AFCDB: L-Aspartic acid (FDB012567)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:14 UTC

Update date

2024-11-29 22:26:46 UTC

Primary ID

FDB012567

Secondary Accession Numbers

FDB030958

Chemical Information

FooDB Name

L-Aspartic acid

Description

Aspartic acid (Asp, D), also known as aspartate, the name of its anion, is one of the 20 natural proteinogenic amino acids which are the building blocks of proteins. As its name indicates, aspartic acid is the carboxylic acid analog of asparagine. As a neurotransmitter, aspartic acid may provide resistance to fatigue and thus lead to endurance, although the evidence to support this idea is not strong. Aspartic acid is a nonessential amino acid, since it can be made from glutamic acid by enzymes using vitamin B6. The amino acid has important roles in the urea cycle and DNA metabolism. Aspartic acid is a major excitatory neurotransmitter, which is sometimes found to be increased in epileptic and stroke patients. It is decreased in depressed patients and in patients with brain atrophy. Aspartic acid supplements are being evaluated. Five grams can raise blood levels. Magnesium and zinc may be natural inhibitors of some of the actions of aspartic acid. Aspartic acid, with the amino acid phenylalanine, is a part of the natural sweetener, aspartame. This sweetener is an advance in artificial sweeteners and is probably safe in normal doses to all except phenylketonurics. The jury is still out on the long-term effects it has on many brain neurohormones. Aspartic acid may be a significant immunostimulant of the thymus and can protect against some of the damaging effects of radiation. Many claims have been made for the special value of administering aspartic acid in the form of potassium and magnesium salts. Since aspartic acid is relatively nontoxic, studies are now in progress to elucidate its pharmacological and therapeutic roles.

CAS Number

56-84-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	142 g/L	ALOGPS
logP	-3.5	ALOGPS
logP	-3.5	ChemAxon
logS	0.03	ALOGPS
pKa (Strongest Acidic)	1.7	ChemAxon
pKa (Strongest Basic)	9.61	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	100.62 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	26.53 m³·mol⁻¹	ChemAxon
Polarizability	11.28 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

Chemical Formula

C4H7NO4

IUPAC name

(2S)-2-aminobutanedioic acid

InChI Identifier

InChI=1S/C4H7NO4/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H,6,7)(H,8,9)/t2-/m0/s1

InChI Key

CKLJMWTZIZZHCS-REOHCLBHSA-N

Isomeric SMILES

N[C@@H](CC(O)=O)C(O)=O

Average Molecular Weight

133.1027

Monoisotopic Molecular Weight

133.037507717

Classification

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
Alpha-amino acid
L-alpha-amino acid
Dicarboxylic acid or derivatives
Fatty acid
Amino acid
Carboxylic acid
Organic oxide
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic oxygen compound
Carbonyl group
Amine
Organic nitrogen compound
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

aspartate family amino acid (CHEBI:17053 )
proteinogenic amino acid (CHEBI:17053 )
L-alpha-amino acid (CHEBI:17053 )
aspartic acid (CHEBI:17053 )
Common amino acids (C00049 )
Amino acids (C00049 )

Ontology

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Tissue and substructures:

All tissues

Organ and components:

Prostate

Biofluid and excreta:

Subcellular:

Cell and elements:

Extracellular

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Biological role:

