MiMeDB: Showing metabocard for Anserine (MMDBc0000500)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:39:11 UTC

Update Date

2024-10-17 08:46:57 UTC

Metabolite ID

MMDBc0000500

Metabolite Identification

Common Name

Anserine

Description

Anserine (beta-alanyl-N-3-methylhistidine) is a dipeptide containing beta-alanine and 3-methylhistidine. It is a derivative of carnosine, which had been methylated. The methyl group of anserine is added to carnosine by the enzyme S-adenosylmethionine: carnosine N-methyltransferase (PMID: 29484990 ). The enzyme is closely related to histamine N-methyltransferase and appears to be present in a majority of anserine-producing species (PMID: 23705015 ). Anserine is a generally a more metabolically stable derivative of carnosine. Anserine can be found in the skeletal muscle and brain of certain mammals (rabbits, cattle), migratory fish and birds. This dipeptide is normally absent from human tissues and body fluids, and its appearance there is usually an artifact of diet. Anserine can also arise from serum carnosinase deficiency. (OMIM 212200 ). Anserine was first discovered in goose muscle in 1929, and was named after this extraction (anser is Latin for goose). Anserine, which is water-soluble, is found at high levels in the muscles of different non-human vertebrates, with poultry, rabbit, tuna, plaice, and salmon having generally higher contents than other marine foods, beef, or pork (PMID: 31908682 ). An increase of urinary anserine excretion has been found in humans after the consumption of chicken, rabbit, and tuna and has been associated with intake of chicken, salmon, and, to a lesser extent, beef (PMID: 31908682 ). Anserine can undergo cleavage to give rise to 3-methylhistidine.(3-MH). The dipeptide balenine, common in some whales, cleaves to form 1-methylhistidine (1-MH) (PMID: 31908682 ). 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 (N-pi 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 of certain foods or various pathophysiological effects when they really were referring to 3MH or vice versa (PMID: 24137022 ). In particular balenine (a whale or snake-specific dipeptide with 1MH) was often confused with anserine (the poultry dipeptide with 3MH). An animal model study of Alzheimer's disease using mice found that treatment with anserine reduced memory loss (PMID: 28974740 ). Anserine reduced glial inflammatory activity (particularly of astrocyte). The study also found that anserine-treated mice had greater pericyte surface area. The greater area of pericytes was commensurate with improved memory. The anserine-treated mice overall performed better on a spatial memory test (Morris Water Maze) (PMID: 28974740 ). A human study on 84 elderly subjects showed that subjects who took anserine and carnosine supplements for one year showed increased blood flow in the prefrontal cortex on MRI (PMID: 29896423 ).

Structure

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

HMDB0000194
     RDKit          3D
Anserine
 33 33  0  0  0  0  0  0  0  0999 V2000
   -4.0174    0.1847   -1.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8596    0.9779   -0.8370 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7313    2.2739   -1.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5565    2.6732   -0.6568 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9451    1.6258   -0.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7717    0.5680   -0.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6271   -0.8012    0.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3359   -1.1138    1.0234 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8234   -0.9534    0.1812 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9802   -0.3110    0.6463 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9814    0.1299    1.8383 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1769   -0.1546   -0.2481 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2306    0.5722    0.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6497    1.8663    0.9378 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3795   -2.5614    1.4708 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4751   -3.3869    1.1222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4260   -2.9287    2.2951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7793   -0.8912   -1.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4614    0.5576   -2.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8003    0.3523   -0.4385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4304    2.8976   -1.7022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0095    1.6951    0.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5106   -1.0993    0.9713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6962   -1.4820   -0.5435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2239   -0.5106    1.9634 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7970   -1.3248   -0.7953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8928    0.3895   -1.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5192   -1.1959   -0.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4062   -0.0345    1.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1410    0.7147   -0.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1962    2.3165    0.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4455    2.4509    1.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1726   -3.4970    1.9031 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
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
  8 15  1  0
 15 16  2  0
 15 17  1  0
  6  2  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  5 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  1
  9 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 17 33  1  0
M  END


