MiMeDB: Showing metabocard for N-Acetyl-L-citrulline (MMDBc0049870)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 22:45:12 UTC

Update Date

2022-12-15 22:52:19 UTC

Metabolite ID

MMDBc0049870

Metabolite Identification

Common Name

N-Acetyl-L-citrulline

Description

N-alpha-Acetyl-L-citrulline, also known as N-acetyl-L-citrulline, N-acetylcitrulline, is an N-acetylated metabolite of citrulline that is part of the arginine biosynthetic pathway. Arginine biosynthesis is notable for its complexity and variability at the genetic level, and by its connection with several other pathways, such as pyrimidine and polyamine biosynthesis, and certain degradative pathways. The initial steps of the arginine biosynthetic pathways proceed via N-acetylated intermediates. The presumed reason for this is that the acetylation prevents the spontaneous cyclization of glutamate derivatives, which leads to proline biosynthesis. N-acetyl-L-ornithine can be transcarbamylated directly by the enzyme acetylornithine transcarbamylase, resulting in N-acetyl-L-citrulline. The enzyme acetylornithine deacetylase can accept N-acetyl-L-citrulline as a substrate and can deacetylate it into citrulline. N-alpha-Acetyl-L-citrulline is found in cases of deficiency of the urea cycle enzyme argininosuccinate synthase (EC 6.3.4.5) that leads to increased concentrations of citrulline and N-acetylcitrulline in the urine (PMID: 14633929 ).

Structure

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

HMDB0000856
     RDKit          3D
N-alpha-Acetyl-L-citrulline
 30 29  0  0  0  0  0  0  0  0999 V2000
   -4.1580   -1.5159   -0.9609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2235   -0.7639   -0.0919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3159   -0.9030    1.1518 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2545    0.0879   -0.6667 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3653    0.8025    0.1810 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0820    0.4722   -0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4337   -0.9519    0.2460 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9216   -1.1151    0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7234   -0.2998    0.8932 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1385   -0.3719    0.7651 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9735    0.4120    1.6033 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6959   -1.1122   -0.0725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5691    2.2572   -0.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4300    2.6356   -0.8454 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8323    3.1852    0.6809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8270   -1.5254   -2.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1805   -1.0884   -0.9516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1785   -2.5720   -0.6161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2266    0.1625   -1.7100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6043    0.5473    1.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7230    1.1167    0.6246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3459    0.7047   -1.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0757   -1.5792   -0.5323 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1359   -1.3274    1.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2097   -2.2018    0.1325 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2117   -0.8599   -1.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3084    0.3400    1.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1976    1.4021    1.3579 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3949    0.0351    2.4923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2545    4.0268    0.9986 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  5 13  1  0
 13 14  2  0
 13 15  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  4 19  1  0
  5 20  1  1
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 11 29  1  0
 15 30  1  0
M  END


  Mrv1652303092022352D          

 15 14  0  0  0  0            999 V2000
10034.109910033.0527    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10033.391410033.4635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10032.675910033.0527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10031.960510033.4635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10031.245110033.0527    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10030.529610033.4635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10029.814310033.0527    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10030.529610034.2894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10034.109910032.2256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10034.824210031.8116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10035.540710032.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10034.824210030.9853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10034.824210033.4635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10035.540710033.0527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10034.824210034.2894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  1  1  0  0  0
  1 13  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0049870

> <DATABASE_NAME>
MIME

> <SMILES>
CC(=O)N[C@@H](CCCNC(N)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H15N3O4/c1-5(12)11-6(7(13)14)3-2-4-10-8(9)15/h6H,2-4H2,1H3,(H,11,12)(H,13,14)(H3,9,10,15)/t6-/m0/s1

> <INCHI_KEY>
WMQMIOYQXNRROC-LURJTMIESA-N

> <FORMULA>
C8H15N3O4

> <MOLECULAR_WEIGHT>
217.2224

> <EXACT_MASS>
217.106255983

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
21.486829058845306

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-5-(carbamoylamino)-2-acetamidopentanoic acid

