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Showing NP-Card for N-Acetylglutamic acid (NP0000536)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:58:12 UTC
NP-MRD IDNP0000536
Secondary Accession NumbersNone
Natural Product Identification
Common NameN-Acetylglutamic acid
DescriptionN-acetyl-L-glutamic acid, also known as N-acetylglutamate (abbreviated NAG) belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N-acetyl-L-glutamic acid is an N-acyl-L-amino acid that is L-glutamic acid in which one of the amine hydrogens is substituted by an acetyl group. N-acetyl-L-glutamic acid is biosynthesized from glutamate and acetylornithine by ornithine acetyltransferase, and from glutamic acid and acetyl-CoA by the enzyme N-acetylglutamate synthase. The reverse reaction, hydrolysis of the acetyl group, is catalyzed by a specific hydrolase. It is the first intermediate involved in the biosynthesis of arginine in prokaryotes and simple eukaryotes and a regulator in the process known as the urea cycle that converts toxic ammonia to urea for excretion from the body in vertebrates. N-Acetyl-L-glutamic acid exists in all living species, ranging from bacteria to humans. In vertebrae and mammals, N-acetylglutamic acid is the allosteric activator molecule to mitochondrial carbamyl phosphate synthetase I (CPSI) which is the first enzyme in the urea cycle. It triggers the production of the first urea cycle intermediate, carbamyl phosphate. CPSI is inactive when N-acetylglutamic acid is not present. In the liver and small intestines, N-acetylglutamic acid-dependent CPSI produces citrulline, the second intermediate in the urea cycle. N-acetylglutamic acid concentrations increase when protein consumption increases due to the accumulation of ammonia that must be secreted through the urea cycle, which supports the role of N-acetylglutamic acid as the cofactor for CPSI. Furthermore, N-acetylglutamic acid can be found in many commonly consumed foods such as soy, corn, and coffee, with cocoa powder containing a notably high concentration. Deficiency in N-acetylglutamic acid in humans is an autosomal recessive disorder that results in blockage of urea production which ultimately increases the concentration of ammonia in the blood (hyperammonemia). This can be caused by defects in the NAGS coding gene or by deficiencies in the precursors essential for its synthesis.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000536 (N-Acetylglutamic acid)


  Mrv1652309042000182D          

 13 12  0  0  0  0            999 V2000
10000.728110000.4124    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.013610000.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.299310000.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.585010000.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.870710000.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.585010001.6496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.7281 9999.5886    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.4437 9999.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1592 9999.5886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4437 9998.3503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.443710000.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.159210000.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.443710001.6496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  1  0  0  0
  1 11  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
  4  6  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
Download

3D MOL for NP0000536 (N-Acetylglutamic acid)

HMDB0001138
     RDKit          3D
N-Acetyl-L-glutamic acid
 24 23  0  0  0  0  0  0  0  0999 V2000
   -3.3142   -0.1497    0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0143   -0.9285    0.5631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2288   -2.2303    0.5424 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8681   -0.3286    0.7817 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3459    0.3068    1.0132 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1085    0.5255   -0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4035   -0.7989   -0.9835 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0709   -0.5037   -2.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3079    0.6919   -2.6584 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4639   -1.5304   -3.0954 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1340    1.7100    1.5044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0629    2.0985    1.6652 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1703    2.5403    1.7721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6055   -0.3402   -0.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1816    0.8991    0.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0590   -0.6215    1.0124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2273   -1.5619    0.8789 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0915   -0.1690    1.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917    1.1363   -0.9890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0241    1.0422   -0.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0908   -1.3935   -0.3197 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4494   -1.3219   -1.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3926   -2.4878   -2.7647 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0166    3.4152    2.2475 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  2  0
  8 10  1  0
  5 11  1  0
 11 12  2  0
 11 13  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  5 18  1  1
  6 19  1  0
  6 20  1  0
  7 21  1  0
  7 22  1  0
 10 23  1  0
 13 24  1  0
M  END
Download

3D SDF for NP0000536 (N-Acetylglutamic acid)


  Mrv1652309042000182D          

 13 12  0  0  0  0            999 V2000
10000.728110000.4124    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.013610000.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.299310000.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.585010000.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.870710000.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.585010001.6496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.7281 9999.5886    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.4437 9999.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1592 9999.5886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4437 9998.3503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.443710000.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.159210000.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.443710001.6496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  1  0  0  0
  1 11  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
  4  6  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0000536

