Bovine Metabolome Database: Showing metabocard for N-Acetyl-L-aspartic acid (BMDB0000812)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:36:58 UTC

Update Date

2020-05-21 16:26:52 UTC

BMDB ID

BMDB0000812

Secondary Accession Numbers

BMDB00812

Metabolite Identification

Common Name

N-Acetyl-L-aspartic acid

Description

N-Acetyl-L-aspartic acid, also known as acetylaspartate or NAA, 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. N-Acetyl-L-aspartic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). N-Acetyl-L-aspartic acid exists in all living organisms, ranging from bacteria to humans. N-acetyl-L-aspartic acid can be converted into acetic acid and L-aspartic acid; which is mediated by the enzyme aspartoacylase. In cattle, N-acetyl-L-aspartic acid is involved in the metabolic pathway called the aspartate metabolism pathway. N-Acetyl-L-aspartic acid is a potentially toxic compound.

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

Expected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm
Mitochondria
Myelin sheath

Physical Properties

State

Solid

Experimental 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

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
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0cdi-0910000000-80f173aa655a9e8604b5	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-008a-0930000000-63ecd768773360e39272	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-001i-0950000000-beff64b09b14e79c535c	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0cdi-0910000000-80f173aa655a9e8604b5	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-008a-0930000000-63ecd768773360e39272	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-001i-0950000000-beff64b09b14e79c535c	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0pvj-0910000000-8952da198dfa2ecb7e21	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-01x1-0930000000-ac192f128bc253b6c299	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000x-9400000000-e45e6641c1b4fdac03e7	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00dl-9541000000-1ca7edd5f216e4355383	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-001i-2900000000-73b8786c25f0b59927c6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00dr-9000000000-f7f7d5d562cbcf3f69fa	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-006x-9000000000-01988ea29217a99519e1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-00di-0900000000-e8fc0d2735d5a8ce1818	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-000i-9800000000-10648516e9c8e71f36ec	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-000i-9000000000-5a1edaf86830da3de4a6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0a4r-9000000000-be6d8862f50bbbceda29	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4l-9000000000-d8e588abce3e75dbb9e6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-0900000000-e8fc0d2735d5a8ce1818	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9800000000-10648516e9c8e71f36ec	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-7d599142d42610746077	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4r-9000000000-be6d8862f50bbbceda29	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4l-9000000000-d8e588abce3e75dbb9e6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-000i-9600000000-f176de6becb0016bc74d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-00or-1900000000-26dc8573491416b97a27	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-000i-9600000000-0cb75d9cdfce88068fbe	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-052r-9400000000-327e451ed714e29b3e49	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-004i-0900000000-7f8ca1d0dd5f77ffad96	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0a4r-9000000000-a67943ff273546b3c435	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-7208631bdea4f3ac52f6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06ei-7900000000-10e9adf8706f97c39bed	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-02h3-9200000000-fb40f9d409269d43e36c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05gi-0900000000-86f974a42eb88002ebd7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-06si-3900000000-06245050379b733be566	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9100000000-e47b08fe049f17160867	View in MoNA
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria
Myelin sheath

Biospecimen Locations

Basal Ganglia
Brain
Fibroblasts
Neuron
Placenta
Prostate Tissue

Pathways

Name	SMPDB/Pathwhiz	KEGG
Aspartate Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Basal Ganglia	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Brain	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Neuron	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Prostate Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000812

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

References

Synthesis Reference

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

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Aspartoacylase

General function:: Amino acid transport and metabolism
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 (By similarity).
Gene Name:: ASPA
Uniprot ID:: P46446
Molecular weight:: 35738.0

Reactions

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

Showing metabocard for N-Acetyl-L-aspartic acid (BMDB0000812)

Structure for BMDB0000812 (N-Acetyl-L-aspartic acid)

Enzymes

Reactions