, and humans (PMID 25287287 ). BCAAs such as leucine have different deficiency symptoms. Valine deficiency is marked by neurological defects in the brain, while isoleucine deficiency is marked by muscle tremors. Persistently low leucine levels can result in decreased appetite, poor feeding, lethargy, poor growth, weight loss, skin rashes, hair loss, and desquamation. Many types of inborn errors of BCAA metabolism exist and these are marked by various abnormalities. The most common form is 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 BCAAs and at least one form is correctable by supplementation with 10 mg of biotin daily. - BCAAs are useful because they are metabolized primarily by muscle. Stress states - e.G surgery, trauma, cirrhosis, infections, fever and starvation--require proportionately more BCAAs than other amino acids and probably proportionately more leucine than either valine or isoleucine. BCAAs and other amino acids are frequently fed intravenously (TPN) to malnourished surgical patients and in some cases of severe trauma. BCAAs, 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. Huntington's chorea and anorexic disorders both are characterized by low serum BCAAs. These diseases, as well as forms of Parkinson's, may respond to BCAA therapy.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001387 (L-Leucine)


  Mrv1652309272007262D          

  9  8  0  0  1  0            999 V2000
    1.7862   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    1.0310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.2063    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3572   -1.0313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  6  4  1  0  0  0  0
  3  6  1  0  0  0  0
  8  3  1  0  0  0  0
  2  8  1  0  0  0  0
  4  5  2  0  0  0  0
  6  7  1  1  0  0  0
  8  9  1  0  0  0  0
M  END
Download

3D MOL for NP0001387 (L-Leucine)

HMDB0000687
     RDKit          3D
L-Leucine
 22 21  0  0  0  0  0  0  0  0999 V2000
   -1.8045   -0.8946    0.8073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1199    0.3943    0.4509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1462    1.2899   -0.2060 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0185    0.2274   -0.4955 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1068   -0.6843    0.0818 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5697   -0.0636    1.2936 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2274   -0.8130   -0.8810 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0686   -1.3261   -2.0144 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5043   -0.3689   -0.5659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8707   -0.6977    1.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3729   -1.3681    1.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7911   -1.5736   -0.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7870    0.9059    1.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0926    2.3225    0.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9664    1.3641   -1.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1882    0.9278    0.0118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3425   -0.2592   -1.4095 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4328    1.2334   -0.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6616   -1.6542    0.3514 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7168    0.9603    1.2128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4117   -0.5169    1.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7639    0.5946   -0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  3 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  1
  6 20  1  0
  6 21  1  0
  9 22  1  0
M  END
Download

3D SDF for NP0001387 (L-Leucine)


  Mrv1652309272007262D          

  9  8  0  0  1  0            999 V2000
    1.7862   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    1.0310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.2063    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3572   -1.0313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  6  4  1  0  0  0  0
  3  6  1  0  0  0  0
  8  3  1  0  0  0  0
  2  8  1  0  0  0  0
  4  5  2  0  0  0  0
  6  7  1  1  0  0  0
  8  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001387

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C6H13NO2

> <MOLECULAR_WEIGHT>
131.1729

> <EXACT_MASS>
131.094628665

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
14.158501021186428

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-4-methylpentanoic acid

> <ALOGPS_LOGP>
-1.82

> <JCHEM_LOGP>
-1.5861571715466434

> <ALOGPS_LOGS>
-0.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7877088821858544

> <JCHEM_PKA_STRONGEST_BASIC>
9.51901425787269

> <JCHEM_POLAR_SURFACE_AREA>
63.31999999999999

> <JCHEM_REFRACTIVITY>
34.1709

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.98e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-leucine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0001387 (L-Leucine)