  Mrv1652305271900032D          

 17 17  0  0  1  0            999 V2000
    2.3194   -1.4830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7063   -0.9310    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8994   -1.1025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4869   -0.3881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0389    0.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7926   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5070    0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5070    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7926    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7926    2.3645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0781    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2215    1.5395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9360    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9360    0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6505    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3649    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0794    1.5395    0.0000 N   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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  8 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000500

> <DATABASE_NAME>
MIME

> <SMILES>
CN1C=NC=C1C[C@H](NC(=O)CCN)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H16N4O3/c1-14-6-12-5-7(14)4-8(10(16)17)13-9(15)2-3-11/h5-6,8H,2-4,11H2,1H3,(H,13,15)(H,16,17)/t8-/m0/s1

> <INCHI_KEY>
MYYIAHXIVFADCU-QMMMGPOBSA-N

> <FORMULA>
C10H16N4O3

> <MOLECULAR_WEIGHT>
240.259

> <EXACT_MASS>
240.122240398

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
24.30257648493638

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.95

> <JCHEM_LOGP>
-4.26466129830276

> <ALOGPS_LOGS>
-1.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.7461992021571

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4429691588256897

> <JCHEM_PKA_STRONGEST_BASIC>
9.125526276418753

> <JCHEM_POLAR_SURFACE_AREA>
110.24

> <JCHEM_REFRACTIVITY>
60.458600000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.01e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
anserine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000194
     RDKit          3D
Anserine
 33 33  0  0  0  0  0  0  0  0999 V2000
   -4.0174    0.1847   -1.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8596    0.9779   -0.8370 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7313    2.2739   -1.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5565    2.6732   -0.6568 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9451    1.6258   -0.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7717    0.5680   -0.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6271   -0.8012    0.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3359   -1.1138    1.0234 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8234   -0.9534    0.1812 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9802   -0.3110    0.6463 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9814    0.1299    1.8383 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1769   -0.1546   -0.2481 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2306    0.5722    0.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6497    1.8663    0.9378 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3795   -2.5614    1.4708 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4751   -3.3869    1.1222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4260   -2.9287    2.2951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7793   -0.8912   -1.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4614    0.5576   -2.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8003    0.3523   -0.4385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4304    2.8976   -1.7022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0095    1.6951    0.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5106   -1.0993    0.9713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6962   -1.4820   -0.5435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2239   -0.5106    1.9634 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7970   -1.3248   -0.7953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8928    0.3895   -1.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5192   -1.1959   -0.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4062   -0.0345    1.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1410    0.7147   -0.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1962    2.3165    0.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4455    2.4509    1.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1726   -3.4970    1.9031 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
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
  8 15  1  0
 15 16  2  0
 15 17  1  0
  6  2  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  5 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  1
  9 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 17 33  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       4.330  -2.768   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       3.185  -1.738   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       1.679  -2.058   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       0.909  -0.724   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       1.939   0.420   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.346  -0.206   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.680   0.564   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.680   2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.346   2.874   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.346   4.414   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.012   2.104   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       6.013   2.874   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       7.347   2.104   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.347   0.564   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.681   2.874   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.014   2.104   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      11.348   2.874   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    2    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0000194
