Record Information
Version1.0
Creation date2010-04-08 22:10:13 UTC
Update date2018-05-29 00:58:57 UTC
Primary IDFDB012535
Secondary Accession Numbers
  • FDB030962
Chemical Information
FooDB NameL-Glutamic acid
Descriptionobtained from acid hydrolysis of proteins. Since 1965 the industrial source of glutamic acid for MSG production has been bacterial fermentation of carbohydrate sources such as molasses and corn starch hydrolysate in the presence of a nitrogen source such as ammonium salts or urea. Annual production approx. 350000t worldwide in 1988. Seasoning additive in food manuf. (as Na, K and NH4 salts). Dietary supplement, nutrient Glutamic acid (abbreviated as Glu or E) is one of the 20 proteinogenic amino acids. It is a non-essential amino acid. L-Glutamic acid is found in many foods, some of which are shortening, red raspberry, prickly pear, and chinese cabbage.
CAS Number56-86-0
Structure
Thumb
Synonyms
SynonymSource
(S)-2-Aminopentanedioic acidChEBI
(S)-Glutamic acidChEBI
Acide glutamiqueChEBI
Acido glutamicoChEBI
Acidum glutamicumChEBI
EChEBI
GluChEBI
GlutamateChEBI
GLUTAMIC ACIDChEBI
L-GluChEBI
L-Glutaminic acidChEBI
L-GlutaminsaeureChEBI
(S)-2-AminopentanedioateGenerator
(S)-GlutamateGenerator
L-GlutaminateGenerator
L-GlutamateGenerator
(2S)-2-AminopentanedioateHMDB
(2S)-2-Aminopentanedioic acidHMDB
(S)-(+)-GlutamateHMDB
(S)-(+)-Glutamic acidHMDB
1-Amino-propane-1,3-dicarboxylateHMDB
1-Amino-propane-1,3-dicarboxylic acidHMDB
1-Aminopropane-1,3-dicarboxylateHMDB
1-Aminopropane-1,3-dicarboxylic acidHMDB
2-AminoglutarateHMDB
2-Aminoglutaric acidHMDB
2-AminopentanedioateHMDB
2-Aminopentanedioic acidHMDB
a-AminoglutarateHMDB
a-Aminoglutaric acidHMDB
a-GlutamateHMDB
a-Glutamic acidHMDB
AciglutHMDB
alpha-AminoglutarateHMDB
alpha-Aminoglutaric acidHMDB
alpha-GlutamateHMDB
alpha-Glutamic acidHMDB
AminoglutarateHMDB
Aminoglutaric acidHMDB
GltHMDB
GlusateHMDB
GlutHMDB
GlutacidHMDB
GlutamicolHMDB
GlutamidexHMDB
GlutaminateHMDB
Glutaminic acidHMDB
GlutaminolHMDB
GlutatonHMDB
L-(+)-GlutamateHMDB
L-(+)-Glutamic acidHMDB
L-a-AminoglutarateHMDB
L-a-Aminoglutaric acidHMDB
L-alpha-AminoglutarateHMDB
L-alpha-Aminoglutaric acidHMDB
D GlutamateHMDB
Glutamate, potassiumHMDB
Glutamic acid, (D)-isomerHMDB
L Glutamic acidHMDB
D-GlutamateHMDB
L GlutamateHMDB
Aluminum L glutamateHMDB
Aluminum L-glutamateHMDB
L-Glutamate, aluminumHMDB
Potassium glutamateHMDB
α-aminoglutaric acid, (S)-biospider
α-glutamic acid, (S)-biospider
2-Aminoglutaric acid, (S)-biospider
a-aminoglutaric acid, (S)-biospider
a-glutamic acid, (S)-biospider
Alpha-aminoglutarate, (S)-biospider
Alpha-aminoglutaric acid, (S)-biospider
Alpha-glutamate, (S)-biospider
Alpha-glutamic acid, (S)-biospider
Glutamic acid; L-formdb_source
L (+)-glutamic acid, alpha-formbiospider
L-glutamic acidmanual
S-1-Aminopropane-1,3-dicarboxylatebiospider
Predicted Properties
PropertyValueSource
Water Solubility80.6 g/LALOGPS
logP-3.5ALOGPS
logP-3.2ChemAxon
logS-0.26ALOGPS
pKa (Strongest Acidic)1.88ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area100.62 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.29 m³·mol⁻¹ChemAxon
Polarizability13.32 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC5H9NO4
IUPAC name(2S)-2-aminopentanedioic acid
InChI IdentifierInChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1
InChI KeyWHUUTDBJXJRKMK-VKHMYHEASA-N
Isomeric SMILESN[C@@H](CCC(O)=O)C(O)=O
Average Molecular Weight147.1293
Monoisotopic Molecular Weight147.053157781
Classification
Description belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid 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 ParentGlutamic acid and derivatives
Alternative Parents
Substituents
  • Glutamic acid or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Amino fatty acid
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Fatty acyl
  • Amino acid
  • Carboxylic acid
  • Organic oxide
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 40.82%; H 6.17%; N 9.52%; O 43.50%DFC
Melting PointMp 224-225 (211-213°, 247-249°)° dec.DFC
Boiling PointNot Available
Experimental Water Solubility8.57 mg/mL at 25 oCBULL,HB et al. (1978)