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H11NO5/c1-4(9)8-5(7(12)13)2-3-6(10)11/h5H,2-3H2,1H3,(H,8,9)(H,10,11)(H,12,13)/t5-/m0/s1

> <INCHI_KEY>
RFMMMVDNIPUKGG-YFKPBYRVSA-N

> <FORMULA>
C7H11NO5

> <MOLECULAR_WEIGHT>
189.1659

> <EXACT_MASS>
189.063722467

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
17.440299050547086

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-acetamidopentanedioic acid

> <ALOGPS_LOGP>
-0.67

> <JCHEM_LOGP>
-1.1130154166666664

> <ALOGPS_LOGS>
-1.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.288470351468538

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.432014588807448

> <JCHEM_PKA_STRONGEST_BASIC>
-1.800828671223234

> <JCHEM_POLAR_SURFACE_AREA>
103.70000000000002

> <JCHEM_REFRACTIVITY>
40.731500000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.86e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-acetyl-L-glutamate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000536 (N-Acetylglutamic acid)

HMDB0001138
     RDKit          3D
N-Acetyl-L-glutamic acid
 24 23  0  0  0  0  0  0  0  0999 V2000
   -3.3142   -0.1497    0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0143   -0.9285    0.5631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2288   -2.2303    0.5424 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8681   -0.3286    0.7817 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3459    0.3068    1.0132 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1085    0.5255   -0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4035   -0.7989   -0.9835 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0709   -0.5037   -2.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3079    0.6919   -2.6584 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4639   -1.5304   -3.0954 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1340    1.7100    1.5044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0629    2.0985    1.6652 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1703    2.5403    1.7721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6055   -0.3402   -0.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1816    0.8991    0.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0590   -0.6215    1.0124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2273   -1.5619    0.8789 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0915   -0.1690    1.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917    1.1363   -0.9890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0241    1.0422   -0.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0908   -1.3935   -0.3197 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4494   -1.3219   -1.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3926   -2.4878   -2.7647 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0166    3.4152    2.2475 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  2  0
  8 10  1  0
  5 11  1  0
 11 12  2  0
 11 13  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  5 18  1  1
  6 19  1  0
  6 20  1  0
  7 21  1  0
  7 22  1  0
 10 23  1  0
 13 24  1  0
M  END
Download

PDB for NP0000536 (N-Acetylglutamic acid)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0    8668.0268667.436   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8666.6928668.206   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8665.3598667.436   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8664.0258668.206   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8662.6928667.436   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8664.0258669.746   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0    8668.0268665.899   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0    8669.3628665.127   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8670.6978665.899   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8669.3628663.587   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8669.3628668.206   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8670.6978667.436   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8669.3628669.746   0.000  0.00  0.00           O+0
CONECT    1    2    7   11                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    1    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    1   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END
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3D PDB for NP0000536 (N-Acetylglutamic acid)

COMPND    HMDB0001138
HETATM    1  C1  UNL     1      -3.314  -0.150   0.298  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.014  -0.929   0.563  1.00  0.00           C  
HETATM    3  O1  UNL     1      -2.229  -2.230   0.542  1.00  0.00           O  
HETATM    4  N1  UNL     1      -0.868  -0.329   0.782  1.00  0.00           N  
HETATM    5  C3  UNL     1       0.346   0.307   1.013  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.108   0.525  -0.325  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.404  -0.799  -0.984  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.071  -0.504  -2.269  1.00  0.00           C  
HETATM    9  O2  UNL     1       2.308   0.692  -2.658  1.00  0.00           O  
HETATM   10  O3  UNL     1       2.464  -1.530  -3.095  1.00  0.00           O  
HETATM   11  C7  UNL     1       0.134   1.710   1.504  1.00  0.00           C  
HETATM   12  O4  UNL     1      -1.063   2.099   1.665  1.00  0.00           O  
HETATM   13  O5  UNL     1       1.170   2.540   1.772  1.00  0.00           O  
HETATM   14  H1  UNL     1      -3.606  -0.340  -0.750  1.00  0.00           H  
HETATM   15  H2  UNL     1      -3.182   0.899   0.517  1.00  0.00           H  
HETATM   16  H3  UNL     1      -4.059  -0.622   1.012  1.00  0.00           H  
HETATM   17  H4  UNL     1      -0.227  -1.562   0.879  1.00  0.00           H  
HETATM   18  H5  UNL     1       1.091  -0.169   1.664  1.00  0.00           H  
HETATM   19  H6  UNL     1       0.492   1.136  -0.989  1.00  0.00           H  
HETATM   20  H7  UNL     1       2.024   1.042  -0.076  1.00  0.00           H  
HETATM   21  H8  UNL     1       2.091  -1.394  -0.320  1.00  0.00           H  
HETATM   22  H9  UNL     1       0.449  -1.322  -1.155  1.00  0.00           H  
HETATM   23  H10 UNL     1       2.393  -2.488  -2.765  1.00  0.00           H  
HETATM   24  H11 UNL     1       1.017   3.415   2.248  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    3    4
CONECT    4    5   17
CONECT    5    6   11   18
CONECT    6    7   19   20
CONECT    7    8   21   22
CONECT    8    9    9   10
CONECT   10   23
CONECT   11   12   12   13
CONECT   13   24
END
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SMILES for NP0000536 (N-Acetylglutamic acid)

