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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 14:44:39 UTC

Update Date

2021-09-26 23:09:46 UTC

HMDB ID

HMDB0255167

Secondary Accession Numbers

None

Metabolite Identification

Common Name

n-methacryloyl-l-histidine methyl ester

Description

n-methacryloyl-l-histidine methyl ester 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. Based on a literature review a significant number of articles have been published on n-methacryloyl-l-histidine methyl ester. This compound has been identified in human blood as reported by (PMID: 31557052 ). N-methacryloyl-l-histidine methyl ester is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically n-methacryloyl-l-histidine methyl ester is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0255167
     RDKit          3D
n-methacryloyl-l-histidine methyl ester
 32 32  0  0  0  0  0  0  0  0999 V2000
    4.8059    0.8980   -0.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7527    0.1018    0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9064   -1.3740    0.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4354    0.6711   -0.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3372    1.9020   -0.3395 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3067   -0.1809   -0.0801 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0563    0.3010   -0.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6302   -0.4323   -1.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0281   -0.0490   -1.7362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3888    0.9838   -2.5858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7506    1.0628   -2.6381 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2285    0.0992   -1.8377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1869   -0.5628   -1.3009 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8229    0.0772    0.9983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2649   -0.4632    1.9833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1501    0.4461    1.1199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8800    0.2211    2.3365 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7806    0.4394    0.1183 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6770    1.9552   -0.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9349   -1.5180    0.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7433   -1.8933   -0.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2168   -1.7177    1.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4097   -1.2048    0.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0212    1.3926   -0.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0526   -0.2934   -2.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6229   -1.5131   -1.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7229    1.6262   -3.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2740   -0.1039   -1.6601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2304   -1.3753   -0.6300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4281    0.8702    3.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9349    0.4620    2.2056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7375   -0.8282    2.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  7 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 13  9  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 17 30  1  0
 17 31  1  0
 17 32  1  0
M  END


  Mrv1652309112116442D          

 17 17  0  0  0  0            999 V2000
    1.6709   -2.8817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0834   -2.1672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6709   -1.4528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9084   -2.1672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3209   -2.8817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3209   -1.4528    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1459   -1.4528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5584   -0.7383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3834   -0.7383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8684   -0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6530   -0.3258    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6530   -1.1508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8684   -1.4057    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5584   -2.1672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1459   -2.8817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3834   -2.1672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7959   -2.8817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  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
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0255167

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)C(CC1=CN=CN1)NC(=O)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C11H15N3O3/c1-7(2)10(15)14-9(11(16)17-3)4-8-5-12-6-13-8/h5-6,9H,1,4H2,2-3H3,(H,12,13)(H,14,15)

> <INCHI_KEY>
LTELWGJDCBOKRL-UHFFFAOYSA-N

> <FORMULA>
C11H15N3O3

> <MOLECULAR_WEIGHT>
237.259

> <EXACT_MASS>
237.111341355

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
23.95054574043093

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 3-(1H-imidazol-5-yl)-2-(2-methylprop-2-enamido)propanoate

> <ALOGPS_LOGP>
0.07

> <JCHEM_LOGP>
-0.23297115700000007

> <ALOGPS_LOGS>
-1.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.088490746762492

