MiMeDB: Showing metabocard for 2-(3-Carboxy-3-aminopropyl)-L-histidine (MMDBc0032905)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:23:48 UTC

Update Date

2024-04-30 19:54:48 UTC

Metabolite ID

MMDBc0032905

Metabolite Identification

Common Name

2-(3-Carboxy-3-aminopropyl)-L-histidine

Description

2-(3-Carboxy-3-aminopropyl)-L-histidine belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. 2-(3-Carboxy-3-aminopropyl)-L-histidine exists in all eukaryotes, ranging from yeast to plants to humans. 2-(3-Carboxy-3-aminopropyl)-L-histidine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 2-(3-carboxy-3-aminopropyl)-L-histidine a potential biomarker for the consumption of these foods. 2-(3-Carboxy-3-aminopropyl)-L-histidine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on 2-(3-Carboxy-3-aminopropyl)-L-histidine.

Structure

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

HMDB0011655
     RDKit          3D
2-(3-Carboxy-3-aminopropyl)-L-histidine
 34 34  0  0  0  0  0  0  0  0999 V2000
   -4.1864   -1.3177    1.5626 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1792   -0.6804    0.2800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8057   -0.6281   -0.3423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8148    0.1226    0.4905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5108    0.0994   -0.2313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2250   -0.4818   -1.4252 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0603   -0.2869   -1.7450 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5961    0.4452   -0.7083 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0013    0.8960   -0.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7828   -0.2118    0.0839 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2043   -0.3688    1.3771 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1929    0.1443    0.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8224    0.2942    1.1422 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8485    0.3200   -1.1260 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6388    0.6757    0.2054 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7345    0.6799    0.2999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1521    1.1684    1.3612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7781    1.3934   -0.8857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3742   -1.9304    1.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3751   -0.6436    2.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8082   -1.3117   -0.4041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8831   -0.1498   -1.3315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4212   -1.6581   -0.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1630    1.1748    0.6552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6624   -0.3092    1.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5640   -0.6248   -2.6152 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0853    1.8628   -0.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3965    1.0142   -1.6527 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6017   -1.1300   -0.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6299   -1.1111    1.9591 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0658    0.5286    1.8661 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5867   -0.1299   -1.9956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6908    1.1935    1.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6943    0.9611   -1.7975 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
  8 15  1  0
  2 16  1  0
 16 17  2  0
 16 18  1  0
 15  5  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  7 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  6
 11 30  1  0
 11 31  1  0
 14 32  1  0
 15 33  1  0
 18 34  1  0
M  END


  Mrv0541 02241201492D          

 18 18  0  0  1  0            999 V2000
   13.7856   -6.8275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5309   -6.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0830   -5.4301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8280   -4.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3125   -3.9780    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8280   -3.3106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0434   -3.5655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0434   -4.3905    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3760   -3.0804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6224   -3.4160    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.9549   -2.9310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0411   -2.1109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2013   -3.2665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5361   -4.2367    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5925   -6.9993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8472   -7.7840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1447   -6.3864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2334   -7.4405    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 15  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 14  1  6  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 18  1  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0032905

> <DATABASE_NAME>
MIME

> <SMILES>
NC(CCC1=NC=C(C[C@H](N)C(O)=O)N1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H16N4O4/c11-6(9(15)16)1-2-8-13-4-5(14-8)3-7(12)10(17)18/h4,6-7H,1-3,11-12H2,(H,13,14)(H,15,16)(H,17,18)/t6?,7-/m0/s1

> <INCHI_KEY>
CJCSNWWKPUXVRD-MLWJPKLSSA-N

> <FORMULA>
C10H16N4O4

> <MOLECULAR_WEIGHT>
256.2584

> <EXACT_MASS>
256.11715502

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
25.5437504836479

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-4-{5-[(2S)-2-amino-2-carboxyethyl]-1H-imidazol-2-yl}butanoic acid

> <ALOGPS_LOGP>
-4.08

> <JCHEM_LOGP>
-6.493360252363875

> <ALOGPS_LOGS>
-1.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
2.232660542859342

