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Showing NP-Card for L-Histidine (NP0001101)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2022-01-25 19:01:18 UTC
NP-MRD IDNP0001101
Secondary Accession NumbersNone
Natural Product Identification
Common NameL-Histidine
DescriptionHistidine (His), also known as L-histidine, 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. Histidine is one of 20 proteinogenic amino acids, i.E., The amino acids used in the biosynthesis of proteins. Histidine is found in all organisms ranging from bacteria to plants to animals. It is classified as an aliphatic, positively charged or basic amino acid. Histidine is a unique amino acid with an imidazole functional group. The acid-base properties of the imidazole side chain are relevant to the catalytic mechanism of many enzymes such as proteases. In catalytic triads, the basic nitrogen of histidine abstracts a proton from serine, threonine, or cysteine to activate it as a nucleophile. In a histidine proton shuttle, histidine is used to quickly shuttle protons. It can do this by abstracting a proton with its basic nitrogen to make a positively charged intermediate and then use another molecule to extract the proton from its acidic nitrogen. Histidine forms complexes with many metal ions. The imidazole sidechain of the histidine residue commonly serves as a ligand in metalloproteins. Histidine was first isolated by German physician Albrecht Kossel in 1896. Histidine is an essential amino acid in humans and other mammals. It was initially thought that it was only essential for infants, but longer-term studies established that it is also essential for adults. Infants four to six months old require 33 mg/kg of histidine. It is not clear how adults make small amounts of histidine, and dietary sources probably account for most of the histidine in the body. Histidine is a precursor for histamine and carnosine biosynthesis. Inborn errors of histidine metabolism, including histidinemia, maple syrup urine disease, propionic acidemia, and tyrosinemia I, exist and are marked by increased histidine levels in the blood. Elevated blood histidine is accompanied by a wide range of symptoms, from mental and physical retardation to poor intellectual functioning, emotional instability, tremor, ataxia and psychosis. Histidine and other imidazole compounds have anti-oxidant, anti-inflammatory and anti-secretory properties (PMID: 9605177 ). The efficacy of L-histidine in protecting inflamed tissue is attributed to the capacity of the imidazole ring to scavenge reactive oxygen species (ROS) generated by cells during acute inflammatory response (PMID: 9605177 ). Histidine, when administered in therapeutic quantities is able to inhibit cytokines and growth factors involved in cell and tissue damage (US patent 6150392). Histidine in medical therapies has its most promising trials in rheumatoid arthritis where up to 4.5 G daily have been used effectively in severely affected patients. Arthritis patients have been found to have low serum histidine levels, apparently because of very rapid removal of histidine from their blood (PMID: 1079527 ). Other patients besides arthritis patients that have been found to be low in serum histidine are those with chronic renal failure. Urinary levels of histidine are reduced in pediatric patients with pneumonia (PMID: 2084459 ). Asthma patients exhibit increased serum levels of histidine over normal controls (PMID: 23517038 ). Serum histidine levels are lower and are negatively associated with inflammation and oxidative stress in obese women (PMID: 23361591 ). Histidine supplementation has been shown to reduce insulin resistance, reduce BMI and fat mass and suppress inflammation and oxidative stress in obese women with metabolic syndrome. Histidine appears to suppress pro-inflammatory cytokine expression, possibly via the NF-κB pathway, in adipocytes (PMID: 23361591 ). Low plasma concentrations of histidine are associated with protein-energy wasting, inflammation, oxidative stress, and greater mortality in chronic kidney disease patients (PMID: 18541578 ). Histidine may have many other possible functions because it is the precursor of the ubiquitous neurohormone-neurotransmitter histamine. Histidine increases histamine in the blood and probably in the brain. Low blood histamine with low serum histidine occurs in rheumatoid arthritis patients. Low blood histamine also occurs in some manic, schizophrenic, high copper and hyperactive groups of psychiatric patients. Histidine is a useful therapy in all patients with low histamine levels (http://Www.Dcnutrition.Com).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001101 (L-Histidine)


