Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:41:52 UTC

Update Date

2021-09-26 22:52:21 UTC

HMDB ID

HMDB0244546

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N-(2-Methylacryloyl)-L-histidine

Description

2-[(1-hydroxy-2-methylprop-2-en-1-ylidene)amino]-3-(1H-imidazol-5-yl)propanoic acid 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 very few articles have been published on 2-[(1-hydroxy-2-methylprop-2-en-1-ylidene)amino]-3-(1H-imidazol-5-yl)propanoic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). N-(2-methylacryloyl)-l-histidine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically N-(2-Methylacryloyl)-L-histidine 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

HMDB0244546
     RDKit          3D
N-(2-Methylacryloyl)-L-histidine
 29 29  0  0  0  0  0  0  0  0999 V2000
    3.2832    1.1224    1.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4008    1.0224    0.2642 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3513    2.0528   -0.7985 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4864   -0.1050    0.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5238   -0.9823    1.1676 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5161   -0.2484   -0.7522 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4118   -1.3382   -0.8007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8419   -0.8658   -0.6974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0592   -0.1362    0.5982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4584   -0.7101    1.7877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5217    0.3077    2.6658 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1855    1.4628    2.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9003    1.1836    0.8034 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2487   -2.1235   -2.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6312   -1.7846   -2.8585 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0259   -3.2259   -2.3070 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3470    0.3941    2.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9691    1.9462    1.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8169    2.9831   -0.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9778    1.6771   -1.6582 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3304    2.2908   -1.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4784    0.4741   -1.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2516   -2.0337    0.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1188   -0.1624   -1.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4794   -1.7780   -0.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6696   -1.7632    1.9507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1591    2.4402    2.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5967    1.8732    0.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1836   -3.9730   -1.6558 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
 13  9  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 16 29  1  0
M  END


  Mrv1533004241521282D          

 16 16  0  0  0  0            999 V2000
    2.7509   -3.6663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1634   -2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7509   -2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9884   -2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4009   -3.6663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4009   -2.2374    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2259   -2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6384   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4634   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9483   -0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7329   -1.1104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7329   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9483   -2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6384   -2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4634   -2.9519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2259   -3.6663    0.0000 O   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
M  END
> <DATABASE_ID>
HMDB0244546

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H13N3O3/c1-6(2)9(14)13-8(10(15)16)3-7-4-11-5-12-7/h4-5,8H,1,3H2,2H3,(H,11,12)(H,13,14)(H,15,16)

> <INCHI_KEY>
ADESRODTHOCWKB-UHFFFAOYSA-N

> <FORMULA>
C10H13N3O3

> <MOLECULAR_WEIGHT>
223.232

> <EXACT_MASS>
223.095691291

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
21.705515373123383

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(1H-imidazol-5-yl)-2-(2-methylprop-2-enamido)propanoic acid

> <ALOGPS_LOGP>
-0.05

> <JCHEM_LOGP>
-1.190286542826571

> <ALOGPS_LOGS>
-1.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.938624402393717

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6814931725263254

> <JCHEM_PKA_STRONGEST_BASIC>
6.751038508729245

> <JCHEM_POLAR_SURFACE_AREA>
95.08

> <JCHEM_REFRACTIVITY>
56.507600000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.40e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(3H-imidazol-4-yl)-2-(2-methylprop-2-enamido)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0244546
     RDKit          3D
N-(2-Methylacryloyl)-L-histidine
 29 29  0  0  0  0  0  0  0  0999 V2000
    3.2832    1.1224    1.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4008    1.0224    0.2642 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3513    2.0528   -0.7985 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4864   -0.1050    0.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5238   -0.9823    1.1676 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5161   -0.2484   -0.7522 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4118   -1.3382   -0.8007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8419   -0.8658   -0.6974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0592   -0.1362    0.5982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4584   -0.7101    1.7877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5217    0.3077    2.6658 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1855    1.4628    2.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9003    1.1836    0.8034 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2487   -2.1235   -2.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6312   -1.7846   -2.8585 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0259   -3.2259   -2.3070 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3470    0.3941    2.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9691    1.9462    1.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8169    2.9831   -0.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9778    1.6771   -1.6582 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3304    2.2908   -1.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4784    0.4741   -1.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2516   -2.0337    0.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1188   -0.1624   -1.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4794   -1.7780   -0.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6696   -1.7632    1.9507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1591    2.4402    2.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5967    1.8732    0.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1836   -3.9730   -1.6558 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
 13  9  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 16 29  1  0
M  END

