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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-10-13 04:27:42 UTC

HMDB ID

HMDB0000194

Secondary Accession Numbers

HMDB00194

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>
HMDB0000194

> <DATABASE_NAME>
hmdb

> <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

View in JSmol View Stereo Labels

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

Chemical Formula

C₁₀H₁₆N₄O₃

Average Molecular Weight

240.259

Monoisotopic Molecular Weight

240.122240398

IUPAC Name

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

Traditional Name

anserine

CAS Registry Number

584-85-0

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 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 17031479)
Saliva (PMID: 22308371)

Tissue

Muscle tissue

Skeletal muscle (HMDB: HMDB0000194)

Organ

Excreta

Biofluid or Excreta

Urine (PMID: 17031479)
Feces (PMID: 27543620)

Cellular substructure

Cytoplasm (HMDB: HMDB0000194)
Membrane (HMDB: HMDB0000194)

Tissue substructure

Muscle (HMDB: HMDB0000194)

Source

Endogenous

Endogenous (HMDB: HMDB0000194)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Lean meat (HMDB: HMDB0000194)

Aquatic origin

Fish

Fish (HMDB: HMDB0000194)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Beta-Alanine metabolism (HMDB: HMDB0000194)
Histidine Metabolism (PathBank: SMP0087314)

Disease pathway

Carnosinuria, Carnosinemia (HMDB: HMDB0000194)
GABA-Transaminase Deficiency (PathBank: SMP0120478)
Histidinemia (PathBank: SMP0120493)

Role

Industrial application

Pharmaceutical industry

Biomarker

Alzheimer's Disease (MarkerDB: MDB00000094)
Eosinophilic esophagitis (MarkerDB: MDB00000094)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	226 - 228 °C	Not Available
Boiling Point	611.30 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	15750 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-2.220 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	155.2	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000009
[M+H]+	Not Available	154.6	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000009

