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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:02:09 UTC
HMDB IDHMDB00168
Secondary Accession NumbersNone
Metabolite Identification
Common NameL-Asparagine
DescriptionAsparagine (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). (http://en.wikipedia.org/wiki/Asparagine).
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 KeyInChIKey=DCXYFEDJOCDNAF-REOHCLBHSA-N
Chemical 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Alanine and aspartate metabolism
  • Component of Aminoacyl-tRNA biosynthesis
  • Component of Nitrogen metabolism
  • Essential amino acid
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
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
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
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
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
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Biofluid Locations
  • Blood
  • Breast Milk
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Location
  • All Tissues
  • Prostate
Pathways
NameSMPDB LinkKEGG Link
Amikacin PathwaySMP00253Not Available
Ammonia RecyclingSMP00009map00910
Arbekacin Action PathwaySMP00713Not Available
Aspartate MetabolismSMP00067map00250
Azithromycin PathwaySMP00247Not Available
Canavan DiseaseSMP00175Not Available
Chloramphenicol Action PathwaySMP00729Not Available
Clarithromycin PathwaySMP00248Not Available
Clindamycin PathwaySMP00249Not Available
Clomocycline PathwaySMP00262Not Available
Demeclocycline PathwaySMP00290Not Available
Doxycycline PathwaySMP00291Not Available
Erythromycin PathwaySMP00250Not Available
Gentamicin PathwaySMP00254Not Available
HypoacetylaspartiaSMP00192Not Available
Josamycin Action PathwaySMP00731Not Available
Kanamycin PathwaySMP00255Not Available
Lincomycin Action PathwaySMP00728Not Available
Lymecycline PathwaySMP00295Not Available
Methacycline Action PathwaySMP00727Not Available
Minocycline PathwaySMP00292Not Available
Neomycin PathwaySMP00256Not Available
Netilmicin PathwaySMP00257Not Available
Oxytetracycline PathwaySMP00293Not Available
Paromomycin Action PathwaySMP00714Not Available
Rolitetracycline Action PathwaySMP00726Not Available
Roxithromycin PathwaySMP00251Not Available
Spectinomycin PathwaySMP00258Not Available
Streptomycin PathwaySMP00259Not Available
Telithromycin PathwaySMP00252Not Available
Tetracycline PathwaySMP00294Not Available
Tigecycline Action PathwaySMP00712Not Available
Tobramycin Action PathwaySMP00711Not Available
Transcription/TranslationSMP00019Not Available
Troleandomycin Action PathwaySMP00730Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified36-87 uMNewborn (0-30 days old)Both
Normal
    • BC Children's Hos...
details
BloodDetected and Quantified33-77 uMInfant (1 - 3 months old)Both
Normal
    • BC Children's Hos...
details
BloodDetected and Quantified23-79 uMChildren (3 months - 6 years old)Both
Normal
    • BC Children's Hos...
details
BloodDetected and Quantified25-75 uMChildren (6 - 18 years old)Both
Normal
    • BC Children's Hos...
details
BloodDetected and Quantified32.9 +/- 7.6 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified41.0 (31.0-51.0) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified48.0 +/- 7.0 uMChildren (1-13 years old)MaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified46.0 +/- 7.0 uMChildren (1-13 years old)FemaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified49.0 +/- 7.0 uMAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified47.0 +/- 9.0 uMAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified35.0 (16.4-57.2) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified82.4 +/- 7.3 uMAdult (>18 years old)BothNormal details
Breast MilkDetected and Quantified16.6 +/- 10.5 uMAdult (>18 years old)Female
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified4.43 (0.0-8.86) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified19.0 +/- 11.1 uMChildren (1-13 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified8.1 +/- 4.9 uMAdult (>18 years old)MaleNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified9.0 +/- 4.2 uMAdult (>18 years old)FemaleNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified5.4 +/- 1.4 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified6.20 (5.90-6.50) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified5.99 +/- 0.92 umol/mmol creatinineAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified4-10 uMChildren (0 - 10 years old)Both
Normal
    • BC Children's Hos...
details
Cerebrospinal Fluid (CSF)Detected and Quantified4-10 uMAdolescent (>11 years old)Both
Normal
    • BC Children's Hos...
