ContaminantDB: L-Asparagine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (9)XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:34:51 UTC

Update Date

2026-05-14 16:24:28 UTC

Accession Number

CHEM003322

Identification

Common Name

L-Asparagine

Class

Small Molecule

Description

Asparagine (Asn) is one of the 20 most common natural amino acids on Earth. It has carboxamide as the side chain's functional group. It is considered a non-essential amino acid. Asparagine is not an essential amino acid, which means that it can be synthesized from central metabolic pathway intermediates in humans and is not required in the diet. The precursor to asparagine is oxaloacetate. Oxaloacetate is converted to aspartate using a transaminase enzyme. The enzyme transfers the amino group from glutamate to oxaloacetate producing alpha-ketoglutarate and aspartate. The enzyme asparagine synthetase produces asparagine, AMP, glutamate, and pyrophosphate from aspartate, glutamine, and ATP. In the asparagine synthetase reaction, ATP is used to activate aspartate, forming beta-aspartyl-AMP. glutamine donates an ammonium group which reacts with beta-aspartyl-AMP to form asparagine and free AMP. Since the asparagine side chain can make efficient hydrogen bond interactions with the peptide backbone, asparagines are often found near the beginning and end of alpha-helices, and in turn motifs in beta sheets. Its role can be thought as capping the hydrogen bond interactions which would otherwise need to be satisfied by the polypeptide backbone. glutamines have an extra methylene group, have more conformational entropy and thus are less useful in this regard. Asparagine also provides key sites for N-linked glycosylation, modification of the protein chain with the addition of carbohydrate chains. A reaction between asparagine and reducing sugars or reactive carbonyls produces acrylamide (acrylic amide) in food when heated to sufficient temperature, i.e. baking. These occur primarily in baked goods such as french fries, potato chips, and roasted coffee. Asparagine was first isolated in 1806 from asparagus juice, in which it is abundant--hence its name--becoming the first amino acid to be isolated. The smell observed in the urine of some individuals after their consumption of asparagus is attributed to a byproduct of the metabolic breakdown of asparagine, asparagine-amino-succinic-acid monoamide. (However, some scientists disagree and implicate other substances in the smell, especially methanethiol). It is biosynthesized from aspartic acid and ammonia by asparagine synthetase.

Contaminant Sources

EAFUS Chemicals
FooDB Chemicals
HMDB Contaminants - Feces
HMDB Contaminants - Urine
HPV EPA Chemicals
My Exposome Chemicals
STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Amine
Animal Toxin
Dietary Supplement
Drug
Food Toxin
Metabolite
Micronutrient
Natural Compound
Non-Essential Amino Acid
Nutraceutical
Organic Compound
Supplement

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S)-2,4-Diamino-4-oxobutanoic acid	ChEBI
(2S)-2-Amino-3-carbamoylpropanoic acid	ChEBI
(S)-2-Amino-3-carbamoylpropanoic acid	ChEBI
(S)-Asparagine	ChEBI
2-Aminosuccinamic acid	ChEBI
alpha-Aminosuccinamic acid	ChEBI
Asn	ChEBI
ASPARAGINE	ChEBI
Aspartamic acid	ChEBI
L-2-Aminosuccinamic acid	ChEBI
L-Asparagin	ChEBI
L-Aspartic acid beta-amide	ChEBI
N	ChEBI
(2S)-2,4-Diamino-4-oxobutanoate	Generator
(2S)-2-Amino-3-carbamoylpropanoate	Generator
(S)-2-Amino-3-carbamoylpropanoate	Generator
2-Aminosuccinamate	Generator
a-Aminosuccinamate	Generator
a-Aminosuccinamic acid	Generator
alpha-Aminosuccinamate	Generator
Α-aminosuccinamate	Generator
Α-aminosuccinamic acid	Generator
Aspartamate	Generator
L-2-Aminosuccinamate	Generator
L-Aspartate b-amide	Generator
L-Aspartate beta-amide	Generator
L-Aspartate β-amide	Generator
L-Aspartic acid b-amide	Generator
L-Aspartic acid β-amide	Generator
(-)-Asparagine	HMDB
(S)-2,4-Diamino-4-oxobutanoate	HMDB
(S)-2,4-Diamino-4-oxobutanoic acid	HMDB
Agedoite	HMDB
alpha Amminosuccinamate	HMDB
alpha Amminosuccinamic acid	HMDB
Altheine	HMDB
Asparagine acid	HMDB
Asparamide	HMDB
Aspartic acid amide	HMDB
Aspartic acid b-amide	HMDB
Aspartic acid beta amide	HMDB
b2,4-(S)-Diamino-4-oxo-utanoate	HMDB
b2,4-(S)-Diamino-4-oxo-utanoic acid	HMDB
Crystal VI	HMDB
L-2,4-Diamino-4-oxobutanoate	HMDB
L-2,4-Diamino-4-oxobutanoic acid	HMDB
L-Aspartamine	HMDB
L-b-Asparagine	HMDB
L-beta-Asparagine	HMDB

