MiMeDB: Showing metabocard for N-Acetylaspartylglutamic acid (MMDBc0000562)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:40:35 UTC

Update Date

2024-04-30 19:33:00 UTC

Metabolite ID

MMDBc0000562

Metabolite Identification

Common Name

N-Acetylaspartylglutamic acid

Description

N-Acetylaspartylglutamate (NAAG) is a neuropeptide found in millimolar concentrations in the brain that is localized to subpopulations of glutamatergic, cholinergic, GABAergic, and noradrenergic neuronal systems. NAAG is released upon depolarization by a Ca(2+)-dependent process and is an agonist at mGluR3 receptors and an antagonist at NMDA receptors. NAAG is catabolized to N-acetylaspartate and glutamate primarily by glutamate carboxypeptidase II, which is expressed on the extracellular surface of astrocytes. The levels of NAAG and the activity of carboxypeptidase II are altered in a regionally specific fashion in several neuropsychiatric disorders (PMID:9361299 ). N-Acetylaspartylglutamic acid (NAAG) is a purported precursor of N-acetylaspartic acid (NAA) and is present at about one-tenth of the concentration of NAA in the brain. NAAG has been reported to activate N-methyl-D-aspartic acid (NMDA) receptors in neurons. Previous immunohistochemical studies in the vertebrate central nervous system (CNS) have suggested that NAAG is exclusively localized to neurons. Recent evidence, however, indicates that NAAG might also be localized to nonneuronal cells within the CNS. Only traces of NAA and NAAG are detectable in other tissues. Some compounds can change levels of NAA and NAAG in the brain. For example, methylphenidate increases the levels of NAA and NAAG in the cerebral cortex; amphetamine also increases NAA concentration in a mature brain by 26%, raising the possibility that other neurochemical systems might be involved in the clinical effects of stimulants (PMID:10603234 ).

Structure

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

HMDB0001067
     RDKit          3D
N-Acetylaspartylglutamic acid
 37 36  0  0  0  0  0  0  0  0999 V2000
   -5.0367   -0.2449    2.2286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0389   -0.4925    1.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2385   -1.4710    0.3832 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9124    0.3169    0.9471 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9887    0.0174   -0.1290 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0863    1.1311   -1.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2092    1.0019   -2.3171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1308    1.6675   -2.3181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4629    0.2016   -3.4220 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6096   -0.1488    0.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3437    0.1049    1.5491 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4022   -0.5935   -0.5135 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8007   -0.7733   -0.1075 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3781    0.5695    0.2114 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8137    0.5878    0.6104 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7150    0.0891   -0.4509 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8752   -1.1421   -0.6226 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3845    1.0153   -1.2581 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8721   -1.7236    1.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7986   -2.2401    1.5042 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0572   -2.0850    1.6267 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4694    0.7848    2.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8732   -0.9653    2.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5942   -0.3010    3.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7249    1.1245    1.5559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3116   -0.9183   -0.6061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0282    2.1258   -0.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1451    1.0582   -1.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3457   -0.1600   -3.6901 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1979   -0.8436   -1.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3750   -1.2344   -0.9247 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2647    1.2666   -0.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7568    1.0240    1.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1052    1.6647    0.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0395   -0.0013    1.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5559    1.9338   -0.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1578   -2.3466    2.5925 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  2  0
  7  9  1  0
  5 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 13 19  1  0
 19 20  2  0
 19 21  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  6
  6 27  1  0
  6 28  1  0
  9 29  1  0
 12 30  1  0
 13 31  1  6
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 18 36  1  0
 21 37  1  0
M  END


  Mrv1652303062020132D          

 21 20  0  0  0  0            999 V2000
10003.124610000.9698    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10003.124610001.7950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.404810002.1943    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10002.404810003.0187    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.690410003.4312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.975710003.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.261210003.4312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.546610003.0187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.261210004.2561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.118410003.4312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.834110003.0187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.118410004.2561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.840310002.2064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.410910000.5563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.698410000.9698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.984010000.5563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.698410001.7950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.840310000.5563    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10004.553810000.9698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.275710000.5686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.553810001.7950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  1 14  1  0  0  0  0
  1 18  1  0  0  0  0
  2  3  1  0  0  0  0
  2 13  2  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  4 10  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000562