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.406674021324164

> <JCHEM_PKA_STRONGEST_BASIC>
6.742660454006466

> <JCHEM_POLAR_SURFACE_AREA>
84.08

> <JCHEM_REFRACTIVITY>
61.276700000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.07e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 3-(3H-imidazol-4-yl)-2-(2-methylprop-2-enamido)propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0255167
     RDKit          3D
n-methacryloyl-l-histidine methyl ester
 32 32  0  0  0  0  0  0  0  0999 V2000
    4.8059    0.8980   -0.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7527    0.1018    0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9064   -1.3740    0.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4354    0.6711   -0.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3372    1.9020   -0.3395 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3067   -0.1809   -0.0801 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0563    0.3010   -0.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6302   -0.4323   -1.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0281   -0.0490   -1.7362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3888    0.9838   -2.5858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7506    1.0628   -2.6381 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2285    0.0992   -1.8377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1869   -0.5628   -1.3009 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8229    0.0772    0.9983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2649   -0.4632    1.9833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1501    0.4461    1.1199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8800    0.2211    2.3365 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7806    0.4394    0.1183 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6770    1.9552   -0.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9349   -1.5180    0.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7433   -1.8933   -0.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2168   -1.7177    1.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4097   -1.2048    0.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0212    1.3926   -0.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0526   -0.2934   -2.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6229   -1.5131   -1.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7229    1.6262   -3.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2740   -0.1039   -1.6601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2304   -1.3753   -0.6300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4281    0.8702    3.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9349    0.4620    2.2056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7375   -0.8282    2.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  7 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 13  9  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 17 30  1  0
 17 31  1  0
 17 32  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       3.119  -5.379   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.889  -4.046   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.119  -2.712   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.429  -4.046   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.199  -5.379   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       6.199  -2.712   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       7.739  -2.712   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.509  -1.378   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.049  -1.378   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.954  -0.132   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      12.419  -0.608   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      12.419  -2.148   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      10.954  -2.624   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       8.509  -4.046   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.739  -5.379   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      10.049  -4.046   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      10.819  -5.379   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    9                                                       
CONECT   14    7   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0255167
HETATM    1  C1  UNL     1       4.806   0.898  -0.018  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.753   0.102   0.037  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.906  -1.374   0.280  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.435   0.671  -0.139  1.00  0.00           C  
HETATM    5  O1  UNL     1       2.337   1.902  -0.340  1.00  0.00           O  
HETATM    6  N1  UNL     1       1.307  -0.181  -0.080  1.00  0.00           N  
HETATM    7  C5  UNL     1      -0.056   0.301  -0.246  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.630  -0.432  -1.434  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.028  -0.049  -1.736  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.389   0.984  -2.586  1.00  0.00           C  
HETATM   11  N2  UNL     1      -3.751   1.063  -2.638  1.00  0.00           N  
HETATM   12  C9  UNL     1      -4.228   0.099  -1.838  1.00  0.00           C  
HETATM   13  N3  UNL     1      -3.187  -0.563  -1.301  1.00  0.00           N  
HETATM   14  C10 UNL     1      -0.823   0.077   0.998  1.00  0.00           C  
HETATM   15  O2  UNL     1      -0.265  -0.463   1.983  1.00  0.00           O  
HETATM   16  O3  UNL     1      -2.150   0.446   1.120  1.00  0.00           O  
HETATM   17  C11 UNL     1      -2.880   0.221   2.336  1.00  0.00           C  
HETATM   18  H1  UNL     1       5.781   0.439   0.118  1.00  0.00           H  
HETATM   19  H2  UNL     1       4.677   1.955  -0.193  1.00  0.00           H  
HETATM   20  H3  UNL     1       4.935  -1.518   0.669  1.00  0.00           H  
HETATM   21  H4  UNL     1       3.743  -1.893  -0.687  1.00  0.00           H  
HETATM   22  H5  UNL     1       3.217  -1.718   1.077  1.00  0.00           H  
HETATM   23  H6  UNL     1       1.410  -1.205   0.088  1.00  0.00           H  
HETATM   24  H7  UNL     1      -0.021   1.393  -0.416  1.00  0.00           H  
HETATM   25  H8  UNL     1       0.053  -0.293  -2.281  1.00  0.00           H  
HETATM   26  H9  UNL     1      -0.623  -1.513  -1.185  1.00  0.00           H  
HETATM   27  H10 UNL     1      -1.723   1.626  -3.123  1.00  0.00           H  
HETATM   28  H11 UNL     1      -5.274  -0.104  -1.660  1.00  0.00           H  
HETATM   29  H12 UNL     1      -3.230  -1.375  -0.630  1.00  0.00           H  
HETATM   30  H13 UNL     1      -2.428   0.870   3.114  1.00  0.00           H  
HETATM   31  H14 UNL     1      -3.935   0.462   2.206  1.00  0.00           H  
HETATM   32  H15 UNL     1      -2.737  -0.828   2.669  1.00  0.00           H  
CONECT    1    2    2   18   19
CONECT    2    3    4
CONECT    3   20   21   22
CONECT    4    5    5    6
CONECT    6    7   23
CONECT    7    8   14   24
CONECT    8    9   25   26
CONECT    9   10   10   13
CONECT   10   11   27
CONECT   11   12   12
CONECT   12   13   28
CONECT   13   29
CONECT   14   15   15   16
CONECT   16   17
CONECT   17   30   31   32
END

