Record Information
Version1.0
Creation date2010-04-08 22:04:42 UTC
Update date2015-10-09 22:28:06 UTC
Primary IDFDB000787
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Asparagine
DescriptionOne of the nonessential amino acids. Dietary supplement, nutrient. Widely distributed in the plant kingdom. Isol. from asparagus, beetroot, peas, beans, etc. Asparagine (abbreviated as Asn or N; Asx or B represent either asparagine or aspartic acid) is one of the 20 most common natural amino acids on Earth. It has carboxamide as the side-chain's functional group. It is not an essential amino acid. Its codons are AAU and AAC. (Wikipedia)
CAS Number70-47-3
Structure
Thumb
Synonyms
SynonymSource
(-)-Asparaginebiospider
(2S)-2-amino-3-CarbamoylpropanoateGenerator
(2S)-2-Amino-3-carbamoylpropanoic acidbiospider
(2S)-2,4-Diamino-4-oxobutanoateGenerator
(2S)-2,4-Diamino-4-oxobutanoic acidbiospider
(S)-2-amino-3-CarbamoylpropanoateGenerator
(S)-2-Amino-3-carbamoylpropanoic acidbiospider
(S)-2-Aminosuccinic acid 4-amidebiospider
(S)-2,4-Diamino-4-oxobutanoatebiospider
(S)-2,4-Diamino-4-oxobutanoic acidbiospider
(S)-Asparaginebiospider
2-AminosuccinamateGenerator
2-Aminosuccinamic acidChEBI
2-Aminosuccinamic acid, L-biospider
a-AminosuccinamateGenerator
a-Aminosuccinamic acidGenerator
AgedoiteHMDB
alpha AmminosuccinamateHMDB
alpha Amminosuccinamic acidHMDB
alpha-AminosuccinamateGenerator
alpha-Aminosuccinamic acidChEBI
AltheineHMDB
AsnChEBI
ASPARAGINEChEBI
Asparagine acidHMDB
Asparagine, 9CI; L-formdb_source
Asparagine, L- (8CI)biospider
AsparamideHMDB
AspartamateGenerator
Aspartamic acidChEBI
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-AminosuccinamateGenerator
L-2-Aminosuccinamic acidbiospider
L-2,4-Diamino-4-oxobutanoatebiospider
L-2,4-Diamino-4-oxobutanoic acidbiospider
L-AsparaginChEBI
L-Asparagine (9CI)biospider
L-Asparataminebiospider
L-Aspartaminebiospider
L-Aspartate b-amideGenerator
L-Aspartate beta-amideGenerator
L-Aspartate β-amideGenerator
L-Aspartic acid 4-amidebiospider
L-Aspartic acid b-amideGenerator
L-Aspartic acid beta-amidebiospider
L-Aspartic acid β-amideGenerator
L-b-Asparaginebiospider
L-beta-Asparaginebiospider
NChEBI
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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 KeyInChIKey=DCXYFEDJOCDNAF-REOHCLBHSA-N
Isomeric SMILESN[C@@H](CC(N)=O)C(O)=O
Average Molecular Weight132
Monoisotopic Molecular Weight132
Classification
DescriptionThis compound belongs to the class of chemical entities known as asparagine and derivatives. These 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
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
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
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) (Non-derivatized)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-MS (Non-derivatized)splash10-02t9-0790000000-b8141f48cbebb90f683eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-02t9-1790000000-1d12ed9b4fb2799da766View 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 - EI-B (Non-derivatized)splash10-00lr-0930000000-79a089d9875e092dd7f2View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0159-0910000000-bedf57998656ab5ebc16View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0159-0910000000-4979c4d028d2dc931263View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0159-0910000000-b7ea3fef61f3940cbddaView in MoNA
GC-MSGC-MS Spectrum - GC-EI-QQ (Non-derivatized)splash10-00di-4931100000-17f149310ce3a0f748d1View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9710000000-6d0afcbcc003347e598eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0uxr-0910000000-2be567239bd3229b1ca1View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-02t9-0790000000-b8141f48cbebb90f683eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-02t9-1790000000-1d12ed9b4fb2799da766View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014u-0961000000-65a5c0999f17110c9939View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00kr-0940000000-0e0e5c7bdbac5ea0e49eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00lr-1920000000-7864dbb1f685e64dd1cfView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000i-1940000000-964ea25da2789805985aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9100000000-5881591331bd059b7e7dView 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 AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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
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).