Record Information
Version1.0
Creation date2010-04-08 22:04:42 UTC
Update date2020-09-17 15:38:24 UTC
Primary IDFDB000787
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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 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 Number70-47-3
Structure
Thumb
Synonyms
SynonymSource
(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
(2S)-2-amino-3-CarbamoylpropanoateGenerator
(S)-2-amino-3-CarbamoylpropanoateGenerator
(S)-2-Aminosuccinic acid 4-amidebiospider
2-Aminosuccinamic acid, L-biospider
Asparagine, 9CI; L-formdb_source
Asparagine, L- (8CI)biospider
L-Asparagine (9CI)biospider
L-Asparataminebiospider
L-Aspartic acid 4-amidebiospider
α-aminosuccinamateGenerator
α-aminosuccinamic acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility168 g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC4H8N2O3
IUPAC name(2S)-2-amino-3-carbamoylpropanoic acid
InChI IdentifierInChI=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
Isomeric SMILESN[C@@H](CC(N)=O)C(O)=O
Average Molecular Weight132.1179
Monoisotopic Molecular Weight132.053492132
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.
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Environmental role:

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 36.36%; H 6.10%; N 21.20%; O 36.33%DFC
Melting PointMp 226-227 dec. (slow heat)DFC
Boiling PointNot Available
Experimental Water Solubility29.4 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP-3.82CHMELIK,J ET AL. (1991)
Experimental pKapKa2 8.6 (NH2)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +33.2 (3M HCl)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSL-Asparagine, 3 TMS, GC-MS Spectrumsplash10-0159-0910000000-bedf57998656ab5ebc16Spectrum
GC-MSL-Asparagine, 3 TMS, GC-MS Spectrumsplash10-0159-0910000000-4979c4d028d2dc931263Spectrum
GC-MSL-Asparagine, non-derivatized, GC-MS Spectrumsplash10-0159-0910000000-b7ea3fef61f3940cbddaSpectrum
GC-MSL-Asparagine, 3 TMS, GC-MS Spectrumsplash10-00di-9710000000-6d0afcbcc003347e598eSpectrum
GC-MSL-Asparagine, 2 TMS, GC-MS Spectrumsplash10-0uxr-0910000000-2be567239bd3229b1ca1Spectrum
GC-MSL-Asparagine, non-derivatized, GC-MS Spectrumsplash10-02t9-0790000000-b8141f48cbebb90f683eSpectrum
GC-MSL-Asparagine, non-derivatized, GC-MS Spectrumsplash10-02t9-1790000000-1d12ed9b4fb2799da766Spectrum
GC-MSL-Asparagine, 4 TMS, GC-MS Spectrumsplash10-014u-0961000000-65a5c0999f17110c9939Spectrum
GC-MSL-Asparagine, 4 TMS, GC-MS Spectrumsplash10-00kr-0940000000-0e0e5c7bdbac5ea0e49eSpectrum
GC-MSL-Asparagine, 3 TMS, GC-MS Spectrumsplash10-00lr-1920000000-7864dbb1f685e64dd1cfSpectrum
GC-MSL-Asparagine, 4 TMS, GC-MS Spectrumsplash10-000i-1940000000-964ea25da2789805985aSpectrum
GC-MSL-Asparagine, non-derivatized, GC-MS Spectrumsplash10-00lr-0930000000-79a089d9875e092dd7f2Spectrum
GC-MSL-Asparagine, non-derivatized, GC-MS Spectrumsplash10-0159-0910000000-bedf57998656ab5ebc16Spectrum
GC-MSL-Asparagine, non-derivatized, GC-MS Spectrumsplash10-0159-0910000000-4979c4d028d2dc931263Spectrum
GC-MSL-Asparagine, non-derivatized, GC-MS Spectrumsplash10-0159-0910000000-b7ea3fef61f3940cbddaSpectrum
GC-MSL-Asparagine, non-derivatized, GC-MS Spectrumsplash10-00di-4931100000-17f149310ce3a0f748d1Spectrum
GC-MSL-Asparagine, non-derivatized, GC-MS Spectrumsplash10-00di-9710000000-6d0afcbcc003347e598eSpectrum
GC-MSL-Asparagine, non-derivatized, GC-MS Spectrumsplash10-0uxr-0910000000-2be567239bd3229b1ca1Spectrum
GC-MSL-Asparagine, non-derivatized, GC-MS Spectrumsplash10-02t9-0790000000-b8141f48cbebb90f683eSpectrum
GC-MSL-Asparagine, non-derivatized, GC-MS Spectrumsplash10-02t9-1790000000-1d12ed9b4fb2799da766Spectrum
GC-MSL-Asparagine, non-derivatized, GC-MS Spectrumsplash10-014u-0961000000-65a5c0999f17110c9939Spectrum
GC-MSL-Asparagine, non-derivatized, GC-MS Spectrumsplash10-00kr-0940000000-0e0e5c7bdbac5ea0e49eSpectrum
GC-MSL-Asparagine, non-derivatized, GC-MS Spectrumsplash10-00lr-1920000000-7864dbb1f685e64dd1cfSpectrum
GC-MSL-Asparagine, non-derivatized, GC-MS Spectrumsplash10-000i-1940000000-964ea25da2789805985aSpectrum