Chemical Formula

C₄H₈N₂O₃

Average Molecular Mass

132.118 g/mol

Monoisotopic Mass

132.053 g/mol

CAS Registry Number

70-47-3

IUPAC Name

(2S)-2-amino-3-carbamoylpropanoic acid

Traditional Name

L-asparagine

SMILES

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

InChI Identifier

InChI=1S/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)/t2-/m0/s1

InChI Key

DCXYFEDJOCDNAF-REOHCLBHSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as asparagine and derivatives. Asparagine and derivatives are compounds containing asparagine or a derivative thereof resulting from reaction of asparagine 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

Asparagine and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

aspartate family amino acid (CHEBI:17196 )
proteinogenic amino acid (CHEBI:17196 )
L-alpha-amino acid (CHEBI:17196 )
asparagine (CHEBI:17196 )
Common amino acids (C00152 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane
Mitochondria

Biofluid Locations

Not Available

Tissue Locations

All Tissues
Prostate

Pathways

Name	SMPDB Link	KEGG Link
Ammonia Recycling	SMP00009	map00910
Aspartate Metabolism	SMP00067	map00250
Transcription/Translation	SMP00019	Not Available
Hartnup Disorder	SMP00189	Not Available

Applications

nutraceutical

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	234-235°C
Boiling Point	Not Available
Solubility	2.94E+004 mg/L (at 25°C)