  Mrv1652309272007392D          

 11 11  0  0  0  0            999 V2000
 9999.978410000.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.6930 9999.7891    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.409010000.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1251 9999.7891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.409010001.0268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.6930 9998.9631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.590810000.2834    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9234 9999.7984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1783 9999.0138    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.0033 9999.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2582 9999.7984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  6  1  1  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
 10 11  2  0  0  0  0
  7  8  2  0  0  0  0
  7 11  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 11  1  0  0  0  0
M  END
Download

3D MOL for NP0001101 (L-Histidine)

HMDB0000177
     RDKit          3D
L-Histidine
 20 20  0  0  0  0  0  0  0  0999 V2000
   -1.4966    1.5834   -0.4622 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4868    0.1893   -0.1990 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3143   -0.5643   -0.7103 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9843   -0.1453   -0.1994 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3438    0.8435    0.6910 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6787    0.8345    0.8390 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1468   -0.1391    0.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1433   -0.7272   -0.5636 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6820   -0.0884    1.2502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8324    0.8268    2.0878 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7036   -1.3965    1.7261 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2591    2.0327    0.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5353    1.7871   -1.4711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3980   -0.2506   -0.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4634   -1.6373   -0.4213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2812   -0.5711   -1.8257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6723    1.5018    1.1775 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2124   -0.3982   -0.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2579   -1.5240   -1.2340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9867   -2.1571    1.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  2  9  1  0
  9 10  2  0
  9 11  1  0
  8  4  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  6
  3 15  1  0
  3 16  1  0
  5 17  1  0
  7 18  1  0
  8 19  1  0
 11 20  1  0
M  END
Download

3D SDF for NP0001101 (L-Histidine)


  Mrv1652309272007392D          

 11 11  0  0  0  0            999 V2000
 9999.978410000.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.6930 9999.7891    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.409010000.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1251 9999.7891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.409010001.0268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.6930 9998.9631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.590810000.2834    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9234 9999.7984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1783 9999.0138    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.0033 9999.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2582 9999.7984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  6  1  1  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
 10 11  2  0  0  0  0
  7  8  2  0  0  0  0
  7 11  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001101

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](CC1=CNC=N1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11)/t5-/m0/s1

> <INCHI_KEY>
HNDVDQJCIGZPNO-YFKPBYRVSA-N

> <FORMULA>
C6H9N3O2

> <MOLECULAR_WEIGHT>
155.1546

> <EXACT_MASS>
155.069476547

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
14.670259477862192

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid

> <ALOGPS_LOGP>
-2.67

> <JCHEM_LOGP>
-3.6160224799542067

> <ALOGPS_LOGS>
-0.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.941172308417478

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8499726767043656

> <JCHEM_PKA_STRONGEST_BASIC>
9.437137464922305

> <JCHEM_POLAR_SURFACE_AREA>
92.0

> <JCHEM_REFRACTIVITY>
38.059

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.13e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-histidine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0001101 (L-Histidine)

HMDB0000177
     RDKit          3D
L-Histidine
 20 20  0  0  0  0  0  0  0  0999 V2000
   -1.4966    1.5834   -0.4622 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4868    0.1893   -0.1990 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3143   -0.5643   -0.7103 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9843   -0.1453   -0.1994 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3438    0.8435    0.6910 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6787    0.8345    0.8390 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1468   -0.1391    0.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1433   -0.7272   -0.5636 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6820   -0.0884    1.2502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8324    0.8268    2.0878 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7036   -1.3965    1.7261 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2591    2.0327    0.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5353    1.7871   -1.4711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3980   -0.2506   -0.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4634   -1.6373   -0.4213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2812   -0.5711   -1.8257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6723    1.5018    1.1775 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2124   -0.3982   -0.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2579   -1.5240   -1.2340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9867   -2.1571    1.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  2  9  1  0
  9 10  2  0
  9 11  1  0
  8  4  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  6
  3 15  1  0
  3 16  1  0
  5 17  1  0
  7 18  1  0
  8 19  1  0
 11 20  1  0
M  END
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PDB for NP0001101 (L-Histidine)