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableChildren (1-13 years old)Not Specified
Normal
details
SalivaDetected and Quantified1.20 +/- 0.809 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified1.24 +/- 0.768 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified1.70 +/- 1.69 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified1.74 +/- 0.972 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified2.17 +/- 1.41 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.580 +/- 0.511 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified1.76 +/- 2.11 uMAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified8.75 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified9.5 (3.0-26.0) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified4.66-16.53 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
UrineDetected and Quantified15.15-53.01 umol/mmol creatinineAdult (>18 years old)BothNormal
    • David F. Putnam C...
details
UrineDetected and Quantified0.96 +/- 0.65 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified10.1 (4.6-17.8) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0 - 77.90 umol/mmol creatinineNewborn (0-30 days old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified0 - 53.03 umol/mmol creatinineInfant (1 - 6 months old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified0 - 32.00 umol/mmol creatinineInfant (6 months - <1 year old)Both
Normal
    • BC Children's Hos...
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0 - 28.15 umol/mmol creatinineChildren (1 - 2 years old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified0 - 26.23 umol/mmol creatinineChildren (2 - 4 years old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified0 - 25.33 umol/mmol creatinineChildren (4 - 13 years old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified0 - 19.56 umol/mmol creatinineAdolescent (13 - 21 years old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified0 - 19.56 umol/mmol creatinineAdult (>21 years old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified25.158 +/- 23.462 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified10.52 +/- 3.85 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified8.8 (4.6-17.7) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified35.7098 +/- 12.6254 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified10.0 (4.6-16.32) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified9.211 (3.289-15.1) umol/mmol creatinineAdult (>18 years old)BothNormal
    details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    BloodDetected and Quantified54.1 +/- 21.7 uMAdult (>18 years old)BothHeart Transplant details
    BloodDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothColorectal cancer details
    BloodDetected and Quantified40.8 +/- 11.5 uMChildren (1-13 years old)BothUremia details
    BloodDetected and Quantified39.9 +/- 3.2 uMAdult (>18 years old)Both
    Epilepsy
    details
    Cerebrospinal Fluid (CSF)Detected and Quantified7.9 +/- 6.4 uMChildren (1-13 years old)Not Specified
    Leukemia
    details
    Cerebrospinal Fluid (CSF)Detected and Quantified11.1 +/- 6.7 uMChildren (1-13 years old)Not Specifiedleukemia details
    Cerebrospinal Fluid (CSF)Detected and Quantified6.01 +/- 0.65 uMAdult (>18 years old)BothSchizophrenia details
    Cerebrospinal Fluid (CSF)Detected and Quantified1.77 +/- 0.16 umol/mmol creatinineAdult (>18 years old)BothAlzheimer's disease details
    FecesDetected but not QuantifiedNot ApplicableChildren (1-13 years old)Not Specified
    Treated celiac disease
    details
    SalivaDetected and Quantified1.68 +/- 2.90 uMAdult (>18 years old)MaleAlzheimer's disease details
    SalivaDetected and Quantified0.97 +/- 1.12 uMAdult (>18 years old)MaleFrontotemporal lobe dementia details
    SalivaDetected and Quantified3.02 +/- 0.83 uMAdult (>18 years old)BothLewy body disease details
    UrineDetected and Quantified35.098 +/- 22.947 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Eosinophilic esophagitis
      • Mordechai, Hien, ...
    details
    UrineDetected and Quantified29.6797 +/- 15.0964 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Eosinophilic esophagitis
      • Mordechai, Hien, ...
    details
    UrineDetected and Quantified28.0762 +/- 31.9291 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Gastroesophageal reflux disease
      • Mordechai, Hien, ...