HMDB0000687
     RDKit          3D
L-Leucine
 22 21  0  0  0  0  0  0  0  0999 V2000
   -1.8045   -0.8946    0.8073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1199    0.3943    0.4509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1462    1.2899   -0.2060 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0185    0.2274   -0.4955 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1068   -0.6843    0.0818 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5697   -0.0636    1.2936 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2274   -0.8130   -0.8810 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0686   -1.3261   -2.0144 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5043   -0.3689   -0.5659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8707   -0.6977    1.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3729   -1.3681    1.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7911   -1.5736   -0.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7870    0.9059    1.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0926    2.3225    0.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9664    1.3641   -1.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1882    0.9278    0.0118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3425   -0.2592   -1.4095 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4328    1.2334   -0.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6616   -1.6542    0.3514 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7168    0.9603    1.2128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4117   -0.5169    1.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7639    0.5946   -0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  3 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  1
  6 20  1  0
  6 21  1  0
  9 22  1  0
M  END
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PDB for NP0001387 (L-Leucine)

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0       3.334  -0.385   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -3.334   0.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.667   0.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.001   0.385   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.001   1.925   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.667  -0.385   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       0.667  -1.925   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -2.001  -0.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.001  -1.925   0.000  0.00  0.00           C+0
CONECT    1    4                                                            
CONECT    2    8                                                            
CONECT    3    6    8                                                       
CONECT    4    1    6    5                                                  
CONECT    5    4                                                            
CONECT    6    4    3    7                                                  
CONECT    7    6                                                            
CONECT    8    3    2    9                                                  
CONECT    9    8                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for NP0001387 (L-Leucine)

COMPND    HMDB0000687
HETATM    1  C1  UNL     1      -1.804  -0.895   0.807  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.120   0.394   0.451  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.146   1.290  -0.206  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.018   0.227  -0.496  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.107  -0.684   0.082  1.00  0.00           C  
HETATM    6  N1  UNL     1       1.570  -0.064   1.294  1.00  0.00           N  
HETATM    7  C6  UNL     1       2.227  -0.813  -0.881  1.00  0.00           C  
HETATM    8  O1  UNL     1       2.069  -1.326  -2.014  1.00  0.00           O  
HETATM    9  O2  UNL     1       3.504  -0.369  -0.566  1.00  0.00           O  
HETATM   10  H1  UNL     1      -2.871  -0.698   1.040  1.00  0.00           H  
HETATM   11  H2  UNL     1      -1.373  -1.368   1.708  1.00  0.00           H  
HETATM   12  H3  UNL     1      -1.791  -1.574  -0.068  1.00  0.00           H  
HETATM   13  H4  UNL     1      -0.787   0.906   1.384  1.00  0.00           H  
HETATM   14  H5  UNL     1      -2.093   2.322   0.213  1.00  0.00           H  
HETATM   15  H6  UNL     1      -1.966   1.364  -1.289  1.00  0.00           H  
HETATM   16  H7  UNL     1      -3.188   0.928   0.012  1.00  0.00           H  
HETATM   17  H8  UNL     1      -0.343  -0.259  -1.409  1.00  0.00           H  
HETATM   18  H9  UNL     1       0.433   1.233  -0.712  1.00  0.00           H  
HETATM   19  H10 UNL     1       0.662  -1.654   0.351  1.00  0.00           H  
HETATM   20  H11 UNL     1       1.717   0.960   1.213  1.00  0.00           H  
HETATM   21  H12 UNL     1       2.412  -0.517   1.699  1.00  0.00           H  
HETATM   22  H13 UNL     1       3.764   0.595  -0.453  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3    4   13
CONECT    3   14   15   16
CONECT    4    5   17   18
CONECT    5    6    7   19
CONECT    6   20   21
CONECT    7    8    8    9
CONECT    9   22
END
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SMILES for NP0001387 (L-Leucine)

CC(C)C[C@H](N)C(O)=O
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INCHI for NP0001387 (L-Leucine)