Essential amino acid

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 36.10%; H 5.30%; N 10.52%; O 48.08%	DFC
Melting Point	Mp 269-271° dec.	DFC
Boiling Point	Not Available
Experimental Water Solubility	5.36 mg/mL at 25 oC	YALKOWSKY,SH & HE,Y (2003)
Experimental logP	-3.89	CHMELIK,J ET AL. (1991)
Experimental pKa	pKa3 9.82-0 (25°,1-COOH)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]D +25.4 (c, 1 in 5M HCl)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	L-Aspartic acid, 3 TMS, GC-MS Spectrum	splash10-0f89-0960000000-5a6a6cb21e9fc0875f84	Spectrum
GC-MS	L-Aspartic acid, 3 TMS, GC-MS Spectrum	splash10-0f89-0950000000-51399a8446c394459765	Spectrum
GC-MS	L-Aspartic acid, 3 TMS, GC-MS Spectrum	splash10-0f89-0950000000-f07e7f52b3c31fd119f5	Spectrum
GC-MS	L-Aspartic acid, 3 TMS, GC-MS Spectrum	splash10-0f89-0950000000-9e175dfa17a8b17a72d2	Spectrum
GC-MS	L-Aspartic acid, non-derivatized, GC-MS Spectrum	splash10-0f89-0950000000-f4475587d5a3b20bfc58	Spectrum
GC-MS	L-Aspartic acid, 3 TMS, GC-MS Spectrum	splash10-00di-9430000000-0cac9a97e698db1672b5	Spectrum
GC-MS	L-Aspartic acid, 2 TMS, GC-MS Spectrum	splash10-03yi-1900000000-ea61b8526ee02ae79b66	Spectrum
GC-MS	L-Aspartic acid, 3 TMS, GC-MS Spectrum	splash10-0f89-1890000000-7da576c8129142b71a1b	Spectrum
GC-MS	L-Aspartic acid, 4 TMS, GC-MS Spectrum	splash10-0pb9-0981000000-ad23d55e348f55115f00	Spectrum
GC-MS	L-Aspartic acid, non-derivatized, GC-MS Spectrum	splash10-001i-0590000000-13cc5a7841854e97f68b	Spectrum
GC-MS	L-Aspartic acid, non-derivatized, GC-MS Spectrum	splash10-0f89-0960000000-5a6a6cb21e9fc0875f84	Spectrum
GC-MS	L-Aspartic acid, non-derivatized, GC-MS Spectrum	splash10-0f89-0950000000-51399a8446c394459765	Spectrum
GC-MS	L-Aspartic acid, non-derivatized, GC-MS Spectrum	splash10-0f89-0950000000-f07e7f52b3c31fd119f5	Spectrum
GC-MS	L-Aspartic acid, non-derivatized, GC-MS Spectrum	splash10-0f89-0950000000-9e175dfa17a8b17a72d2	Spectrum
GC-MS	L-Aspartic acid, non-derivatized, GC-MS Spectrum	splash10-0f89-0950000000-f4475587d5a3b20bfc58	Spectrum
GC-MS	L-Aspartic acid, non-derivatized, GC-MS Spectrum	splash10-0g4i-6946100000-0ae49e3be0f2f1f92065	Spectrum
GC-MS	L-Aspartic acid, non-derivatized, GC-MS Spectrum	splash10-00di-9430000000-0cac9a97e698db1672b5	Spectrum
GC-MS	L-Aspartic acid, non-derivatized, GC-MS Spectrum	splash10-03yi-1900000000-ea61b8526ee02ae79b66	Spectrum
GC-MS	L-Aspartic acid, non-derivatized, GC-MS Spectrum	splash10-0f89-1890000000-7da576c8129142b71a1b	Spectrum
GC-MS	L-Aspartic acid, non-derivatized, GC-MS Spectrum	splash10-0pb9-0981000000-ad23d55e348f55115f00	Spectrum
Predicted GC-MS	L-Aspartic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000f-9100000000-b7db3377089f4c95001b	Spectrum
Predicted GC-MS	L-Aspartic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01w4-9610000000-0f1463c6395830708e12	Spectrum
Predicted GC-MS	L-Aspartic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Aspartic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Aspartic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0079-9300000000-92f9914d94078d96f5cf	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-9000000000-c467d10f2b7e21ed1734	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00dl-9000000000-87f0c58226f5a2f3ac8a	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0900000000-fde7ef1951fddff4b817	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0uk9-8900000000-2d7e5609618437e59272	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-4b43567f4a446aed0828	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-4900000000-45382d9abd25be948e5b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-3f39a9b758e282358ac0	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-3900000000-44d361ad09ff9a30dd14	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-18e1dba62e6b803e17b8	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0002-0930000000-d97f9518a2d516d830c5	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-02ai-0962100000-909bb894b2c1318afee4	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-00di-9000000000-f2059dd438fcf62f62e1	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03dr-7900000000-8b7b89ed34530e331024	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-014i-0190000000-58a78949f4b93de22aab	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0921000000-214b6b969fdc4216ca71	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03dr-6900000000-4918748927dd097d2879	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0900000000-88dc2f1093f261e76201	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0290000000-a8856f56645a2961baac	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-001i-0900000000-8cf9870557ca9adc3374	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-000i-9400000000-81b2804a712625a2d9c4	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-000i-9000000000-9bf77ba12ad952f84ac0	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-00di-9000000000-e08bfb96c5fd8c9b9db7	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-876e30f6c9ed061091fe	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-00dl-9000000000-6c0d44d4e3853e5701a3	2012-08-31	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 400 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