Experimental logP-3.69HANSCH,C ET AL. (1995)
Experimental pKapKa3 9.6 (25°,NH2)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D +46.8 (c, 2 in 5M 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)splash10-0002-2950000000-2d6edc93ec5f8dee2223View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-002b-0940000000-4e285988bc537825d94dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00dj-9630000000-1ecc76aab86283892139View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-8910000000-00f65ced0c55aa4ad169View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0032-3980000000-3069de5b6c49e4176968View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-0790000000-79d3e289c22cb183faa1View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-2950000000-2d6edc93ec5f8dee2223View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-002b-0940000000-4e285988bc537825d94dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-QQ (Non-derivatized)splash10-00ea-6932100000-30d3f5dcc198a5971e96View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dj-9630000000-1ecc76aab86283892139View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-8910000000-00f65ced0c55aa4ad169View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0032-3980000000-3069de5b6c49e4176968View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0znc-9300000000-f88e86b78a4cee99a2d4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-8290000000-f99e03763f636e557887View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-003r-6900000000-95b0a084dc076f9c7b91View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9000000000-c37d4c80a14ec029ef63View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a59-9000000000-6f1888aa71bcb0adf76cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004j-0900000000-5fa8a338dcd2f2a6bdd2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004i-0900000000-16763200aa07f7629ad4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-03di-3900000000-d9cfc5187aa799f6f978View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0900000000-10ee9a593e13550bec1cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-0900000000-4d045a3c1fc6e56f801bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-9000000000-c3c7f8f3754109a0c25bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004i-0900000000-48bfae26c69408b7f0aeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-0900000000-82c2a681e7522a7bb1d1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-0905010000-af1c9ec4d0062fa6960eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-01q9-9700000000-2b967b896a6e48914512View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0900000000-1434321646181ea894a0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0900000000-11fadb2530828eedad8aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-006t-0941100000-07d051890cb1d9e5c856View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-9200000000-f8619d11f1f54d836bb1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0900000000-ea2dd00e79ef06e8dc04View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0900000000-3e239d4014c95a2ef873View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-b548959edce39d319cf4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0udi-0900000000-40d901f655797db2cd0fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0udi-1900000000-f997527a39900ac431c7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0udi-7900000000-60816f0601a4e6d25ffbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0007-9000000000-6ee821f657c604d1afcaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-000t-0900000000-7c02624abe56da9247a2View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C 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 ID30572
ChEMBL IDCHEMBL575060
KEGG Compound IDC00025
Pubchem Compound ID33032
Pubchem Substance IDNot Available
ChEBI ID16015
Phenol-Explorer IDNot Available
DrugBank IDDB00142
HMDB IDHMDB00148
CRC / DFC (Dictionary of Food Compounds) IDHHT64-G:HHT63-F
EAFUS ID1507
Dr. Duke IDGLUTAMINIC-ACID|L-GLUTAMIC-ACID|GLUTAMIC-ACID|GLUTAMIC-ACID(FREE)