CC(=O)N[C@@H](CCC(O)=O)C(O)=O
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INCHI for NP0000536 (N-Acetylglutamic acid)

InChI=1S/C7H11NO5/c1-4(9)8-5(7(12)13)2-3-6(10)11/h5H,2-3H2,1H3,(H,8,9)(H,10,11)(H,12,13)/t5-/m0/s1
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View in JSmolView NMR Assignments
Synonyms
ValueSource
(S)-2-(Acetylamino)pentanedioic acidChEBI
Ac-glu-OHChEBI
Acetyl-L-glutamic acidChEBI
Acetylglutamic acidChEBI
L-N-Acetylglutamic acidChEBI
N-Ac-glu-OHChEBI
N-ACETYL-L-glutamATEChEBI
N-Acetylglutamic acidChEBI
(S)-2-(Acetylamino)pentanedioateGenerator
Acetyl-L-glutamateGenerator
AcetylglutamateGenerator
L-N-AcetylglutamateGenerator
N-AcetylglutamateGenerator
N-Acetylglutamic acid semialdehydeHMDB
N-Acetylglutamate, potassium salt, (L)-isomerHMDB
N-Acetylglutamate, (D)-isomerHMDB
N-Acetylglutamate, calcium salt (1:1), (L)-isomerHMDB
N-Acetylglutamate, dipotassium salt, (L)-isomerHMDB
N-Acetylglutamate, disodium salt, (L)-isomerHMDB
N-Acetylglutamate, calcium salt, (L)-isomerHMDB
N-Acetylglutamate, magnesium salt, (L)-isomerHMDB
Sodium N-acetylglutamateHMDB
N-Acetylglutamate, (DL)-isomerHMDB
N-Acetylglutamate, monosodium salt, (L)-isomerHMDB
N-Acetyl-L-glutaminic acidHMDB
alpha-(N-Acetyl)-L-glutamic acidHMDB
Α-(N-acetyl)-L-glutamic acidHMDB
NAcGluHMDB
N-Acetyl-L-glutamic acidGenerator, KEGG
Chemical FormulaC7H11NO5
Average Mass189.1659 Da
Monoisotopic Mass189.06372 Da
IUPAC Name(2S)-2-acetamidopentanedioic acid
Traditional NameN-acetyl-L-glutamate
CAS Registry Number1188-37-0
SMILES
CC(=O)N[C@@H](CCC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C7H11NO5/c1-4(9)8-5(7(12)13)2-3-6(10)11/h5H,2-3H2,1H3,(H,8,9)(H,10,11)(H,12,13)/t5-/m0/s1
InChI KeyRFMMMVDNIPUKGG-YFKPBYRVSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Actinidia chinensisFooDB
Agaricus bisporusFooDB
AgaveFooDB
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosumFooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Aloysia triphyllaFooDB
AmaranthusFooDB
Amelanchier alnifoliaFooDB
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anethum graveolensFooDB
Angelica keiskeiFooDB
Annona cherimolaFooDB
Annona muricataFooDB
Annona reticulataFooDB
Annona squamosaFooDB
Anser anserFooDB
Anthriscus cerefoliumFooDB
Apis ceranaLOTUS Database
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arachis hypogaeaFooDB
Arctium lappaFooDB
Armoracia rusticanaFooDB
Artemisia dracunculusFooDB
Artemisia vulgarisFooDB
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Asparagus officinalisFooDB
Attalea speciosaFooDB
Auricularia auricula-judaeFooDB
Auricularia polytrichaFooDB
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Basella albaFooDB
Benincasa hispidaFooDB
Bertholletia excelsaFooDB
Beta vulgarisFooDB
Beta vulgaris ssp. ciclaFooDB
Bison bisonFooDB
Borago officinalisFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica alboglabraFooDB
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridisFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensisFooDB
Brassica rapa var. rapaFooDB
Brassica ruvoFooDB
Brosimum alicastrumFooDB
Bubalus bubalisFooDB
Byrsonima crassifoliaFooDB
Cajanus cajanFooDB
Canarium ovatumFooDB
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Capsicum annuum L.FooDB
Capsicum annuum var. annuumFooDB
Capsicum chinenseFooDB
Capsicum pubescensFooDB
Carica papaya L.FooDB