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       5.135  -6.844   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.905  -5.510   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.135  -4.176   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.445  -5.510   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.215  -6.844   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       8.215  -4.176   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       9.755  -4.176   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.525  -2.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.065  -2.843   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.970  -1.597   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      14.435  -2.073   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      14.435  -3.613   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      12.970  -4.089   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      10.525  -5.510   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      12.065  -5.510   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       9.755  -6.844   0.000  0.00  0.00           O+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                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0244546
HETATM    1  C1  UNL     1       3.283   1.122   1.222  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.401   1.022   0.264  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.351   2.053  -0.798  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.486  -0.105   0.269  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.524  -0.982   1.168  1.00  0.00           O  
HETATM    6  N1  UNL     1       0.516  -0.248  -0.752  1.00  0.00           N  
HETATM    7  C5  UNL     1      -0.412  -1.338  -0.801  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.842  -0.866  -0.697  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.059  -0.136   0.598  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.458  -0.710   1.788  1.00  0.00           C  
HETATM   11  N2  UNL     1      -2.522   0.308   2.666  1.00  0.00           N  
HETATM   12  C9  UNL     1      -2.186   1.463   2.082  1.00  0.00           C  
HETATM   13  N3  UNL     1      -1.900   1.184   0.803  1.00  0.00           N  
HETATM   14  C10 UNL     1      -0.249  -2.123  -2.027  1.00  0.00           C  
HETATM   15  O2  UNL     1       0.631  -1.785  -2.858  1.00  0.00           O  
HETATM   16  O3  UNL     1      -1.026  -3.226  -2.307  1.00  0.00           O  
HETATM   17  H1  UNL     1       3.347   0.394   2.008  1.00  0.00           H  
HETATM   18  H2  UNL     1       3.969   1.946   1.240  1.00  0.00           H  
HETATM   19  H3  UNL     1       2.817   2.983  -0.411  1.00  0.00           H  
HETATM   20  H4  UNL     1       2.978   1.677  -1.658  1.00  0.00           H  
HETATM   21  H5  UNL     1       1.330   2.291  -1.135  1.00  0.00           H  
HETATM   22  H6  UNL     1       0.478   0.474  -1.501  1.00  0.00           H  
HETATM   23  H7  UNL     1      -0.252  -2.034   0.068  1.00  0.00           H  
HETATM   24  H8  UNL     1      -2.119  -0.162  -1.494  1.00  0.00           H  
HETATM   25  H9  UNL     1      -2.479  -1.778  -0.714  1.00  0.00           H  
HETATM   26  H10 UNL     1      -2.670  -1.763   1.951  1.00  0.00           H  
HETATM   27  H11 UNL     1      -2.159   2.440   2.588  1.00  0.00           H  
HETATM   28  H12 UNL     1      -1.597   1.873   0.056  1.00  0.00           H  
HETATM   29  H13 UNL     1      -1.184  -3.973  -1.656  1.00  0.00           H  
CONECT    1    2    2   17   18
CONECT    2    3    4
CONECT    3   19   20   21
CONECT    4    5    5    6
CONECT    6    7   22
CONECT    7    8   14   23
CONECT    8    9   24   25
CONECT    9   10   10   13
CONECT   10   11   26
CONECT   11   12   12
CONECT   12   13   27
CONECT   13   28
CONECT   14   15   15   16
CONECT   16   29
END

HMDB0244546
     RDKit          3D
N-(2-Methylacryloyl)-L-histidine
 29 29  0  0  0  0  0  0  0  0999 V2000
    3.2832    1.1224    1.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4008    1.0224    0.2642 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3513    2.0528   -0.7985 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4864   -0.1050    0.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5238   -0.9823    1.1676 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5161   -0.2484   -0.7522 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4118   -1.3382   -0.8007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8419   -0.8658   -0.6974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0592   -0.1362    0.5982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4584   -0.7101    1.7877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5217    0.3077    2.6658 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1855    1.4628    2.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9003    1.1836    0.8034 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2487   -2.1235   -2.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6312   -1.7846   -2.8585 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0259   -3.2259   -2.3070 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3470    0.3941    2.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9691    1.9462    1.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8169    2.9831   -0.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9778    1.6771   -1.6582 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3304    2.2908   -1.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4784    0.4741   -1.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2516   -2.0337    0.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1188   -0.1624   -1.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4794   -1.7780   -0.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6696   -1.7632    1.9507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1591    2.4402    2.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5967    1.8732    0.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1836   -3.9730   -1.6558 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
 13  9  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 16 29  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-[(1-Hydroxy-2-methylprop-2-en-1-ylidene)amino]-3-(1H-imidazol-5-yl)propanoate	Generator

