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Showing NP-Card for N-Acetyl-L-aspartic acid (NP0000081)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-09 22:33:30 UTC
NP-MRD IDNP0000081
Secondary Accession NumbersNone
Natural Product Identification
Common NameN-Acetyl-L-aspartic acid
DescriptionN-Acetyl-L-Aspartic acid (NAA) or N-Acetylaspartic acid, belongs to the class of organic compounds known as N-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. N-alpha-Acetyl-L-aspartic acid can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-Acetyl-L-aspartic acid is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-aspartic acid. N-acetyl amino acids can be produced either via direct synthesis of specific N-acetyltransferases or via the proteolytic degradation of N-acetylated proteins by specific hydrolases. N-terminal acetylation of proteins is a widespread and highly conserved process in eukaryotes that is involved in protection and stability of proteins (PMID: 16465618 ). About 85% of all human proteins and 68% of all yeast proteins are acetylated at their N-terminus (PMID: 21750686 ). Several proteins from prokaryotes and archaea are also modified by N-terminal acetylation. The majority of eukaryotic N-terminal-acetylation reactions occur through N-acetyltransferase enzymes or NAT’s (PMID: 30054468 ). These enzymes consist of three main oligomeric complexes NatA, NatB, and NatC, which are composed of at least a unique catalytic subunit and one unique ribosomal anchor. The substrate specificities of different NAT enzymes are mainly determined by the identities of the first two N-terminal residues of the target protein. The human NatA complex co-translationally acetylates N-termini that bear a small amino acid (A, S, T, C, and occasionally V and G) (PMID: 30054468 ). NatA also exists in a monomeric state and can post-translationally acetylate acidic N-termini residues (D-, E-). NatB and NatC acetylate N-terminal methionine with further specificity determined by the identity of the second amino acid. N-acetylated amino acids, such as N-acetylaspartate can be released by an N-acylpeptide hydrolase from peptides generated by proteolytic degradation (PMID: 16465618 ). In addition to the NAT enzymes and protein-based acetylation, N-acetylation of free aspartic acid can also occur. In particular, N-Acetyl-L-aspartic acid can be synthesized in neurons from the amino acid aspartate and acetyl coenzyme A (acetyl CoA). Specifically, the enzyme known as aspartate N-acetyltransferase (EC 2.3.1.17) Catalyzes the transfer of the acetyl group of acetyl CoA to the amino group of aspartate. N-Acetyl-L-aspartic acid is the second most concentrated molecule in the brain after the amino acid glutamate. The various functions served by N-acetylaspartic acid are still under investigation, but the primary proposed functions include (1) acting as a neuronal osmolyte that is involved in fluid balance in the brain, (2) serving as a source of acetate for lipid and myelin synthesis in oligodendrocytes (the glial cells that myelinate neuronal axons), (3) serving as a precursor for the synthesis of the important dipeptide neurotransmitter N-acetylaspartylglutamate (NAAG), and (4) playing a potential role in energy production from the amino acid glutamate in neuronal mitochondria. High neurotransmitter (i.E. N-acetylaspartic acid) levels can lead to abnormal neural signaling, delayed or arrested intellectual development, and difficulties with general motor skills. When present in sufficiently high levels, N-acetylaspartic acid can be a neurotoxin, an acidogen, and a metabotoxin. A neurotoxin is a compound that disrupts or attacks neural tissue. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of N-acetylaspartic acid are associated with Canavan disease. Because N-acetylaspartic acid functions as an organic acid and high levels of organic acids can lead to a condition known as acidosis. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. Infants with acidosis have symptoms that include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart abnormalities, seizures, coma, and possibly death. Many affected children with organic acidemias experience intellectual disability or delayed development. In adults, acidosis or acidemia is characterized by headaches, confusion, feeling tired, tremors, sleepiness, and flapping tremors. Many N-acetylamino acids, including N-acetylaspartic acid, are classified as uremic toxins if present in high abundance in the serum or plasma (PMID: 26317986 ; PMID: 20613759 ). Uremic toxins are a diverse group of endogenously produced molecules that, if not properly cleared or eliminated by the kidneys, can cause kidney damage, cardiovascular disease and neurological deficits (PMID: 18287557 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000081 (N-Acetyl-L-aspartic acid)

