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Showing NP-Card for 3-Methylhistidine (NP0000907)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2023-04-27 22:22:29 UTC
NP-MRD IDNP0000907
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Methylhistidine
Description3-Methylhistidine, also known as 3-MHis or 3MH, belongs to the class of organic compounds known as histidine and derivatives. 3MH is also classified as a methylamino acid. Methylamino acids are primarily proteogenic amino acids (found in proteins) which have been methylated (in situ) on their side chains by various methyltransferase enzymes. 3-Methylhistidine is also classified as a member of the class of compounds known as L-alpha-amino acids. L-alpha-Amino acids are alpha amino acids which have the L-configuration of the alpha-carbon atom. 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. 3-Methylhistidine is generated from histidine residues found in proteins. Histidine can be methylated at either the N1 or N3 position of its imidazole ring, yielding the isomers 1-methylhistidine (1MH; also referred to as pi-methylhistidine) or 3-methylhistidine (3MH; tau-methylhistidine), respectively. There is considerable confusion with regard to the nomenclature of the methylated nitrogen atoms on the imidazole ring of histidine and other histidine-containing peptides such as anserine. In particular, older literature (mostly prior to the year 2000) designated anserine (Npi methylated) as beta-alanyl-N1-methyl-histidine, whereas according to standard IUPAC nomenclature, anserine is correctly named as beta-alanyl-N3-methyl-histidine. As a result, many papers published prior to the year 2000 incorrectly identified 1MH as a specific marker for dietary consumption or various pathophysiological effects when they really were referring to 3MH (PMID: 24137022 ). Histidine methylation on the 3- or tau site is mediated by the enzyme known as METTL18. METTL18 is a nuclear methyltransferase protein that contains a functional nuclear localization signal and accumulates in nucleoli. Urinary concentrations of 3-methylhistidine can be used as a biomarker for skeletal muscle protein breakdown in humans who have been subject to muscle injury (PMID: 16079625 ). 3-Methylhistidine is formed by the posttranslational methylation of histidine residues of the main myofibrillar proteins actin and myosin. During protein catabolism, 3-methylhistidine is released but cannot be reutilized. Therefore, the plasma concentration and urine excretion of 3-methylhistidine are sensitive markers of myofibrillar protein degradation (PMID: 32235743 ). Approximately 75% of 3-methylhistidine is estimated to originate from skeletal muscle (PMID: 32235743 ). In addition to the degradation of muscle proteins, the 3-methylhistidine level is affected by the degradation of intestinal proteins and meat intake. 3-Methylhistidine exists in all eukaryotes, ranging from yeast to humans. In humans, 3-methylhistidine is involved in methylhistidine metabolism. 3-Methylhistidine has been found to be associated with several diseases such as diabetes mellitus type 2, eosinophilic esophagitis, and kidney disease. The normal concentration of 3-methylhistidine in the urine of healthy adult humans has been detected and quantified in a range of 3.63–69.27 Micromoles per millimole (umol/mmol) of creatinine, with most studies reporting the average urinary concentration between 15–20 umol/mmol of creatinine. The average concentration of 3-methylhistidine in human blood plasma has been detected and quantified at 2.85 Micromolar (uM) with a range of 0.0–5.9 UM. As a general rule, urinary 1MH is associated with white meat intake (p< 0.001), Whereas urinary 3MH is associated with red meat intake (p< 0.001) (PMID: 34091671 ).
Structure
Data?1628564082
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000907 (3-Methylhistidine)


  Mrv1652310151922162D          

 13 13  0  0  1  0            999 V2000
   -0.8843    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1467    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    1.9393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    3.5893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    3.5893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    2.7643    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  2  1  0  0  0  0
  7  6  1  0  0  0  0
  6  8  1  1  0  0  0
  9  3  1  0  0  0  0
  9  4  2  0  0  0  0
 10  1  1  0  0  0  0
 10  4  1  0  0  0  0
 10  5  1  0  0  0  0
 11  7  2  0  0  0  0
 12  7  1  0  0  0  0
  6 13  1  1  0  0  0
M  END
Download

3D MOL for NP0000907 (3-Methylhistidine)