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H16N2O8/c1-5(14)12-7(4-9(17)18)10(19)13-6(11(20)21)2-3-8(15)16/h6-7H,2-4H2,1H3,(H,12,14)(H,13,19)(H,15,16)(H,17,18)(H,20,21)/t6-,7-/m0/s1

> <INCHI_KEY>
OPVPGKGADVGKTG-BQBZGAKWSA-N

> <FORMULA>
C11H16N2O8

> <MOLECULAR_WEIGHT>
304.255

> <EXACT_MASS>
304.090665483

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
27.74784794760162

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(2S)-3-carboxy-2-acetamidopropanamido]pentanedioic acid

> <ALOGPS_LOGP>
-1.10

> <JCHEM_LOGP>
-2.291346324

> <ALOGPS_LOGS>
-1.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
3.724444616747219

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1274533847684935

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9551503529465353

> <JCHEM_POLAR_SURFACE_AREA>
170.1

> <JCHEM_REFRACTIVITY>
64.0643

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.29e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-acetylaspartylglutamic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001067
     RDKit          3D
N-Acetylaspartylglutamic acid
 37 36  0  0  0  0  0  0  0  0999 V2000
   -5.0367   -0.2449    2.2286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0389   -0.4925    1.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2385   -1.4710    0.3832 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9124    0.3169    0.9471 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9887    0.0174   -0.1290 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0863    1.1311   -1.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2092    1.0019   -2.3171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1308    1.6675   -2.3181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4629    0.2016   -3.4220 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6096   -0.1488    0.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3437    0.1049    1.5491 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4022   -0.5935   -0.5135 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8007   -0.7733   -0.1075 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3781    0.5695    0.2114 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8137    0.5878    0.6104 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7150    0.0891   -0.4509 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8752   -1.1421   -0.6226 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3845    1.0153   -1.2581 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8721   -1.7236    1.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7986   -2.2401    1.5042 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0572   -2.0850    1.6267 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4694    0.7848    2.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8732   -0.9653    2.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5942   -0.3010    3.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7249    1.1245    1.5559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3116   -0.9183   -0.6061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0282    2.1258   -0.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1451    1.0582   -1.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3457   -0.1600   -3.6901 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1979   -0.8436   -1.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3750   -1.2344   -0.9247 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2647    1.2666   -0.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7568    1.0240    1.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1052    1.6647    0.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0395   -0.0013    1.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5559    1.9338   -0.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1578   -2.3466    2.5925 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  2  0
  7  9  1  0
  5 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 13 19  1  0
 19 20  2  0
 19 21  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  6
  6 27  1  0
  6 28  1  0
  9 29  1  0
 12 30  1  0
 13 31  1  6
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 18 36  1  0
 21 37  1  0
M  END

HEADER    PROTEIN                                 06-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAR-20         0                                  
HETATM    1  C   UNK     0    8672.4998668.477   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8672.4998670.017   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0    8671.1568670.763   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0    8671.1568672.302   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8669.8228673.072   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8668.4888672.302   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8667.1548673.072   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8665.8208672.302   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8667.1548674.611   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8672.4888673.072   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8673.8248672.302   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8672.4888674.611   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8673.8358670.785   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0    8671.1678667.705   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8669.8378668.477   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0    8668.5038667.705   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0    8669.8378670.017   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0    8673.8358667.705   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0    8675.1678668.477   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8676.5158667.728   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0    8675.1678670.017   0.000  0.00  0.00           O+0
CONECT    1    2   14   18                                                  
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    4   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    2                                                            
CONECT   14    1   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    1   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

