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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-05-30 20:55:58 UTC

HMDB ID

HMDB0000812

Secondary Accession Numbers

HMDB00812

Metabolite Identification

Common Name

N-Acetyl-L-aspartic acid

Description

N-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‚Äôs (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

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

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(S)-2-(Acetylamino)butanedioic acid	ChEBI
(S)-2-(Acetylamino)succinic acid	ChEBI
Acetyl-L-aspartic acid	ChEBI
Acetylaspartic acid	ChEBI
L-N-Acetylaspartic acid	ChEBI
N-Acetylaspartic acid	ChEBI
NAA	ChEBI
(S)-2-(Acetylamino)butanedioate	Generator
(S)-2-(Acetylamino)succinate	Generator
Acetyl-L-aspartate	Generator
Acetylaspartate	Generator
L-N-Acetylaspartate	Generator
N-Acetylaspartate	Generator
N-Acetyl-L-aspartate	Generator
(2S)-2-Acetamidobutanedioate	HMDB
(2S)-2-Acetamidobutanedioic acid	HMDB
N-Acetyl-S-aspartate	HMDB
N-Acetyl-S-aspartic acid	HMDB
N-Acetyl aspartate	HMDB
N-Acetylaspartate, monopotassium salt	HMDB
Acetyl aspartic acid	HMDB

Chemical Formula

C₆H₉NO₅

Average Molecular Weight

175.1394

Monoisotopic Molecular Weight

175.048072403

IUPAC Name

(2S)-2-acetamidobutanedioic acid

Traditional Name

acetyl-L-aspartic acid

CAS Registry Number

997-55-7

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 Key

OTCCIMWXFLJLIA-BYPYZUCNSA-N

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Aspartic 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 Framework

Aliphatic acyclic compounds

External Descriptors

N-acetyl-L-amino acid (CHEBI:21547 )
N-acyl-L-aspartic acid (CHEBI:21547 )

Ontology

Physiological effect

Health effect

Nervous system disorder

Central nervous system disorder

Psychiatric disorder

Schizophrenia (HMDB: HMDB0000812)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 16139832)
Cerebrospinal Fluid (CSF) (PMID: 2375630)
Saliva (HMDB: HMDB0000812)
Cerebrospinal fluid (HMDB: HMDB0000812)

Cell

Fibroblast

Fibroblast (HMDB: HMDB0000812)

Tissue

Basal Ganglia (HMDB: HMDB0000812)

Organ

Excreta

Biofluid or Excreta

Urine (PMID: 8087979)
Feces (PMID: 26505825)

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0000812)

Organ substructure

Hippocampus (HMDB: HMDB0000812)
Thalamus (HMDB: HMDB0000812)

Temporal Lobe (HMDB: HMDB0000812)

Source

Endogenous

Endogenous (HMDB: HMDB0000812)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Aspartate Metabolism (HMDB: HMDB0000812)
Aspartate Metabolism (HMDB: HMDB0000812)

Disease pathway

Canavan Disease (HMDB: HMDB0000812)
Hypoacetylaspartia (PathBank: SMP0120722)
Hypoacetylaspartia (HMDB: HMDB0000812)

Role

Industrial application

Food and nutrition

Nutritional supplement (HMDB: HMDB0000812)

Nutraceutical (HMDB: HMDB0000812)

Pharmaceutical industry

Biomarker

Canavan disease (MarkerDB: MDB00000259)

Indirect biological role

Metabotoxin

Metabotoxin (HMDB: HMDB0000812)

Biological role

Metabolite (HMDB: HMDB0000812)
Metabolite (HMDB: HMDB0000812)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	137 - 140 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	675 mg/mL	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	129.212	30932474
[M-H]-	Not Available	130.8	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000034