> <ALOGPS_LOGP>
-1.96

> <JCHEM_LOGP>
-1.8510329956666667

> <ALOGPS_LOGS>
-1.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.030159592147147

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.872733207277384

> <JCHEM_PKA_STRONGEST_BASIC>
-1.4604347442751138

> <JCHEM_POLAR_SURFACE_AREA>
121.52000000000001

> <JCHEM_REFRACTIVITY>
50.772800000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.57e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-acetyl-L-citrulline

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000856
     RDKit          3D
N-alpha-Acetyl-L-citrulline
 30 29  0  0  0  0  0  0  0  0999 V2000
   -4.1580   -1.5159   -0.9609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2235   -0.7639   -0.0919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3159   -0.9030    1.1518 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2545    0.0879   -0.6667 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3653    0.8025    0.1810 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0820    0.4722   -0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4337   -0.9519    0.2460 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9216   -1.1151    0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7234   -0.2998    0.8932 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1385   -0.3719    0.7651 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9735    0.4120    1.6033 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6959   -1.1122   -0.0725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5691    2.2572   -0.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4300    2.6356   -0.8454 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8323    3.1852    0.6809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8270   -1.5254   -2.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1805   -1.0884   -0.9516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1785   -2.5720   -0.6161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2266    0.1625   -1.7100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6043    0.5473    1.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7230    1.1167    0.6246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3459    0.7047   -1.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0757   -1.5792   -0.5323 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1359   -1.3274    1.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2097   -2.2018    0.1325 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2117   -0.8599   -1.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3084    0.3400    1.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1976    1.4021    1.3579 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3949    0.0351    2.4923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2545    4.0268    0.9986 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  5 13  1  0
 13 14  2  0
 13 15  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  4 19  1  0
  5 20  1  1
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 11 29  1  0
 15 30  1  0
M  END

HEADER    PROTEIN                                 09-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-MAR-20         0                                  
HETATM    1  C   UNK     0    8730.3388728.365   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8728.9978729.132   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8727.6628728.365   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8726.3268729.132   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0    8724.9918728.365   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0    8723.6558729.132   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0    8722.3208728.365   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0    8723.6558730.674   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0    8730.3388726.821   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0    8731.6728726.048   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8733.0098726.821   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8731.6728724.506   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0    8731.6728729.132   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0    8733.0098728.365   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0    8731.6728730.674   0.000  0.00  0.00           O+0
CONECT    1    2    9   13                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    1   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    1   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

COMPND    HMDB0000856
HETATM    1  C1  UNL     1      -4.158  -1.516  -0.961  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.224  -0.764  -0.092  1.00  0.00           C  
HETATM    3  O1  UNL     1      -3.316  -0.903   1.152  1.00  0.00           O  
HETATM    4  N1  UNL     1      -2.255   0.088  -0.667  1.00  0.00           N  
HETATM    5  C3  UNL     1      -1.365   0.802   0.181  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.082   0.472  -0.001  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.434  -0.952   0.246  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.922  -1.115   0.019  1.00  0.00           C  
HETATM    9  N2  UNL     1       2.723  -0.300   0.893  1.00  0.00           N  
HETATM   10  C7  UNL     1       4.139  -0.372   0.765  1.00  0.00           C  
HETATM   11  N3  UNL     1       4.973   0.412   1.603  1.00  0.00           N  
HETATM   12  O2  UNL     1       4.696  -1.112  -0.072  1.00  0.00           O  
HETATM   13  C8  UNL     1      -1.569   2.257  -0.020  1.00  0.00           C  
HETATM   14  O3  UNL     1      -2.430   2.636  -0.845  1.00  0.00           O  
HETATM   15  O4  UNL     1      -0.832   3.185   0.681  1.00  0.00           O  
HETATM   16  H1  UNL     1      -3.827  -1.525  -2.021  1.00  0.00           H  
HETATM   17  H2  UNL     1      -5.180  -1.088  -0.952  1.00  0.00           H  
HETATM   18  H3  UNL     1      -4.178  -2.572  -0.616  1.00  0.00           H  
HETATM   19  H4  UNL     1      -2.227   0.162  -1.710  1.00  0.00           H  
HETATM   20  H5  UNL     1      -1.604   0.547   1.249  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.723   1.117   0.625  1.00  0.00           H  
HETATM   22  H7  UNL     1       0.346   0.705  -1.067  1.00  0.00           H  
HETATM   23  H8  UNL     1      -0.076  -1.579  -0.532  1.00  0.00           H  
HETATM   24  H9  UNL     1       0.136  -1.327   1.232  1.00  0.00           H  
HETATM   25  H10 UNL     1       2.210  -2.202   0.133  1.00  0.00           H  
HETATM   26  H11 UNL     1       2.212  -0.860  -1.020  1.00  0.00           H  
HETATM   27  H12 UNL     1       2.308   0.340   1.617  1.00  0.00           H  
HETATM   28  H13 UNL     1       5.198   1.402   1.358  1.00  0.00           H  
HETATM   29  H14 UNL     1       5.395   0.035   2.492  1.00  0.00           H  
HETATM   30  H15 UNL     1      -1.255   4.027   0.999  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    3    4
CONECT    4    5   19
CONECT    5    6   13   20
CONECT    6    7   21   22
CONECT    7    8   23   24
CONECT    8    9   25   26
CONECT    9   10   27
CONECT   10   11   12   12
CONECT   11   28   29
CONECT   13   14   14   15
CONECT   15   30
END

