Milk Composition Database: Showing metabocard for L-Asparagine (BMDB0000168)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:20:27 UTC

Update Date

2020-06-04 20:48:06 UTC

MCDB ID

BMDB0000168

Secondary Accession Numbers

BMDB00168

Metabolite Identification

Common 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 exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Asparagine exists in all living species, ranging from bacteria to humans. L-Asparagine is a potentially toxic compound. L-Asparagine has been found to be associated with several diseases known as pregnancy, cystic fibrosis, gout, and leukemia; also l-asparagine has been linked to the inborn metabolic disorders including celiac disease.

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 Weight

132.1179

Monoisotopic Molecular Weight

132.053492132

IUPAC Name

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

Traditional Name

L-asparagine

CAS Registry Number

70-47-3

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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	234 - 235 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	29.4 mg/mL	Not Available
LogP	-3.82	CHMELIK,J ET AL. (1991)

Predicted Properties

Property	Value	Source
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	Deposition Date	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	2014-06-16	View 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	2014-06-16	View 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	2014-06-16	View 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	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0uxr-0910000000-2be567239bd3229b1ca1	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-02t9-0790000000-b8141f48cbebb90f683e	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-02t9-1790000000-1d12ed9b4fb2799da766	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-014u-0961000000-65a5c0999f17110c9939	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-00kr-0940000000-0e0e5c7bdbac5ea0e49e	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-00lr-1920000000-7864dbb1f685e64dd1cf	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-000i-1940000000-964ea25da2789805985a	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00lr-0930000000-79a089d9875e092dd7f2	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0159-0910000000-bedf57998656ab5ebc16	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0159-0910000000-4979c4d028d2dc931263	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0159-0910000000-b7ea3fef61f3940cbdda	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-QQ (Non-derivatized)	splash10-00di-4931100000-17f149310ce3a0f748d1	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9710000000-6d0afcbcc003347e598e	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0uxr-0910000000-2be567239bd3229b1ca1	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-02t9-0790000000-b8141f48cbebb90f683e	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-02t9-1790000000-1d12ed9b4fb2799da766	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014u-0961000000-65a5c0999f17110c9939	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00kr-0940000000-0e0e5c7bdbac5ea0e49e	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00lr-1920000000-7864dbb1f685e64dd1cf	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-000i-1940000000-964ea25da2789805985a	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-9100000000-5881591331bd059b7e7d	2016-09-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0080-9400000000-e5c7e19f427eea6d71b0	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-9000000000-afc1214100db1168b095	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00dl-9000000000-57e977cd87e9a86d482b	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-6fb96f5aa291359dba29	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-76f11e6fe5657c35d15f	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-e944486273dbfde4cae4	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-27ad91a86be0c4d86c3c	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-b8b7a3431b66246ad613	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-03fa294ec740e189dd99	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-cee2081406fc25ab6169	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-cd79afa0c27f65e54adc	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-01q9-0943200000-5a24322ba0ce2f410155	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03di-0900000000-fc3086cc1bb0c06a4c11	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03di-3900000000-2d74d8232e7523f3b1c9	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0900000000-fa61c6fa9a87ce4905bb	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-01q9-0942200000-757da8b3406485c997b0	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-014i-9000000000-eac18512f2d22ab7a7ef	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03di-0900000000-8df6d5b6cf94bf081c89	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0900000000-18079004a95c252da208	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-001i-0900000000-e6b1f9b4982e6cdc863d	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-03di-5900000000-7b9c09b3b6de28972f97	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-00dl-9100000000-2ea95ead344d62e230a4	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-defacc365589bc4437d7	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-fd60db4d5e35794c45ae	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-001i-3900000000-fd0f1034b5c1e40435c0	2012-08-31	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Not Available	2021-10-10	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2021-10-10	View 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)	Not Available	2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected but not Quantified	Not Applicable	PMID: 23438684	details
Detected and Quantified	6 +/- 1 uM	PMID: 30994344	details
Detected and Quantified	7 +/- 1 uM	PMID: 30994344	details
Detected and Quantified	8 +/- 1 uM	PMID: 30994344	details
Detected and Quantified	6 +/- 2 uM	PMID: 30994344	details
Detected and Quantified	6.6 +/- 0.3 uM	PMID: 30994344	details
Detected and Quantified	6.5 +/- 0.2 uM	PMID: 30994344	details
Detected and Quantified	6.5 +/- 0.3 uM	PMID: 30994344	details
Detected and Quantified	5.3 +/- 0.2 uM	PMID: 30994344	details

External Links

HMDB ID

HMDB0000168

DrugBank ID

DB00174

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

6267

PDB ID

Not Available

ChEBI ID

17196

References

Synthesis Reference

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

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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. [PubMed:23438684 ]
A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Showing metabocard for L-Asparagine (BMDB0000168)

Structure for BMDB0000168 (L-Asparagine)