Predicted Molecular Properties

Property	Value	Source
Water Solubility	21.1 g/L	ALOGPS
logP	-0.79	ALOGPS
logP	-1.4	ChemAxon
logS	-0.92	ALOGPS
pKa (Strongest Acidic)	3.41	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	103.7 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	35.98 m³·mol⁻¹	ChemAxon
Polarizability	15.29 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	140.143	31661259
DarkChem	[M-H]-	132.854	31661259
AllCCS	[M+H]+	139.651	32859911
AllCCS	[M-H]-	132.727	32859911
DeepCCS	[M+H]+	131.325	30932474
DeepCCS	[M-H]-	128.525	30932474
DeepCCS	[M-2H]-	164.848	30932474
DeepCCS	[M+Na]+	140.284	30932474
AllCCS	[M+H]+	139.7	32859911
AllCCS	[M+H-H2O]+	135.8	32859911
AllCCS	[M+NH4]+	143.2	32859911
AllCCS	[M+Na]+	144.2	32859911
AllCCS	[M-H]-	132.7	32859911
AllCCS	[M+Na-2H]-	134.3	32859911
AllCCS	[M+HCOO]-	136.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Acetyl-L-aspartic acid	CC(=O)N[C@@H](CC(O)=O)C(O)=O	2646.2	Standard polar	33892256
N-Acetyl-L-aspartic acid	CC(=O)N[C@@H](CC(O)=O)C(O)=O	1453.6	Standard non polar	33892256
N-Acetyl-L-aspartic acid	CC(=O)N[C@@H](CC(O)=O)C(O)=O	1774.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Acetyl-L-aspartic acid,1TMS,isomer #1	CC(=O)N[C@@H](CC(=O)O[Si](C)(C)C)C(=O)O	1567.1	Semi standard non polar	33892256
N-Acetyl-L-aspartic acid,1TMS,isomer #2	CC(=O)N[C@@H](CC(=O)O)C(=O)O[Si](C)(C)C	1525.7	Semi standard non polar	33892256
N-Acetyl-L-aspartic acid,1TMS,isomer #3	CC(=O)N([C@@H](CC(=O)O)C(=O)O)[Si](C)(C)C	1623.5	Semi standard non polar	33892256
N-Acetyl-L-aspartic acid,2TMS,isomer #1	CC(=O)N[C@@H](CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1667.9	Semi standard non polar	33892256
N-Acetyl-L-aspartic acid,2TMS,isomer #2	CC(=O)N([C@@H](CC(=O)O[Si](C)(C)C)C(=O)O)[Si](C)(C)C	1654.7	Semi standard non polar	33892256
N-Acetyl-L-aspartic acid,2TMS,isomer #3	CC(=O)N([C@@H](CC(=O)O)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1646.7	Semi standard non polar	33892256
N-Acetyl-L-aspartic acid,3TMS,isomer #1	CC(=O)N([C@@H](CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1691.7	Semi standard non polar	33892256
N-Acetyl-L-aspartic acid,3TMS,isomer #1	CC(=O)N([C@@H](CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1718.2	Standard non polar	33892256
N-Acetyl-L-aspartic acid,3TMS,isomer #1	CC(=O)N([C@@H](CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1890.3	Standard polar	33892256
N-Acetyl-L-aspartic acid,1TBDMS,isomer #1	CC(=O)N[C@@H](CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	1824.7	Semi standard non polar	33892256
N-Acetyl-L-aspartic acid,1TBDMS,isomer #2	CC(=O)N[C@@H](CC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	1781.0	Semi standard non polar	33892256
N-Acetyl-L-aspartic acid,1TBDMS,isomer #3	CC(=O)N([C@@H](CC(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C	1849.9	Semi standard non polar	33892256
N-Acetyl-L-aspartic acid,2TBDMS,isomer #1	CC(=O)N[C@@H](CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2095.1	Semi standard non polar	33892256
N-Acetyl-L-aspartic acid,2TBDMS,isomer #2	CC(=O)N([C@@H](CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2126.8	Semi standard non polar	33892256
N-Acetyl-L-aspartic acid,2TBDMS,isomer #3	CC(=O)N([C@@H](CC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2093.7	Semi standard non polar	33892256
N-Acetyl-L-aspartic acid,3TBDMS,isomer #1	CC(=O)N([C@@H](CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2350.4	Semi standard non polar	33892256
N-Acetyl-L-aspartic acid,3TBDMS,isomer #1	CC(=O)N([C@@H](CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2343.0	Standard non polar	33892256
N-Acetyl-L-aspartic acid,3TBDMS,isomer #1	CC(=O)N([C@@H](CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2312.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-L-aspartic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0cdi-0910000000-80f173aa655a9e8604b5	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-L-aspartic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-008a-0930000000-63ecd768773360e39272	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-L-aspartic acid GC-MS (3 TMS)	splash10-001i-0950000000-beff64b09b14e79c535c	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-L-aspartic acid GC-EI-TOF (Non-derivatized)	splash10-0cdi-0910000000-80f173aa655a9e8604b5	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-L-aspartic acid GC-EI-TOF (Non-derivatized)	splash10-008a-0930000000-63ecd768773360e39272	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-L-aspartic acid GC-MS (Non-derivatized)	splash10-001i-0950000000-beff64b09b14e79c535c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-L-aspartic acid GC-EI-TOF (Non-derivatized)	splash10-0pvj-0910000000-8952da198dfa2ecb7e21	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-L-aspartic