L-Asparagine (PAMDB000069)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000069
Identification
Name: L-Asparagine
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. 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. (http://en.wikipedia.org/wiki/Asparagine)
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • α-aminosuccinamate
  • α-aminosuccinamic acid
  • (-)-Asparagine
  • (S)-2,4-Diamino-4-oxobutanoate
  • (S)-2,4-Diamino-4-oxobutanoic acid
  • (S)-Asparagine
  • 2,4-Diamino-4-oxo-(S)-Butanoate
  • 2,4-Diamino-4-oxo-(S)-Butanoic acid
  • 2,4-diamino-4-Oxobutanoate, (S)-
  • 2,4-diamino-4-oxobutanoic acid, (S)-
  • 2-Aminosuccinamate
  • 2-Aminosuccinamate, L-
  • 2-Aminosuccinamic acid
  • 2-aminosuccinamic acid, L-
  • a Amminosuccinamate
  • a Amminosuccinamic acid
  • A-Aminosuccinamate
  • A-Aminosuccinamic acid
  • Agedoite
  • Alpha Amminosuccinamate
  • Alpha Amminosuccinamic acid
  • Alpha-Aminosuccinamate
  • Alpha-Aminosuccinamic acid
  • Altheine
  • Asn
  • Asparagine
  • Asparagine acid
  • Asparamide
  • Aspartamate
  • Aspartamic acid
  • Aspartate β-amide
  • Aspartate amide
  • Aspartate b amide
  • Aspartate b-amide
  • Aspartate beta amide
  • Aspartate beta-amide
  • Aspartate β amide
  • Aspartate β-amide
  • Aspartic acid β-amide
  • Aspartic acid amide
  • Aspartic acid b amide
  • Aspartic acid b-amide
  • Aspartic acid beta amide
  • Aspartic acid beta-amide
  • Aspartic acid β amide
  • Aspartic acid β-amide
  • B2,4-(S)-diamino-4-oxo-utanoate
  • B2,4-(S)-diamino-4-oxo-utanoic acid
  • Butanoate, 2,4-diamino-4-oxo-, (S)-
  • Butanoic acid, 2,4-diamino-4-oxo-, (S)-
  • Crystal VI
  • L-β-asparagine
  • L-2,4-Diamino-4-oxobutanoate
  • L-2,4-Diamino-4-oxobutanoic acid
  • L-2-Aminosuccinamate
  • L-2-Aminosuccinamic acid
  • L-Asparagine
  • L-Asparatamine
  • L-Aspartamine
  • L-b-Asparagine
  • L-beta-Asparagine
  • L-β-Asparagine
  • N
  • α Amminosuccinamate
  • α Amminosuccinamic acid
  • α-Aminosuccinamate
  • α-Aminosuccinamic acid
Chemical Formula: C4H8N2O3
Average Molecular Weight: 132.1179
Monoisotopic Molecular Weight: 132.053492132
InChI Key: DCXYFEDJOCDNAF-REOHCLBHSA-N
InChI:InChI=1S/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)/t2-/m0/s1
CAS number: 70-47-3
IUPAC Name:(2S)-2-amino-3-carbamoylpropanoic acid
Traditional IUPAC Name: L-asparagine
SMILES:N[C@@H](CC(N)=O)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct Parent L-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • Fatty amide
  • Primary carboxylic acid amide
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: 234-235 °C
Experimental Properties:
PropertyValueSource
Water Solubility:29.4 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP:-3.82 [CHMELIK,J ET AL. (1991)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility168.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity28.35 m3·mol-1ChemAxon
Polarizability11.68 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
L-Asparagine + Water > L-Aspartic acid + Ammonium
L-Aspartic acid + Adenosine triphosphate + L-Glutamine + Water > Adenosine monophosphate + L-Asparagine + L-Glutamate + Hydrogen ion + Pyrophosphate
L-Asparagine + Adenosine triphosphate + tRNA(Asn) + tRNA(Asn) <> Adenosine monophosphate + L-Asparaginyl-tRNA(Asn) + Pyrophosphate + L-Asparaginyl-tRNA(Asn)
L-Aspartic acid + Adenosine triphosphate + Ammonium > Adenosine monophosphate + L-Asparagine + Hydrogen ion + Pyrophosphate
Adenosine triphosphate + L-Aspartic acid + Ammonia <> Adenosine monophosphate + Pyrophosphate + L-Asparagine
L-Asparagine + Water <> L-Aspartic acid + Ammonia
Adenosine triphosphate + L-Aspartic acid + L-Glutamine + Water <> Adenosine monophosphate + Pyrophosphate + L-Asparagine + L-Glutamate
Adenosine triphosphate + L-Asparagine + tRNA(Asn) <> Adenosine monophosphate + Pyrophosphate + L-Asparaginyl-tRNA(Asn)
L-Asparagine + Water > Hydrogen ion + L-Aspartic acid + Ammonia
gly-asn + Water > Glycine + L-Asparagine
Adenosine triphosphate + L-Aspartic acid + L-Glutamine + Water + Ammonia <> Adenosine monophosphate + Pyrophosphate + L-Asparagine + L-Glutamate
Adenosine triphosphate + L-Aspartic acid + Ammonia + L-Aspartic acid > Adenosine monophosphate + L-Asparagine + Pyrophosphate + L-Asparagine
Adenosine triphosphate + L-Aspartic acid + L-Glutamine + Water + L-Aspartic acid > Adenosine monophosphate + Pyrophosphate + L-Asparagine + L-Glutamic acid + L-Asparagine + L-Glutamate
L-Asparagine + Adenosine triphosphate + Hydrogen ion + tRNA(Asn) + L-Asparagine > Pyrophosphate + Adenosine monophosphate + L-asparaginyl-tRNA(Asn)
L-Aspartic acid + Water + Adenosine triphosphate + L-Glutamine + L-Aspartic acid > L-Asparagine + Hydrogen ion + Adenosine monophosphate + L-Glutamic acid + Pyrophosphate + L-Asparagine + L-Glutamate
L-Aspartic acid + Adenosine triphosphate + Ammonium + L-Aspartic acid > L-Asparagine + Adenosine monophosphate + Pyrophosphate + Hydrogen ion + L-Asparagine
L-Asparagine + Water + L-Asparagine > L-Aspartic acid + Ammonium + L-Aspartic acid