InChI=1S/C6H13NO2/c1-4(2)3-5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t5-/m0/s1
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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 Mass131.1729 Da
Monoisotopic Mass131.09463 Da
IUPAC Name(2S)-2-amino-4-methylpentanoic acid
Traditional NameL-leucine
CAS Registry Number61-90-5
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 KeyROHFNLRQFUQHCH-YFKPBYRVSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-02-14View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)v.dorna83@yahoo.comNot AvailableNot Available2021-08-03View Spectrum
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Abies balsameaLOTUS Database
Abramis bramaFooDB
Abutilon indicumLOTUS Database
Achillea millefoliumLOTUS Database
AcipenseridaeFooDB
Actinidia chinensisFooDB
Agaricus bisporusFooDB
Agaricus campestrisLOTUS Database
AgaveFooDB
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosumFooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Aloysia triphyllaFooDB
Amanita muscariaLOTUS Database
AmaranthusFooDB
Amaranthus spinosusLOTUS Database
Amelanchier alnifoliaFooDB
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anarhichas lupusFooDB
AnatidaeFooDB
Anethum graveolensFooDB
Angelica keiskeiFooDB
AnguilliformesFooDB
Annona cherimolaFooDB
Annona muricataFooDB
Annona reticulataFooDB
Annona squamosaFooDB
Anthriscus cerefoliumFooDB
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaeaFooDB
Arctium lappaFooDB
Armoracia rusticanaFooDB
Artemia salinaLOTUS Database
Artemisia absinthiumLOTUS Database
Artemisia dracunculusFooDB
Artemisia vulgarisFooDB
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Asparagus officinalisFooDB
AstacideaFooDB
Attalea speciosaFooDB
Auricularia auricula-judaeFooDB
Auricularia polytrichaFooDB
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Basella albaFooDB
Belone beloneFooDB
Benincasa hispidaFooDB
Bertholletia excelsaFooDB
Beta vulgarisFooDB
Beta vulgaris ssp. ciclaFooDB
BivalviaFooDB
Borago officinalisFooDB
Bos taurusFooDB
BrachyuraFooDB
Brassica alboglabraFooDB
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridisFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensisFooDB
Brassica rapa var. rapaFooDB
Brassica ruvoFooDB
Brosimum alicastrumFooDB
Byrsonima crassifoliaFooDB
Cajanus cajanFooDB
Calendula officinalisLOTUS Database
Canarium ovatumFooDB
Cancer magisterFooDB
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsicum annuumKNApSAcK Database
Capsicum annuum L.FooDB
Capsicum annuum var. annuumFooDB
Capsicum chinenseFooDB
Capsicum pubescensFooDB
Carica papaya L.FooDB
CarideaFooDB
Carissa macrocarpaFooDB
Carthamus tinctoriusFooDB
Carum carviFooDB
CaryaFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Castanea crenataFooDB
Castanea mollissimaFooDB
Castanea sativaFooDB
Catha edulisLOTUS Database
Ceratonia siliquaFooDB
CervidaeFooDB
Chamaemelum nobileFooDB
Chamerion angustifoliumFooDB
Chenopodium albumFooDB
Chenopodium quinoaFooDB
Chionoecetes opilioFooDB
Chlamydomonas reinhardtiiLOTUS Database
Chrysanthemum coronariumFooDB
Cicer arietinumFooDB
CichlidaeFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
Cinnamomum aromaticumFooDB
Cinnamomum verumFooDB
CirsiumFooDB
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus latifoliaFooDB
Citrus limonFooDB
Citrus maximaFooDB
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Claviceps purpureaLOTUS Database
ClupeinaeFooDB
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colchicum trigynumLOTUS Database
Colocasia esculentaFooDB
ColumbidaeFooDB
Corchorus olitoriusFooDB
CoregonusFooDB
Coriandrum sativum L.FooDB
CorylusFooDB