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  C   UNK     0    8666.6268667.043   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8667.9608666.273   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8669.2978667.043   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8670.6348666.273   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8669.2978668.583   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0    8667.9608664.731   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0    8664.0368667.196   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0    8662.7908666.290   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0    8663.2668664.826   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0    8664.8068664.826   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8665.2828666.290   0.000  0.00  0.00           C+0
CONECT    1    2   11                                                       
CONECT    2    1    3    6                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    2                                                            
CONECT    7    8   11                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10   11    9                                                       
CONECT   11   10    7    1                                                  
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for NP0001101 (L-Histidine)

COMPND    HMDB0000177
HETATM    1  N1  UNL     1      -1.497   1.583  -0.462  1.00  0.00           N  
HETATM    2  C1  UNL     1      -1.487   0.189  -0.199  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.314  -0.564  -0.710  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.984  -0.145  -0.199  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.344   0.843   0.691  1.00  0.00           C  
HETATM    6  N2  UNL     1       2.679   0.834   0.839  1.00  0.00           N  
HETATM    7  C5  UNL     1       3.147  -0.139   0.058  1.00  0.00           C  
HETATM    8  N3  UNL     1       2.143  -0.727  -0.564  1.00  0.00           N  
HETATM    9  C6  UNL     1      -1.682  -0.088   1.250  1.00  0.00           C  
HETATM   10  O1  UNL     1      -1.832   0.827   2.088  1.00  0.00           O  
HETATM   11  O2  UNL     1      -1.704  -1.397   1.726  1.00  0.00           O  
HETATM   12  H1  UNL     1      -2.259   2.033   0.064  1.00  0.00           H  
HETATM   13  H2  UNL     1      -1.535   1.787  -1.471  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.398  -0.251  -0.705  1.00  0.00           H  
HETATM   15  H4  UNL     1      -0.463  -1.637  -0.421  1.00  0.00           H  
HETATM   16  H5  UNL     1      -0.281  -0.571  -1.826  1.00  0.00           H  
HETATM   17  H6  UNL     1       0.672   1.502   1.177  1.00  0.00           H  
HETATM   18  H7  UNL     1       4.212  -0.398  -0.040  1.00  0.00           H  
HETATM   19  H8  UNL     1       2.258  -1.524  -1.234  1.00  0.00           H  
HETATM   20  H9  UNL     1      -1.987  -2.157   1.101  1.00  0.00           H  
CONECT    1    2   12   13
CONECT    2    3    9   14
CONECT    3    4   15   16
CONECT    4    5    5    8
CONECT    5    6   17
CONECT    6    7    7
CONECT    7    8   18
CONECT    8   19
CONECT    9   10   10   11
CONECT   11   20
END
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SMILES for NP0001101 (L-Histidine)

N[C@@H](CC1=CNC=N1)C(O)=O
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INCHI for NP0001101 (L-Histidine)