HMDB0255167
     RDKit          3D
n-methacryloyl-l-histidine methyl ester
 32 32  0  0  0  0  0  0  0  0999 V2000
    4.8059    0.8980   -0.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7527    0.1018    0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9064   -1.3740    0.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4354    0.6711   -0.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3372    1.9020   -0.3395 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3067   -0.1809   -0.0801 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0563    0.3010   -0.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6302   -0.4323   -1.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0281   -0.0490   -1.7362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3888    0.9838   -2.5858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7506    1.0628   -2.6381 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2285    0.0992   -1.8377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1869   -0.5628   -1.3009 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8229    0.0772    0.9983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2649   -0.4632    1.9833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1501    0.4461    1.1199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8800    0.2211    2.3365 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7806    0.4394    0.1183 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6770    1.9552   -0.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9349   -1.5180    0.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7433   -1.8933   -0.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2168   -1.7177    1.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4097   -1.2048    0.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0212    1.3926   -0.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0526   -0.2934   -2.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6229   -1.5131   -1.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7229    1.6262   -3.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2740   -0.1039   -1.6601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2304   -1.3753   -0.6300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4281    0.8702    3.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9349    0.4620    2.2056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7375   -0.8282    2.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  7 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 13  9  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 17 30  1  0
 17 31  1  0
 17 32  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
N-Methacryloyl-L-his methyl ester	MeSH

Chemical Formula

C₁₁H₁₅N₃O₃

Average Molecular Weight

237.259

Monoisotopic Molecular Weight

237.111341355

IUPAC Name

methyl 3-(1H-imidazol-5-yl)-2-(2-methylprop-2-enamido)propanoate

Traditional Name

methyl 3-(3H-imidazol-4-yl)-2-(2-methylprop-2-enamido)propanoate

CAS Registry Number

Not Available

SMILES

COC(=O)C(CC1=CN=CN1)NC(=O)C(C)=C

InChI Identifier

InChI=1S/C11H15N3O3/c1-7(2)10(15)14-9(11(16)17-3)4-8-5-12-6-13-8/h5-6,9H,1,4H2,2-3H3,(H,12,13)(H,14,15)

