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

Functional Ontology

Physical Properties

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-008a-9110000000-2f66d9e2bd58d8fdfe22	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-008a-9220000000-c098b7478e4e2469402c	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a4i-0910000000-e359d14a1164b571973e	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-0900000000-3ae24b5b69cb5463a956	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0002-7930000000-344e4a7f3b532ce31015	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-0090000000-66959f5b2f8cd0fed35d	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-014r-0950000000-27db9dc4c4fbe3889f7d	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-014i-3900000000-e8dd832f2b9453b196fb	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0a4i-9500000000-91673df79b5fb9e1373b	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4i-9100000000-468135f3bc158f013255	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0006-0090000000-5545eb5f0143bc37b54c	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0006-0690000000-65defef60d9fd6e60fe8	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0a4i-1900000000-1ecb5ca2c9f4935af629	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0a4j-5900000000-24168da8606d1994f23b	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-052b-9400000000-08a9a8a8d83e5958d60e	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-00di-0920000000-fdb3cabe02ef9f20956d	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-0a4i-0900000000-39c6787170775cf28b30	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-0a4i-1900000000-a9ee2ab9908f584909b4	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-0aor-6900000000-934d365646fde55d5c16	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-0a4i-0900000000-440a3e57f35809ac4568	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-052g-3950000000-656f64d2f4533d03073e	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-014r-0960000000-1ec10daf4624249b1d5b	2012-08-31	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00xu-1970000000-1e25ebc6c091a98fd2e9	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-3910000000-731cfc3c9901fad1d44b	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-3900000000-307d922cb29b8694f151	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-1490000000-b93b05b7108f994cf9f6	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0079-5950000000-42d4878fd04fd2f8210e	2016-09-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Human Proteins and Enzymes

Human Pathways

Metabolic Reactions

Health Effects and Bioactivity

Microbial Sources

Exposure Sources

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

References

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 ]
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Showing metabocard for Anserine (MMDBc0000500)

MOL for #<Metabolite:0x00007fd5990ce060>

3D MOL for #<Metabolite:0x00007fd5990ce060>

3D SDF for #<Metabolite:0x00007fd5990ce060>

3D-SDF for #<Metabolite:0x00007fd5990ce060>

PDB for #<Metabolite:0x00007fd5990ce060>

3D PDB for #<Metabolite:0x00007fd5990ce060>

SMILES for #<Metabolite:0x00007fd5990ce060>

INCHI for #<Metabolite:0x00007fd5990ce060>

Structure for #<Metabolite:0x00007fd5990ce060>

3D Structure for #<Metabolite:0x00007fd5990ce060>