HETATM    1  C1  UNL     1      -4.017   0.185  -1.208  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.860   0.978  -0.837  1.00  0.00           N  
HETATM    3  C2  UNL     1      -2.731   2.274  -1.153  1.00  0.00           C  
HETATM    4  N2  UNL     1      -1.556   2.673  -0.657  1.00  0.00           N  
HETATM    5  C3  UNL     1      -0.945   1.626  -0.028  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.772   0.568  -0.148  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.627  -0.801   0.348  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.336  -1.114   1.023  1.00  0.00           C  
HETATM    9  N3  UNL     1       0.823  -0.953   0.181  1.00  0.00           N  
HETATM   10  C7  UNL     1       1.980  -0.311   0.646  1.00  0.00           C  
HETATM   11  O1  UNL     1       1.981   0.130   1.838  1.00  0.00           O  
HETATM   12  C8  UNL     1       3.177  -0.155  -0.248  1.00  0.00           C  
HETATM   13  C9  UNL     1       4.231   0.572   0.559  1.00  0.00           C  
HETATM   14  N4  UNL     1       3.650   1.866   0.938  1.00  0.00           N  
HETATM   15  C10 UNL     1      -0.379  -2.561   1.471  1.00  0.00           C  
HETATM   16  O2  UNL     1       0.475  -3.387   1.122  1.00  0.00           O  
HETATM   17  O3  UNL     1      -1.426  -2.929   2.295  1.00  0.00           O  
HETATM   18  H1  UNL     1      -3.779  -0.891  -1.256  1.00  0.00           H  
HETATM   19  H2  UNL     1      -4.461   0.558  -2.169  1.00  0.00           H  
HETATM   20  H3  UNL     1      -4.800   0.352  -0.439  1.00  0.00           H  
HETATM   21  H4  UNL     1      -3.430   2.898  -1.702  1.00  0.00           H  
HETATM   22  H5  UNL     1       0.009   1.695   0.457  1.00  0.00           H  
HETATM   23  H6  UNL     1      -2.511  -1.099   0.971  1.00  0.00           H  
HETATM   24  H7  UNL     1      -1.696  -1.482  -0.544  1.00  0.00           H  
HETATM   25  H8  UNL     1      -0.224  -0.511   1.963  1.00  0.00           H  
HETATM   26  H9  UNL     1       0.797  -1.325  -0.795  1.00  0.00           H  
HETATM   27  H10 UNL     1       2.893   0.390  -1.159  1.00  0.00           H  
HETATM   28  H11 UNL     1       3.519  -1.196  -0.473  1.00  0.00           H  
HETATM   29  H12 UNL     1       4.406  -0.035   1.472  1.00  0.00           H  
HETATM   30  H13 UNL     1       5.141   0.715  -0.051  1.00  0.00           H  
HETATM   31  H14 UNL     1       3.196   2.317   0.115  1.00  0.00           H  
HETATM   32  H15 UNL     1       4.445   2.451   1.284  1.00  0.00           H  
HETATM   33  H16 UNL     1      -2.173  -3.497   1.903  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    6
CONECT    3    4    4   21
CONECT    4    5
CONECT    5    6    6   22
CONECT    6    7
CONECT    7    8   23   24
CONECT    8    9   15   25
CONECT    9   10   26
CONECT   10   11   11   12
CONECT   12   13   27   28
CONECT   13   14   29   30
CONECT   14   31   32
CONECT   15   16   16   17
CONECT   17   33
END

HMDB0000194
     RDKit          3D
Anserine
 33 33  0  0  0  0  0  0  0  0999 V2000
   -4.0174    0.1847   -1.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8596    0.9779   -0.8370 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7313    2.2739   -1.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5565    2.6732   -0.6568 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9451    1.6258   -0.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7717    0.5680   -0.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6271   -0.8012    0.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3359   -1.1138    1.0234 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8234   -0.9534    0.1812 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9802   -0.3110    0.6463 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9814    0.1299    1.8383 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1769   -0.1546   -0.2481 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2306    0.5722    0.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6497    1.8663    0.9378 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3795   -2.5614    1.4708 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4751   -3.3869    1.1222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4260   -2.9287    2.2951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7793   -0.8912   -1.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4614    0.5576   -2.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8003    0.3523   -0.4385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4304    2.8976   -1.7022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0095    1.6951    0.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5106   -1.0993    0.9713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6962   -1.4820   -0.5435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2239   -0.5106    1.9634 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7970   -1.3248   -0.7953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8928    0.3895   -1.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5192   -1.1959   -0.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4062   -0.0345    1.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1410    0.7147   -0.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1962    2.3165    0.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4455    2.4509    1.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1726   -3.4970    1.9031 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
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
  8 15  1  0
 15 16  2  0
 15 17  1  0
  6  2  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  5 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  1
  9 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 17 33  1  0
M  END