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.629480153597954

> <JCHEM_PKA_STRONGEST_BASIC>
9.77576919184479

> <JCHEM_POLAR_SURFACE_AREA>
155.32

> <JCHEM_REFRACTIVITY>
61.1437

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.71e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-4-{4-[(2S)-2-amino-2-carboxyethyl]-3H-imidazol-2-yl}butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0011655
     RDKit          3D
2-(3-Carboxy-3-aminopropyl)-L-histidine
 34 34  0  0  0  0  0  0  0  0999 V2000
   -4.1864   -1.3177    1.5626 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1792   -0.6804    0.2800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8057   -0.6281   -0.3423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8148    0.1226    0.4905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5108    0.0994   -0.2313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2250   -0.4818   -1.4252 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0603   -0.2869   -1.7450 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5961    0.4452   -0.7083 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0013    0.8960   -0.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7828   -0.2118    0.0839 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2043   -0.3688    1.3771 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1929    0.1443    0.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8224    0.2942    1.1422 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8485    0.3200   -1.1260 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6388    0.6757    0.2054 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7345    0.6799    0.2999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1521    1.1684    1.3612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7781    1.3934   -0.8857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3742   -1.9304    1.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3751   -0.6436    2.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8082   -1.3117   -0.4041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8831   -0.1498   -1.3315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4212   -1.6581   -0.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1630    1.1748    0.6552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6624   -0.3092    1.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5640   -0.6248   -2.6152 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0853    1.8628   -0.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3965    1.0142   -1.6527 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6017   -1.1300   -0.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6299   -1.1111    1.9591 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0658    0.5286    1.8661 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5867   -0.1299   -1.9956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6908    1.1935    1.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6943    0.9611   -1.7975 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
  8 15  1  0
  2 16  1  0
 16 17  2  0
 16 18  1  0
 15  5  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  7 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  6
 11 30  1  0
 11 31  1  0
 14 32  1  0
 15 33  1  0
 18 34  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      25.733 -12.745   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      25.258 -11.280   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      26.288 -10.136   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      25.812  -8.671   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      26.717  -7.426   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      25.812  -6.180   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.348  -6.656   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      24.348  -8.196   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      23.102  -5.750   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.695  -6.377   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      20.449  -5.471   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      20.610  -3.940   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      19.042  -6.097   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0      21.534  -7.909   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      27.239 -13.065   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      27.715 -14.530   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      28.270 -11.921   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0      24.702 -13.889   0.000  0.00  0.00           N+0
CONECT    1    2   15   18                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    4    7                                                       
CONECT    9    7   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10                                                            
CONECT   15    1   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    1                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0011655
HETATM    1  N1  UNL     1      -4.186  -1.318   1.563  1.00  0.00           N  
HETATM    2  C1  UNL     1      -4.179  -0.680   0.280  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.806  -0.628  -0.342  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.815   0.123   0.491  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.511   0.099  -0.231  1.00  0.00           C  
HETATM    6  N2  UNL     1      -0.225  -0.482  -1.425  1.00  0.00           N  
HETATM    7  C5  UNL     1       1.060  -0.287  -1.745  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.596   0.445  -0.708  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.001   0.896  -0.631  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.783  -0.212   0.084  1.00  0.00           C  
HETATM   11  N3  UNL     1       3.204  -0.369   1.377  1.00  0.00           N  
HETATM   12  C9  UNL     1       5.193   0.144   0.074  1.00  0.00           C  
HETATM   13  O1  UNL     1       5.822   0.294   1.142  1.00  0.00           O  
HETATM   14  O2  UNL     1       5.848   0.320  -1.126  1.00  0.00           O  
HETATM   15  N4  UNL     1       0.639   0.676   0.205  1.00  0.00           N  
HETATM   16  C10 UNL     1      -4.734   0.680   0.300  1.00  0.00           C  
HETATM   17  O3  UNL     1      -5.152   1.168   1.361  1.00  0.00           O  
HETATM   18  O4  UNL     1      -4.778   1.393  -0.886  1.00  0.00           O  
HETATM   19  H1  UNL     1      -3.374  -1.930   1.714  1.00  0.00           H  
HETATM   20  H2  UNL     1      -4.375  -0.644   2.332  1.00  0.00           H  
HETATM   21  H3  UNL     1      -4.808  -1.312  -0.404  1.00  0.00           H  
HETATM   22  H4  UNL     1      -2.883  -0.150  -1.331  1.00  0.00           H  
HETATM   23  H5  UNL     1      -2.421  -1.658  -0.503  1.00  0.00           H  
HETATM   24  H6  UNL     1      -2.163   1.175   0.655  1.00  0.00           H  
HETATM   25  H7  UNL     1      -1.662  -0.309   1.486  1.00  0.00           H  
HETATM   26  H8  UNL     1       1.564  -0.625  -2.615  1.00  0.00           H  
HETATM   27  H9  UNL     1       3.085   1.863  -0.065  1.00  0.00           H  
HETATM   28  H10 UNL     1       3.396   1.014  -1.653  1.00  0.00           H  
HETATM   29  H11 UNL     1       3.602  -1.130  -0.539  1.00  0.00           H  
HETATM   30  H12 UNL     1       3.630  -1.111   1.959  1.00  0.00           H  
HETATM   31  H13 UNL     1       3.066   0.529   1.866  1.00  0.00           H  
HETATM   32  H14 UNL     1       5.587  -0.130  -1.996  1.00  0.00           H  
HETATM   33  H15 UNL     1       0.691   1.194   1.109  1.00  0.00           H  
HETATM   34  H16 UNL     1      -4.694   0.961  -1.797  1.00  0.00           H  
CONECT    1    2   19   20
CONECT    2    3   16   21
CONECT    3    4   22   23
CONECT    4    5   24   25
CONECT    5    6    6   15
CONECT    6    7
CONECT    7    8    8   26
CONECT    8    9   15
CONECT    9   10   27   28
CONECT   10   11   12   29
CONECT   11   30   31
CONECT   12   13   13   14
CONECT   14   32
CONECT   15   33
CONECT   16   17   17   18
CONECT   18   34
END