COMPND    HMDB0001067
HETATM    1  C1  UNL     1      -5.037  -0.245   2.229  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.039  -0.493   1.141  1.00  0.00           C  
HETATM    3  O1  UNL     1      -4.238  -1.471   0.383  1.00  0.00           O  
HETATM    4  N1  UNL     1      -2.912   0.317   0.947  1.00  0.00           N  
HETATM    5  C3  UNL     1      -1.989   0.017  -0.129  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.086   1.131  -1.166  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.209   1.002  -2.317  1.00  0.00           C  
HETATM    8  O2  UNL     1      -0.131   1.668  -2.318  1.00  0.00           O  
HETATM    9  O3  UNL     1      -1.463   0.202  -3.422  1.00  0.00           O  
HETATM   10  C6  UNL     1      -0.610  -0.149   0.358  1.00  0.00           C  
HETATM   11  O4  UNL     1      -0.344   0.105   1.549  1.00  0.00           O  
HETATM   12  N2  UNL     1       0.402  -0.593  -0.514  1.00  0.00           N  
HETATM   13  C7  UNL     1       1.801  -0.773  -0.108  1.00  0.00           C  
HETATM   14  C8  UNL     1       2.378   0.570   0.211  1.00  0.00           C  
HETATM   15  C9  UNL     1       3.814   0.588   0.610  1.00  0.00           C  
HETATM   16  C10 UNL     1       4.715   0.089  -0.451  1.00  0.00           C  
HETATM   17  O5  UNL     1       4.875  -1.142  -0.623  1.00  0.00           O  
HETATM   18  O6  UNL     1       5.384   1.015  -1.258  1.00  0.00           O  
HETATM   19  C11 UNL     1       1.872  -1.724   1.035  1.00  0.00           C  
HETATM   20  O7  UNL     1       0.799  -2.240   1.504  1.00  0.00           O  
HETATM   21  O8  UNL     1       3.057  -2.085   1.627  1.00  0.00           O  
HETATM   22  H1  UNL     1      -5.469   0.785   2.091  1.00  0.00           H  
HETATM   23  H2  UNL     1      -5.873  -0.965   2.170  1.00  0.00           H  
HETATM   24  H3  UNL     1      -4.594  -0.301   3.228  1.00  0.00           H  
HETATM   25  H4  UNL     1      -2.725   1.125   1.556  1.00  0.00           H  
HETATM   26  H5  UNL     1      -2.312  -0.918  -0.606  1.00  0.00           H  
HETATM   27  H6  UNL     1      -2.028   2.126  -0.671  1.00  0.00           H  
HETATM   28  H7  UNL     1      -3.145   1.058  -1.558  1.00  0.00           H  
HETATM   29  H8  UNL     1      -2.346  -0.160  -3.690  1.00  0.00           H  
HETATM   30  H9  UNL     1       0.198  -0.844  -1.518  1.00  0.00           H  
HETATM   31  H10 UNL     1       2.375  -1.234  -0.925  1.00  0.00           H  
HETATM   32  H11 UNL     1       2.265   1.267  -0.660  1.00  0.00           H  
HETATM   33  H12 UNL     1       1.757   1.024   1.026  1.00  0.00           H  
HETATM   34  H13 UNL     1       4.105   1.665   0.814  1.00  0.00           H  
HETATM   35  H14 UNL     1       4.039  -0.001   1.530  1.00  0.00           H  
HETATM   36  H15 UNL     1       5.556   1.934  -0.886  1.00  0.00           H  
HETATM   37  H16 UNL     1       3.158  -2.347   2.592  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    3    4
CONECT    4    5   25
CONECT    5    6   10   26
CONECT    6    7   27   28
CONECT    7    8    8    9
CONECT    9   29
CONECT   10   11   11   12
CONECT   12   13   30
CONECT   13   14   19   31
CONECT   14   15   32   33
CONECT   15   16   34   35
CONECT   16   17   17   18
CONECT   18   36
CONECT   19   20   20   21
CONECT   21   37
END

HMDB0001067
     RDKit          3D
N-Acetylaspartylglutamic acid
 37 36  0  0  0  0  0  0  0  0999 V2000
   -5.0367   -0.2449    2.2286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0389   -0.4925    1.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2385   -1.4710    0.3832 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9124    0.3169    0.9471 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9887    0.0174   -0.1290 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0863    1.1311   -1.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2092    1.0019   -2.3171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1308    1.6675   -2.3181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4629    0.2016   -3.4220 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6096   -0.1488    0.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3437    0.1049    1.5491 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4022   -0.5935   -0.5135 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8007   -0.7733   -0.1075 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3781    0.5695    0.2114 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8137    0.5878    0.6104 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7150    0.0891   -0.4509 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8752   -1.1421   -0.6226 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3845    1.0153   -1.2581 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8721   -1.7236    1.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7986   -2.2401    1.5042 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0572   -2.0850    1.6267 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4694    0.7848    2.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8732   -0.9653    2.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5942   -0.3010    3.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7249    1.1245    1.5559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3116   -0.9183   -0.6061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0282    2.1258   -0.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1451    1.0582   -1.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3457   -0.1600   -3.6901 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1979   -0.8436   -1.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3750   -1.2344   -0.9247 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2647    1.2666   -0.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7568    1.0240    1.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1052    1.6647    0.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0395   -0.0013    1.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5559    1.9338   -0.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1578   -2.3466    2.5925 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  2  0
  7  9  1  0
  5 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 13 19  1  0
 19 20  2  0
 19 21  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  6
  6 27  1  0
  6 28  1  0
  9 29  1  0
 12 30  1  0
 13 31  1  6
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 18 36  1  0
 21 37  1  0
M  END

Synonyms

Value	Source
Isospaglumic acid	ChEBI
N-Ac-D-e	ChEBI
N-Acetyl-1-aspartylglutamic acid	ChEBI
N-Acetyl-L-asp-L-glu	ChEBI
NAAG	ChEBI
Isospaglumate	Generator
N-Acetyl-1-aspartylglutamate	Generator
N-Acetylaspartylglutamate	Generator
N-Acetyl-L-alpha-aspartylglutamic acid	HMDB
N-Acetyl-aspartyl-glutamate	HMDB
N-Acetyl-1-asp-glu	HMDB
N-(N-Acetyl-L-alpha-aspartyl)-L-glutamic acid	HMDB
Naaxia	HMDB
NAAGA	HMDB
N-Acetyl-aspartyl-glutamic acid	HMDB
Acetyl-alpha-L-aspartylglutamic acid	HMDB
Acetyl-α-L-aspartylglutamic acid	HMDB
N-(N-Acetylaspartyl)glutamic acid	HMDB
N-Acetyl-L-alpha-aspartyl-L-glutamic acid	HMDB
N-Acetyl-L-aspartyl-L-glutamic acid	HMDB
N-Acetyl-L-α-aspartyl-L-glutamic acid	HMDB
N-Acetyl-alpha-L-aspartyl-L-glutamic acid	HMDB
N-Acetyl-alpha-aspartylglutamic acid	HMDB
N-Acetyl-α-L-aspartyl-L-glutamic acid	HMDB
N-Acetyl-α-aspartylglutamic acid	HMDB
alpha-Spaglumic acid	HMDB
Α-spaglumic acid	HMDB
N-Acetylaspartylglutamic acid	HMDB

Molecular Formula

C₁₁H₁₆N₂O₈

Average Mass

304.255

Monoisotopic Mass

304.090665483

IUPAC Name

(2S)-2-[(2S)-3-carboxy-2-acetamidopropanamido]pentanedioic acid

Traditional Name

N-acetylaspartylglutamic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C11H16N2O8/c1-5(14)12-7(4-9(17)18)10(19)13-6(11(20)21)2-3-8(15)16/h6-7H,2-4H2,1H3,(H,12,14)(H,13,19)(H,15,16)(H,17,18)(H,20,21)/t6-,7-/m0/s1

InChI Key

OPVPGKGADVGKTG-BQBZGAKWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Glutamic acid or derivatives
Aspartic acid or derivatives
N-acyl-l-alpha-amino acid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Tricarboxylic acid or derivatives
Fatty amide
N-acyl-amine
Fatty acyl
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dipeptide (CHEBI:73688 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	3.29 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-2.3	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.13	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	170.1 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	64.06 m³·mol⁻¹	ChemAxon
Polarizability	27.75 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	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0002-0900000000-2f2be5e8f2f3cf8bb047	2019-11-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001r-9600000000-b3b345b7a22f2cdfac08	2019-11-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001r-9000000000-20ed6fe2510cf8b50b0a	2019-11-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-004i-2900000000-81d2ffd85e7709309bd4	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udr-0497000000-ed40c363bb0654b17709	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0k92-0960000000-074698ba2f1202824307	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pdj-6900000000-9345f44975a2885c78fb	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0933000000-2b2dfb7f42861c249784	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-067j-1900000000-520ccb836d0a005b4049	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9700000000-eade3ae8efd1db0c4733	2021-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)		2019-11-14	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
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)		2019-11-14	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Placenta
Urine