InChI=1S/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11)/t5-/m0/s1
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View in JSmol
Synonyms
ValueSource
(S)-4-(2-Amino-2-carboxyethyl)imidazoleChEBI
(S)-alpha-Amino-1H-imidazole-4-propanoic acidChEBI
(S)-alpha-Amino-1H-imidazole-4-propionic acidChEBI
HChEBI
HisChEBI
HISTIDINEChEBI
L-(-)-HistidineChEBI
L-HistidinChEBI
(S)-a-Amino-1H-imidazole-4-propanoateGenerator
(S)-a-Amino-1H-imidazole-4-propanoic acidGenerator
(S)-alpha-Amino-1H-imidazole-4-propanoateGenerator
(S)-Α-amino-1H-imidazole-4-propanoateGenerator
(S)-Α-amino-1H-imidazole-4-propanoic acidGenerator
(S)-a-Amino-1H-imidazole-4-propionateGenerator
(S)-a-Amino-1H-imidazole-4-propionic acidGenerator
(S)-alpha-Amino-1H-imidazole-4-propionateGenerator
(S)-Α-amino-1H-imidazole-4-propionateGenerator
(S)-Α-amino-1H-imidazole-4-propionic acidGenerator
(S)-1H-Imidazole-4-alanineHMDB
(S)-2-Amino-3-(4-imidazolyl)propionsaeureHMDB
(S)-HistidineHMDB
(S)1H-Imidazole-4-alanineHMDB
3-(1H-Imidazol-4-yl)-L-alanineHMDB
Amino-1H-imidazole-4-propanoateHMDB
Amino-1H-imidazole-4-propanoic acidHMDB
Amino-4-imidazoleproprionateHMDB
Amino-4-imidazoleproprionic acidHMDB
Glyoxaline-5-alanineHMDB
Histidine, L isomerHMDB
Histidine, L-isomerHMDB
L-Isomer histidineHMDB
L-HistidineKEGG
Chemical FormulaC6H9N3O2
Average Mass155.1546 Da
Monoisotopic Mass155.06948 Da
IUPAC Name(2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid
Traditional NameL-histidine
CAS Registry Number71-00-1
SMILES
N[C@@H](CC1=CN=CN1)C(O)=O
InChI Identifier
InChI=1S/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11)/t5-/m0/s1
InChI KeyHNDVDQJCIGZPNO-YFKPBYRVSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-01-25View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)Varshavi.d262021-09-05View 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)varshavi.d26@gmail.comNot AvailableNot Available2021-07-25View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)varshavi.d26@gmail.comNot AvailableNot Available2021-07-25View Spectrum
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Abramis bramaFooDB
Abutilon indicumLOTUS Database
Achillea millefoliumLOTUS Database
AcipenserFooDB
AcipenseridaeFooDB
Actinidia chinensisFooDB
Agaricus bisporusFooDB
AgaveFooDB
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosumFooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Alosa sapidissimaFooDB
Aloysia triphyllaFooDB
AmaranthusFooDB
Amelanchier alnifoliaFooDB
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anarhichas lupusFooDB
AnatidaeFooDB
Anethum graveolensFooDB
Angelica keiskeiFooDB
AnguillaFooDB
AnguilliformesFooDB
Annona cherimolaFooDB
Annona muricataFooDB
Annona reticulataFooDB
Annona squamosaFooDB
Anoplopoma fimbriaFooDB
Anthriscus cerefoliumFooDB
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Aplodinotus grunniensFooDB
Aplysina insularisLOTUS Database
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaeaFooDB
Archosargus probatocephalusFooDB
Arctium lappaFooDB
Armoracia rusticanaFooDB
Arripis truttaLOTUS Database
Artemia salinaLOTUS Database
Artemisia dracunculusFooDB
Artemisia vulgarisFooDB
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Asparagus officinalisFooDB
AstacideaFooDB
Astragalus hamosusLOTUS Database
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
Bison bisonFooDB
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
Brosme brosmeFooDB
Bubalus bubalisFooDB
BuccinidaeFooDB
Byrsonima crassifoliaFooDB