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	154.57	31661259
DarkChem	[M-H]-	154.295	31661259
AllCCS	[M+H]+	155.096	32859911
AllCCS	[M-H]-	154.548	32859911
DeepCCS	[M+H]+	150.661	30932474
DeepCCS	[M-H]-	148.303	30932474
DeepCCS	[M-2H]-	182.032	30932474
DeepCCS	[M+Na]+	156.883	30932474
AllCCS	[M+H]+	155.1	32859911
AllCCS	[M+H-H2O]+	151.6	32859911
AllCCS	[M+NH4]+	158.3	32859911
AllCCS	[M+Na]+	159.3	32859911
AllCCS	[M-H]-	154.5	32859911
AllCCS	[M+Na-2H]-	155.0	32859911
AllCCS	[M+HCOO]-	155.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.6 minutes	32390414
Predicted by Siyang on May 30, 2022	9.0563 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	8.8 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	422.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	349.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	243.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	50.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	162.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	61.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	299.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	242.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	1006.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	541.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	45.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	626.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	186.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	257.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	742.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	746.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	392.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Anserine	CN1C=NC=C1C[C@H](NC(=O)CCN)C(O)=O	3285.6	Standard polar	33892256
Anserine	CN1C=NC=C1C[C@H](NC(=O)CCN)C(O)=O	2333.8	Standard non polar	33892256
Anserine	CN1C=NC=C1C[C@H](NC(=O)CCN)C(O)=O	2408.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Anserine,1TMS,isomer #1	CN1C=NC=C1C[C@H](NC(=O)CCN)C(=O)O[Si](C)(C)C	2402.9	Semi standard non polar	33892256
Anserine,1TMS,isomer #2	CN1C=NC=C1C[C@H](NC(=O)CCN[Si](C)(C)C)C(=O)O	2498.8	Semi standard non polar	33892256
Anserine,1TMS,isomer #3	CN1C=NC=C1C[C@@H](C(=O)O)N(C(=O)CCN)[Si](C)(C)C	2320.9	Semi standard non polar	33892256
Anserine,2TMS,isomer #1	CN1C=NC=C1C[C@H](NC(=O)CCN[Si](C)(C)C)C(=O)O[Si](C)(C)C	2514.8	Semi standard non polar	33892256
Anserine,2TMS,isomer #1	CN1C=NC=C1C[C@H](NC(=O)CCN[Si](C)(C)C)C(=O)O[Si](C)(C)C	2352.8	Standard non polar	33892256
Anserine,2TMS,isomer #1	CN1C=NC=C1C[C@H](NC(=O)CCN[Si](C)(C)C)C(=O)O[Si](C)(C)C	3248.9	Standard polar	33892256
Anserine,2TMS,isomer #2	CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)CCN)[Si](C)(C)C	2326.9	Semi standard non polar	33892256
Anserine,2TMS,isomer #2	CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)CCN)[Si](C)(C)C	2276.0	Standard non polar	33892256
Anserine,2TMS,isomer #2	CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)CCN)[Si](C)(C)C	3439.2	Standard polar	33892256
Anserine,2TMS,isomer #3	CN1C=NC=C1C[C@@H](C(=O)O)N(C(=O)CCN[Si](C)(C)C)[Si](C)(C)C	2403.0	Semi standard non polar	33892256
Anserine,2TMS,isomer #3	CN1C=NC=C1C[C@@H](C(=O)O)N(C(=O)CCN[Si](C)(C)C)[Si](C)(C)C	2415.1	Standard non polar	33892256
Anserine,2TMS,isomer #3	CN1C=NC=C1C[C@@H](C(=O)O)N(C(=O)CCN[Si](C)(C)C)[Si](C)(C)C	3309.7	Standard polar	33892256
Anserine,2TMS,isomer #4	CN1C=NC=C1C[C@H](NC(=O)CCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2626.2	Semi standard non polar	33892256
Anserine,2TMS,isomer #4	CN1C=NC=C1C[C@H](NC(=O)CCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2523.0	Standard non polar	33892256
Anserine,2TMS,isomer #4	CN1C=NC=C1C[C@H](NC(=O)CCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O	3481.3	Standard polar	33892256
Anserine,3TMS,isomer #1	CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)CCN[Si](C)(C)C)[Si](C)(C)C	2413.9	Semi standard non polar	33892256
Anserine,3TMS,isomer #1	CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)CCN[Si](C)(C)C)[Si](C)(C)C	2405.7	Standard non polar	33892256
Anserine,3TMS,isomer #1	CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)CCN[Si](C)(C)C)[Si](C)(C)C	2927.8	Standard polar	33892256
Anserine,3TMS,isomer #2	CN1C=NC=C1C[C@H](NC(=O)CCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2622.7	Semi standard non polar	33892256
Anserine,3TMS,isomer #2	CN1C=NC=C1C[C@H](NC(=O)CCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2471.8	Standard non polar	33892256
Anserine,3TMS,isomer #2	CN1C=NC=C1C[C@H](NC(=O)CCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	3053.3	Standard polar	33892256