Carissa macrocarpaFooDB
Carthamus tinctoriusFooDB
Carum carviFooDB
CaryaFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Castanea crenataFooDB
Castanea mollissimaFooDB
Castanea sativaFooDB
Ceratonia siliquaFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chamaemelum nobileFooDB
Chamerion angustifoliumFooDB
Chenopodium albumFooDB
Chenopodium quinoaFooDB
Chrysanthemum coronariumFooDB
Cicer arietinumFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
Cinnamomum aromaticumFooDB
Cinnamomum verumFooDB
CirsiumFooDB
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus latifoliaFooDB
Citrus limonFooDB
Citrus maximaFooDB
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colocasia esculentaFooDB
ColumbaFooDB
ColumbidaeFooDB
Corchorus olitoriusFooDB
Coriandrum sativum L.FooDB
CorylusFooDB
Corylus avellanaFooDB
Crateva religiosaFooDB
Crocus sativusFooDB
Cucumis meloFooDB
Cucumis metuliferusFooDB
Cucumis sativus L.FooDB
CucurbitaFooDB
Cucurbita maximaFooDB
Cucurbita moschataFooDB
Cuminum cyminumFooDB
Curcuma longaFooDB
Cydonia oblongaFooDB
Cymbopogon citratusFooDB
Cynara cardunculusFooDB
Cynara scolymusFooDB
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Dimocarpus longanFooDB
DioscoreaFooDB
Dioscorea pentaphyllaFooDB
DiospyrosFooDB
Diospyros kakiFooDB
Diospyros virginianaFooDB
Dromaius novaehollandiaeFooDB
Durio zibethinusFooDB
Dysphania ambrosioidesFooDB
ElaeisFooDB
Eleocharis dulcisFooDB
Elettaria cardamomumFooDB
Empetrum nigrumFooDB
Equus caballusFooDB
Eragrostis tefFooDB
Eriobotrya japonicaFooDB
Eruca vesicaria subsp. SativaFooDB
Eugenia javanicaFooDB
Eugenia unifloraFooDB
Eutrema japonicumFooDB
Fagopyrum esculentumFooDB
Fagopyrum tataricumFooDB
FagusFooDB
Feijoa sellowianaFooDB
Ficus caricaFooDB
Flammulina velutipesFooDB
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
Gallus gallusFooDB
Garcinia mangostanaFooDB
Gaylussacia baccataFooDB
Ginkgo bilobaFooDB
Glycine maxFooDB
GossypiumFooDB
Grifola frondosaFooDB
Hedysarum alpinumFooDB
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
Hibiscus sabbariffaFooDB
Hippophae rhamnoidesFooDB
Homo sapiensLOTUS Database
Hordeum vulgareFooDB
Hypericum japonicumLOTUS Database
Hyssopus officinalis L.FooDB
Illicium verumFooDB
Ipomoea aquaticaFooDB
Ipomoea batatasFooDB
JuglansFooDB
Juglans ailanthifoliaFooDB
Juglans cinereaFooDB
Juglans nigra L.FooDB
Juglans regiaFooDB
Lablab purpureusFooDB
Lactuca sativaFooDB
Lagenaria sicerariaFooDB
Lagopus mutaFooDB
Lathyrus sativusFooDB
Laurus nobilis L.FooDB
Lens culinarisFooDB
Lentinus edodesFooDB
Lepidium sativumFooDB
LeporidaeFooDB
Lepus timidusFooDB
Levisticum officinaleFooDB
Linum usitatissimumFooDB
Litchi chinensisFooDB
Luffa aegyptiacaFooDB
LupinusFooDB
Lupinus albusFooDB
MacadamiaFooDB
Macadamia tetraphyllaFooDB
Malpighia emarginataFooDB
MalusFooDB
Malus pumilaFooDB
Mammea americanaFooDB
Mangifera indicaFooDB
Manihot esculentaFooDB
Manilkara zapotaFooDB
Maranta arundinaceaFooDB
Matricaria recutitaFooDB
Matteuccia struthiopterisFooDB
Medicago sativaFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Melissa officinalis L.FooDB
MenthaFooDB
Mentha aquaticaFooDB
Mentha arvensisFooDB
Mentha spicataFooDB
Mentha x piperitaFooDB
Mespilus germanicaFooDB
Metroxylon saguFooDB
Momordica charantiaFooDB
MorchellaceaeFooDB
Morella rubraFooDB
Moringa oleiferaFooDB
MorusFooDB