HMDB0000856
     RDKit          3D
N-alpha-Acetyl-L-citrulline
 30 29  0  0  0  0  0  0  0  0999 V2000
   -4.1580   -1.5159   -0.9609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2235   -0.7639   -0.0919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3159   -0.9030    1.1518 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2545    0.0879   -0.6667 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3653    0.8025    0.1810 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0820    0.4722   -0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4337   -0.9519    0.2460 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9216   -1.1151    0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7234   -0.2998    0.8932 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1385   -0.3719    0.7651 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9735    0.4120    1.6033 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6959   -1.1122   -0.0725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5691    2.2572   -0.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4300    2.6356   -0.8454 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8323    3.1852    0.6809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8270   -1.5254   -2.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1805   -1.0884   -0.9516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1785   -2.5720   -0.6161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2266    0.1625   -1.7100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6043    0.5473    1.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7230    1.1167    0.6246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3459    0.7047   -1.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0757   -1.5792   -0.5323 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1359   -1.3274    1.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2097   -2.2018    0.1325 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2117   -0.8599   -1.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3084    0.3400    1.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1976    1.4021    1.3579 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3949    0.0351    2.4923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2545    4.0268    0.9986 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  5 13  1  0
 13 14  2  0
 13 15  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  4 19  1  0
  5 20  1  1
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 11 29  1  0
 15 30  1  0
M  END

Synonyms

Value	Source
(2S)-2-(Acetylamino)-5-[(aminocarbonyl)amino]pentanoic acid	ChEBI
(S)-2-ACETAMIDO-5-ureidopentanoIC ACID	ChEBI
(2S)-2-(Acetylamino)-5-[(aminocarbonyl)amino]pentanoate	Generator
(S)-2-ACETAMIDO-5-ureidopentanoate	Generator
N-a-Acetyl-L-citrulline	Generator
N-Α-acetyl-L-citrulline	Generator
N-Acetyl-L-citrulline	HMDB
N2-Acetyl-N5-(aminocarbonyl)-L-ornithine	HMDB
Nalpha-acetyl-L-citrulline	HMDB
Nalpha-acetylcitrulline	HMDB
Nα-acetyl-L-citrulline	HMDB
Nα-acetylcitrulline	HMDB
alpha-N-Acetylcitrulline	HMDB
Α-N-acetylcitrulline	HMDB

Molecular Formula

C₈H₁₅N₃O₄

Average Mass

217.2224

Monoisotopic Mass

217.106255983

IUPAC Name

(2S)-5-(carbamoylamino)-2-acetamidopentanoic acid

Traditional Name

N-acetyl-L-citrulline

CAS Registry Number

Not Available

SMILES

CC(=O)N[C@@H](CCCNC(N)=O)C(O)=O

InChI Identifier

InChI=1S/C8H15N3O4/c1-5(12)11-6(7(13)14)3-2-4-10-8(9)15/h6H,2-4H2,1H3,(H,11,12)(H,13,14)(H3,9,10,15)/t6-/m0/s1