      
  Mrv1652305271900222D          

 12 11  0  0  0  0            999 V2000
10000.3567 9999.5885    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.6428 9999.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9285 9999.5885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2140 9999.1751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.928510000.4123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.356710000.4123    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.072310000.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.785810000.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.072310001.6497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.0723 9999.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7858 9999.5885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.0723 9998.3502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  6  0  0  0
  1 10  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  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
M  END
Download

3D MOL for NP0000081 (N-Acetyl-L-aspartic acid)

HMDB0000812
     RDKit          3D
N-Acetyl-L-aspartic acid
 21 20  0  0  0  0  0  0  0  0999 V2000
   -3.1013   -1.1183   -0.0739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7454   -0.8489   -0.7545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6320   -1.4916   -1.8638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8299   -0.0320   -0.2027 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1205    0.8115    0.3627 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1603    0.2285    1.2436 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0399   -0.7760    0.6568 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9145   -1.3058    1.4299 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0137   -1.2013   -0.6555 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6841    1.8704   -0.5627 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2150    2.0619   -1.7099 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7407    2.6464   -0.1351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9436   -1.4430    0.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6006   -1.9194   -0.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7182   -0.2098   -0.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0277   -0.2374   -1.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4879    1.5255    1.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6337   -0.2573    2.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7337    1.0646    1.7099 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2175   -2.1903   -0.8492 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5576    2.8222   -0.7191 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
  1 13  1  0
  1 14  1  0
  1 15  1  0
  4 16  1  0
  5 17  1  1
  6 18  1  0
  6 19  1  0
  9 20  1  0
 12 21  1  0
M  END
Download

3D SDF for NP0000081 (N-Acetyl-L-aspartic acid)

      
  Mrv1652305271900222D          

 12 11  0  0  0  0            999 V2000
10000.3567 9999.5885    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.6428 9999.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9285 9999.5885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2140 9999.1751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.928510000.4123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.356710000.4123    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.072310000.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.785810000.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.072310001.6497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.0723 9999.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7858 9999.5885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.0723 9998.3502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  6  0  0  0
  1 10  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  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
M  END
> <DATABASE_ID>
NP0000081

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H9NO5/c1-3(8)7-4(6(11)12)2-5(9)10/h4H,2H2,1H3,(H,7,8)(H,9,10)(H,11,12)/t4-/m0/s1

> <INCHI_KEY>
OTCCIMWXFLJLIA-BYPYZUCNSA-N

> <FORMULA>
C6H9NO5

> <MOLECULAR_WEIGHT>
175.1394

> <EXACT_MASS>
175.048072403

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
15.285189586226192

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.79

> <JCHEM_LOGP>
-1.4016766216666667

> <ALOGPS_LOGS>
-0.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.3336803807969115

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4130365160445932

> <JCHEM_PKA_STRONGEST_BASIC>
-1.988558845428103

> <JCHEM_POLAR_SURFACE_AREA>
103.69999999999999

> <JCHEM_REFRACTIVITY>
35.9765

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.11e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetyl-L-aspartic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000081 (N-Acetyl-L-aspartic acid)

HMDB0000812
     RDKit          3D
N-Acetyl-L-aspartic acid
 21 20  0  0  0  0  0  0  0  0999 V2000
   -3.1013   -1.1183   -0.0739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7454   -0.8489   -0.7545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6320   -1.4916   -1.8638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8299   -0.0320   -0.2027 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1205    0.8115    0.3627 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1603    0.2285    1.2436 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0399   -0.7760    0.6568 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9145   -1.3058    1.4299 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0137   -1.2013   -0.6555 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6841    1.8704   -0.5627 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2150    2.0619   -1.7099 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7407    2.6464   -0.1351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9436   -1.4430    0.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6006   -1.9194   -0.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7182   -0.2098   -0.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0277   -0.2374   -1.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4879    1.5255    1.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6337   -0.2573    2.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7337    1.0646    1.7099 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2175   -2.1903   -0.8492 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5576    2.8222   -0.7191 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
  1 13  1  0
  1 14  1  0
  1 15  1  0
  4 16  1  0
  5 17  1  1
  6 18  1  0
  6 19  1  0
  9 20  1  0
 12 21  1  0
M  END
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PDB for NP0000081 (N-Acetyl-L-aspartic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0    8667.3338665.899   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8666.0008665.127   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8664.6678665.899   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8663.3338665.127   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8664.6678667.436   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0    8667.3338667.436   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0    8668.6688668.206   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8670.0008667.436   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    8668.6688669.746   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8668.6688665.127   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8670.0008665.899   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8668.6688663.587   0.000  0.00  0.00           O+0
CONECT    1    2    6   10                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    1    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    1   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END
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3D PDB for NP0000081 (N-Acetyl-L-aspartic acid)