Chemical Formula

C₁₀H₁₃N₃O₃

Average Molecular Weight

223.232

Monoisotopic Molecular Weight

223.095691291

IUPAC Name

3-(1H-imidazol-5-yl)-2-(2-methylprop-2-enamido)propanoic acid

Traditional Name

3-(3H-imidazol-4-yl)-2-(2-methylprop-2-enamido)propanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C10H13N3O3/c1-6(2)9(14)13-8(10(15)16)3-7-4-11-5-12-7/h4-5,8H,1,3H2,2H3,(H,11,12)(H,13,14)(H,15,16)

InChI Key

ADESRODTHOCWKB-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
N-acyl-alpha amino acid or derivatives
Imidazolyl carboxylic acid derivative
Azole
Imidazole
Heteroaromatic compound
Secondary carboxylic acid amide
Carboxamide group
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Azacycle
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
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)

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	-0.05	ALOGPS
logP	-1.2	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	3.68	ChemAxon
pKa (Strongest Basic)	6.75	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	95.08 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	56.51 m³·mol⁻¹	ChemAxon
Polarizability	21.71 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
DeepCCS	[M+H]+	142.885	30932474
DeepCCS	[M-H]-	140.527	30932474
DeepCCS	[M-2H]-	175.548	30932474
DeepCCS	[M+Na]+	150.772	30932474
AllCCS	[M+H]+	150.2	32859911
AllCCS	[M+H-H2O]+	146.5	32859911
AllCCS	[M+NH4]+	153.7	32859911
AllCCS	[M+Na]+	154.7	32859911
AllCCS	[M-H]-	149.2	32859911
AllCCS	[M+Na-2H]-	149.7	32859911
AllCCS	[M+HCOO]-	150.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-(2-Methylacryloyl)-L-histidine	CC(=C)C(=O)NC(CC1=CN=CN1)C(O)=O	2997.6	Standard polar	33892256
N-(2-Methylacryloyl)-L-histidine	CC(=C)C(=O)NC(CC1=CN=CN1)C(O)=O	1424.2	Standard non polar	33892256
N-(2-Methylacryloyl)-L-histidine	CC(=C)C(=O)NC(CC1=CN=CN1)C(O)=O	2219.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-(2-Methylacryloyl)-L-histidine,2TMS,isomer #1	C=C(C)C(=O)N(C(CC1=CN=C[NH]1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2093.5	Semi standard non polar	33892256
N-(2-Methylacryloyl)-L-histidine,2TMS,isomer #1	C=C(C)C(=O)N(C(CC1=CN=C[NH]1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2039.6	Standard non polar	33892256
N-(2-Methylacryloyl)-L-histidine,2TMS,isomer #1	C=C(C)C(=O)N(C(CC1=CN=C[NH]1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2689.6	Standard polar	33892256
N-(2-Methylacryloyl)-L-histidine,2TMS,isomer #2	C=C(C)C(=O)NC(CC1=CN=CN1[Si](C)(C)C)C(=O)O[Si](C)(C)C	2287.7	Semi standard non polar	33892256
N-(2-Methylacryloyl)-L-histidine,2TMS,isomer #2	C=C(C)C(=O)NC(CC1=CN=CN1[Si](C)(C)C)C(=O)O[Si](C)(C)C	2029.5	Standard non polar	33892256
N-(2-Methylacryloyl)-L-histidine,2TMS,isomer #2	C=C(C)C(=O)NC(CC1=CN=CN1[Si](C)(C)C)C(=O)O[Si](C)(C)C	2813.5	Standard polar	33892256
N-(2-Methylacryloyl)-L-histidine,2TMS,isomer #3	C=C(C)C(=O)N(C(CC1=CN=CN1[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2206.5	Semi standard non polar	33892256
N-(2-Methylacryloyl)-L-histidine,2TMS,isomer #3	C=C(C)C(=O)N(C(CC1=CN=CN1[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2146.1	Standard non polar	33892256
N-(2-Methylacryloyl)-L-histidine,2TMS,isomer #3	C=C(C)C(=O)N(C(CC1=CN=CN1[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2833.6	Standard polar	33892256
N-(2-Methylacryloyl)-L-histidine,3TMS,isomer #1	C=C(C)C(=O)N(C(CC1=CN=CN1[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2218.7	Semi standard non polar	33892256
N-(2-Methylacryloyl)-L-histidine,3TMS,isomer #1	C=C(C)C(=O)N(C(CC1=CN=CN1[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2132.0	Standard non polar	33892256
N-(2-Methylacryloyl)-L-histidine,3TMS,isomer #1	C=C(C)C(=O)N(C(CC1=CN=CN1[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2533.8	Standard polar	33892256
N-(2-Methylacryloyl)-L-histidine,2TBDMS,isomer #1	C=C(C)C(=O)N(C(CC1=CN=C[NH]1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2552.3	Semi standard non polar	33892256
N-(2-Methylacryloyl)-L-histidine,2TBDMS,isomer #1	C=C(C)C(=O)N(C(CC1=CN=C[NH]1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2485.6	Standard non polar	33892256