Corylus avellanaFooDB
Crassostrea gigasFooDB
Crassostrea virginicaFooDB
Crateva religiosaFooDB
Crocus sativusFooDB
Cucumis meloFooDB
Cucumis metuliferusFooDB
Cucumis sativus L.FooDB
CucurbitaFooDB
Cucurbita foetidissimaLOTUS Database
Cucurbita maximaFooDB
Cucurbita moschataFooDB
Cuminum cyminumFooDB
Curcuma domesticaKNApSAcK Database
Curcuma longaPlant
CyclopteridaeFooDB
Cydonia oblongaFooDB
Cymbopogon citratusFooDB
Cynara cardunculusFooDB
Cynara scolymusFooDB
Cyperus aromaticusLOTUS Database
Daphnia pulexLOTUS Database
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
    • David M. Alabran, and Ahmed F. Mabrouk. Carrot flavor. Sugars and free nitrogenous compounds in f...
Dimocarpus longanFooDB
DioscoreaFooDB
Dioscorea pentaphyllaFooDB
DiospyrosFooDB
Diospyros kakiFooDB
Diospyros virginianaFooDB
Durio zibethinusFooDB
Dysphania ambrosioidesFooDB
ElaeisFooDB
Eleocharis dulcisFooDB
Elettaria cardamomumFooDB
Empetrum nigrumFooDB
EngraulidaeFooDB
Eragrostis tefFooDB
Eriobotrya japonicaFooDB
Eruca vesicaria subsp. SativaFooDB
Esox luciusFooDB
EucheumaFooDB
Eugenia javanicaFooDB
Eugenia unifloraFooDB
Euphrasia strictaLOTUS Database
Eutrema japonicumFooDB
Fagopyrum esculentumFooDB
Fagopyrum tataricumFooDB
FagusFooDB
Feijoa sellowianaFooDB
Ficus caricaFooDB
Flammulina velutipesFooDB
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
GadiformesFooDB
GadusFooDB
Gallus gallusFooDB
Garcinia mangostanaFooDB
GastropodaFooDB
Gaylussacia baccataFooDB
Ginkgo bilobaFooDB
Glycine maxFooDB
GossypiumFooDB
Grifola frondosaFooDB
Hansenia weberbauerianaLOTUS Database
Hedysarum alpinumFooDB
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
Hibiscus sabbariffaFooDB
HippoglossusFooDB
Hippoglossus hippoglossusFooDB
Hippophae rhamnoidesFooDB
Homo sapiensLOTUS Database
Hoplostethus atlanticusFooDB
Hordeum vulgareFooDB
Hypholoma fasciculareLOTUS Database
Hyssopus officinalis L.FooDB
Ictalurus punctatusFooDB
Illicium verumFooDB
Indigofera hirsutaLOTUS Database
Iochroma fuchsioidesLOTUS Database
Ipomoea aquaticaFooDB
Ipomoea batatasFooDB
Jatropha gossypifoliaLOTUS Database
JuglansFooDB
Juglans ailanthifoliaFooDB
Juglans cinereaFooDB
Juglans nigra L.FooDB
Juglans regiaFooDB
Katsuwonus pelamisFooDB
Lablab purpureusFooDB
Lactuca sativaFooDB
Lagenaria sicerariaFooDB
Lagopus mutaFooDB
Lathyrus sativusFooDB
Laurus nobilis L.FooDB
Lens culinarisFooDB
Lentinus edodesFooDB
Lepidium sativumFooDB
LeporidaeFooDB
Lepus timidusFooDB
Levisticum officinaleFooDB
Limanda limandaFooDB
Linum usitatissimumFooDB
Litchi chinensisFooDB
Litoria verreauxiiLOTUS Database
Lota lotaFooDB
Luffa aegyptiacaFooDB
LupinusFooDB
Lupinus albusFooDB
MacadamiaFooDB
Macadamia tetraphyllaFooDB
Malpighia emarginataFooDB
MalusFooDB
Malus pumilaFooDB
Mammea americanaFooDB
Mangifera indicaFooDB
Manihot esculentaFooDB
Manilkara zapotaFooDB
Maranta arundinaceaFooDB
Marthasterias glacialisLOTUS Database
Matricaria recutitaFooDB
Matteuccia struthiopterisFooDB
Medicago sativaFooDB
Melanogrammus aeglefinusFooDB
Meleagris gallopavoFooDB
Melissa officinalis L.FooDB
MenthaFooDB
Mentha aquaticaFooDB
Mentha arvensisFooDB
Mentha spicataFooDB
Mentha x piperitaFooDB
Merlangius merlangusFooDB
Mespilus germanicaFooDB
Metroxylon saguFooDB
Micromesistius poutassouFooDB
Microstomus kittFooDB
Molva molvaFooDB
Momordica charantiaFooDB
Morchella angusticepsLOTUS Database
MorchellaceaeFooDB
Morella rubraFooDB
Moringa oleiferaFooDB
MorusFooDB
Morus nigraFooDB
Mus musculusLOTUS Database
Musa acuminataFooDB
Musa x paradisiacaFooDB
MyricaFooDB
Myristica fragransFooDB
MytilidaeFooDB
NelumboFooDB
Nelumbo nuciferaFooDB
Nephelium lappaceumFooDB
NephropidaeFooDB
