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Showing Compound Levoglutamide (FDB012164)

Record Information
Version1.0
Creation date2010-04-08 22:10:01 UTC
Update date2019-11-26 03:06:18 UTC
Primary IDFDB012164
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLevoglutamide
DescriptionLevoglutamide, also known as glutamin or HGLN, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Levoglutamide is a very strong basic compound (based on its pKa). Levoglutamide is a mild, cocoa, and custard tasting compound. Levoglutamide is found, on average, in the highest concentration within a few different foods, such as wheats, broccoli, and red beetroots and in a lower concentration in potato, green bell peppers, and japanese pumpkins. Levoglutamide has also been detected, but not quantified in, several different foods, such as cow milks, wild celeries, cow milks, common sages, and wild leeks. This could make levoglutamide a potential biomarker for the consumption of these foods.
CAS Number56-85-9
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
2,5-Diamino-5-oxopentanoic acidChEBI
2-Amino-4-carbamoylbutanoic acidChEBI
2-Aminoglutaramic acidChEBI
Glutamic acid gamma-amideChEBI
GlutaminChEBI
Glutaminsaeure-5-amidChEBI
HGLNChEBI
2,5-Diamino-5-oxopentanoateGenerator
2-Amino-4-carbamoylbutanoateGenerator
2-AminoglutaramateGenerator
Glutamate g-amideGenerator
Glutamate gamma-amideGenerator
Glutamate γ-amideGenerator
Glutamic acid g-amideGenerator
Glutamic acid γ-amideGenerator
PolyglutamineMeSH
Poly(glutamine)MeSH
PolyQMeSH
(2S)-2-amino-4-carbamoylbutanoatebiospider
(2S)-2-amino-4-carbamoylbutanoic acidbiospider
(2S)-2,5-diamino-5-oxopentanoatebiospider
(2S)-2,5-diamino-5-oxopentanoic acidbiospider
(S)-2,5-Diamino-5-oxopentanoatebiospider
(S)-2,5-Diamino-5-oxopentanoic acidbiospider
2-Aminoglutaramic acid, L-biospider
CebrogenHMDB
Energlutdb_source
FEMA 3684db_source
gamma-GlutamineHMDB
GlavaminHMDB
GluminHMDB
Glutamate 5-amideGenerator
Glutamate amideGenerator
Glutamic acid 5-amideChEBI
Glutamic acid amideChEBI
GLUTAMINEChEBI
Glutamine, 9CI; L-formdb_source
Glutavendb_source
Iperphosdb_source
L-(+)-glutaminebiospider
L-2-AminoglutaramateGenerator
L-2-Aminoglutaramic acidbiospider
L-2-Aminoglutaramidic acidbiospider
L-Glutamate g-amideGenerator
L-Glutamate gamma-amideGenerator
L-Glutamate γ-amideGenerator
L-Glutamic acid 5-amidebiospider
L-Glutamic acid g-amideGenerator
L-glutamic acid gamma-amidebiospider
L-Glutamic acid γ-amideGenerator
L-GlutamidHMDB
L-GlutamideHMDB
L-GlutaminChEBI
L-glutaminebiospider
L-Glutaminsaeure-5-amidChEBI
LevoglutamidHMDB
LevoglutamidaHMDB
Levoglutamide, INNdb_source
LevoglutamidumHMDB
LevoglutaminaHMDB
Memorildb_source
QChEBI
StimulinaHMDB
Predicted Properties
PropertyValueSource
Water Solubility3.44 g/LALOGPS
logP-3.4ALOGPS
logP-5.8ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)-0.46ChemAxon
pKa (Strongest Basic)13.07ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.4 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity44.05 m³·mol⁻¹ChemAxon
Polarizability13.93 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H10N2O3
IUPAC name2-amino-4-(C-hydroxycarbonimidoyl)butanoic acid
InChI IdentifierInChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)
InChI KeyZDXPYRJPNDTMRX-UHFFFAOYSA-N
Isomeric SMILESNC(CCC(O)=N)C(O)=O
Average Molecular Weight146.1445
Monoisotopic Molecular Weight146.069142196
Classification
Description Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Fatty acid
  • Amino acid
  • Carboximidic acid
  • Carboximidic acid derivative
  • 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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 41.09%; H 6.90%; N 19.17%; O 32.84%DFC
Melting PointMp 184-185° dec.DFC
Boiling PointNot Available
Experimental Water Solubility41.3 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP-3.64CHMELIK,J ET AL. (1991)
Experimental pKapKa2 9.01 (25°, 0.1M KNO3)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +46.5 (5M HCl)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSLevoglutamide, 2 TMS, GC-MS Spectrumsplash10-0a4i-0900000000-f5c3e469b28e7ddd1ed2Spectrum
GC-MSLevoglutamide, 3 TMS, GC-MS Spectrumsplash10-0fb9-1942000000-b99e36f8a6678634505eSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ugj-2900000000-31acb66301700f32a8bb2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-9600000000-62ca6d658ffe481161922015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-fac990fe6ddad443984e2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1900000000-639fa6841a11c86d9c0e2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004m-7900000000-df522f5e8b34040213292015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-0cf14bf810f9866ab61d2015-05-27View Spectrum
NMRNot Available
ChemSpider ID5746
ChEMBL IDCHEMBL930
KEGG Compound IDC00064
Pubchem Compound ID5961
Pubchem Substance IDNot Available
ChEBI ID18050
Phenol-Explorer IDNot Available
DrugBank IDDB00130
HMDB IDHMDB00641
CRC / DFC (Dictionary of Food Compounds) IDHDW07-E:HDW08-F
EAFUS ID1509
Dr. Duke IDGLUTAMINE
BIGG ID33714
KNApSAcK IDC00001359
HET IDGLN
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1037431
SuperScent IDNot Available
Wikipedia IDL-Glutamine
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 alcoholic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti depressant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti sicklingDUKE
anti ulcer49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.DUKE
catabolicDUKE
Enzymes
NameGene NameUniProt ID
Glycine N-acyltransferase-like protein 1GLYATL1Q969I3
Asparagine synthetase [glutamine-hydrolyzing]ASNSP08243
Kynurenine--oxoglutarate transaminase 1CCBL1Q16773
Glutamine synthetaseGLULP15104
Glutaminase liver isoform, mitochondrialGLS2Q9UI32
Glutaminase kidney isoform, mitochondrialGLSO94925
CTP synthase 2CTPS2Q9NRF8
Glutamine--fructose-6-phosphate aminotransferase [isomerizing] 2GFPT2O94808
Glutamine--fructose-6-phosphate aminotransferase [isomerizing] 1GFPT1Q06210
Glutamine--tRNA ligaseQARSP47897
Phosphoribosylformylglycinamidine synthasePFASO15067
Glutamyl-tRNA(Gln) amidotransferase subunit B, mitochondrialPET112O75879
Glutamyl-tRNA(Gln) amidotransferase subunit A, mitochondrialQRSL1Q9H0R6
Pathways
NameSMPDB LinkKEGG Link
Amino Sugar MetabolismSMP00045 map00520
Ammonia RecyclingSMP00009 map00910
Glutamate MetabolismSMP00072 map00250
Phenylacetate MetabolismSMP00126 map00360
Purine MetabolismSMP00050 map00230
Pyrimidine MetabolismSMP00046 map00240
Transcription/TranslationSMP00019 Not Available
Urea CycleSMP00059 map00330
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
mild
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
milky
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
custard
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
cocoa
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
oily
  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).