N-(2-Methylacryloyl)-L-histidine,2TBDMS,isomer #1	C=C(C)C(=O)N(C(CC1=CN=C[NH]1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2836.3	Standard polar	33892256
N-(2-Methylacryloyl)-L-histidine,2TBDMS,isomer #2	C=C(C)C(=O)NC(CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2756.0	Semi standard non polar	33892256
N-(2-Methylacryloyl)-L-histidine,2TBDMS,isomer #2	C=C(C)C(=O)NC(CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2460.0	Standard non polar	33892256
N-(2-Methylacryloyl)-L-histidine,2TBDMS,isomer #2	C=C(C)C(=O)NC(CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2896.4	Standard polar	33892256
N-(2-Methylacryloyl)-L-histidine,2TBDMS,isomer #3	C=C(C)C(=O)N(C(CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2682.1	Semi standard non polar	33892256
N-(2-Methylacryloyl)-L-histidine,2TBDMS,isomer #3	C=C(C)C(=O)N(C(CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2542.8	Standard non polar	33892256
N-(2-Methylacryloyl)-L-histidine,2TBDMS,isomer #3	C=C(C)C(=O)N(C(CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2917.4	Standard polar	33892256
N-(2-Methylacryloyl)-L-histidine,3TBDMS,isomer #1	C=C(C)C(=O)N(C(CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2883.9	Semi standard non polar	33892256
N-(2-Methylacryloyl)-L-histidine,3TBDMS,isomer #1	C=C(C)C(=O)N(C(CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2743.3	Standard non polar	33892256
N-(2-Methylacryloyl)-L-histidine,3TBDMS,isomer #1	C=C(C)C(=O)N(C(CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2795.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-(2-Methylacryloyl)-L-histidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-015c-9200000000-b6e50ba1dbe844392fbb	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(2-Methylacryloyl)-L-histidine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(2-Methylacryloyl)-L-histidine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(2-Methylacryloyl)-L-histidine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(2-Methylacryloyl)-L-histidine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(2-Methylacryloyl)-L-histidine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(2-Methylacryloyl)-L-histidine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(2-Methylacryloyl)-L-histidine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Methylacryloyl)-L-histidine 10V, Positive-QTOF	splash10-05fr-0490000000-7bc838e6047764865585	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Methylacryloyl)-L-histidine 20V, Positive-QTOF	splash10-03dr-0900000000-3a80cde5ebff96514271	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Methylacryloyl)-L-histidine 40V, Positive-QTOF	splash10-01po-9300000000-a5339094b9a7d5d2afeb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Methylacryloyl)-L-histidine 10V, Negative-QTOF	splash10-00di-1390000000-05d6c7aafdd4377a7652	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Methylacryloyl)-L-histidine 20V, Negative-QTOF	splash10-001i-9310000000-f9c15c7866a0f8ce3976	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Methylacryloyl)-L-histidine 40V, Negative-QTOF	splash10-00kf-9400000000-8f66627301961c1dd4d5	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	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

292103

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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-(2-Methylacryloyl)-L-histidine (HMDB0244546)

MOL for HMDB0244546 (N-(2-Methylacryloyl)-L-histidine)

3D MOL for HMDB0244546 (N-(2-Methylacryloyl)-L-histidine)

3D SDF for HMDB0244546 (N-(2-Methylacryloyl)-L-histidine)

3D-SDF for HMDB0244546 (N-(2-Methylacryloyl)-L-histidine)

PDB for HMDB0244546 (N-(2-Methylacryloyl)-L-histidine)

3D PDB for HMDB0244546 (N-(2-Methylacryloyl)-L-histidine)

SMILES for HMDB0244546 (N-(2-Methylacryloyl)-L-histidine)

INCHI for HMDB0244546 (N-(2-Methylacryloyl)-L-histidine)

Structure for HMDB0244546 (N-(2-Methylacryloyl)-L-histidine)

3D Structure for HMDB0244546 (N-(2-Methylacryloyl)-L-histidine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra