NP-MRD: Showing NP-Card for N-Acetylaspartylglutamic acid (NP0000671)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2024-09-17 15:42:38 UTC

NP-MRD ID

NP0000671

Secondary Accession Numbers

None

Natural Product 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>
NP0000671

> <DATABASE_NAME>
NP-MRD

> <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

View in JSmol View NMR Assignments

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, ChEBI

Chemical Formula

C₁₁H₁₆N₂O₈

Average Mass

304.2533 Da

Monoisotopic Mass

304.09067 Da

IUPAC Name

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

Traditional Name

N-acetylaspartylglutamic acid

CAS Registry Number

3106-85-2

SMILES

CC(=O)NC(CC(O)=O)C(=O)NC(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)

InChI Key

OPVPGKGADVGKTG-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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 )

Physical Properties

State

Solid

Experimental Properties

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

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

External Links

HMDB ID

HMDB0001067

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

General References

Coyle JT: The nagging question of the function of N-acetylaspartylglutamate. Neurobiol Dis. 1997;4(3-4):231-8. [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. [PubMed:10603234 ]
Chen L, Chao Y, Cheng P, Li N, Zheng H, Yang Y: UPLC-QTOF/MS-Based Metabolomics Reveals the Protective Mechanism of Hydrogen on Mice with Ischemic Stroke. Neurochem Res. 2019 Aug;44(8):1950-1963. doi: 10.1007/s11064-019-02829-x. Epub 2019 Jun 24. [PubMed:31236794 ]
Raider K, Ma D, Harris JL, Fuentes I, Rogers RS, Wheatley JL, Geiger PC, Yeh HW, Choi IY, Brooks WM, Stanford JA: A high fat diet alters metabolic and bioenergetic function in the brain: A magnetic resonance spectroscopy study. Neurochem Int. 2016 Jul;97:172-80. doi: 10.1016/j.neuint.2016.04.008. Epub 2016 Apr 26. [PubMed:27125544 ]

Showing NP-Card for N-Acetylaspartylglutamic acid (NP0000671)

MOL for NP0000671 (N-Acetylaspartylglutamic acid)

3D MOL for NP0000671 (N-Acetylaspartylglutamic acid)

3D SDF for NP0000671 (N-Acetylaspartylglutamic acid)

3D-SDF for NP0000671 (N-Acetylaspartylglutamic acid)

PDB for NP0000671 (N-Acetylaspartylglutamic acid)

3D PDB for NP0000671 (N-Acetylaspartylglutamic acid)

SMILES for NP0000671 (N-Acetylaspartylglutamic acid)

INCHI for NP0000671 (N-Acetylaspartylglutamic acid)

Structure for NP0000671 (N-Acetylaspartylglutamic acid)

3D Structure for NP0000671 (N-Acetylaspartylglutamic acid)