Morus nigraFooDB
Musa acuminataFooDB
Musa x paradisiacaFooDB
MyricaFooDB
Myristica fragransFooDB
NelumboFooDB
Nelumbo nuciferaFooDB
Nephelium lappaceumFooDB
Numida meleagrisFooDB
Nuphar luteaFooDB
Ocimum basilicumFooDB
OdocoileusFooDB
Oenothera biennisFooDB
Olea europaeaFooDB
OpuntiaFooDB
Opuntia cochenilliferaFooDB
Opuntia macrorhizaFooDB
Origanum majoranaFooDB
Origanum onitesFooDB
Origanum vulgareFooDB
Origanum X majoricumFooDB
OryctolagusFooDB
Oryza rufipogonFooDB
Oryza sativaFooDB
Ovis ariesFooDB
Pachyrhizus erosusFooDB
Panax ginsengFooDB
Pangium eduleFooDB
Panicum miliaceumFooDB
Paraburkholderia phymatum-
Passiflora edulisFooDB
Pastinaca sativaFooDB
Pediomelum esculentumFooDB
Perideridia oreganaFooDB
Persea americanaFooDB
Petasites japonicusFooDB
Petroselinum crispumFooDB
Phaseolus coccineusFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Phoenix dactyliferaFooDB
Photinia melanocarpaFooDB
Phyllostachys edulisFooDB
PhysalisFooDB
Physalis philadelphica var. immaculataFooDB
Phytolacca americanaFooDB
Pimenta dioicaFooDB
Pimpinella anisumFooDB
PinusFooDB
Pinus edulisFooDB
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
Pleurotus ostreatusFooDB
Polygonum alpinumFooDB
Portulaca oleraceaFooDB
Pouteria sapotaFooDB
Prunus armeniacaFooDB
Prunus aviumFooDB
Prunus avium L.FooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Prunus persica var. persicaFooDB
Prunus tomentosaFooDB
Prunus virginianaFooDB
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Punica granatumFooDB
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
QuercusFooDB
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativusFooDB
Rheum rhabarbarumFooDB
Ribes aureumFooDB
Ribes glandulosumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
RosaFooDB
Rubus arcticusFooDB
Rubus chamaemorusFooDB
Rubus idaeusFooDB
Rubus occidentalisFooDB
Rubus spectabilisFooDB
RumexFooDB
Rumex acetosaFooDB
Rumex articusFooDB
Sagittaria latifoliaFooDB
Salix pulchraFooDB
Salmonella entericaLOTUS Database
Salvia elegansFooDB
Salvia hispanicaFooDB
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Satureja hortensis L.FooDB
Satureja montanaFooDB
Scorzonera hispanicaFooDB
Secale cerealeFooDB
Sechium eduleFooDB
Sesamum indicumFooDB
Sesbania bispinosaFooDB
Sinapis albaFooDB
SisymbriumFooDB
Solanum lycopersicumFooDB
Solanum lycopersicum var. cerasiformeFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum quitoenseFooDB
Solanum tuberosumFooDB
Sorbus aucupariaFooDB
Sorghum bicolorFooDB
Spinacia oleraceaFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Synechococcus elongatusLOTUS Database
Syzygium aromaticumFooDB
Syzygium cuminiFooDB
Syzygium jambosFooDB
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Tetragonia tetragonioidesFooDB
ThelespermaFooDB
Thymus pulegioidesFooDB
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia L.FooDB
Tragopogon porrifoliusFooDB
Trigonella foenum-graecumFooDB
TriticumFooDB
Triticum aestivumFooDB
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Trypanosoma bruceiLOTUS Database
Typha angustifoliaFooDB
VacciniumFooDB
Vaccinium angustifoliumFooDB
Vaccinium angustifolium X Vaccinium corymbosumFooDB
Vaccinium arboreumFooDB
Vaccinium corymbosumFooDB
Vaccinium deliciosumFooDB
Vaccinium elliottiiFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtilloidesFooDB
Vaccinium myrtillusFooDB