acid GC-EI-TOF (Non-derivatized)	splash10-01x1-0930000000-ac192f128bc253b6c299	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-aspartic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-000x-9400000000-e45e6641c1b4fdac03e7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-aspartic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00dl-9541000000-1ca7edd5f216e4355383	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-aspartic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-aspartic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-aspartic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-aspartic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-aspartic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-aspartic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-aspartic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-aspartic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-aspartic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-aspartic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-aspartic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-aspartic acid GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-aspartic acid GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-aspartic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-001i-2900000000-73b8786c25f0b59927c6	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-aspartic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-00dr-9000000000-f7f7d5d562cbcf3f69fa	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-aspartic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-006x-9000000000-01988ea29217a99519e1	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-aspartic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-00di-0900000000-e8fc0d2735d5a8ce1818	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-aspartic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-000i-9800000000-10648516e9c8e71f36ec	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-aspartic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-000i-9000000000-5a1edaf86830da3de4a6	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-aspartic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-0a4r-9000000000-be6d8862f50bbbceda29	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-aspartic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-0a4l-9000000000-d8e588abce3e75dbb9e6	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-aspartic acid LC-ESI-QQ , negative-QTOF	splash10-00di-0900000000-e8fc0d2735d5a8ce1818	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-aspartic acid LC-ESI-QQ , negative-QTOF	splash10-000i-9800000000-10648516e9c8e71f36ec	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-aspartic acid LC-ESI-QQ , negative-QTOF	splash10-000i-9000000000-7d599142d42610746077	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-aspartic acid LC-ESI-QQ , negative-QTOF	splash10-0a4r-9000000000-be6d8862f50bbbceda29	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-aspartic acid LC-ESI-QQ , negative-QTOF	splash10-0a4l-9000000000-d8e588abce3e75dbb9e6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-aspartic acid , negative-QTOF	splash10-000i-9600000000-f176de6becb0016bc74d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-aspartic acid , positive-QTOF	splash10-00or-1900000000-26dc8573491416b97a27	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-aspartic acid 35V, Negative-QTOF	splash10-000i-9600000000-0cb75d9cdfce88068fbe	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-aspartic acid 10V, Negative-QTOF	splash10-052r-9400000000-327e451ed714e29b3e49	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-aspartic acid 35V, Negative-QTOF	splash10-004i-0900000000-7f8ca1d0dd5f77ffad96	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-aspartic acid 30V, Negative-QTOF	splash10-0a4r-9000000000-a67943ff273546b3c435	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-L-aspartic acid 10V, Positive-QTOF	splash10-0a4i-0900000000-7208631bdea4f3ac52f6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-L-aspartic acid 20V, Positive-QTOF	splash10-06ei-7900000000-10e9adf8706f97c39bed	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-L-aspartic acid 40V, Positive-QTOF	splash10-02h3-9200000000-fb40f9d409269d43e36c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-L-aspartic acid 10V, Negative-QTOF	splash10-05gi-0900000000-86f974a42eb88002ebd7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-L-aspartic acid 20V, Negative-QTOF	splash10-06si-3900000000-06245050379b733be566	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-L-aspartic acid 40V, Negative-QTOF	splash10-0a4l-9100000000-e47b08fe049f17160867	2017-09-01	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva
Urine