HMDB0000479
     RDKit          3D
3-Methylhistidine
 23 23  0  0  0  0  0  0  0  0999 V2000
    2.5476    0.2005    1.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9711   -0.1153    0.1925 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6456   -0.3774   -0.9204 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7654   -0.6192   -1.9048 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5101   -0.5044   -1.3903 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6434   -0.1865   -0.0678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4200    0.0358    0.9323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7983   -0.0574    0.3328 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9744   -1.3497   -0.2389 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0319    1.0830   -0.5579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8028    2.2326   -0.0564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4642    1.0608   -1.8526 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9708   -0.7243    1.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7894    0.6257    2.1705 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3376    0.9822    1.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7420   -0.3860   -0.9867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3696   -0.6532   -1.9698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2841   -0.7052    1.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3414    1.0692    1.3681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5120    0.0063    1.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5391   -1.3659   -1.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2729   -2.0412    0.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1121    1.7894   -2.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
  6  2  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  3 16  1  0
  5 17  1  0
  7 18  1  0
  7 19  1  0
  8 20  1  1
  9 21  1  0
  9 22  1  0
 12 23  1  0
M  END
Download

3D SDF for NP0000907 (3-Methylhistidine)


  Mrv1652310151922162D          

 13 13  0  0  1  0            999 V2000
   -0.8843    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1467    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    1.9393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    3.5893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    3.5893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    2.7643    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  2  1  0  0  0  0
  7  6  1  0  0  0  0
  6  8  1  1  0  0  0
  9  3  1  0  0  0  0
  9  4  2  0  0  0  0
 10  1  1  0  0  0  0
 10  4  1  0  0  0  0
 10  5  1  0  0  0  0
 11  7  2  0  0  0  0
 12  7  1  0  0  0  0
  6 13  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0000907

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@](N)(CC1=CN=CN1C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H11N3O2/c1-10-4-9-3-5(10)2-6(8)7(11)12/h3-4,6H,2,8H2,1H3,(H,11,12)/t6-/m0/s1

> <INCHI_KEY>
JDHILDINMRGULE-LURJTMIESA-N

> <FORMULA>
C7H11N3O2

> <MOLECULAR_WEIGHT>
169.1811

> <EXACT_MASS>
169.085126611

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
16.579381016239893

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.89

> <JCHEM_LOGP>
-3.3952407273413714

> <ALOGPS_LOGS>
-1.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.960164078727427

> <JCHEM_PKA_STRONGEST_BASIC>
9.428858911874197

> <JCHEM_POLAR_SURFACE_AREA>
81.14

> <JCHEM_REFRACTIVITY>
42.9557

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.93e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,methylhistidine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000907 (3-Methylhistidine)

HMDB0000479
     RDKit          3D
3-Methylhistidine
 23 23  0  0  0  0  0  0  0  0999 V2000
    2.5476    0.2005    1.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9711   -0.1153    0.1925 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6456   -0.3774   -0.9204 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7654   -0.6192   -1.9048 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5101   -0.5044   -1.3903 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6434   -0.1865   -0.0678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4200    0.0358    0.9323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7983   -0.0574    0.3328 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9744   -1.3497   -0.2389 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0319    1.0830   -0.5579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8028    2.2326   -0.0564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4642    1.0608   -1.8526 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9708   -0.7243    1.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7894    0.6257    2.1705 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3376    0.9822    1.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7420   -0.3860   -0.9867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3696   -0.6532   -1.9698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2841   -0.7052    1.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3414    1.0692    1.3681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5120    0.0063    1.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5391   -1.3659   -1.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2729   -2.0412    0.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1121    1.7894   -2.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
  6  2  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  3 16  1  0
  5 17  1  0
  7 18  1  0
  7 19  1  0
  8 20  1  1
  9 21  1  0
  9 22  1  0
 12 23  1  0
M  END
Download

PDB for NP0000907 (3-Methylhistidine)

HEADER    PROTEIN                                 15-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-OCT-19         0                                  
HETATM    1  C   UNK     0      -1.651   1.651   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.274   5.930   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -1.608   3.620   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       1.830  -0.290   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      -0.186   1.175   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0      -1.608   6.700   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.060   6.700   0.000  0.00  0.00           O+0
HETATM   13  H   UNK     0       1.060   5.160   0.000  0.00  0.00           H+0
CONECT    1   10                                                            
CONECT    2    5    6                                                       
CONECT    3    5    9                                                       
CONECT    4    9   10                                                       
CONECT    5    2    3   10                                                  
CONECT    6    2    7    8   13                                             
CONECT    7    6   11   12                                                  
CONECT    8    6                                                            
CONECT    9    3    4                                                       
CONECT   10    1    4    5                                                  
CONECT   11    7                                                            
CONECT   12    7                                                            
CONECT   13    6                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END
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3D PDB for NP0000907 (3-Methylhistidine)