HMDB0011655
     RDKit          3D
2-(3-Carboxy-3-aminopropyl)-L-histidine
 34 34  0  0  0  0  0  0  0  0999 V2000
   -4.1864   -1.3177    1.5626 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1792   -0.6804    0.2800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8057   -0.6281   -0.3423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8148    0.1226    0.4905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5108    0.0994   -0.2313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2250   -0.4818   -1.4252 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0603   -0.2869   -1.7450 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5961    0.4452   -0.7083 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0013    0.8960   -0.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7828   -0.2118    0.0839 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2043   -0.3688    1.3771 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1929    0.1443    0.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8224    0.2942    1.1422 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8485    0.3200   -1.1260 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6388    0.6757    0.2054 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7345    0.6799    0.2999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1521    1.1684    1.3612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7781    1.3934   -0.8857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3742   -1.9304    1.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3751   -0.6436    2.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8082   -1.3117   -0.4041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8831   -0.1498   -1.3315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4212   -1.6581   -0.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1630    1.1748    0.6552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6624   -0.3092    1.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5640   -0.6248   -2.6152 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0853    1.8628   -0.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3965    1.0142   -1.6527 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6017   -1.1300   -0.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6299   -1.1111    1.9591 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0658    0.5286    1.8661 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5867   -0.1299   -1.9956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6908    1.1935    1.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6943    0.9611   -1.7975 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
  8 15  1  0
  2 16  1  0
 16 17  2  0
 16 18  1  0
 15  5  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  7 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  6
 11 30  1  0
 11 31  1  0
 14 32  1  0
 15 33  1  0
 18 34  1  0
M  END

