Livestock Metabolome Database: Showing metabocard for N-Acetyl-L-aspartic acid (LMDB00250)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:45:40 UTC

Update Date

2016-07-20 20:58:44 UTC

Lmdb

LMDB00250

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N-Acetyl-L-aspartic acid

Description

N-Acetylaspartic acid is a derivative of aspartic acid. It is the second most concentrated molecule in the brain after the amino acid glutamate. It is synthesized in neurons from the amino acid aspartate and acetyl coenzyme A. The various functions served by N-acetylaspartic acid are still under investigation, but the primary proposed functions include:. 1) A neuronal osmolyte that is involved in fluid balance in the brain 2) A source of acetate for lipid and myelin synthesis in oligodendrocytes, the glial cells that myelinate neuronal axons 3) A precursor for the synthesis of the important neuronal dipeptide N-acetylaspartylglutamate 4)N-Acetylaspartic acid may also be involved in energy production from the amino acid glutamate in neuronal mitochondria.

Structure

MOL SDF PDB SMILES InChI

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

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

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
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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0cdi-0910000000-80f173aa655a9e8604b5	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-008a-0930000000-63ecd768773360e39272	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-001i-0950000000-beff64b09b14e79c535c	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0cdi-0910000000-80f173aa655a9e8604b5	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-008a-0930000000-63ecd768773360e39272	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-001i-0950000000-beff64b09b14e79c535c	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0pvj-0910000000-8952da198dfa2ecb7e21	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-01x1-0930000000-ac192f128bc253b6c299	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000x-9400000000-e45e6641c1b4fdac03e7	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00dl-9541000000-1ca7edd5f216e4355383	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-001i-2900000000-73b8786c25f0b59927c6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00dr-9000000000-f7f7d5d562cbcf3f69fa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-006x-9000000000-01988ea29217a99519e1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-00di-0900000000-e8fc0d2735d5a8ce1818	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-000i-9800000000-10648516e9c8e71f36ec	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-000i-9000000000-5a1edaf86830da3de4a6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0a4r-9000000000-be6d8862f50bbbceda29	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4l-9000000000-d8e588abce3e75dbb9e6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-0900000000-e8fc0d2735d5a8ce1818	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9800000000-10648516e9c8e71f36ec	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-7d599142d42610746077	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4r-9000000000-be6d8862f50bbbceda29	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4l-9000000000-d8e588abce3e75dbb9e6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-000i-9600000000-f176de6becb0016bc74d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-00or-1900000000-26dc8573491416b97a27	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-000i-9600000000-0cb75d9cdfce88068fbe	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-052r-9400000000-327e451ed714e29b3e49	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-004i-0900000000-7f8ca1d0dd5f77ffad96	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0a4r-9000000000-a67943ff273546b3c435	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-7208631bdea4f3ac52f6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06ei-7900000000-10e9adf8706f97c39bed	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-02h3-9200000000-fb40f9d409269d43e36c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05gi-0900000000-86f974a42eb88002ebd7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-06si-3900000000-06245050379b733be566	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9100000000-e47b08fe049f17160867	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Brain
Cerebrospinal Fluid (CSF)
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Brain	Detected but not Quantified	Not Applicable	Not Available	Ovine	25959287	details
Cerebrospinal Fluid (CSF)	Detected but not Quantified	Not Applicable	Not Available	Ovine	17510975	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	23255817	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	22761248	details