COMPND    HMDB0000479
HETATM    1  C1  UNL     1       2.548   0.200   1.495  1.00  0.00           C  
HETATM    2  N1  UNL     1       1.971  -0.115   0.192  1.00  0.00           N  
HETATM    3  C2  UNL     1       2.646  -0.377  -0.920  1.00  0.00           C  
HETATM    4  N2  UNL     1       1.765  -0.619  -1.905  1.00  0.00           N  
HETATM    5  C3  UNL     1       0.510  -0.504  -1.390  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.643  -0.187  -0.068  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.420   0.036   0.932  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.798  -0.057   0.333  1.00  0.00           C  
HETATM    9  N3  UNL     1      -1.974  -1.350  -0.239  1.00  0.00           N  
HETATM   10  C7  UNL     1      -2.032   1.083  -0.558  1.00  0.00           C  
HETATM   11  O1  UNL     1      -1.803   2.233  -0.056  1.00  0.00           O  
HETATM   12  O2  UNL     1      -2.464   1.061  -1.853  1.00  0.00           O  
HETATM   13  H1  UNL     1       2.971  -0.724   1.920  1.00  0.00           H  
HETATM   14  H2  UNL     1       1.789   0.626   2.171  1.00  0.00           H  
HETATM   15  H3  UNL     1       3.338   0.982   1.378  1.00  0.00           H  
HETATM   16  H4  UNL     1       3.742  -0.386  -0.987  1.00  0.00           H  
HETATM   17  H5  UNL     1      -0.370  -0.653  -1.970  1.00  0.00           H  
HETATM   18  H6  UNL     1      -0.284  -0.705   1.751  1.00  0.00           H  
HETATM   19  H7  UNL     1      -0.341   1.069   1.368  1.00  0.00           H  
HETATM   20  H8  UNL     1      -2.512   0.006   1.224  1.00  0.00           H  
HETATM   21  H9  UNL     1      -2.539  -1.366  -1.113  1.00  0.00           H  
HETATM   22  H10 UNL     1      -2.273  -2.041   0.474  1.00  0.00           H  
HETATM   23  H11 UNL     1      -3.112   1.789  -2.180  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3    6
CONECT    3    4    4   16
CONECT    4    5
CONECT    5    6    6   17
CONECT    6    7
CONECT    7    8   18   19
CONECT    8    9   10   20
CONECT    9   21   22
CONECT   10   11   11   12
CONECT   12   23
END
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SMILES for NP0000907 (3-Methylhistidine)

[H][C@](N)(CC1=CN=CN1C)C(O)=O
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INCHI for NP0000907 (3-Methylhistidine)