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0159-0910000000-bedf57998656ab5ebc16View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0159-0910000000-4979c4d028d2dc931263View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0159-0910000000-b7ea3fef61f3940cbddaView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9710000000-6d0afcbcc003347e598eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0uxr-0910000000-2be567239bd3229b1ca1View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-02t9-0790000000-b8141f48cbebb90f683eView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-02t9-1790000000-1d12ed9b4fb2799da766View in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-014u-0961000000-65a5c0999f17110c9939View in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-00kr-0940000000-0e0e5c7bdbac5ea0e49eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00lr-1920000000-7864dbb1f685e64dd1cfView in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-000i-1940000000-964ea25da2789805985aView in MoNA
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0080-9400000000-e5c7e19f427eea6d71b0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9000000000-afc1214100db1168b095View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00dl-9000000000-57e977cd87e9a86d482bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-6fb96f5aa291359dba29View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-76f11e6fe5657c35d15fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-e944486273dbfde4cae4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-27ad91a86be0c4d86c3cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-b8b7a3431b66246ad613View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-03fa294ec740e189dd99View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-cee2081406fc25ab6169View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-cd79afa0c27f65e54adcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-01q9-0943200000-5a24322ba0ce2f410155View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0900000000-fc3086cc1bb0c06a4c11View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-3900000000-2d74d8232e7523f3b1c9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0900000000-fa61c6fa9a87ce4905bbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-01q9-0942200000-757da8b3406485c997b0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-014i-9000000000-eac18512f2d22ab7a7efView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0900000000-8df6d5b6cf94bf081c89View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0900000000-18079004a95c252da208View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-001i-0900000000-e6b1f9b4982e6cdc863dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-03di-5900000000-7b9c09b3b6de28972f97View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00dl-9100000000-2ea95ead344d62e230a4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-defacc365589bc4437d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-fd60db4d5e35794c45aeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-001i-3900000000-fd0f1034b5c1e40435c0View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
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  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Mohrmann K, van Eijndhoven MA, Schinkel AH, Schellens JH: Absence of N-linked glycosylation does not affect plasma membrane localization of breast cancer resistance protein (BCRP/ABCG2). Cancer Chemother Pharmacol. 2005 Oct;56(4):344-50. Epub 2005 May 5. Pubmed: 15875186
  • 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. Pubmed: 15911239
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  • Xu L, Wang Y, Gillespie D, Meissner G: Two rings of negative charges in the cytosolic vestibule of type-1 ryanodine receptor modulate ion fluxes. Biophys J. 2006 Jan 15;90(2):443-53. Epub 2005 Oct 20. Pubmed: 16239337
Synthesis Reference: Wang, Fangda. Preparation of L-b-asparagine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 8 pp.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID17196
HMDB IDHMDB00168
Pubchem Compound ID6267
Kegg IDC00152
ChemSpider ID6031
WikipediaAsn
BioCyc IDASN
EcoCyc IDASN
Ligand ExpoASN_LFZW

Enzymes

Protein Details
• L-asparaginase 2
General function:
Involved in asparaginase activity
Specific function:
L-asparagine + H(2)O = L-aspartate + NH(3)
Gene Name:
ansB
Locus Tag:
PA1337
Molecular weight:
38.6 kDa
Reactions
L-asparagine + H(2)O = L-aspartate + NH(3).
Protein Details
• L-asparaginase 1
General function:
Involved in asparaginase activity
Specific function:
L-asparagine + H(2)O = L-aspartate + NH(3)
Gene Name:
ansA
Locus Tag:
PA2253
Molecular weight:
34.8 kDa
Reactions
L-asparagine + H(2)O = L-aspartate + NH(3).

Transporters

Protein Details
• Uncharacterized amino-acid ABC transporter ATP-binding protein yecC
General function:
Involved in nucleotide binding
Specific function:
Probably part of a binding-protein-dependent transport system yecCS for an amino acid. Probably responsible for energy coupling to the transport system
Gene Name:
yecC
Locus Tag:
PA5152
Molecular weight:
28.4 kDa