Cajanus cajanFooDB
Calendula officinalisLOTUS Database
Callinectes sapidusFooDB
Canarium ovatumFooDB
Cancer magisterFooDB
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Capsicum annuum L.FooDB
Capsicum annuum var. annuumFooDB
Capsicum chinenseFooDB
Capsicum pubescensFooDB
Carica papayaKNApSAcK Database
Carica papaya L.FooDB
CarideaFooDB
Carissa macrocarpaFooDB
Carthamus tinctoriusFooDB
Carum carviFooDB
CaryaFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Castanea crenataFooDB
Castanea mollissimaFooDB
Castanea sativaFooDB
Catha edulisLOTUS Database
Catostomus commersoniiFooDB
Ceratonia siliquaFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chamaemelum nobileFooDB
Chamerion angustifoliumFooDB
Chanos chanosFooDB
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
Clupea harengus harengusFooDB
Clupea pallasiiFooDB
ClupeinaeFooDB
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colocasia esculentaFooDB
ColumbaFooDB
ColumbidaeFooDB
Coprinopsis atramentariaLOTUS Database
Corchorus olitoriusFooDB
CoregonusFooDB
Coregonus artediFooDB
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 longaFooDB
CyclopteridaeFooDB
Cydonia oblongaFooDB
Cymbopogon citratusFooDB
Cynara cardunculusFooDB
Cynara scolymusFooDB
Cyprinus carpioFooDB
Daphnia pulexLOTUS Database
Datura stramoniumLOTUS 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
Dromaius novaehollandiaeFooDB
Durio zibethinusFooDB
Dysphania ambrosioidesFooDB
ElaeisFooDB
Eleocharis dulcisFooDB
Elettaria cardamomumFooDB
Empetrum nigrumFooDB
EngraulidaeFooDB
Engraulis encrasicolusFooDB
EpinephelusFooDB
Epipremnum pinnatumLOTUS Database
Equus caballusFooDB
Eragrostis tefFooDB
Eriobotrya japonicaFooDB
Eruca vesicaria subsp. SativaFooDB
Esox luciusFooDB
EucheumaFooDB
Eugenia javanicaFooDB
Eugenia unifloraFooDB
Eutrema japonicumFooDB
Fagopyrum esculentumFooDB
Fagopyrum tataricumFooDB
FagusFooDB
Feijoa sellowianaFooDB
Ficus caricaFooDB
Flammulina velutipesFooDB
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
GadiformesFooDB
GadusFooDB
Gadus macrocephalusFooDB
Gadus morhuaFooDB
Gallus gallusFooDB
Garcinia mangostanaFooDB
GastropodaFooDB
Gaylussacia baccataFooDB
Ginkgo bilobaFooDB
Glycine maxFooDB
GossypiumFooDB
Gossypium hirsutumLOTUS Database
Grifola frondosaFooDB
Hedysarum alpinumFooDB
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
Hibiscus sabbariffaFooDB
HippoglossusFooDB
Hippoglossus hippoglossusFooDB
Hippoglossus stenolepisFooDB
Hippophae rhamnoidesFooDB
Hippospongia communisLOTUS Database
Homarus americanusFooDB
Homo sapiensLOTUS Database
Hoplostethus atlanticusFooDB
Hordeum vulgareFooDB
Hyssopus officinalis L.FooDB
Ictalurus punctatusFooDB
Illicium verumFooDB
Indigofera schimperiLOTUS Database
Ipomoea aquaticaFooDB
Ipomoea batatasFooDB
JuglansFooDB
Juglans ailanthifoliaFooDB
Juglans cinereaFooDB
Juglans nigra L.FooDB
Juglans regiaFooDB
Juncus roemerianusLOTUS Database
Katsuwonus pelamisFooDB
Lablab purpureusFooDB
Lactuca sativaFooDB
Lagenaria sicerariaFooDB
Lagopus mutaFooDB
LaminariaFooDB
Lathyrus sativusFooDB
Laurus nobilis L.FooDB
Leiostomus xanthurusFooDB
Lens culinarisFooDB
Lentinus edodesFooDB
Lepidium sativumFooDB
Lepomis gibbosusFooDB
LeporidaeFooDB
Lepus timidusFooDB
Levisticum officinaleFooDB
Limanda limandaFooDB
Linum usitatissimumFooDB
Litchi chinensisFooDB
Lophius piscatoriusFooDB
Lopholatilus chamaeleonticepsFooDB
Lota lotaFooDB
Luffa aegyptiacaFooDB
LupinusFooDB
Lupinus albusFooDB
LutjanidaeFooDB
MacadamiaFooDB
Macadamia tetraphyllaFooDB