InChI=1S/C7H11N3O2/c1-10-4-9-3-5(10)2-6(8)7(11)12/h3-4,6H,2,8H2,1H3,(H,11,12)/t6-/m0/s1
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View in JSmol
Synonyms
ValueSource
(2S)-2-Amino-3-(1-methyl-1H-imidazol-5-yl)propanoic acidChEBI
3-Methyl-L-histidineChEBI
N(Pai)-methyl-L-histidineChEBI
N-pros-Methyl-L-histidineChEBI
Tau-methylhistidineChEBI
(2S)-2-Amino-3-(1-methyl-1H-imidazol-5-yl)propanoateGenerator
3-N-Methyl-L-histidineHMDB
L-3-MethylhistidineHMDB
N(pros)-Methyl-L-histidineHMDB
N3-Methyl-L-histidineHMDB
Tau-methyl-L-histidineHMDB
3-Methylhistidine hydrideHMDB
N(Tau)-methylhistidineHMDB
3-Methylhistidine dihydrochlorideHMDB
N Tau-methylhistidineHMDB
N(Pi)-methyl-L-histidineHMDB
Pi-methyl-L-histidineHMDB
3-MethylhistidineChEBI
Chemical FormulaC7H11N3O2
Average Mass169.1811 Da
Monoisotopic Mass169.08513 Da
IUPAC Name(2S)-2-amino-3-(1-methyl-1H-imidazol-5-yl)propanoic acid
Traditional Name3,methylhistidine
CAS Registry Number368-16-1
SMILES
[H][C@](N)(CC1=CN=CN1C)C(O)=O
InChI Identifier
InChI=1S/C7H11N3O2/c1-10-4-9-3-5(10)2-6(8)7(11)12/h3-4,6H,2,8H2,1H3,(H,11,12)/t6-/m0/s1
InChI KeyJDHILDINMRGULE-LURJTMIESA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2023-04-27View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, experimental)Ahselim2023-04-27View 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 IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)V.dorna832021-08-02View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Apis ceranaLOTUS Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Cannabis sativaCannabisDB
      Not Available
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Trypanosoma bruceiLOTUS Database
Species Where Detected
Species NameSourceReference
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
  • N-substituted imidazole
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Amino acid
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen 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 PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility200 mg/mL at 25 °CBeilstein Handbook of Organic Chemistry (Handbuch der Organischen Chemie), 4th Edition
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.93 g/LALOGPS
logP-2.9ALOGPS
logP-3.4ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)1.96ChemAxon
pKa (Strongest Basic)9.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area81.14 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity42.96 m³·mol⁻¹ChemAxon
Polarizability16.58 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000479
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB093613
KNApSAcK IDC00050709
Chemspider ID58494
KEGG Compound IDC01152
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link3-Methylhistidine
METLIN ID5466
PubChem Compound64969
PDB IDNot Available
ChEBI ID27596
Good Scents IDrw1191881
References
General References
  1. Sjolin J, Stjernstrom H, Henneberg S, Hambraeus L, Friman G: Evaluation of urinary 3-methylhistidine excretion in infection by measurements of 1-methylhistidine and the creatinine ratios. Am J Clin Nutr. 1989 Jan;49(1):62-70. [PubMed:2912013 ]
  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. Bucciante G, Mencini A, Boninsegna A, Branca D, Scutari A, Scutari G: 3-Methylhistidine urinary excretion as an index of skeletal muscle protein metabolism: reference values. G Clin Med. 1985 Nov-Dec;66(11-12):451-8. [PubMed:3835089 ]
  4. Schmitz JE: [Effect of metabolism-oriented substrate administration on energy and protein metabolism in polytraumatized artificial respiration patients]. Infusionsther Klin Ernahr. 1984 Aug;11(4):205-18. [PubMed:6434422 ]
  5. McKeran RO, Halliday D, Purkiss P: Comparison of human myofibrillar protein catabolic rate derived from 3-methylhistidine excretion with synthetic rate from muscle biopsies during L-[alpha-15N]lysine infusion. Clin Sci Mol Med. 1978 May;54(5):471-5. [PubMed:750147 ]
  6. Teahon K, Rideout JM: A sensitive and specific high performance liquid chromatographic assay for imidazole dipeptides and 3-methylhistidine in human muscle biopsies, serum and urine. Biomed Chromatogr. 1992 Jan-Feb;6(1):16-9. [PubMed:1600369 ]
  7. Adlerberth A, Jagenburg R, Lindstedt G, Stenstrom G, Hasselgren PO: Effects of thyroid hormone and beta-adrenoceptor blocking agents on urinary excretion of 3-methylhistidine and plasma amino acids in man. Eur J Clin Invest. 1986 Aug;16(4):316-20. [PubMed:3093243 ]
  8. Wang Z, Deurenberg P, Matthews DE, Heymsfield SB: Urinary 3-methylhistidine excretion: association with total body skeletal muscle mass by computerized axial tomography. JPEN J Parenter Enteral Nutr. 1998 Mar-Apr;22(2):82-6. [PubMed:9527964 ]
