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Record Information
Version1.0
Creation Date2016-09-30 22:20:27 UTC
Update Date2020-06-04 20:48:06 UTC
MCDB ID BMDB0000168
Secondary Accession Numbers
  • BMDB00168
Metabolite Identification
Common NameL-Asparagine
DescriptionL-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
Thumb
Synonyms
ValueSource
(2S)-2,4-Diamino-4-oxobutanoic acidChEBI
(2S)-2-Amino-3-carbamoylpropanoic acidChEBI
(S)-2-Amino-3-carbamoylpropanoic acidChEBI
(S)-AsparagineChEBI
2-Aminosuccinamic acidChEBI
alpha-Aminosuccinamic acidChEBI
AsnChEBI
ASPARAGINEChEBI
Aspartamic acidChEBI
L-2-Aminosuccinamic acidChEBI
L-AsparaginChEBI
L-Aspartic acid beta-amideChEBI
NChEBI
(2S)-2,4-Diamino-4-oxobutanoateGenerator
(2S)-2-Amino-3-carbamoylpropanoateGenerator
(S)-2-Amino-3-carbamoylpropanoateGenerator
2-AminosuccinamateGenerator
a-AminosuccinamateGenerator
a-Aminosuccinamic acidGenerator
alpha-AminosuccinamateGenerator
Α-aminosuccinamateGenerator
Α-aminosuccinamic acidGenerator
AspartamateGenerator
L-2-AminosuccinamateGenerator
L-Aspartate b-amideGenerator
L-Aspartate beta-amideGenerator
L-Aspartate β-amideGenerator
L-Aspartic acid b-amideGenerator
L-Aspartic acid β-amideGenerator
(-)-AsparagineHMDB
(S)-2,4-Diamino-4-oxobutanoateHMDB
(S)-2,4-Diamino-4-oxobutanoic acidHMDB
AgedoiteHMDB
alpha AmminosuccinamateHMDB
alpha Amminosuccinamic acidHMDB
AltheineHMDB
Asparagine acidHMDB
AsparamideHMDB
Aspartic acid amideHMDB
Aspartic acid b-amideHMDB
Aspartic acid beta amideHMDB
b2,4-(S)-Diamino-4-oxo-utanoateHMDB
b2,4-(S)-Diamino-4-oxo-utanoic acidHMDB
Crystal VIHMDB
L-2,4-Diamino-4-oxobutanoateHMDB
L-2,4-Diamino-4-oxobutanoic acidHMDB
L-AspartamineHMDB
L-b-AsparagineHMDB
L-beta-AsparagineHMDB
Chemical FormulaC4H8N2O3
Average Molecular Weight132.1179
Monoisotopic Molecular Weight132.053492132
IUPAC Name(2S)-2-amino-3-carbamoylpropanoic acid
Traditional NameL-asparagine
CAS Registry Number70-47-3
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 KeyDCXYFEDJOCDNAF-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAsparagine 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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point234 - 235 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility29.4 mg/mLNot Available
LogP-3.82CHMELIK,J ET AL. (1991)
Predicted Properties
PropertyValueSource
logP-3.4ALOGPS
logP-4.3ChemAxon
logS0.1ALOGPS
pKa (Strongest Acidic)2ChemAxon
pKa (Strongest Basic)8.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area106.41 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity28.35 m³·mol⁻¹ChemAxon
Polarizability11.68 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0159-0910000000-bedf57998656ab5ebc162014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0159-0910000000-4979c4d028d2dc9312632014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0159-0910000000-b7ea3fef61f3940cbdda2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9710000000-6d0afcbcc003347e598e2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0uxr-0910000000-2be567239bd3229b1ca12014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-02t9-0790000000-b8141f48cbebb90f683e2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-02t9-1790000000-1d12ed9b4fb2799da7662014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-014u-0961000000-65a5c0999f17110c99392014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-00kr-0940000000-0e0e5c7bdbac5ea0e49e2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00lr-1920000000-7864dbb1f685e64dd1cf2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-000i-1940000000-964ea25da2789805985a2014-06-16View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00lr-0930000000-79a089d9875e092dd7f22017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0159-0910000000-bedf57998656ab5ebc162017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0159-0910000000-4979c4d028d2dc9312632017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0159-0910000000-b7ea3fef61f3940cbdda2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-QQ (Non-derivatized)splash10-00di-4931100000-17f149310ce3a0f748d12017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9710000000-6d0afcbcc003347e598e2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0uxr-0910000000-2be567239bd3229b1ca12017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-02t9-0790000000-b8141f48cbebb90f683e2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-02t9-1790000000-1d12ed9b4fb2799da7662017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014u-0961000000-65a5c0999f17110c99392017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00kr-0940000000-0e0e5c7bdbac5ea0e49e2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00lr-1920000000-7864dbb1f685e64dd1cf2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000i-1940000000-964ea25da2789805985a2017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9100000000-5881591331bd059b7e7d2016-09-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0080-9400000000-e5c7e19f427eea6d71b02012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9000000000-afc1214100db1168b0952012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00dl-9000000000-57e977cd87e9a86d482b2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-6fb96f5aa291359dba292012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-76f11e6fe5657c35d15f2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-e944486273dbfde4cae42012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-27ad91a86be0c4d86c3c2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-b8b7a3431b66246ad6132012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-03fa294ec740e189dd992012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-cee2081406fc25ab61692012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-cd79afa0c27f65e54adc2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-01q9-0943200000-5a24322ba0ce2f4101552012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0900000000-fc3086cc1bb0c06a4c112012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-3900000000-2d74d8232e7523f3b1c92012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0900000000-fa61c6fa9a87ce4905bb2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-01q9-0942200000-757da8b3406485c997b02012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-014i-9000000000-eac18512f2d22ab7a7ef2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0900000000-8df6d5b6cf94bf081c892012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0900000000-18079004a95c252da2082012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-001i-0900000000-e6b1f9b4982e6cdc863d2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-03di-5900000000-7b9c09b3b6de28972f972012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00dl-9100000000-2ea95ead344d62e230a42012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-defacc365589bc4437d72012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-fd60db4d5e35794c45ae2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-001i-3900000000-fd0f1034b5c1e40435c02012-08-31View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Not Available2016-10-22View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Not Available2021-10-10View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not Available2021-10-10View 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 Available2012-12-04View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not Available2012-12-05View Spectrum
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
Detected and Quantified6 +/- 1 uM details
Detected and Quantified7 +/- 1 uM details
Detected and Quantified8 +/- 1 uM details
Detected and Quantified6 +/- 2 uM details
Detected and Quantified6.6 +/- 0.3 uM details
Detected and Quantified6.5 +/- 0.2 uM details
Detected and Quantified6.5 +/- 0.3 uM details
Detected and Quantified5.3 +/- 0.2 uM details
HMDB IDHMDB0000168
DrugBank IDDB00174
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000787
KNApSAcK IDC00001341
Chemspider ID6031
KEGG Compound IDC00152
BioCyc IDASN
BiGG ID34055
Wikipedia LinkAsparagine
METLIN ID14
PubChem Compound6267
PDB IDNot Available
ChEBI ID17196
References
Synthesis ReferenceWang, Fangda. Preparation of L-b-asparagine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 8 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. 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.