Tissue Locations

Basal Ganglia
Brain
Fibroblasts
Neuron
Placenta
Prostate

Pathways

Name	SMPDB/PathBank	KEGG
Aspartate Metabolism
Canavan Disease		Not Available
Hypoacetylaspartia		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22007635	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.81 +/- 0.38 uM	Adult (>18 years old)	Both	Normal	7595563	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Saliva	Detected and Quantified	0.827 +/- 0.521 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	1.08 +/- 0.586 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	1.54 +/- 1.13 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.658 +/- 0.331 uM	Adult (>18 years old)	Male	Normal	Sugimoto et al. (...	details
Urine	Detected and Quantified	10.0 +/- 2.1 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	3354621	details
Urine	Detected and Quantified	33.2 (4.9-65.5) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	8087979	details
Urine	Detected and Quantified	18.0 (0.1-43.9) umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	8087979	details
Urine	Detected and Quantified	10.3 (6.1-15.4) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	7.7 (3.1-18.7) umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	10.657 +/- 6.879 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	2.9-5.4 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	27012787	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	11.3 umol/mmol creatinine	Children (1-13 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	1.65 +/- 1.50 umol/mmol creatinine	Children (1-13 years old)	Both	Normal	16139832	details
Urine	Detected and Quantified	0.83 +/- 0.83 umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	16139832	details
Urine	Detected and Quantified	0.40 +/- 0.43 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16139832	details
Urine	Detected and Quantified	<44.29 umol/mmol creatinine	Children (1 - 18 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	28157703	details
Urine	Detected and Quantified	26.26 (18.78-40.70) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Analysis of 40 NI...	details
Urine	Detected and Quantified	4.0 (1.3-7.0) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	2.6-3.9 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	27012787	details
Urine	Detected and Quantified	4.66 +/- 1.14 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	7067131	details
Urine	Detected and Quantified	7.0 +/- 1.84 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	7067131	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	920-1370 uM	Children (1-13 years old)	Not Specified	Canavan disease	3354621	details
Blood	Detected and Quantified	16.96 +/- 19.57 uM	Adult (>18 years old)	Both	Canavan disease	16139832	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Schizophrenia	22007635	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.80 +/- 0.62 uM	Adult (>18 years old)	Both	Schizophrenia	7595563	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	380.0 (0.0-760.0) uM	Adult (>18 years old)	Both	Canavan Disease	2375630	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	obese	26505825	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected and Quantified	1299.5-3680.9 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Canavan disease	3354621	details
Urine	Detected and Quantified	14.079 +/- 11.359 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	1872.03 +/- 631.86 umol/mmol creatinine	Adult (>18 years old)	Both	Canavan disease	16139832	details
Urine	Detected and Quantified	306.820 +/- 184.100 umol/mmol creatinine	Children (1-13 years old)	Not Available	Canavan disease	2512436	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

Associated Disorders and Diseases

Disease References

Canavan disease
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 ] 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 ] Matalon R, Michals K, Sebesta D, Deanching M, Gashkoff P, Casanova J: Aspartoacylase deficiency and N-acetylaspartic aciduria in patients with Canavan disease. Am J Med Genet. 1988 Feb;29(2):463-71. doi: 10.1002/ajmg.1320290234. [PubMed:3354621 ] Matalon R, Kaul R, Casanova J, Michals K, Johnson A, Rapin I, Gashkoff P, Deanching M: SSIEM Award. Aspartoacylase deficiency: the enzyme defect in Canavan disease. J Inherit Metab Dis. 1989;12 Suppl 2:329-31. [PubMed:2512436 ]
Schizophrenia
Do KQ, Lauer CJ, Schreiber W, Zollinger M, Gutteck-Amsler U, Cuenod M, Holsboer F: gamma-Glutamylglutamine and taurine concentrations are decreased in the cerebrospinal fluid of drug-naive patients with schizophrenic disorders. J Neurochem. 1995 Dec;65(6):2652-62. [PubMed:7595563 ] Xuan J, Pan G, Qiu Y, Yang L, Su M, Liu Y, Chen J, Feng G, Fang Y, Jia W, Xing Q, He L: Metabolomic profiling to identify potential serum biomarkers for schizophrenia and risperidone action. J Proteome Res. 2011 Dec 2;10(12):5433-43. doi: 10.1021/pr2006796. Epub 2011 Nov 8. [PubMed:22007635 ]
Obesity
Haro C, Montes-Borrego M, Rangel-Zuniga OA, Alcala-Diaz JF, Gomez-Delgado F, Perez-Martinez P, Delgado-Lista J, Quintana-Navarro GM, Tinahones FJ, Landa BB, Lopez-Miranda J, Camargo A, Perez-Jimenez F: Two Healthy Diets Modulate Gut Microbial Community Improving Insulin Sensitivity in a Human Obese Population. J Clin Endocrinol Metab. 2016 Jan;101(1):233-42. doi: 10.1210/jc.2015-3351. Epub 2015 Oct 27. [PubMed:26505825 ]
Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