Predicted Properties

Property	Value	Source
Water Solubility	168 g/L	ALOGPS
logP	-3.4	ALOGPS
logP	-4.3	ChemAxon
logS	0.1	ALOGPS
pKa (Strongest Acidic)	2	ChemAxon
pKa (Strongest Basic)	8.43	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	106.41 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	28.35 m³·mol⁻¹	ChemAxon
Polarizability	11.68 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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) (3 TMS)	splash10-0159-0910000000-bedf57998656ab5ebc16	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-0159-0910000000-4979c4d028d2dc931263	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0159-0910000000-b7ea3fef61f3940cbdda	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-00di-9710000000-6d0afcbcc003347e598e	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0uxr-0910000000-2be567239bd3229b1ca1	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-02t9-0790000000-b8141f48cbebb90f683e	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-02t9-1790000000-1d12ed9b4fb2799da766	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-014u-0961000000-65a5c0999f17110c9939	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-00kr-0940000000-0e0e5c7bdbac5ea0e49e	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-00lr-1920000000-7864dbb1f685e64dd1cf	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-000i-1940000000-964ea25da2789805985a	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00lr-0930000000-79a089d9875e092dd7f2	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0159-0910000000-bedf57998656ab5ebc16	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0159-0910000000-4979c4d028d2dc931263	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0159-0910000000-b7ea3fef61f3940cbdda	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-QQ (Non-derivatized)	splash10-00di-4931100000-17f149310ce3a0f748d1	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9710000000-6d0afcbcc003347e598e	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0uxr-0910000000-2be567239bd3229b1ca1	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-02t9-0790000000-b8141f48cbebb90f683e	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-02t9-1790000000-1d12ed9b4fb2799da766	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014u-0961000000-65a5c0999f17110c9939	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00kr-0940000000-0e0e5c7bdbac5ea0e49e	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00lr-1920000000-7864dbb1f685e64dd1cf	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-000i-1940000000-964ea25da2789805985a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-9100000000-5881591331bd059b7e7d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0080-9400000000-e5c7e19f427eea6d71b0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-9000000000-afc1214100db1168b095	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00dl-9000000000-57e977cd87e9a86d482b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-6fb96f5aa291359dba29	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-76f11e6fe5657c35d15f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-e944486273dbfde4cae4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-27ad91a86be0c4d86c3c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-b8b7a3431b66246ad613	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-03fa294ec740e189dd99	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-cee2081406fc25ab6169	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-cd79afa0c27f65e54adc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-01q9-0943200000-5a24322ba0ce2f410155	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03di-0900000000-fc3086cc1bb0c06a4c11	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03di-3900000000-2d74d8232e7523f3b1c9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0900000000-fa61c6fa9a87ce4905bb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-01q9-0942200000-757da8b3406485c997b0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-014i-9000000000-eac18512f2d22ab7a7ef	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03di-0900000000-8df6d5b6cf94bf081c89	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0900000000-18079004a95c252da208	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-001i-0900000000-e6b1f9b4982e6cdc863d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-03di-5900000000-7b9c09b3b6de28972f97	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-00dl-9100000000-2ea95ead344d62e230a4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-defacc365589bc4437d7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-fd60db4d5e35794c45ae	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-001i-3900000000-fd0f1034b5c1e40435c0	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
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Asparagine, a non-essential amino acid is important in the metabolism of toxic ammonia in the body through the action of asparagine synthase which attaches ammonia to aspartic acid in an amidation reaction. Asparagine is also used as a structural component in many proteins.

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Used for nutritional supplementation, also for treating dietary shortage or imbalance.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00174

HMDB ID

HMDB0000168

FooDB ID

FDB000787

Phenol Explorer ID

Not Available

KNApSAcK ID

C00001341

BiGG ID

34055

BioCyc ID

ASN

METLIN ID

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

References

Synthesis Reference

Sang C. Park, “Pharmaceutical preparation containing L-aspartate or L-asparagine for preventing ethanol toxicity, and process for preparation thereof.” U.S. Patent US5389359, issued November, 1991.

MSDS

Link

General References

1. Wang, Fangda. Preparation of L-b-asparagine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 8 pp.

2. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.

3. A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)

4. Wang, Fangda. Preparation of L-b-asparagine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 8 pp.

5. Starczynowski DT, Reynolds JG, Gilmore TD: Mutations of tumor necrosis factor alpha-responsive serine residues within the C-terminal transactivation domain of human transcription factor REL enhance its in vitro transforming ability. Oncogene. 2005 Nov 10;24(49):7355-68.

6. Fischer D, Schroers A, Blumcke I, Urbach H, Zerres K, Mortier W, Vorgerd M, Schroder R: Consequences of a novel caveolin-3 mutation in a large German family. Ann Neurol. 2003 Feb;53(2):233-41.

7. Filho JC, Bergstrom J, Stehle P, Furst P: Simultaneous measurements of free amino acid patterns of plasma, muscle and erythrocytes in healthy human subjects. Clin Nutr. 1997 Dec;16(6):299-305.

8. Peng CT, Wu KH, Lan SJ, Tsai JJ, Tsai FJ, Tsai CH: Amino acid concentrations in cerebrospinal fluid in children with acute lymphoblastic leukemia undergoing chemotherapy. Eur J Cancer. 2005 May;41(8):1158-63. Epub 2005 Apr 14.

9. Sun S, Han J, Ralph WM Jr, Chandrasekaran A, Liu K, Auborn KJ, Carter TH: Endoplasmic reticulum stress as a correlate of cytotoxicity in human tumor cells exposed to diindolylmethane in vitro. Cell Stress Chaperones. 2004 Mar;9(1):76-87.