COMPND    HMDB0000812
HETATM    1  C1  UNL     1      -3.101  -1.118  -0.074  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.745  -0.849  -0.755  1.00  0.00           C  
HETATM    3  O1  UNL     1      -1.632  -1.492  -1.864  1.00  0.00           O  
HETATM    4  N1  UNL     1      -0.830  -0.032  -0.203  1.00  0.00           N  
HETATM    5  C3  UNL     1       0.120   0.812   0.363  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.160   0.228   1.244  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.040  -0.776   0.657  1.00  0.00           C  
HETATM    8  O2  UNL     1       2.915  -1.306   1.430  1.00  0.00           O  
HETATM    9  O3  UNL     1       2.014  -1.201  -0.656  1.00  0.00           O  
HETATM   10  C6  UNL     1       0.684   1.870  -0.563  1.00  0.00           C  
HETATM   11  O4  UNL     1       0.215   2.062  -1.710  1.00  0.00           O  
HETATM   12  O5  UNL     1       1.741   2.646  -0.135  1.00  0.00           O  
HETATM   13  H1  UNL     1      -2.944  -1.443   0.969  1.00  0.00           H  
HETATM   14  H2  UNL     1      -3.601  -1.919  -0.633  1.00  0.00           H  
HETATM   15  H3  UNL     1      -3.718  -0.210  -0.157  1.00  0.00           H  
HETATM   16  H4  UNL     1       0.028  -0.237  -1.238  1.00  0.00           H  
HETATM   17  H5  UNL     1      -0.488   1.526   1.073  1.00  0.00           H  
HETATM   18  H6  UNL     1       0.634  -0.257   2.110  1.00  0.00           H  
HETATM   19  H7  UNL     1       1.734   1.065   1.710  1.00  0.00           H  
HETATM   20  H8  UNL     1       2.217  -2.190  -0.849  1.00  0.00           H  
HETATM   21  H9  UNL     1       2.558   2.822  -0.719  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3    3    4
CONECT    4    5   16
CONECT    5    6   10   17
CONECT    6    7   18   19
CONECT    7    8    8    9
CONECT    9   20
CONECT   10   11   11   12
CONECT   12   21
END
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SMILES for NP0000081 (N-Acetyl-L-aspartic acid)

CC(=O)N[C@@H](CC(O)=O)C(O)=O
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INCHI for NP0000081 (N-Acetyl-L-aspartic acid)