Vaccinium ovalifoliumFooDB
Vaccinium ovatumFooDB
Vaccinium oxycoccosFooDB
Vaccinium parvifoliumFooDB
Vaccinium reticulatumFooDB
Vaccinium stamineumFooDB
Vaccinium uliginosumFooDB
Vaccinium vitis-idaeaFooDB
Valerianella locustaFooDB
VanillaFooDB
Verbena officinalisFooDB
Viburnum eduleFooDB
Vicia fabaFooDB
Vigna aconitifoliaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna umbellataFooDB
Vigna unguiculataFooDB
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
Vigna unguiculata var. sesquipedalisFooDB
VitisFooDB
Vitis aestivalisFooDB
Vitis labruscaFooDB
Vitis rotundifoliaFooDB
Vitis viniferaLOTUS Database
Vitis vinifera L.FooDB
Xanthosoma sagittifoliumFooDB
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Zizania aquaticaFooDB
Ziziphus zizyphusFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGlutamic acid and derivatives
Alternative Parents
Substituents
  • Glutamic acid or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point199 - 201 °CNot Available
Boiling Point495.00 to 496.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility52 mg/mLNot Available
LogP-2.131 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility18.6 g/LALOGPS
logP-0.67ALOGPS
logP-1.1ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)3.43ChemAxon
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area103.7 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity40.73 m³·mol⁻¹ChemAxon
Polarizability17.44 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001138
DrugBank IDDB04075
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031019
KNApSAcK IDC00053528
Chemspider ID64077
KEGG Compound IDC00624
BioCyc IDACETYL-GLU
BiGG IDNot Available
Wikipedia LinkN-Acetylglutamic_acid
METLIN IDNot Available
PubChem Compound70914
PDB IDNot Available
ChEBI ID17533
Good Scents IDrw1265511
References
General References
  1. Zhang W, Holzknecht RA, Butkowski RJ, Tuchman M: Immunochemical analysis of carbamyl phosphate synthetase I and ornithine transcarbamylase deficient livers: elevated N-acetylglutamate level in a liver lacking carbamyl phosphate synthetase protein. Clin Invest Med. 1990 Aug;13(4):183-8. [PubMed:2208834 ]
  2. Tavazzi B, Lazzarino G, Leone P, Amorini AM, Bellia F, Janson CG, Di Pietro V, Ceccarelli L, Donzelli S, Francis JS, Giardina B: Simultaneous high performance liquid chromatographic separation of purines, pyrimidines, N-acetylated amino acids, and dicarboxylic acids for the chemical diagnosis of inborn errors of metabolism. Clin Biochem. 2005 Nov;38(11):997-1008. Epub 2005 Sep 1. [PubMed:16139832 ]
  3. Sugahara K, Zhang J, Kodama H: Liquid chromatographic-mass spectrometric analysis of N-acetylamino acids in human urine. J Chromatogr B Biomed Appl. 1994 Jul 1;657(1):15-21. [PubMed:7952062 ]
  4. Tuchman M, Holzknecht RA: N-acetylglutamate content in liver and gut of normal and fasted mice, normal human livers, and livers of individuals with carbamyl phosphate synthetase or ornithine transcarbamylase deficiency. Pediatr Res. 1990 Apr;27(4 Pt 1):408-12. [PubMed:2342831 ]
  5. Vockley J, Vockley CM, Lin SP, Tuchman M, Wu TC, Lin CY, Seashore MR: Normal N-acetylglutamate concentration measured in liver from a new patient with N-acetylglutamate synthetase deficiency: physiologic and biochemical implications. Biochem Med Metab Biol. 1992 Feb;47(1):38-46. [PubMed:1562355 ]