    details
    Associated Disorders and Diseases
    Disease References
    Alzheimer's disease
    1. Fonteh AN, Harrington RJ, Tsai A, Liao P, Harrington MG: Free amino acid and dipeptide changes in the body fluids from Alzheimer's disease subjects. Amino Acids. 2007 Feb;32(2):213-24. Epub 2006 Oct 10. [17031479 ]
    Epilepsy
    1. Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. [14992292 ]
    Schizophrenia
    1. Do KQ, Lauer CJ, Schreiber W, Zollinger M, Gutteck-Amsler U, Cuenod M, Holsboer F: gamma-Glutamylglutamine and taurine concentrations are decreased in the cerebrospinal fluid of drug-naive patients with schizophrenic disorders. J Neurochem. 1995 Dec;65(6):2652-62. [7595563 ]
    Leukemia
    1. 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. [15911239 ]
    Uremia
    1. Canepa A, Filho JC, Gutierrez A, Carrea A, Forsberg AM, Nilsson E, Verrina E, Perfumo F, Bergstrom J: Free amino acids in plasma, red blood cells, polymorphonuclear leukocytes, and muscle in normal and uraemic children. Nephrol Dial Transplant. 2002 Mar;17(3):413-21. [11865086 ]
    Associated OMIM IDs
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB000787
    KNApSAcK IDC00001341
    Chemspider ID6031
    KEGG Compound IDC00152
    BioCyc IDASN
    BiGG ID34055
    Wikipedia LinkAsn
    NuGOwiki LinkHMDB00168
    Metagene LinkHMDB00168
    METLIN ID14
    PubChem Compound6267
    PDB IDASN
    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. Rip JW, Coulter-Mackie MB, Rupar CA, Gordon BA: Purification and structure of human liver aspartylglucosaminidase. Biochem J. 1992 Dec 15;288 ( Pt 3):1005-10. [1281977 ]
    2. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. [19212411 ]
    3. Hagenfeldt L, Bjerkenstedt L, Edman G, Sedvall G, Wiesel FA: Amino acids in plasma and CSF and monoamine metabolites in CSF: interrelationship in healthy subjects. J Neurochem. 1984 Mar;42(3):833-7. [6198473 ]
    4. 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. [15911239 ]
    5. Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6. [12297216 ]
    6. Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. [14992292 ]
    7. 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. [16027730 ]
    8. 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. [12557291 ]
    9. Filho JC, Bergstrom J, Stehle P, Furst P: Simultaneous measurements of free amino acid patternsof plasma, muscle and erythrocytes in healthy human subjects. Clin Nutr. 1997 Dec;16(6):299-305. [16844612 ]
    10. 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. [15270080 ]
    11. Takamatsu S, Inoue N, Katsumata T, Nakamura K, Fujibayashi Y, Takeuchi M: The relationship between the branch-forming glycosyltransferases and cell surface sugar chain structures. Biochemistry. 2005 Apr 26;44(16):6343-9. [15835923 ]
    12. Chiara F, Goumans MJ, Forsberg H, Ahgren A, Rasola A, Aspenstrom P, Wernstedt C, Hellberg C, Heldin CH, Heuchel R: A gain of function mutation in the activation loop of platelet-derived growth factor beta-receptor deregulates its kinase activity. J Biol Chem. 2004 Oct 8;279(41):42516-27. Epub 2004 Jul 28. [15284236 ]
    13. 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. [16239337 ]
    14. Poon CJ, Plaas AH, Keene DR, McQuillan DJ, Last K, Fosang AJ: N-linked keratan sulfate in the aggrecan interglobular domain potentiates aggrecanase activity. J Biol Chem. 2005 Jun 24;280(25):23615-21. Epub 2005 Apr 22. [15849197 ]
    15. Ahlman B, Andersson K, Leijonmarck CE, Ljungqvist O, Hedenborg L, Wernerman J: Short-term starvation alters the free amino acid content of the human intestinal mucosa. Clin Sci (Lond). 1994 Jun;86(6):653-62. [7914846 ]
    16. Avramis VI, Panosyan EH: Pharmacokinetic/pharmacodynamic relationships of asparaginase formulations: the past, the present and recommendations for the future. Clin Pharmacokinet. 2005;44(4):367-93. [15828851 ]
    17. 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. [15875186 ]

    Enzymes

    General function:
    Involved in asparagine synthase (glutamine-hydrolyzing) activity
    Specific function:
    Not Available
    Gene Name:
    ASNS
    Uniprot ID:
    P08243
    Molecular weight:
    62167.855
    Reactions
    Adenosine triphosphate + L-Aspartic acid + L-Glutamine + Water → Adenosine monophosphate + Pyrophosphate + L-Asparagine + L-Glutamic aciddetails
    General function:
    Involved in nucleotide binding
    Specific function:
    Not Available
    Gene Name:
    NARS
    Uniprot ID:
    O43776
    Molecular weight:
    62942.425
    Reactions
    Adenosine triphosphate + L-Asparagine + tRNA(Asn) → Adenosine monophosphate + Pyrophosphate + L-asparaginyl-tRNA(Asn)details
    Adenosine triphosphate + L-Asparagine + tRNA(Asn) → Adenosine monophosphate + Pyrophosphate + L-Asparaginyl-tRNA(Asn)details
    General function:
    Involved in dolichyl-diphosphooligosaccharide-protein glycotransferase activity
    Specific function:
    Essential subunit of the N-oligosaccharyl transferase (OST) complex which catalyzes the transfer of a high mannose oligosaccharide from a lipid-linked oligosaccharide donor to an asparagine residue within an Asn-X-Ser/Thr consensus motif in nascent polypeptide chains.