InChI=1S/C6H9NO5/c1-3(8)7-4(6(11)12)2-5(9)10/h4H,2H2,1H3,(H,7,8)(H,9,10)(H,11,12)/t4-/m0/s1
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View in JSmol
Synonyms
ValueSource
(S)-2-(Acetylamino)butanedioic acidChEBI
(S)-2-(Acetylamino)succinic acidChEBI
Acetyl-L-aspartic acidChEBI
Acetylaspartic acidChEBI
L-N-Acetylaspartic acidChEBI
N-Acetylaspartic acidChEBI
NAAChEBI
(S)-2-(Acetylamino)butanedioateGenerator
(S)-2-(Acetylamino)succinateGenerator
Acetyl-L-aspartateGenerator
AcetylaspartateGenerator
L-N-AcetylaspartateGenerator
N-AcetylaspartateGenerator
N-Acetyl-L-aspartateGenerator
(2S)-2-AcetamidobutanedioateHMDB
(2S)-2-Acetamidobutanedioic acidHMDB
N-Acetyl-S-aspartateHMDB
N-Acetyl-S-aspartic acidHMDB
N-Acetyl aspartateHMDB
N-Acetylaspartate, monopotassium saltHMDB
Acetyl aspartic acidHMDB
Chemical FormulaC6H9NO5
Average Mass175.1394 Da
Monoisotopic Mass175.04807 Da
IUPAC Name(2S)-2-acetamidobutanedioic acid
Traditional Nameacetyl-L-aspartic acid
CAS Registry Number997-55-7
SMILES
CC(=O)N[C@@H](CC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C6H9NO5/c1-3(8)7-4(6(11)12)2-5(9)10/h4H,2H2,1H3,(H,7,8)(H,9,10)(H,11,12)/t4-/m0/s1
InChI KeyOTCCIMWXFLJLIA-BYPYZUCNSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)V.dorna832021-07-21View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Homo sapiensLOTUS Database
Homo sapiens (Urine)Animalia
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic 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 ParentAspartic acid and derivatives
Alternative Parents
Substituents
  • Aspartic acid or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point137 - 140 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility675 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility21.1 g/LALOGPS
logP-0.79ALOGPS
logP-1.4ChemAxon
logS-0.92ALOGPS
pKa (Strongest Acidic)3.41ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area103.7 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity35.98 m³·mol⁻¹ChemAxon
Polarizability15.29 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000812
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022260
KNApSAcK IDNot Available
Chemspider ID58576
KEGG Compound IDC01042
BioCyc IDCPD-420
BiGG ID36685
Wikipedia LinkN-acetylaspartic_acid
METLIN ID5776
PubChem Compound65065
PDB IDNot Available
ChEBI ID21547
Good Scents IDrw1408501
References
General References
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  2. Kaul R, Gao GP, Balamurugan K, Matalon R: Cloning of the human aspartoacylase cDNA and a common missense mutation in Canavan disease. Nat Genet. 1993 Oct;5(2):118-23. [PubMed:8252036 ]
  3. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
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  13. Clementi V, Tonon C, Lodi R, Malucelli E, Barbiroli B, Iotti S: Assessment of glutamate and glutamine contribution to in vivo N-acetylaspartate quantification in human brain by (1)H-magnetic resonance spectroscopy. Magn Reson Med. 2005 Dec;54(6):1333-9. [PubMed:16265633 ]
  14. Rothstein JD, Tsai G, Kuncl RW, Clawson L, Cornblath DR, Drachman DB, Pestronk A, Stauch BL, Coyle JT: Abnormal excitatory amino acid metabolism in amyotrophic lateral sclerosis. Ann Neurol. 1990 Jul;28(1):18-25. [PubMed:2375630 ]
  15. Surendran S, Matalon KM, Szucs S, Tyring SK, Matalon R: Metabolic changes in the knockout mouse for Canavan's disease: implications for patients with Canavan's disease. J Child Neurol. 2003 Sep;18(9):611-5. [PubMed:14572139 ]
  16. Gordon N: Canavan disease: a review of recent developments. Eur J Paediatr Neurol. 2001;5(2):65-9. [PubMed:11589315 ]
  17. Zhu XH, Chen W: Observed BOLD effects on cerebral metabolite resonances in human visual cortex during visual stimulation: a functional (1)H MRS study at 4 T. Magn Reson Med. 2001 Nov;46(5):841-7. [PubMed:11675633 ]
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  21. Kvittingen EA, Guldal G, Borsting S, Skalpe IO, Stokke O, Jellum E: N-acetylaspartic aciduria in a child with a progressive cerebral atrophy. Clin Chim Acta. 1986 Aug 15;158(3):217-27. [PubMed:3769199 ]
  22. Gideon P, Henriksen O, Sperling B, Christiansen P, Olsen TS, Jorgensen HS, Arlien-Soborg P: Early time course of N-acetylaspartate, creatine and phosphocreatine, and compounds containing choline in the brain after acute stroke. A proton magnetic resonance spectroscopy study. Stroke. 1992 Nov;23(11):1566-72. [PubMed:1440704 ]
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  26. Toyohara T, Akiyama Y, Suzuki T, Takeuchi Y, Mishima E, Tanemoto M, Momose A, Toki N, Sato H, Nakayama M, Hozawa A, Tsuji I, Ito S, Soga T, Abe T: Metabolomic profiling of uremic solutes in CKD patients. Hypertens Res. 2010 Sep;33(9):944-52. doi: 10.1038/hr.2010.113. Epub 2010 Jul 8. [PubMed:20613759 ]
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