AFCDB: L-Asparagine (FDB000787)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:42 UTC

Update date

2020-09-17 15:38:24 UTC

Primary ID

FDB000787

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

L-Asparagine

Description

L-Asparagine, also known as Asn or aspartamic acid, 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. L-Asparagine is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. L-Asparagine is a very strong basic compound (based on its pKa). L-Asparagine exists in all living species, ranging from bacteria to humans. Within humans, L-asparagine participates in a number of enzymatic reactions. In particular, L-asparagine and L-glutamic acid can be biosynthesized from L-aspartic acid and L-glutamine through the action of the enzyme asparagine synthetase [glutamine-hydrolyzing]. In addition, L-asparagine can be converted into L-aspartic acid through the action of the enzyme isoaspartyl peptidase/l-asparaginase. In humans, L-asparagine is involved in aspartate metabolism. L-Asparagine is an odorless tasting compound. Outside of the human body, L-Asparagine is found, on average, in the highest concentration within a few different foods, such as white lupines, wheats, and oats and in a lower concentration in sacred lotus, parsnips, and pineapples. L-Asparagine has also been detected, but not quantified in, several different foods, such as colorado pinyons, opium poppies, lentils, green beans, and watermelons. This could make L-asparagine a potential biomarker for the consumption of these foods. L-Asparagine is a potentially toxic compound. An optically active form of asparagine having L-configuration.

CAS Number

70-47-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C4H8N2O3

IUPAC name

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

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

Isomeric SMILES

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

Average Molecular Weight

132.1179

Monoisotopic Molecular Weight

132.053492132

Classification

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 )

Ontology

Leukemia

Disposition

Route of exposure:

Enteral:

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

Environmental role:

Environmental contaminant

Industrial application:

Food and nutrition:

Nutritional supplement

Pharmaceutical industry:

Pharmaceutical

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 36.36%; H 6.10%; N 21.20%; O 36.33%	DFC
Melting Point	Mp 226-227 dec. (slow heat)	DFC
Boiling Point	Not Available
Experimental Water Solubility	29.4 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	-3.82	CHMELIK,J ET AL. (1991)
Experimental pKa	pKa2 8.6 (NH2)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]D +33.2 (3M 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-Asparagine, 3 TMS, GC-MS Spectrum	splash10-0159-0910000000-bedf57998656ab5ebc16	Spectrum
GC-MS	L-Asparagine, 3 TMS, GC-MS Spectrum	splash10-0159-0910000000-4979c4d028d2dc931263	Spectrum
GC-MS	L-Asparagine, non-derivatized, GC-MS Spectrum	splash10-0159-0910000000-b7ea3fef61f3940cbdda	Spectrum
GC-MS	L-Asparagine, 3 TMS, GC-MS Spectrum	splash10-00di-9710000000-6d0afcbcc003347e598e	Spectrum
GC-MS	L-Asparagine, 2 TMS, GC-MS Spectrum	splash10-0uxr-0910000000-2be567239bd3229b1ca1	Spectrum
GC-MS	L-Asparagine, non-derivatized, GC-MS Spectrum	splash10-02t9-0790000000-b8141f48cbebb90f683e	Spectrum
GC-MS	L-Asparagine, non-derivatized, GC-MS Spectrum	splash10-02t9-1790000000-1d12ed9b4fb2799da766	Spectrum
GC-MS	L-Asparagine, 4 TMS, GC-MS Spectrum	splash10-014u-0961000000-65a5c0999f17110c9939	Spectrum
GC-MS	L-Asparagine, 4 TMS, GC-MS Spectrum	splash10-00kr-0940000000-0e0e5c7bdbac5ea0e49e	Spectrum
GC-MS	L-Asparagine, 3 TMS, GC-MS Spectrum	splash10-00lr-1920000000-7864dbb1f685e64dd1cf	Spectrum
GC-MS	L-Asparagine, 4 TMS, GC-MS Spectrum	splash10-000i-1940000000-964ea25da2789805985a	Spectrum
GC-MS	L-Asparagine, non-derivatized, GC-MS Spectrum	splash10-00lr-0930000000-79a089d9875e092dd7f2	Spectrum
GC-MS	L-Asparagine, non-derivatized, GC-MS Spectrum	splash10-0159-0910000000-bedf57998656ab5ebc16	Spectrum
GC-MS	L-Asparagine, non-derivatized, GC-MS Spectrum	splash10-0159-0910000000-4979c4d028d2dc931263	Spectrum
GC-MS	L-Asparagine, non-derivatized, GC-MS Spectrum	splash10-0159-0910000000-b7ea3fef61f3940cbdda	Spectrum
GC-MS	L-Asparagine, non-derivatized, GC-MS Spectrum	splash10-00di-4931100000-17f149310ce3a0f748d1	Spectrum
GC-MS	L-Asparagine, non-derivatized, GC-MS Spectrum	splash10-00di-9710000000-6d0afcbcc003347e598e	Spectrum
GC-MS	L-Asparagine, non-derivatized, GC-MS Spectrum	splash10-0uxr-0910000000-2be567239bd3229b1ca1	Spectrum
GC-MS	L-Asparagine, non-derivatized, GC-MS Spectrum	splash10-02t9-0790000000-b8141f48cbebb90f683e	Spectrum
GC-MS	L-Asparagine, non-derivatized, GC-MS Spectrum	splash10-02t9-1790000000-1d12ed9b4fb2799da766	Spectrum
GC-MS	L-Asparagine, non-derivatized, GC-MS Spectrum	splash10-014u-0961000000-65a5c0999f17110c9939	Spectrum
GC-MS	L-Asparagine, non-derivatized, GC-MS Spectrum	splash10-00kr-0940000000-0e0e5c7bdbac5ea0e49e	Spectrum
GC-MS	L-Asparagine, non-derivatized, GC-MS Spectrum	splash10-00lr-1920000000-7864dbb1f685e64dd1cf	Spectrum
GC-MS	L-Asparagine, non-derivatized, GC-MS Spectrum	splash10-000i-1940000000-964ea25da2789805985a	Spectrum
Predicted GC-MS	L-Asparagine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000f-9100000000-5881591331bd059b7e7d	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0080-9400000000-e5c7e19f427eea6d71b0	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-9000000000-afc1214100db1168b095	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00dl-9000000000-57e977cd87e9a86d482b	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-6fb96f5aa291359dba29	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-76f11e6fe5657c35d15f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-e944486273dbfde4cae4	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-27ad91a86be0c4d86c3c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-b8b7a3431b66246ad613	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-03fa294ec740e189dd99	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-cee2081406fc25ab6169	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-cd79afa0c27f65e54adc	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-01q9-0943200000-5a24322ba0ce2f410155	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03di-0900000000-fc3086cc1bb0c06a4c11	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03di-3900000000-2d74d8232e7523f3b1c9	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0900000000-fa61c6fa9a87ce4905bb	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-01q9-0942200000-757da8b3406485c997b0	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-014i-9000000000-eac18512f2d22ab7a7ef	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03di-0900000000-8df6d5b6cf94bf081c89	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0900000000-18079004a95c252da208	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-001i-0900000000-e6b1f9b4982e6cdc863d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-03di-5900000000-7b9c09b3b6de28972f97	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-00dl-9100000000-2ea95ead344d62e230a4	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-defacc365589bc4437d7	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-fd60db4d5e35794c45ae	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-001i-3900000000-fd0f1034b5c1e40435c0	2012-08-31	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 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	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 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, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