Synonyms

Value	Source
beta-Alanyl-3-methyl-L-histidine	ChEBI
beta-Alanyl-N(pai)-methyl-L-histidine	ChEBI
b-Alanyl-3-methyl-L-histidine	Generator
Β-alanyl-3-methyl-L-histidine	Generator
b-Alanyl-N(pai)-methyl-L-histidine	Generator
Β-alanyl-N(pai)-methyl-L-histidine	Generator
L-Anserine	HMDB
L-N-b-Alanyl-3-methyl-histidine	HMDB
L-N-beta-Alanyl-3-methyl-histidine	HMDB
N-b-Alanyl-3-methyl-L-histidine	HMDB
N-beta-Alanyl-3-methyl-L-histidine	HMDB
Balanine	HMDB
Beta Alanyl 3 methylhistidine	HMDB
Beta-Alanyl-3-methylhistidine	HMDB
Ophidine	HMDB

Molecular Formula

C₁₀H₁₆N₄O₃

Average Mass

240.259

Monoisotopic Mass

240.122240398

IUPAC Name

(2S)-2-(3-aminopropanamido)-3-(1-methyl-1H-imidazol-5-yl)propanoic acid

Traditional Name

anserine

CAS Registry Number

Not Available

SMILES

CN1C=NC=C1C[C@H](NC(=O)CCN)C(O)=O

InChI Identifier

InChI=1S/C10H16N4O3/c1-14-6-12-5-7(14)4-8(10(16)17)13-9(15)2-3-11/h5-6,8H,2-4,11H2,1H3,(H,13,15)(H,16,17)/t8-/m0/s1

InChI Key

MYYIAHXIVFADCU-QMMMGPOBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Hybrid peptides

Direct Parent

Hybrid peptides

Alternative Parents

Substituents

Hybrid peptide
Histidine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Imidazolyl carboxylic acid derivative
N-substituted imidazole
Azole
Imidazole
Heteroaromatic compound
Amino acid or derivatives
Amino acid
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid derivative
Carboxylic acid
Azacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Primary aliphatic amine
Carbonyl group
Organic nitrogen compound
Amine
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Primary amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

beta-alanine derivative (CHEBI:18323 )
dipeptide (CHEBI:18323 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	4.01 g/L	ALOGPS
logP	-3	ALOGPS
logP	-4.3	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	3.44	ChemAxon
pKa (Strongest Basic)	9.13	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	110.24 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	60.46 m³·mol⁻¹	ChemAxon
Polarizability	24.3 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Brain
Feces
Placenta
Prostate
Saliva
Skeletal Muscle
Urine

Tissue Locations

Brain
Placenta
Prostate
Skeletal Muscle

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192131	Beta-Ala-His dipeptidase	Unknown	Q96KN2	Homo sapiens
MMDBp0195610	Carnosine synthase 1	Unknown	A5YM72	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank
1-Methylhistidine Metabolism