17053

Phenol-Explorer ID

Not Available

DrugBank ID

DB00128

HMDB ID

HMDB00191

CRC / DFC (Dictionary of Food Compounds) ID

HJB19-Y:HJB17-W

EAFUS ID

264

Dr. Duke ID

ASPARAGINIC-ACID|ASPARAGIC-ACID|ASPARTIC-ACID|L-ASPARTIC-ACID

BIGG ID

33663

KNApSAcK ID

C00001342

HET ID

ASP

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1037291

SuperScent ID

Not Available

Wikipedia ID

Aspartic_acid

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti morphinic			DUKE
neuroexcitant			DUKE
roborant			DUKE
neurotransmitter	25512	An endogenous compound that is used to transmit information across the synapse between a neuron and another cell.	CHEBI

Enzymes

Name	Gene Name	UniProt ID
Aspartate aminotransferase, cytoplasmic	GOT1	P17174
Aspartate aminotransferase, mitochondrial	GOT2	P00505
Asparagine synthetase [glutamine-hydrolyzing]	ASNS	P08243
Isoaspartyl peptidase/L-asparaginase	ASRGL1	Q7L266
60 kDa lysophospholipase	ASPG	Q86U10
Lysozyme C	LYZ	P61626
Putative aspartate aminotransferase, cytoplasmic 2	GOT1L1	Q8NHS2
Glutamate decarboxylase 2	GAD2	Q05329
Glutamate decarboxylase 1	GAD1	Q99259
Argininosuccinate synthase	ASS1	P00966
Aspartoacylase	ASPA	P45381
Aspartoacylase-2	ACY3	Q96HD9
Ribonuclease pancreatic	RNASE1	P07998
Aspartate aminotransferase	GIG18	Q2TU84
Aspartate--tRNA ligase, cytoplasmic	DARS	P14868
Multifunctional protein ADE2	PAICS	P22234
N(4)-(beta-N-acetylglucosaminyl)-L-asparaginase	AGA	P20933
Aspartate--tRNA ligase, mitochondrial	DARS2	Q6PI48

Pathways

Name	SMPDB Link	KEGG Link
Ammonia Recycling	SMP00009	map00910
Arginine and Proline Metabolism	SMP00020	map00330
Aspartate Metabolism	SMP00067	map00250
Beta-Alanine Metabolism	SMP00007	map00410
Malate-Aspartate Shuttle	SMP00129	Not Available
Transcription/Translation	SMP00019	Not Available
Urea Cycle	SMP00059	map00330
Metabolism and Physiological Effects of Orotic acid	SMP0124870	Not Available
Metabolism and Physiological Effects of Uridine	SMP0124871	Not Available
Metabolsim and Physiological Effects of Argininic acid	SMP0125504	Not Available
Metabolism and Physiological Effects of N-alpha-Acetyl-L-arginine	SMP0125530	Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
odorless	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

L-Aspartic acid (FDB012567)

Structure for FDB012567 (L-Aspartic acid)