Malpighia emarginataFooDB
MalusFooDB
Malus pumilaFooDB
Mammea americanaFooDB
Mangifera indicaKNApSAcK Database
Manihot esculentaFooDB
Manilkara zapotaFooDB
Maranta arundinaceaFooDB
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
Micropogonias undulatusFooDB
Microstomus kittFooDB
Molva molvaFooDB
Momordica charantiaFooDB
MorchellaceaeFooDB
Morella rubraFooDB
Moringa oleiferaFooDB
Morone saxatilisFooDB
MorusFooDB
Morus nigraFooDB
Mugil cephalusFooDB
Mus musculusLOTUS Database
Musa acuminataFooDB
Musa x paradisiacaFooDB
MyricaFooDB
Myristica fragransFooDB
MytilidaeFooDB
Mytilus edulisFooDB
NelumboFooDB
Nelumbo nuciferaFooDB
Nephelium lappaceumFooDB
NephropidaeFooDB
Nephrops norvegicusFooDB
Neptunea antiquaLOTUS Database
Nicotiana tabacumLOTUS Database
Numida meleagrisFooDB
Nuphar luteaFooDB
Ocimum basilicumFooDB
Octopus vulgarisFooDB
Oenothera biennisFooDB
Olea europaeaFooDB
Oncorhynchus gorbuschaFooDB
Oncorhynchus ketaFooDB
Oncorhynchus kisutchFooDB
Oncorhynchus mykissFooDB
Oncorhynchus nerkaFooDB
Oncorhynchus tshawytschaFooDB
Ophiodon elongatusFooDB
OpuntiaFooDB
Opuntia cochenilliferaFooDB
Opuntia ficus-indicaLOTUS Database
Opuntia macrorhizaFooDB
Origanum majoranaFooDB
Origanum onitesFooDB
Origanum vulgareFooDB
Origanum X majoricumFooDB
OryctolagusFooDB
Oryza rufipogonFooDB
Oryza sativaFooDB
OsmeridaeFooDB
Osmerus mordaxFooDB
Ovis ariesFooDB
Pachyrhizus erosusFooDB
PalinuridaeFooDB
Panax ginsengFooDB
Pangium eduleFooDB
Panicum miliaceumFooDB
PapaverFooDB
Paralithodes camtschaticusFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
PectinidaeFooDB
Pediomelum esculentumFooDB
Peprilus triacanthusFooDB
PerciformesFooDB
PercoideiFooDB
Perideridia oreganaFooDB
Persea americanaFooDB
Petasites japonicusFooDB
Petroselinum crispumFooDB
Phaseolus coccineusFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Phoenix dactyliferaFooDB
Photinia melanocarpaFooDB
Phyllostachys edulisFooDB
PhysalisFooDB
Physalis philadelphica var. immaculataFooDB
Phytolacca americanaFooDB
Picea pungensLOTUS Database
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
PollachiusFooDB
Pollachius pollachiusFooDB
Polygonum alpinumFooDB
Pomatomus saltatrixFooDB
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
Salmo trutta forma truttaFooDB
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
Scomberomorus cavallaFooDB
Scomberomorus maculatusFooDB
ScombridaeFooDB
Scophthalmus maximusFooDB
Scorzonera hispanicaFooDB
SebastesFooDB
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
SoleidaeFooDB
Sorbus aucupariaFooDB
Sorghum bicolorFooDB
Spermacoce pusillaLOTUS Database
Spinacia oleraceaFooDB
SpirulinaFooDB
SqualiformesFooDB
Squalus acanthiasFooDB
Stellaria mediaLOTUS Database
Stenodus leucichthysFooDB
Stenotomus chrysopsFooDB
Struthio camelusFooDB
Suaeda aegyptiacaLOTUS Database
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Syzygium aromaticumFooDB
Syzygium cuminiFooDB
Syzygium jambosFooDB
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Telekia speciosaLOTUS Database
Tetragonia tetragonioidesFooDB
TeuthidaFooDB
Thalassiosira pseudonanaLOTUS Database
ThelespermaFooDB
Theobroma cacaoFooDB
ThunnusFooDB
Thunnus albacaresFooDB
Thunnus thynnusFooDB
Thymus pulegioidesFooDB
Thymus transcaucasicusLOTUS Database
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia L.FooDB
Trachinotus carolinusFooDB
Trachurus symmetricusFooDB
Tragopogon porrifoliusFooDB
Trapa natansLOTUS Database
Treculia africanaLOTUS Database