271900 (Canavan disease)
181500 (Schizophrenia)
601665 (Obesity)
114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022260

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

N-acetylaspartic_acid

METLIN ID

5776

PubChem Compound

65065

PDB ID

Not Available

ChEBI ID

21547

Food Biomarker Ontology

Not Available

VMH ID

NACASP

MarkerDB ID

MDB00000259

Good Scents ID

Not Available

References

Synthesis Reference

Montoro, Fernando; Calatayud, Jose; Vilar, Angel. N-Acetyl-L-aspartic acid. Span. (1983), 5 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Sass JO, Mohr V, Olbrich H, Engelke U, Horvath J, Fliegauf M, Loges NT, Schweitzer-Krantz S, Moebus R, Weiler P, Kispert A, Superti-Furga A, Wevers RA, Omran H: Mutations in ACY1, the gene encoding aminoacylase 1, cause a novel inborn error of metabolism. Am J Hum Genet. 2006 Mar;78(3):401-9. Epub 2006 Jan 18. [PubMed:16465618 ]
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 ]
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 ]
Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
Wevers RA, Engelke U, Wendel U, de Jong JG, Gabreels FJ, Heerschap A: Standardized method for high-resolution 1H-NMR of cerebrospinal fluid. Clin Chem. 1995 May;41(5):744-51. [PubMed:7729054 ]
Tedeschi G, Bonavita S, Banerjee TK, Virta A, Schiffmann R: Diffuse central neuronal involvement in Fabry disease: a proton MRS imaging study. Neurology. 1999 May 12;52(8):1663-7. [PubMed:10331696 ]
Tacke U, Olbrich H, Sass JO, Fekete A, Horvath J, Ziyeh S, Kleijer WJ, Rolland MO, Fisher S, Payne S, Vargiami E, Zafeiriou DI, Omran H: Possible genotype-phenotype correlations in children with mild clinical course of Canavan disease. Neuropediatrics. 2005 Aug;36(4):252-5. [PubMed:16138249 ]
Rocca MA, Mezzapesa DM, Falini A, Ghezzi A, Martinelli V, Scotti G, Comi G, Filippi M: Evidence for axonal pathology and adaptive cortical reorganization in patients at presentation with clinically isolated syndromes suggestive of multiple sclerosis. Neuroimage. 2003 Apr;18(4):847-55. [PubMed:12725761 ]
Izumiyama H, Abe T, Tanioka D, Fukuda A, Kunii N: Clinicopathological examination of glioma by proton magnetic resonance spectroscopy background. Brain Tumor Pathol. 2004;21(1):39-46. [PubMed:15696968 ]
Bal D, Gryff-Keller A, Gradowska W: Absolute configuration of N-acetylaspartate in urine from patients with Canavan disease. J Inherit Metab Dis. 2005;28(4):607-9. [PubMed:15902566 ]
Manji HK, Moore GJ, Chen G: Clinical and preclinical evidence for the neurotrophic effects of mood stabilizers: implications for the pathophysiology and treatment of manic-depressive illness. Biol Psychiatry. 2000 Oct 15;48(8):740-54. [PubMed:11063971 ]
Vermathen P, Laxer KD, Matson GB, Weiner MW: Hippocampal structures: anteroposterior N-acetylaspartate differences in patients with epilepsy and control subjects as shown with proton MR spectroscopic imaging. Radiology. 2000 Feb;214(2):403-10. [PubMed:10671587 ]
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 ]
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 ]
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 ]
Gordon N: Canavan disease: a review of recent developments. Eur J Paediatr Neurol. 2001;5(2):65-9. [PubMed:11589315 ]
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 ]
Lam WW, Wang ZJ, Zhao H, Berry GT, Kaplan P, Gibson J, Kaplan BS, Bilaniuk LT, Hunter JV, Haselgrove JC, Zimmermann RA: 1H MR spectroscopy of the basal ganglia in childhood: a semiquantitative analysis. Neuroradiology. 1998 May;40(5):315-23. [PubMed:9638674 ]
Martin RC, Sawrie S, Hugg J, Gilliam F, Faught E, Kuzniecky R: Cognitive correlates of 1H MRSI-detected hippocampal abnormalities in temporal lobe epilepsy. Neurology. 1999 Dec 10;53(9):2052-8. [PubMed:10599780 ]
Trope I, Lopez-Villegas D, Lenkinski RE: Magnetic resonance imaging and spectroscopy of regional brain structure in a 10-year-old boy with elevated blood lead levels. Pediatrics. 1998 Jun;101(6):E7. [PubMed:9606249 ]
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 ]
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Enzymes