    Gene Name:
    RPN1
    Uniprot ID:
    P04843
    Molecular weight:
    68568.81
    General function:
    Involved in dolichyl-diphosphooligosaccharide-protein glycotransferase activity
    Specific function:
    Essential subunit of the N-oligosaccharyl transferase (OST) complex which catalyzes the transfer of a high mannose oligosaccharide from a lipid-linked oligosaccharide donor to an asparagine residue within an Asn-X-Ser/Thr consensus motif in nascent polypeptide chains.
    Gene Name:
    DDOST
    Uniprot ID:
    P39656
    Molecular weight:
    50701.205
    General function:
    Involved in dolichyl-diphosphooligosaccharide-protein glycotransferase activity
    Specific function:
    Essential subunit of the N-oligosaccharyl transferase (OST) complex which catalyzes the transfer of a high mannose oligosaccharide from a lipid-linked oligosaccharide donor to an asparagine residue within an Asn-X-Ser/Thr consensus motif in nascent polypeptide chains.
    Gene Name:
    RPN2
    Uniprot ID:
    P04844
    Molecular weight:
    67722.73
    General function:
    Involved in oligosaccharyl transferase activity
    Specific function:
    Catalytic subunit of the N-oligosaccharyl transferase (OST) complex which catalyzes the transfer of a high mannose oligosaccharide from a lipid-linked oligosaccharide donor to an asparagine residue within an Asn-X-Ser/Thr consensus motif in nascent polypeptide chains. N-glycosylation occurs cotranslationally and the complex associates with the Sec61 complex at the channel-forming translocon complex that mediates protein translocation across the endoplasmic reticulum (ER). SST3A seems to be involved in complex substrate specificity. STT3A is present in the majority of OST complexes and mediates cotranslational N-glycosylation of most sites on target proteins, while STT3B-containing complexes are required for efficient cotranslational glycosylation and mediate glycosylation of sites that have been skipped by STT3A.
    Gene Name:
    STT3A
    Uniprot ID:
    P46977
    Molecular weight:
    80528.83
    General function:
    Involved in dolichyl-diphosphooligosaccharide-protein g
    Specific function:
    Essential subunit of the N-oligosaccharyl transferase (OST) complex which catalyzes the transfer of a high mannose oligosaccharide from a lipid-linked oligosaccharide donor to an asparagine residue within an Asn-X-Ser/Thr consensus motif in nascent polypeptide chains. N-glycosylation occurs cotranslationally and the complex associates with the Sec61 complex at the channel-forming translocon complex that mediates protein translocation across the endoplasmic reticulum (ER). Loss of the DAD1 protein triggers apoptosis (By similarity).