InChI Key

LTELWGJDCBOKRL-UHFFFAOYSA-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
N-acyl-alpha amino acid or derivatives
Alpha-amino acid ester
Imidazolyl carboxylic acid derivative
Fatty acid ester
Fatty acyl
Heteroaromatic compound
Methyl ester
Imidazole
Azole
Secondary carboxylic acid amide
Carboxylic acid ester
Carboxamide group
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.07	ALOGPS
logP	-0.23	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	12.41	ChemAxon
pKa (Strongest Basic)	6.74	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	84.08 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	61.28 m³·mol⁻¹	ChemAxon
Polarizability	23.95 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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
DeepCCS	[M+H]+	154.13	30932474
DeepCCS	[M-H]-	151.772	30932474
DeepCCS	[M-2H]-	184.713	30932474
DeepCCS	[M+Na]+	160.223	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	9.4946 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.81 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	736.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	235.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	83.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	160.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	41.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	270.3 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	287.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	629.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	639.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	140.0 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	878.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	171.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	182.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	376.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	427.3 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	189.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
n-methacryloyl-l-histidine methyl ester	COC(=O)C(CC1=CN=CN1)NC(=O)C(C)=C	2658.6	Standard polar	33892256
n-methacryloyl-l-histidine methyl ester	COC(=O)C(CC1=CN=CN1)NC(=O)C(C)=C	1386.1	Standard non polar	33892256
n-methacryloyl-l-histidine methyl ester	COC(=O)C(CC1=CN=CN1)NC(=O)C(C)=C	2140.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
n-methacryloyl-l-histidine methyl ester,1TMS,isomer #1	C=C(C)C(=O)NC(CC1=CN=CN1[Si](C)(C)C)C(=O)OC	2172.6	Semi standard non polar	33892256
n-methacryloyl-l-histidine methyl ester,1TMS,isomer #1	C=C(C)C(=O)NC(CC1=CN=CN1[Si](C)(C)C)C(=O)OC	1964.3	Standard non polar	33892256
n-methacryloyl-l-histidine methyl ester,1TMS,isomer #1	C=C(C)C(=O)NC(CC1=CN=CN1[Si](C)(C)C)C(=O)OC	3047.2	Standard polar	33892256
n-methacryloyl-l-histidine methyl ester,1TMS,isomer #2	C=C(C)C(=O)N(C(CC1=CN=C[NH]1)C(=O)OC)[Si](C)(C)C	1993.9	Semi standard non polar	33892256
n-methacryloyl-l-histidine methyl ester,1TMS,isomer #2	C=C(C)C(=O)N(C(CC1=CN=C[NH]1)C(=O)OC)[Si](C)(C)C	1990.1	Standard non polar	33892256
n-methacryloyl-l-histidine methyl ester,1TMS,isomer #2	C=C(C)C(=O)N(C(CC1=CN=C[NH]1)C(=O)OC)[Si](C)(C)C	2899.0	Standard polar	33892256
n-methacryloyl-l-histidine methyl ester,2TMS,isomer #1	C=C(C)C(=O)N(C(CC1=CN=CN1[Si](C)(C)C)C(=O)OC)[Si](C)(C)C	2143.3	Semi standard non polar	33892256
n-methacryloyl-l-histidine methyl ester,2TMS,isomer #1	C=C(C)C(=O)N(C(CC1=CN=CN1[Si](C)(C)C)C(=O)OC)[Si](C)(C)C	2053.3	Standard non polar	33892256
n-methacryloyl-l-histidine methyl ester,2TMS,isomer #1	C=C(C)C(=O)N(C(CC1=CN=CN1[Si](C)(C)C)C(=O)OC)[Si](C)(C)C	2672.1	Standard polar	33892256
n-methacryloyl-l-histidine methyl ester,1TBDMS,isomer #1	C=C(C)C(=O)NC(CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)OC	2396.2	Semi standard non polar	33892256
n-methacryloyl-l-histidine methyl ester,1TBDMS,isomer #1	C=C(C)C(=O)NC(CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)OC	2163.3	Standard non polar	33892256
n-methacryloyl-l-histidine methyl ester,1TBDMS,isomer #1	C=C(C)C(=O)NC(CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)OC	3072.4	Standard polar	33892256
n-methacryloyl-l-histidine methyl ester,1TBDMS,isomer #2	C=C(C)C(=O)N(C(CC1=CN=C[NH]1)C(=O)OC)[Si](C)(C)C(C)(C)C	2231.6	Semi standard non polar	33892256
n-methacryloyl-l-histidine methyl ester,1TBDMS,isomer #2	C=C(C)C(=O)N(C(CC1=CN=C[NH]1)C(=O)OC)[Si](C)(C)C(C)(C)C	2227.2	Standard non polar	33892256
n-methacryloyl-l-histidine methyl ester,1TBDMS,isomer #2	C=C(C)C(=O)N(C(CC1=CN=C[NH]1)C(=O)OC)[Si](C)(C)C(C)(C)C	2964.4	Standard polar	33892256
n-methacryloyl-l-histidine methyl ester,2TBDMS,isomer #1	C=C(C)C(=O)N(C(CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)OC)[Si](C)(C)C(C)(C)C	2581.7	Semi standard non polar	33892256
n-methacryloyl-l-histidine methyl ester,2TBDMS,isomer #1	C=C(C)C(=O)N(C(CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)OC)[Si](C)(C)C(C)(C)C	2462.7	Standard non polar	33892256
n-methacryloyl-l-histidine methyl ester,2TBDMS,isomer #1	C=C(C)C(=O)N(C(CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)OC)[Si](C)(C)C(C)(C)C	2797.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - n-methacryloyl-l-histidine methyl ester GC-MS (Non-derivatized) - 70eV, Positive	splash10-00or-9510000000-65f8c2d13251181f0250	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - n-methacryloyl-l-histidine methyl ester GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

86021246

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for n-methacryloyl-l-histidine methyl ester (HMDB0255167)

MOL for HMDB0255167 (n-methacryloyl-l-histidine methyl ester)

3D MOL for HMDB0255167 (n-methacryloyl-l-histidine methyl ester)

3D SDF for HMDB0255167 (n-methacryloyl-l-histidine methyl ester)

3D-SDF for HMDB0255167 (n-methacryloyl-l-histidine methyl ester)

PDB for HMDB0255167 (n-methacryloyl-l-histidine methyl ester)

3D PDB for HMDB0255167 (n-methacryloyl-l-histidine methyl ester)

SMILES for HMDB0255167 (n-methacryloyl-l-histidine methyl ester)

INCHI for HMDB0255167 (n-methacryloyl-l-histidine methyl ester)

Structure for HMDB0255167 (n-methacryloyl-l-histidine methyl ester)

3D Structure for HMDB0255167 (n-methacryloyl-l-histidine methyl ester)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

NMR Spectra