Trifolium pratense L.KNApSAcK Database
Trifolium repensPlant
Trifolium repens L.KNApSAcK Database
Trigonella foenum-graecumKNApSAcK Database
Trisopterus esmarkiiFooDB
TriticumFooDB
Triticum aestivumFooDB
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Trypanosoma bruceiLOTUS Database
Typha angustifoliaFooDB
Undaria pinnatifidaFooDB
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
Valerianella locustaFooDB
VanillaFooDB
Verbena officinalisFooDB
Verpa bohemicaLOTUS Database
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
Virola surinamensisFooDB
VitisFooDB
Vitis aestivalisFooDB
Vitis labruscaFooDB
Vitis rotundifoliaFooDB
Vitis vinifera L.FooDB
Xanthosoma sagittifoliumFooDB
Xiphias gladiusFooDB
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Zizania aquaticaFooDB
Ziziphus zizyphusFooDB
Zoarces americanusFooDB
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 histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine 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 ParentHistidine and derivatives
Alternative Parents
Substituents
  • Histidine or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Imidazolyl carboxylic acid derivative
  • Aralkylamine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Amino acid
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary amine
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point287 °CNot Available
Boiling Point458.87 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility45.6 mg/mLNot Available
LogP-3.32Chmelík, J., Hudecek, J., Putyera, K., Makovicka, J., Kalous, V., & Chmelíková, J. (1991). Characterization of the hydrophobic properties of amino acids on the basis of their partition and distribution coefficients in the 1-octanol-water system. Collection of Czechoslovak chemical communications, 56(10), 2030-2041.
Predicted Properties
PropertyValueSource
Water Solubility71.3 g/LALOGPS
logP-2.7ALOGPS
logP-3.6ChemAxon
logS-0.34ALOGPS
pKa (Strongest Acidic)1.85ChemAxon
pKa (Strongest Basic)9.44ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity38.06 m³·mol⁻¹ChemAxon
Polarizability14.67 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000177
DrugBank IDDB00117
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011856
KNApSAcK IDC00001363
Chemspider ID6038
KEGG Compound IDC00135
BioCyc IDHIS
BiGG ID33985
Wikipedia LinkL-histidine
METLIN ID21
PubChem Compound6274
PDB IDNot Available
ChEBI ID15971
Good Scents IDrw1037461
References
General References
  1. Xiao B, Jing C, Kelly G, Walker PA, Muskett FW, Frenkiel TA, Martin SR, Sarma K, Reinberg D, Gamblin SJ, Wilson JR: Specificity and mechanism of the histone methyltransferase Pr-Set7. Genes Dev. 2005 Jun 15;19(12):1444-54. Epub 2005 Jun 2. [PubMed:15933069 ]
  2. 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 ]
  3. Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. [PubMed:2026685 ]
  4. Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. [PubMed:12097436 ]
  5. 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 ]
  6. Wevers RA, Engelke U, Wendel U, de Jong JG, Gabreels FJ, Heerschap A: Standardized method for high-resolution 1H-NMR of cerebrospinal fluid. Clin Chem. 1995 May;41(5):744-51. [PubMed:7729054 ]
  7. 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 ]
  8. 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 ]
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  26. Effective method for the amelioration and prevention of tissue and cellular damage [Link]