  9. Nygren J, Thorell A, Brismar K, Essen P, Wernerman J, McNurlan MA, Garlick PJ, Ljungqvist O: Glucose flux is normalized by compensatory hyperinsulinaemia in growth hormone-induced insulin resistance in healthy subjects, while skeletal muscle protein synthesis remains unchanged. Clin Sci (Lond). 2002 Apr;102(4):457-64. [PubMed:11914108 ]
  10. Elia M, Carter A, Bacon S, Winearls CG, Smith R: Clinical usefulness of urinary 3-methylhistidine excretion in indicating muscle protein breakdown. Br Med J (Clin Res Ed). 1981 Jan 31;282(6261):351-4. [PubMed:6780020 ]
  11. Rathmacher JA, Flakoll PJ, Nissen SL: A compartmental model of 3-methylhistidine metabolism in humans. Am J Physiol. 1995 Jul;269(1 Pt 1):E193-8. [PubMed:7631776 ]
  12. Lunyong VE, Friedman Z: Myofibrillar protein degradation in premature infants with respiratory distress as assessed by 3-methylhistidine and creatinine excretions. Am J Clin Nutr. 1982 Sep;36(3):485-91. [PubMed:7113954 ]
  13. Buchholz-Wimmer GB, Wimmer W, Herbertz L, Reinauer H: [3-Methylhistidine as a parameter for the determination of muscle proteolysis in the post-stress syndrome and in diabetes mellitus]. Infusionsther Klin Ernahr. 1984 Jun;11(3):168-74. [PubMed:6434416 ]
  14. Vesali RF, Klaude M, Thunblad L, Rooyackers OE, Wernerman J: Contractile protein breakdown in human leg skeletal muscle as estimated by [2H3]-3-methylhistidine: a new method. Metabolism. 2004 Aug;53(8):1076-80. [PubMed:15281022 ]
  15. Bird SP, Tarpenning KM, Marino FE: Independent and combined effects of liquid carbohydrate/essential amino acid ingestion on hormonal and muscular adaptations following resistance training in untrained men. Eur J Appl Physiol. 2006 May;97(2):225-38. Epub 2006 Mar 24. [PubMed:16456674 ]
  16. Lamisse F, May MA, Couet C, Constans T, Bacq Y, Delarue J, Lamagnere JP, Colombat P, Garrigue MA: [Changes in nutritional status at the initial phase of treatment of cancers and malignant hemopathies]. Rev Med Interne. 1987 May-Jun;8(3):257-61. [PubMed:3616232 ]
  17. Neuhauser M, Bergstrom J, Chao L, Holmstrom J, Nordlund L, Vinnars E, Furst P: Urinary excretion of 3-methylhistidine as an index of muscle protein catabolism in postoperative trauma: the effect of parenteral nutrition. Metabolism. 1980 Dec;29(12):1206-13. [PubMed:6779092 ]
  18. Emery PW, Rennie MJ: Elimination by formaldehyde of interference with 3-methylhistidine determination: application of the method to the study of muscle protein degradation. Anal Biochem. 1982 Oct;126(1):67-73. [PubMed:7181118 ]
  19. Tomas FM, Ballard FJ, Pope LM: Age-dependent changes in the rate of myofibrillar protein degradation in humans as assessed by 3-methylhistidine and creatinine excretion. Clin Sci (Lond). 1979 Apr;56(4):341-6. [PubMed:477219 ]
  20. Long CL, Dillard DR, Bodzin JH, Geiger JW, Blakemore WS: Validity of 3-methylhistidine excretion as an indicator of skeletal muscle protein breakdown in humans. Metabolism. 1988 Sep;37(9):844-9. [PubMed:3138511 ]
  21. Young VR, Munro HN: Ntau-methylhistidine (3-methylhistidine) and muscle protein turnover: an overview. Fed Proc. 1978 Jul;37(9):2291-300. [PubMed:350635 ]
  22. Boldyrev AA, Aldini G, Derave W: Physiology and pathophysiology of carnosine. Physiol Rev. 2013 Oct;93(4):1803-45. doi: 10.1152/physrev.00039.2012. [PubMed:24137022 ]
  23. Said MY, Rodriguez-Nino A, Post A, Schutten JC, Kieneker LM, Gomes-Neto AW, van Londen M, Oste MC, Borgonjen-van den Berg KJ, Nolte IM, van den Berg E, de Blaauw P, van der Krogt J, Heiner-Fokkema MR, Navis G, Yard BA, Bakker SJ: Meat intake and risk of mortality and graft failure in kidney transplant recipients. Am J Clin Nutr. 2021 Jun 5. pii: 6294068. doi: 10.1093/ajcn/nqab185. [PubMed:34091671 ]
  24. Chinkes DL: Methods for measuring tissue protein breakdown rate in vivo. Curr Opin Clin Nutr Metab Care. 2005 Sep;8(5):534-7. doi: 10.1097/01.mco.0000170754.25372.37. [PubMed:16079625 ]
  25. Holecek M: Histidine in Health and Disease: Metabolism, Physiological Importance, and Use as a Supplement. Nutrients. 2020 Mar 22;12(3). pii: nu12030848. doi: 10.3390/nu12030848. [PubMed:32235743 ]
  26. Nagy-Szakal D, Barupal DK, Lee B, Che X, Williams BL, Kahn EJR, Ukaigwe JE, Bateman L, Klimas NG, Komaroff AL, Levine S, Montoya JG, Peterson DL, Levin B, Hornig M, Fiehn O, Lipkin WI: Insights into myalgic encephalomyelitis/chronic fatigue syndrome phenotypes through comprehensive metabolomics. Sci Rep. 2018 Jul 3;8(1):10056. doi: 10.1038/s41598-018-28477-9. [PubMed:29968805 ]