17196

Phenol-Explorer ID

Not Available

DrugBank ID

DB00174

HMDB ID

HMDB00168

CRC / DFC (Dictionary of Food Compounds) ID

BCF96-C:BHH57-K

EAFUS ID

261

Dr. Duke ID

L-ASPARAGINE|ASPARAGINE|ASPARAGIN

BIGG ID

34055

KNApSAcK ID

C00001341

HET ID

ASN

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1039271

SuperScent ID

Not Available

Wikipedia ID

Asparagine

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 sickling			DUKE
diuretic	35498	An agent that promotes the excretion of urine through its effects on kidney function.	DUKE

Enzymes

Name	Gene Name	UniProt ID
Asparagine synthetase [glutamine-hydrolyzing]	ASNS	P08243
Asparagine--tRNA ligase, cytoplasmic	NARS	O43776
Dolichyl-diphosphooligosaccharide--protein glycosyltransferase subunit 1	RPN1	P04843
Dolichyl-diphosphooligosaccharide--protein glycosyltransferase 48 kDa subunit	DDOST	P39656
Dolichyl-diphosphooligosaccharide--protein glycosyltransferase subunit 2	RPN2	P04844
Dolichyl-diphosphooligosaccharide--protein glycosyltransferase subunit STT3A	STT3A	P46977
Dolichyl-diphosphooligosaccharide--protein glycosyltransferase subunit DAD1	DAD1	P61803
Isoaspartyl peptidase/L-asparaginase	ASRGL1	Q7L266
Dolichyl-diphosphooligosaccharide--protein glycosyltransferase subunit STT3B	STT3B	Q8TCJ2
60 kDa lysophospholipase	ASPG	Q86U10
Probable asparagine--tRNA ligase, mitochondrial	NARS2	Q96I59

Pathways

Name	SMPDB Link	KEGG Link
Ammonia Recycling	SMP00009	map00910
Aspartate Metabolism	SMP00067	map00250
Transcription/Translation	SMP00019	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

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

L-Asparagine (FDB000787)

Structure for FDB000787 (L-Asparagine)