BIGG ID33561
KNApSAcK IDC00001358
HET IDGGL
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1025121
SuperScent IDNot Available
Wikipedia IDGlutamic_acid
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 alkaliDUKE
anti epileptic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti hyperammonemicDUKE
anti lithicDUKE
anti prostatiticDUKE
anti retardationDUKE
anxiolytic35474 Anxiolytic drugs are agents that alleviate anxiety, tension, and anxiety disorders, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions.DUKE
neurotoxic50910 A poison that interferes with the functions of the nervous system.DUKE
neurotransmitter25512 An endogenous compound that is used to transmit information across the synapse between a neuron and another cell.CHEBI
Enzymes
NameGene NameUniProt ID
Tyrosine aminotransferaseTATP17735
Aspartate aminotransferase, cytoplasmicGOT1P17174
Aspartate aminotransferase, mitochondrialGOT2P00505
Aminoadipate-semialdehyde synthaseAASSA4D0W4
Branched-chain-amino-acid aminotransferase, cytosolicBCAT1P54687
Branched-chain-amino-acid aminotransferase, mitochondrialBCAT2O15382
Alanine--glyoxylate aminotransferase 2, mitochondrialAGXT2Q9BYV1
Glutathione synthetaseGSSP48637
Kynurenine--oxoglutarate transaminase 3CCBL2Q6YP21
Ornithine aminotransferase, mitochondrialOATP04181
4-aminobutyrate aminotransferase, mitochondrialABATP80404
Alanine aminotransferase 1GPTP24298
Alanine aminotransferase 2GPT2Q8TD30
Glutamate--cysteine ligase catalytic subunitGCLCP48506
Bifunctional glutamate/proline--tRNA ligaseEPRSP07814
Phosphoserine aminotransferasePSAT1Q9Y617
Asparagine synthetase [glutamine-hydrolyzing]ASNSP08243
Putative aspartate aminotransferase, cytoplasmic 2GOT1L1Q8NHS2
Gamma-glutamyltranspeptidase 1GGT1P19440
Gamma-glutamyltransferase 7GGT7Q9UJ14
Gamma-glutamyltransferase 6GGT6Q6P531
Gamma-glutamyltransferase 5GGT5P36269
Glutamate decarboxylase 2GAD2Q05329
Glutamate decarboxylase 1GAD1Q99259
Arginine decarboxylaseADCQ96A70
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrialAADATQ8N5Z0
Kynurenine--oxoglutarate transaminase 1CCBL1Q16773
Glutamyl aminopeptidaseENPEPQ07075
Delta-1-pyrroline-5-carboxylate synthaseALDH18A1P54886
Glutamine synthetaseGLULP15104
Glutaminase liver isoform, mitochondrialGLS2Q9UI32
Glutaminase kidney isoform, mitochondrialGLSO94925
Formimidoyltransferase-cyclodeaminaseFTCDO95954
CTP synthase 2CTPS2Q9NRF8
Probable glutamate--tRNA ligase, mitochondrialEARS2Q5JPH6
Glutamine--fructose-6-phosphate aminotransferase [isomerizing] 2GFPT2O94808
Glutamine--fructose-6-phosphate aminotransferase [isomerizing] 1GFPT1Q06210
Phosphoribosylformylglycinamidine synthasePFASO15067
Glutamyl-tRNA(Gln) amidotransferase subunit B, mitochondrialPET112O75879
Glutamyl-tRNA(Gln) amidotransferase subunit A, mitochondrialQRSL1Q9H0R6
Glutamate--cysteine ligase regulatory subunitGCLMP48507
N-acetylglutamate synthase, mitochondrialNAGSQ8N159
Folylpolyglutamate synthase, mitochondrialFPGSQ05932
5-oxoprolinaseOPLAHO14841
Glutamate receptor, ionotropic kainate 1GRIK1P39086
Glutamate receptor, ionotropic kainate 3GRIK3Q13003
Glutamate receptor 1GRIA1P42261
Mitochondrial glutamate carrier 2SLC25A18Q9H1K4
LengsinLGSNQ5TDP6
Mitochondrial glutamate carrier 1SLC25A22Q9H936
Aspartate aminotransferaseGIG18Q2TU84
Aspartyl aminopeptidaseDNPEPQ9ULA0
Pathways
NameSMPDB LinkKEGG Link
Alanine MetabolismSMP00055 map00250
Amino Sugar MetabolismSMP00045 map00520
Ammonia RecyclingSMP00009 map00910
Arginine and Proline MetabolismSMP00020 map00330
Cysteine MetabolismSMP00013 map00270
Folate MetabolismSMP00053 map00670
Glucose-Alanine CycleSMP00127 Not Available
Glutamate MetabolismSMP00072 map00250
Glutathione MetabolismSMP00015 map00480
Glycine and Serine MetabolismSMP00004 map00260
Histidine MetabolismSMP00044 map00340
Malate-Aspartate ShuttleSMP00129 Not Available
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.
yeast
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
baked
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bread
  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— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.