Nephrops norvegicusFooDB
Neptunea antiquaLOTUS Database
Nicotiana tabacumLOTUS Database
Nuphar luteaFooDB
Ocimum basilicumFooDB
Octopus vulgarisFooDB
Oenothera biennisFooDB
Olea europaeaFooDB
Oncorhynchus gorbuschaFooDB
Oncorhynchus ketaFooDB
Oncorhynchus kisutchFooDB
Oncorhynchus mykissFooDB
Oncorhynchus nerkaFooDB
Oncorhynchus tshawytschaFooDB
Onobrychis kacheticaLOTUS Database
OpuntiaFooDB
Opuntia cochenilliferaFooDB
Opuntia ficus-indicaLOTUS Database
Opuntia macrorhizaFooDB
Origanum majoranaFooDB
Origanum onitesFooDB
Origanum vulgareFooDB
Origanum X majoricumFooDB
Oryza rufipogonFooDB
Oryza sativaFooDB
OsmeridaeFooDB
Ovis ariesFooDB
Pachyrhizus erosusFooDB
PalinuridaeFooDB
Panax ginsengFooDB
Pangium eduleFooDB
Panicum miliaceumFooDB
PapaverFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
PectinidaeFooDB
Pediomelum esculentumFooDB
Pentaclethra macrophyllaLOTUS Database
PerciformesFooDB
Perideridia oreganaFooDB
Persea americanaFooDB
Petasites japonicusFooDB
Petroselinum crispumFooDB
Phaseolus coccineusFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
Phoenix dactyliferaFooDB
Photinia melanocarpaFooDB
Phyllostachys edulisFooDB
PhysalisFooDB
Physalis philadelphica var. immaculataFooDB
Phytolacca americanaFooDB
Pimenta dioicaFooDB
Pimpinella anisumFooDB
PinusFooDB
Pinus densifloraLOTUS Database
Pinus edulisFooDB
Pinus ponderosaLOTUS Database
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
PleuronectidaeFooDB
PleuronectiformesFooDB
Pleurotus ostreatusFooDB
Pogostemon cablinLOTUS Database
PollachiusFooDB
Polygonum alpinumFooDB
Portulaca oleraceaFooDB
Pouteria sapotaFooDB
Prunus armeniacaFooDB
Prunus aviumFooDB
Prunus avium L.FooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Prunus persica var. persicaFooDB
Prunus tomentosaFooDB
Prunus virginianaFooDB
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Puccinia graminisLOTUS Database
Punica granatumFooDB
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
QuercusFooDB
RanidaeFooDB
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativusFooDB
Reinhardtius hippoglossoidesFooDB
Rheum rhabarbarumFooDB
Ribes aureumFooDB
Ribes glandulosumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
Ripariosida hermaphroditaLOTUS Database
RosaFooDB
Rubus arcticusFooDB
Rubus chamaemorusFooDB
Rubus idaeusFooDB
Rubus occidentalisFooDB
Rubus spectabilisFooDB
RumexFooDB
Rumex acetosaFooDB
Rumex articusFooDB
Saccharina japonicaFooDB
Sagittaria latifoliaFooDB
Salix pulchraFooDB
Salmo salarFooDB
Salmonella entericaLOTUS Database
SalmonidaeFooDB
SalvelinusFooDB
Salvelinus namaycushFooDB
Salvia elegansFooDB
Salvia hispanicaFooDB
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Sander luciopercaFooDB
Satureja hortensis L.FooDB
Satureja montanaFooDB
Scolopendra subspinipesLOTUS Database
ScombridaeFooDB
Scophthalmus maximusFooDB
Scorzonera hispanicaFooDB
Sebastes alutusFooDB
Sebastes viviparusFooDB
Secale cerealeFooDB
Sechium eduleFooDB
Senna obtusifoliaLOTUS Database
SepiidaeFooDB
Seriola lalandiFooDB
Sesamum indicumFooDB
Sesbania bispinosaFooDB
SiluriformesFooDB
Sinapis albaFooDB
SisymbriumFooDB
Solanum lycopersicumFooDB
Solanum lycopersicum var. cerasiformeFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum quitoenseFooDB
Solanum tuberosumFooDB
Sorbus aucupariaFooDB
Sorghum bicolorFooDB
Spermacoce pusillaLOTUS Database
Spinacia oleraceaFooDB
Squalus acanthiasFooDB
Stellaria mediaLOTUS Database
Stenodus leucichthysFooDB
Stratiotes aloidesLOTUS Database
Suaeda aegyptiacaLOTUS Database
Suaeda nudifloraLOTUS Database
Sus scrofa domesticaFooDB
Swertia angustifoliaLOTUS Database
Syzygium aromaticumFooDB
Syzygium cuminiFooDB