Anserine,3TMS,isomer #3	CN1C=NC=C1C[C@@H](C(=O)O)N(C(=O)CCN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2558.7	Semi standard non polar	33892256
Anserine,3TMS,isomer #3	CN1C=NC=C1C[C@@H](C(=O)O)N(C(=O)CCN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2563.4	Standard non polar	33892256
Anserine,3TMS,isomer #3	CN1C=NC=C1C[C@@H](C(=O)O)N(C(=O)CCN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	3114.6	Standard polar	33892256
Anserine,4TMS,isomer #1	CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)CCN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2582.3	Semi standard non polar	33892256
Anserine,4TMS,isomer #1	CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)CCN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2540.2	Standard non polar	33892256
Anserine,4TMS,isomer #1	CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)CCN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2792.4	Standard polar	33892256
Anserine,1TBDMS,isomer #1	CN1C=NC=C1C[C@H](NC(=O)CCN)C(=O)O[Si](C)(C)C(C)(C)C	2676.5	Semi standard non polar	33892256
Anserine,1TBDMS,isomer #2	CN1C=NC=C1C[C@H](NC(=O)CCN[Si](C)(C)C(C)(C)C)C(=O)O	2732.7	Semi standard non polar	33892256
Anserine,1TBDMS,isomer #3	CN1C=NC=C1C[C@@H](C(=O)O)N(C(=O)CCN)[Si](C)(C)C(C)(C)C	2598.1	Semi standard non polar	33892256
Anserine,2TBDMS,isomer #1	CN1C=NC=C1C[C@H](NC(=O)CCN[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2949.3	Semi standard non polar	33892256
Anserine,2TBDMS,isomer #1	CN1C=NC=C1C[C@H](NC(=O)CCN[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2750.8	Standard non polar	33892256
Anserine,2TBDMS,isomer #1	CN1C=NC=C1C[C@H](NC(=O)CCN[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3277.2	Standard polar	33892256
Anserine,2TBDMS,isomer #2	CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCN)[Si](C)(C)C(C)(C)C	2812.6	Semi standard non polar	33892256
Anserine,2TBDMS,isomer #2	CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCN)[Si](C)(C)C(C)(C)C	2704.1	Standard non polar	33892256
Anserine,2TBDMS,isomer #2	CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCN)[Si](C)(C)C(C)(C)C	3410.3	Standard polar	33892256
Anserine,2TBDMS,isomer #3	CN1C=NC=C1C[C@@H](C(=O)O)N(C(=O)CCN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2915.2	Semi standard non polar	33892256
Anserine,2TBDMS,isomer #3	CN1C=NC=C1C[C@@H](C(=O)O)N(C(=O)CCN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2794.2	Standard non polar	33892256
Anserine,2TBDMS,isomer #3	CN1C=NC=C1C[C@@H](C(=O)O)N(C(=O)CCN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3309.7	Standard polar	33892256
Anserine,2TBDMS,isomer #4	CN1C=NC=C1C[C@H](NC(=O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	3066.3	Semi standard non polar	33892256
Anserine,2TBDMS,isomer #4	CN1C=NC=C1C[C@H](NC(=O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	2882.3	Standard non polar	33892256
Anserine,2TBDMS,isomer #4	CN1C=NC=C1C[C@H](NC(=O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	3461.2	Standard polar	33892256
Anserine,3TBDMS,isomer #1	CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3090.0	Semi standard non polar	33892256
Anserine,3TBDMS,isomer #1	CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2969.7	Standard non polar	33892256
Anserine,3TBDMS,isomer #1	CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3131.5	Standard polar	33892256
Anserine,3TBDMS,isomer #2	CN1C=NC=C1C[C@H](NC(=O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3292.1	Semi standard non polar	33892256
Anserine,3TBDMS,isomer #2	CN1C=NC=C1C[C@H](NC(=O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3057.7	Standard non polar	33892256
Anserine,3TBDMS,isomer #2	CN1C=NC=C1C[C@H](NC(=O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3202.5	Standard polar	33892256
Anserine,3TBDMS,isomer #3	CN1C=NC=C1C[C@@H](C(=O)O)N(C(=O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3240.2	Semi standard non polar	33892256
Anserine,3TBDMS,isomer #3	CN1C=NC=C1C[C@@H](C(=O)O)N(C(=O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3100.4	Standard non polar	33892256
Anserine,3TBDMS,isomer #3	CN1C=NC=C1C[C@@H](C(=O)O)N(C(=O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3244.9	Standard polar	33892256
Anserine,4TBDMS,isomer #1	CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3421.1	Semi standard non polar	33892256
Anserine,4TBDMS,isomer #1	CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3240.6	Standard non polar	33892256
Anserine,4TBDMS,isomer #1	CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3106.4	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