    Gene Name:
    DAD1
    Uniprot ID:
    P61803
    Molecular weight:
    12496.55
    General function:
    Involved in hydrolase activity
    Specific function:
    Has both L-asparaginase and beta-aspartyl peptidase activity. May be involved in the production of L-aspartate, which can act as an excitatory neurotransmitter in some brain regions. Is highly active with L-Asp beta-methyl ester. Besides, has catalytic activity toward beta-aspartyl dipeptides and their methyl esters, including beta-L-Asp-L-Phe, beta-L-Asp-L-Phe methyl ester (aspartame), beta-L-Asp-L-Ala, beta-L-Asp-L-Leu and beta-L-Asp-L-Lys. Does not have aspartylglucosaminidase activity and is inactive toward GlcNAc-L-Asn. Likewise, has no activity toward glutamine.
    Gene Name:
    ASRGL1
    Uniprot ID:
    Q7L266
    Molecular weight:
    32054.325
    Reactions
    L-Asparagine + Water → L-Aspartic acid + Ammoniadetails
    General function:
    Involved in oligosaccharyl transferase activity
    Specific function:
    Catalytic subunit of the N-oligosaccharyl transferase (OST) complex which catalyzes the transfer of a high mannose oligosaccharide from a lipid-linked oligosaccharide donor to an asparagine residue within an Asn-X-Ser/Thr consensus motif in nascent polypeptide chains. N-glycosylation occurs cotranslationally and the complex associates with the Sec61 complex at the channel-forming translocon complex that mediates protein translocation across the endoplasmic reticulum (ER). STT3B is present in a small subset of OST complexes and mediates both cotranslational and post-translational N-glycosylation of target proteins: STT3B-containing complexes are required for efficient cotranslational glycosylation and while they are less competent than STT3A-containing complexes for cotranslational glycosylation, they have the ability to mediate glycosylation of some nascent sites that are not accessible for STT3A. STT3B-containing complexes also act post-translationally and mediate modification of skipped glycosylation sites in unfolded proteins. Plays a role in ER-associated degradation (ERAD) pathway that mediates ubiquitin-dependent degradation of misfolded endoplasmic reticulum proteins by mediating N-glycosylation of unfolded proteins, which are then recognized by the ERAD pathway and targeted for degradation. Mediates glycosylation of the disease variant AMYL-TTR 'Asp-38' of TTR at 'Asn-118', leading to its degradation.
    Gene Name:
    STT3B
    Uniprot ID:
    Q8TCJ2
    Molecular weight:
    93673.495
    General function:
    Involved in asparaginase activity
    Specific function:
    Exhibits lysophospholipase, transacylase, PAF acetylhydrolase and asparaginase activities.
    Gene Name:
    ASPG
    Uniprot ID:
    Q86U10
    Molecular weight:
    60882.4
    Reactions
    L-Asparagine + Water → L-Aspartic acid + Ammoniadetails
    General function:
    Involved in nucleotide binding
    Specific function:
    Not Available
    Gene Name:
    NARS2
    Uniprot ID:
    Q96I59
    Molecular weight:
    54089.64
    Reactions
    Adenosine triphosphate + L-Asparagine + tRNA(Asn) → Adenosine monophosphate + Pyrophosphate + L-asparaginyl-tRNA(Asn)details
    Adenosine triphosphate + L-Asparagine + tRNA(Asn) → Adenosine monophosphate + Pyrophosphate + L-Asparaginyl-tRNA(Asn)details

    Transporters

    General function:
    Involved in sodium:dicarboxylate symporter activity
    Specific function:
    Has a broad substrate specificity, a preference for zwitterionic amino acids, and a sodium-dependence. It accepts as substrates all neutral amino acids, including glutamine, asparagine, and branched-chain and aromatic amino acids, and excludes methylated amino acids, anionic amino acids, and cationic amino acids. Act as a cell surface receptor for feline endogenous virus RD114, baboon M7 endogenous virus and type D simian retroviruses
    Gene Name:
    SLC1A5
    Uniprot ID:
    Q15758
    Molecular weight:
    56597.6
    General function:
    Amino acid transport and metabolism
    Specific function:
    Sodium-dependent amino acid/proton antiporter. Mediates electrogenic cotransport of glutamine and sodium ions in exchange for protons. Also recognizes histidine, asparagine and alanine. May mediate amino acid transport in either direction under physiological conditions. May play a role in nitrogen metabolism and synaptic transmission
    Gene Name:
    SLC38A3
    Uniprot ID:
    Q99624
    Molecular weight:
    55772.4