Predicted GC-MSL-Asparagine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000f-9100000000-5881591331bd059b7e7dSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-01q9-0943200000-5a24322ba0ce2f410155Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0900000000-fc3086cc1bb0c06a4c11Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-3900000000-2d74d8232e7523f3b1c9Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0900000000-fa61c6fa9a87ce4905bbSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-01q9-0942200000-757da8b3406485c997b0Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-014i-9000000000-eac18512f2d22ab7a7efSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0900000000-8df6d5b6cf94bf081c89Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0900000000-18079004a95c252da208Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-001i-0900000000-e6b1f9b4982e6cdc863dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-03di-5900000000-7b9c09b3b6de28972f97Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00dl-9100000000-2ea95ead344d62e230a4Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-defacc365589bc4437d7Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-fd60db4d5e35794c45aeSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0900000000-e6b1f9b4982e6cdc863dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-5900000000-0cb113c77622352647ebSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00dl-9100000000-2ea95ead344d62e230a4Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-defacc365589bc4437d7Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-fd60db4d5e35794c45aeSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-03di-0900000000-fc3086cc1bb0c06a4c11Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-03di-3900000000-2d74d8232e7523f3b1c9Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-0900000000-fa61c6fa9a87ce4905bbSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-014i-9000000000-eac18512f2d22ab7a7efSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-03di-0900000000-8df6d5b6cf94bf081c89Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-0900000000-18079004a95c252da208Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03di-9800000000-7fcb00d7edfb8465c112Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,1H] 2D NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID6031
ChEMBL IDCHEMBL58832
KEGG Compound IDC00152
Pubchem Compound ID6267
Pubchem Substance IDNot Available
ChEBI ID17196
Phenol-Explorer IDNot Available
DrugBank IDDB00174
HMDB IDHMDB00168
CRC / DFC (Dictionary of Food Compounds) IDBCF96-C:BHH57-K
EAFUS ID261
Dr. Duke IDL-ASPARAGINE|ASPARAGINE|ASPARAGIN
BIGG ID34055
KNApSAcK IDC00001341
HET IDASN
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1039271
SuperScent IDNot Available
Wikipedia IDAsparagine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti sicklingDUKE
diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
Enzymes
NameGene NameUniProt ID
Asparagine synthetase [glutamine-hydrolyzing]ASNSP08243
Asparagine--tRNA ligase, cytoplasmicNARSO43776
Dolichyl-diphosphooligosaccharide--protein glycosyltransferase subunit 1RPN1P04843
Dolichyl-diphosphooligosaccharide--protein glycosyltransferase 48 kDa subunitDDOSTP39656
Dolichyl-diphosphooligosaccharide--protein glycosyltransferase subunit 2RPN2P04844
Dolichyl-diphosphooligosaccharide--protein glycosyltransferase subunit STT3ASTT3AP46977
Dolichyl-diphosphooligosaccharide--protein glycosyltransferase subunit DAD1DAD1P61803
Isoaspartyl peptidase/L-asparaginaseASRGL1Q7L266
Dolichyl-diphosphooligosaccharide--protein glycosyltransferase subunit STT3BSTT3BQ8TCJ2
60 kDa lysophospholipaseASPGQ86U10
Probable asparagine--tRNA ligase, mitochondrialNARS2Q96I59
Pathways
NameSMPDB LinkKEGG Link
Ammonia RecyclingSMP00009 map00910
Aspartate MetabolismSMP00067 map00250
Transcription/TranslationSMP00019 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
odorless
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).