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Alzheimer's disease		Association	Human Blood	HMDB	17031479
Alzheimer's disease	Slight Decrease	Association	Human Urine	HMDB	17031479
Eosinophilic esophagitis	Slight Decrease	Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Firmicutes	1	Human stool; Human ; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria/Eubacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Indirect association between microbiota composition and metabolites measured in host biospecimen
Eukaryota/Fungi	Ascomycota	3	Human feces; Human saliva	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	0.457	0.214			uM	Elderly (>65 years old)	Both	Alzheimer's disease	HMDB	17031479
Human Urine	Detected and Quantified	8.0	5.0			umol/mmol creatinine	Adult (>18 years old)	Both	Alzheimer's disease	HMDB	17031479
Human Blood	Detected and Quantified	41.0	10.0			uM	Adult (>18 years old)	Both	Normal	HMDB	9267323
Human Urine	Detected and Quantified	7.0		3.3	20.0	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	12.808	6.444			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	14.842	5.257			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	16.16				umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	Shaykhutdinov RA, MacInnis GD, Dowlatabadi R, Weljie AM, Vogel HJ. Quantitative analysis of metabolite concentrations in human urine samples using 13C{1H} NMR spectroscopy. Metabolomics. 2009
Human Urine	Detected and Quantified	<15.95				umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Urine	Detected and Quantified	<31.33				umol/mmol creatinine	Infant (0-1 year old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Urine	Detected and Quantified	<4.30				umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Urine	Detected and Quantified	<41.74				umol/mmol creatinine	Adolescent (13-18 years old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Urine	Detected and Quantified	<45.021				umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Urine	Detected and Quantified	<92.76				umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Brain	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Skeletal muscle	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	21389975
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	21736852
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000194

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Anserine

METLIN ID

5209

PubChem Compound

112072

PDB ID

Not Available

ChEBI ID

18323

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Abe H, Okuma E, Sekine H, Maeda A, Yoshiue S: Human urinary excretion of L-histidine-related compounds after ingestion of several meats and fish muscle. Int J Biochem. 1993 Sep;25(9):1245-9. doi: 10.1016/0020-711x(93)90074-o. [PubMed:8224369 ]
Tan KM, Candlish JK: Carnosine and anserine as modulators of neutrophil function. Clin Lab Haematol. 1998 Aug;20(4):239-44. doi: 10.1046/j.1365-2257.1998.00123.x. [PubMed:9777271 ]
Pagnano MW, Hanssen AD, Lewallen DG, Stuart MJ: Flexion instability after primary posterior cruciate retaining total knee arthroplasty. Clin Orthop Relat Res. 1998 Nov;(356):39-46. doi: 10.1097/00003086-199811000-00008. [PubMed:9917666 ]
Magana Loarte JE, Perez Franco J, Sanchez Sanchez G: [Is therapy with local infiltrations feasible in primary care consultations?]. Aten Primaria. 1999 Jan;23(1):4-7. [PubMed:10079554 ]
Boldyrev A, Abe H: Metabolic transformation of neuropeptide carnosine modifies its biological activity. Cell Mol Neurobiol. 1999 Feb;19(1):163-75. doi: 10.1023/a:1006933028389. [PubMed:10079975 ]
Kang I, Han SW: Anserine bursitis in patients with osteoarthritis of the knee. South Med J. 2000 Feb;93(2):207-9. [PubMed:10701790 ]
Harris RC, Tallon MJ, Dunnett M, Boobis L, Coakley J, Kim HJ, Fallowfield JL, Hill CA, Sale C, Wise JA: The absorption of orally supplied beta-alanine and its effect on muscle carnosine synthesis in human vastus lateralis. Amino Acids. 2006 May;30(3):279-89. doi: 10.1007/s00726-006-0299-9. Epub 2006 Mar 24. [PubMed:16554972 ]
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 ]
Drozak J, Chrobok L, Poleszak O, Jagielski AK, Derlacz R: Molecular identification of carnosine N-methyltransferase as chicken histamine N-methyltransferase-like protein (hnmt-like). PLoS One. 2013 May 21;8(5):e64805. doi: 10.1371/journal.pone.0064805. Print 2013. [PubMed:23705015 ]
Kwiatkowski S, Kiersztan A, Drozak J: Biosynthesis of Carnosine and Related Dipeptides in Vertebrates. Curr Protein Pept Sci. 2018;19(8):771-789. doi: 10.2174/1389203719666180226155657. [PubMed:29484990 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Anserine (MMDBc0000500)

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