Syzygium jambosFooDB
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Telekia speciosaLOTUS Database
Tetragonia tetragonioidesFooDB
ThelespermaFooDB
Theobroma cacaoFooDB
ThunnusFooDB
Thunnus albacaresFooDB
Thymus pulegioidesFooDB
Thymus transcaucasicusLOTUS Database
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia L.FooDB
Tragopogon porrifoliusFooDB
Trigonella foenum-graecumFooDB
Trisopterus esmarkiiFooDB
TriticumFooDB
Triticum aestivumFooDB
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Trypanosoma bruceiLOTUS Database
Typha angustifoliaFooDB
VacciniumFooDB
Vaccinium angustifoliumFooDB
Vaccinium angustifolium X Vaccinium corymbosumFooDB
Vaccinium arboreumFooDB
Vaccinium corymbosumFooDB
Vaccinium deliciosumFooDB
Vaccinium elliottiiFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtilloidesFooDB
Vaccinium myrtillusFooDB
Vaccinium ovalifoliumFooDB
Vaccinium ovatumFooDB
Vaccinium oxycoccosFooDB
Vaccinium parvifoliumFooDB
Vaccinium reticulatumFooDB
Vaccinium stamineumFooDB
Vaccinium uliginosumFooDB
Vaccinium vitis-idaeaFooDB
Valeriana officinalisLOTUS Database
Valerianella locustaFooDB
VanillaFooDB
Verbena officinalisFooDB
Viburnum eduleFooDB
Vicia fabaFooDB
Vigna aconitifoliaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna umbellataFooDB
Vigna unguiculataFooDB
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
Vigna unguiculata var. sesquipedalisFooDB
Viscum albumLOTUS Database
Vitellaria paradoxaFooDB
VitisFooDB
Vitis aestivalisFooDB
Vitis labruscaFooDB
Vitis rotundifoliaFooDB
Vitis vinifera L.FooDB
Xanthosoma sagittifoliumFooDB
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Zizania aquaticaFooDB
Ziziphus zizyphusFooDB
Species Where Detected
Species NameSourceReference
Escherichia coliKNApSAcK Database
Homo sapiens (Serum)KNApSAcK Database
Homo sapiens (Urine)KNApSAcK Database
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point268 - 288 °CNot Available
Boiling Point563.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility21.5 mg/mLNot Available
LogP-1.52Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
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
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
Good Scents IDrw1030281
References
General References
  1. 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. [PubMed:19212411 ]
  2. 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. [PubMed:6696735 ]
  3. 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. [PubMed:6198473 ]
  4. 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. [PubMed:15911239 ]
  5. Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6. [PubMed:12297216 ]
  6. 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. [PubMed:14992292 ]
  7. 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. [PubMed:12101068 ]
  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. [PubMed:7061706 ]
  9. 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. [PubMed:9773842 ]
  10. 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. [PubMed:1512514 ]
  11. Mero A: Leucine supplementation and intensive training. Sports Med. 1999 Jun;27(6):347-58. [PubMed:10418071 ]
  12. 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. [PubMed:6847871 ]
  13. 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. [PubMed:15930465 ]
  14. 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. [PubMed:10582553 ]
  15. Lynch CJ, Adams SH: Branched-chain amino acids in metabolic signalling and insulin resistance. Nat Rev Endocrinol. 2014 Dec;10(12):723-36. doi: 10.1038/nrendo.2014.171. Epub 2014 Oct 7. [PubMed:25287287 ]
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