Synonyms

Value	Source
2-(3-Carboxy-3-aminopropyl)-L-histidine	ChEBI
2-(3-amino-3-Carboxypropyl)-L-histidine	HMDB
2-amino-4-[[4-(2-amino-2-Carboxy-ethyl)-1H-imidazol-2-yl]] butanoate	HMDB
2-amino-4-[[4-(2-amino-2-Carboxy-ethyl)-1H-imidazol-2-yl]] butanoic acid	HMDB

Molecular Formula

C₁₀H₁₆N₄O₄

Average Mass

256.2584

Monoisotopic Mass

256.11715502

IUPAC Name

2-amino-4-{5-[(2S)-2-amino-2-carboxyethyl]-1H-imidazol-2-yl}butanoic acid

Traditional Name

2-amino-4-{4-[(2S)-2-amino-2-carboxyethyl]-3H-imidazol-2-yl}butanoic acid

CAS Registry Number

Not Available

SMILES

NC(CCC1=NC=C(C[C@H](N)C(O)=O)N1)C(O)=O

InChI Identifier

InChI=1S/C10H16N4O4/c11-6(9(15)16)1-2-8-13-4-5(14-8)3-7(12)10(17)18/h4,6-7H,1-3,11-12H2,(H,13,14)(H,15,16)(H,17,18)/t6?,7-/m0/s1

InChI Key

CJCSNWWKPUXVRD-MLWJPKLSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Histidine and derivatives

Alternative Parents

Substituents

Histidine or derivatives
Alpha-amino acid
L-alpha-amino acid
Imidazolyl carboxylic acid derivative
Aralkylamine
Dicarboxylic acid or derivatives
Azole
Imidazole
Heteroaromatic compound
Amino acid
Carboxylic acid
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Primary amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:17144 )
L-histidine derivative (CHEBI:17144 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	8.71 g/L	ALOGPS
logP	-4.1	ALOGPS
logP	-6.5	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	1.63	ChemAxon
pKa (Strongest Basic)	9.78	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	155.32 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	61.14 m³·mol⁻¹	ChemAxon
Polarizability	25.54 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

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-02mu-5940000000-c3310ff9a24aa7c862e6	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-001i-3592000000-a21b1849129fc09978d0	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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dl-0490000000-b169c82b73ecee75fb2e	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02tc-0930000000-88b257572c5443b2894a	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kr-1900000000-34de02163a51cec0b920	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0190000000-6fb3de3d4334b0f51e46	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-1790000000-4f147519032e14741316	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-7910000000-b899dda5046bb04ed5ec	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4r-0190000000-c2328930b95b5240880d	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052u-1950000000-d39ef30f4993bac546fc	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01bc-2900000000-34f57b5e9afde72e67e1	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-6b70ce39004c223ed447	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01vo-0590000000-de801a6acbb75116fe8e	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00y0-1900000000-c344db411f89e38f99b3	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192074	Diphthine synthase	Unknown	Q9H2P9	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0010699	S-Adenosylhomocysteine	S-Adenosylmethionine	Diphthamide biosynthesis 5	S-Adenosyl-L-Methionine:2- (3-Carboxy-3-Aminopropyl)-L-Histidine Methyltransferase	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0011655

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028346

KNApSAcK ID

Not Available

Chemspider ID

389308

KEGG Compound ID

C04441

BioCyc ID

2-3-CARBOXY-3-AMINOPROPYL-L-HISTIDINE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440342

PDB ID

Not Available

ChEBI ID

17144

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]

Showing metabocard for 2-(3-Carboxy-3-aminopropyl)-L-histidine (MMDBc0032905)

MOL for #<Metabolite:0x00007fe27b651458>

3D MOL for #<Metabolite:0x00007fe27b651458>

3D SDF for #<Metabolite:0x00007fe27b651458>

3D-SDF for #<Metabolite:0x00007fe27b651458>

PDB for #<Metabolite:0x00007fe27b651458>

3D PDB for #<Metabolite:0x00007fe27b651458>

SMILES for #<Metabolite:0x00007fe27b651458>

INCHI for #<Metabolite:0x00007fe27b651458>

Structure for #<Metabolite:0x00007fe27b651458>

3D Structure for #<Metabolite:0x00007fe27b651458>