Enzyme Details

1. Aspartoacylase

General function:: Involved in hydrolase activity, acting on ester bonds
Specific function:: Catalyzes the deacetylation of N-acetylaspartic acid (NAA) to produce acetate and L-aspartate. NAA occurs in high concentration in brain and its hydrolysis NAA plays a significant part in the maintenance of intact white matter. In other tissues it act as a scavenger of NAA from body fluids.
Gene Name:: ASPA
Uniprot ID:: P45381
Molecular weight:: 35734.79

Reactions

N-Acetyl-L-aspartic acid + Water → Acetic acid + L-Aspartic acid	details

Enzyme Details

2. Aspartoacylase-2

General function:: Involved in hydrolase activity, acting on ester bonds
Specific function:: Plays an important role in deacetylating mercapturic acids in kidney proximal tubules (By similarity).
Gene Name:: ACY3
Uniprot ID:: Q96HD9
Molecular weight:: Not Available

Reactions

N-Acetyl-L-aspartic acid + Water → Acetic acid + L-Aspartic acid	details

Enzyme Details

3. N-acetylaspartyl-glutamate synthetase A

General function:: Involved in catalytic activity
Specific function:: Catalyzes the synthesis of N-acetylaspartyl-glutamate (NAAG).
Gene Name:: RIMKLA
Uniprot ID:: Q8IXN7
Molecular weight:: 42863.8

Reactions

Adenosine triphosphate + N-Acetyl-L-aspartic acid + L-Glutamic acid → ADP + Phosphate + N-acetylaspartyl-glutamate	details

Enzyme Details

4. Beta-citryl-glutamate synthase B

General function:: Involved in catalytic activity
Specific function:: Catalyzes the synthesis of beta-citryl-glutamate and N-acetyl-aspartyl-glutamate. Beta-citryl-glutamate is synthesized more efficiently than N-acetyl-aspartyl-glutamate (By similarity).
Gene Name:: RIMKLB
Uniprot ID:: Q9ULI2
Molecular weight:: 42463.575

Reactions

Adenosine triphosphate + N-Acetyl-L-aspartic acid + L-Glutamic acid → ADP + Phosphate + N-acetylaspartyl-glutamate	details

Enzyme Details

5. N-acetylaspartate synthetase

General function:: Not Available
Specific function:: Plays a role in the regulation of lipogenesis by producing N-acetylaspartate acid (NAA), a brain-specific metabolite. NAA occurs in high concentration in brain and its hydrolysis plays a significant part in the maintenance of intact white matter. Promotes dopamine uptake by regulating TNF-alpha expression. Attenuates methamphetamine-induced inhibition of dopamine uptake.
Gene Name:: NAT8L
Uniprot ID:: Q8N9F0
Molecular weight:: 32836.875

Reactions

Acetyl-CoA + L-Aspartic acid → Coenzyme A + N-Acetyl-L-aspartic acid	details

Showing metabocard for N-Acetyl-L-aspartic acid (HMDB0000812)

MOL for HMDB0000812 (N-Acetyl-L-aspartic acid)

3D MOL for HMDB0000812 (N-Acetyl-L-aspartic acid)

3D SDF for HMDB0000812 (N-Acetyl-L-aspartic acid)

3D-SDF for HMDB0000812 (N-Acetyl-L-aspartic acid)

PDB for HMDB0000812 (N-Acetyl-L-aspartic acid)

3D PDB for HMDB0000812 (N-Acetyl-L-aspartic acid)

SMILES for HMDB0000812 (N-Acetyl-L-aspartic acid)

INCHI for HMDB0000812 (N-Acetyl-L-aspartic acid)

Structure for HMDB0000812 (N-Acetyl-L-aspartic acid)

3D Structure for HMDB0000812 (N-Acetyl-L-aspartic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

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