Tissue Locations

Placenta

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

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Canavan disease	Slight Increase	Association	Human Cerebrospinal Fluid (CSF)	HMDB	16802726
Canavan disease		Association	Human Cerebrospinal Fluid (CSF)	HMDB	10333125
Schizophrenia		Association	Human Urine	HMDB	7595563

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	1		Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Cerebrospinal fluid (csf)	Detected and Quantified	16.37		3.55	37.30	uM	Children (1-13 years old)	Not Specified	Canavan disease	HMDB	16802726
Human Cerebrospinal fluid (csf)	Detected and Quantified	18.7		0.0	37.4	uM	Adult (>18 years old)	Both	Canavan disease	HMDB	10333125
Human Cerebrospinal fluid (csf)	Detected and Quantified	43		0.0	203.58	uM	Children (1-13 years old)	Not Specified	Pelizaeus Merzbacher Disease	HMDB	16802726
Human Urine	Detected and Quantified	2.1	0.9			umol/mmol creatinine	Adult (>18 years old)	Both	Schizophrenia	HMDB	7595563
Human Cerebrospinal fluid (csf)	Detected and Quantified	2.2	0.87			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	7595563
Human Urine	Detected and Quantified	2.35	1.08			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	7067131
Human Urine	Detected and Quantified	2.7	0.92			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	7067131
Human Cerebrospinal fluid (csf)	Detected and Quantified	3.42		0.0	12.68	uM	Children (1-13 years old)	Not Specified	Normal	HMDB	16802726
Human Cerebrospinal fluid (csf)	Detected and Quantified	4.55		0.7	8.4	uM	Adult (>18 years old)	Both	Normal	HMDB	10333125
Human Blood	Detected and Quantified	4.89	0.12			uM	Adult (>18 years old)	Both	Normal	HMDB	16139832
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0001067

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022406

KNApSAcK ID

Not Available

Chemspider ID

164080

KEGG Compound ID

C12270

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

N-Acetylaspartylglutamic_acid

METLIN ID

Not Available

PubChem Compound

188803

PDB ID

Not Available

ChEBI ID

73688

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Coyle JT: The nagging question of the function of N-acetylaspartylglutamate. Neurobiol Dis. 1997;4(3-4):231-8. doi: 10.1006/nbdi.1997.0153. [PubMed:9361299 ]
Ma D, Zhang J, Sugahara K, Ageta T, Nakayama K, Kodama H: Simultaneous determination of N-acetylaspartic acid, N-acetylglutamic acid, and N-acetylaspartylglutamic acid in whole brain of 3-mercaptopropionic acid-treated rats using liquid chromatography-atmospheric pressure chemical ionization mass spectrometry. Anal Biochem. 1999 Dec 15;276(2):124-8. doi: 10.1006/abio.1999.4352. [PubMed:10603234 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for N-Acetylaspartylglutamic acid (MMDBc0000562)

MOL for #<Metabolite:0x00007fdb0a8fae48>

3D MOL for #<Metabolite:0x00007fdb0a8fae48>

3D SDF for #<Metabolite:0x00007fdb0a8fae48>

3D-SDF for #<Metabolite:0x00007fdb0a8fae48>

PDB for #<Metabolite:0x00007fdb0a8fae48>

3D PDB for #<Metabolite:0x00007fdb0a8fae48>

SMILES for #<Metabolite:0x00007fdb0a8fae48>

INCHI for #<Metabolite:0x00007fdb0a8fae48>

Structure for #<Metabolite:0x00007fdb0a8fae48>

3D Structure for #<Metabolite:0x00007fdb0a8fae48>