Brain
Placenta
Prostate
Skeletal Muscle

Pathways

Name	SMPDB/PathBank	KEGG
beta-Alanine metabolism	Not Available
GABA-Transaminase Deficiency		Not Available
Ureidopropionase Deficiency		Not Available
Carnosinuria, carnosinemia		Not Available
Histidine metabolism

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	41.0 +/- 10.0 uM	Adult (>18 years old)	Both	Normal	9267323	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Urine	Detected and Quantified	<45.021 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	<5.921 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Not Available	details
Urine	Detected and Quantified	<15.95 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	<41.74 umol/mmol creatinine	Adolescent (13-18 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	<4.30 umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	16.16 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	Shaykhutdinov RA,...	details
Urine	Detected and Quantified	<92.76 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	<31.33 umol/mmol creatinine	Infant (0-1 year old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21736852	details
Urine	Detected and Quantified	14.842 +/- 5.257 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21389975	details
Urine	Detected and Quantified	7.0 (3.3 -20.0) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.457 +/- 0.214 uM	Elderly (>65 years old)	Both	Alzheimer's disease	17031479	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected and Quantified	8.0 +/- 5.0 umol/mmol creatinine	Adult (>18 years old)	Both	Alzheimer's disease	17031479	details
Urine	Detected and Quantified	12.808 +/- 6.444 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details

Associated Disorders and Diseases

Disease References

Alzheimer's disease
Fonteh AN, Harrington RJ, Tsai A, Liao P, Harrington MG: Free amino acid and dipeptide changes in the body fluids from Alzheimer's disease subjects. Amino Acids. 2007 Feb;32(2):213-24. Epub 2006 Oct 10. [PubMed:17031479 ]
Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

104300 (Alzheimer's disease)
114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

External Links

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

VMH ID

Not Available

MarkerDB ID

MDB00000094

Good Scents ID

rw1692971

References

Synthesis Reference

Yudaev, N. A. Biosynthesis of anserine. Doklady Akademii Nauk SSSR (1952), 82 615-17.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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 ]
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. Epub 2006 Mar 24. [PubMed:16554972 ]
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. [PubMed:9917666 ]
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. [PubMed:8224369 ]
Kang I, Han SW: Anserine bursitis in patients with osteoarthritis of the knee. South Med J. 2000 Feb;93(2):207-9. [PubMed:10701790 ]
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 ]
Tan KM, Candlish JK: Carnosine and anserine as modulators of neutrophil function. Clin Lab Haematol. 1998 Aug;20(4):239-44. [PubMed:9777271 ]
Boldyrev A, Abe H: Metabolic transformation of neuropeptide carnosine modifies its biological activity. Cell Mol Neurobiol. 1999 Feb;19(1):163-75. [PubMed:10079975 ]
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 ]
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 ]
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 ]

Enzymes

Enzyme Details

1. Beta-Ala-His dipeptidase

General function:: Involved in metallopeptidase activity
Specific function:: Preferential hydrolysis of the beta-Ala-|-His dipeptide (carnosine), and also anserine, Xaa-|-His dipeptides and other dipeptides including homocarnosine
Gene Name:: CNDP1
Uniprot ID:: Q96KN2
Molecular weight:: 56691.6

Enzyme Details

2. Carnosine synthase 1

General function:: Involved in catalytic activity
Specific function:: Catalyzes the synthesis of carnosine and homocarnosine. Carnosine is synthesized more efficiently than homocarnosine.
Gene Name:: CARNS1
Uniprot ID:: A5YM72
Molecular weight:: 101318.725

Reactions

Adenosine triphosphate + Methylhistidine + beta-Alanine → Adenosine monophosphate + Pyrophosphate + Anserine	details

Showing metabocard for Anserine (HMDB0000194)

MOL for HMDB0000194 (Anserine)

3D MOL for HMDB0000194 (Anserine)

3D SDF for HMDB0000194 (Anserine)

3D-SDF for HMDB0000194 (Anserine)

PDB for HMDB0000194 (Anserine)

3D PDB for HMDB0000194 (Anserine)

SMILES for HMDB0000194 (Anserine)

INCHI for HMDB0000194 (Anserine)

Structure for HMDB0000194 (Anserine)

3D Structure for HMDB0000194 (Anserine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

Reactions