InChI Key

WMQMIOYQXNRROC-LURJTMIESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-L-alpha-amino acids

Alternative Parents

Substituents

N-acyl-l-alpha-amino acid
Fatty acid
Acetamide
Carboxamide group
Carbonic acid derivative
Secondary carboxylic acid amide
Urea
Carboxylic acid
Monocarboxylic acid or derivatives
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N-acetyl-L-amino acid (CHEBI:49002 )
N-acetylcitrulline (CHEBI:49002 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	3.57 g/L	ALOGPS
logP	-2	ALOGPS
logP	-1.9	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	3.87	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	121.52 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	50.77 m³·mol⁻¹	ChemAxon
Polarizability	21.49 Å³	ChemAxon
Number of Rings	0	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	splash10-0006-9400000000-7401e8328e755c9a54fe	2017-08-28	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00e9-0900000000-b7f7505693c52ea91fa5	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-001i-2900000000-a96ef51f6b478a3b6d30	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9200000000-9441d923bf5fa62ab976	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-001i-7900000000-05a0d30dc4911b7ae9fc	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05xr-0930000000-3b9d796f05634936c485	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06w9-1900000000-ff1ced7b78fd0b206b4a	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-5900000000-a4e2e243a03648720a7c	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00xu-3920000000-b2b92b49a0c49064919f	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05dl-4900000000-3deaf4d3cb14ff42b7e0	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-4bb42e23506bdcaba7c4	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01b9-1940000000-d843dcf3f292d83e02a5	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-3900000000-8ae141fbcff3973274ff	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-568f68b2bbb834a48941	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0gb9-0490000000-c345f9ff031271a70e8c	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0900-0910000000-6d0541054b5eb47b749e	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dl-9300000000-129aa9c775d01121bb1b	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

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

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0008261	N2-Acetylornithine	N-Acetyl-L-citrulline	Not Available		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
Bacteria	Proteobacteria	175	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Metabolic reconstruction
Bacteria	Firmicutes	303	Pig ; Human feces; Human ; Cattle ; Human subgingival plaque	Metabolic reconstruction
Bacteria	Actinobacteria	121	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	123	Human feces; Human appendix biopsy; Human ; Human stool; Human urine; Human gastric fluid; Human saliva; Human subgingival plaque	Metabolic reconstruction
Bacteria	Synergistetes	4	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Bacteria	Fusobacteria	9	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	2		Metabolic reconstruction
Bacteria	Tenericutes	4	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1		Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction

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

HMDB0000856

DrugBank ID

DB02368

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB031018

KNApSAcK ID

Not Available

Chemspider ID

571213

KEGG Compound ID

C15532

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

656979

PDB ID

Not Available

ChEBI ID

49002

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Engelke UF, Liebrand-van Sambeek ML, de Jong JG, Leroy JG, Morava E, Smeitink JA, Wevers RA: N-acetylated metabolites in urine: proton nuclear magnetic resonance spectroscopic study on patients with inborn errors of metabolism. Clin Chem. 2004 Jan;50(1):58-66. doi: 10.1373/clinchem.2003.020214. Epub 2003 Nov 18. [PubMed:14633929 ]

Showing metabocard for N-Acetyl-L-citrulline (MMDBc0049870)

MOL for #<Metabolite:0x00007fece19cbaa0>

3D MOL for #<Metabolite:0x00007fece19cbaa0>

3D SDF for #<Metabolite:0x00007fece19cbaa0>

3D-SDF for #<Metabolite:0x00007fece19cbaa0>

PDB for #<Metabolite:0x00007fece19cbaa0>

3D PDB for #<Metabolite:0x00007fece19cbaa0>

SMILES for #<Metabolite:0x00007fece19cbaa0>

INCHI for #<Metabolite:0x00007fece19cbaa0>

Structure for #<Metabolite:0x00007fece19cbaa0>

3D Structure for #<Metabolite:0x00007fece19cbaa0>