Record Information
Version1.0
Creation date2010-04-08 22:10:13 UTC
Update date2024-11-29 22:27:57 UTC
Primary IDFDB012535
Secondary Accession Numbers
  • FDB030962
Chemical Information
FooDB NameL-Glutamic acid
DescriptionL-glutamic acid (abbreviated Glu or E), also referred to as glutamate (the anion), is a non-essential amino acid, one of the 20 amino acids used in the biosynthesis of proteins. L-glutamic acid exists in all living species, from bacteria to humans. In humans, dietary proteins are broken down by digestion into amino acids, which serves as metabolic fuel or other functional roles in the body. Glutamate is a component amino acid in many protein rich foods including the gluten protein in flour and is found as a free acid in cheeses and soya sauce. It is used as a flavor enhancer as a sodium salt known as monosodium glutamate. Glutamate is a key molecule in cellular metabolism. Glutamate is the most abundant fast excitatory neurotransmitter in the mammalian nervous system. At chemical synapses, glutamate is stored in vesicles. Nerve impulses trigger release of glutamate from the pre-synaptic cell. In the opposing post-synaptic cell, glutamate receptors, such as the N-methyl-d-aspartate acid (NMDA) receptor, bind glutamate and are activated. Because of its role in synaptic plasticity, it is believed that glutamic acid is involved in cognitive functions like learning and memory in the brain. Glutamate transporters are found in neuronal and glial membranes. They rapidly remove glutamate from the extracellular space. In brain injury or disease, glutamate can accumulate outside cells, causing glutamate excitotoxicity. Excitotoxicity occurs when neurons are exposed to high levels of glutamate or other neurotransmitters, causing persistent activation of the and α-amino-3-hydroxy-5-methylisoxazole propionic acid (AMPA) receptors and voltage-gated calcium channels. This results in a lethal influx of extracellular calcium leading to neuronal damage and eventual cell death. Cell death arises from damage to mitochondria by the excessively high intracellular calcium, which open mitochondrial pores, causing mitochondria to swell. Reactive oxygen species (ROS) may also be released by mitochondria into the intracellular space. Excess glutamate and calcium trigger apoptosis by further activating transcription factors for pro-apoptotic genes, or downregulating transcription factors for anti-apoptotic genes. Glutamate excitotoxicity causes other health consequences. In ischemic stroke and brain trauma, the severely reduced blood supply leads to flooding of glutamate and aspartate into the extra-neuronal space ( PMID: 16314180). Glutamate excitotoxicity is associated with diseases like amyotrophic lateral sclerosis, multiple sclerosis, lathyrism, and Alzheimer's disease (PMID: 20229265) and in epileptic seizures. Microinjection of glutamic acid into neurons produces spontaneous depolarization around one second apart which is like a paroxysmal depolarizing shift seen in epileptic attacks. This change in the resting membrane potential at seizure foci could cause spontaneous opening of voltage activated calcium channels, leading to glutamic acid release and further depolarization. Moreover, glutamic acid is associated with N-acetylglutamate synthetase deficiency, which is an inborn error of metabolism.
CAS Number56-86-0
Structure
Thumb
Synonyms
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSL-Glutamic acid, 3 TMS, GC-MS Spectrumsplash10-0002-2950000000-2d6edc93ec5f8dee2223Spectrum
GC-MSL-Glutamic acid, non-derivatized, GC-MS Spectrumsplash10-002b-0940000000-4e285988bc537825d94dSpectrum
GC-MSL-Glutamic acid, 3 TMS, GC-MS Spectrumsplash10-00dj-9630000000-1ecc76aab86283892139Spectrum
GC-MSL-Glutamic acid, 2 TMS, GC-MS Spectrumsplash10-001i-8910000000-00f65ced0c55aa4ad169Spectrum
GC-MSL-Glutamic acid, 3 TMS, GC-MS Spectrumsplash10-0032-3980000000-3069de5b6c49e4176968Spectrum
GC-MSL-Glutamic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0790000000-79d3e289c22cb183faa1Spectrum
GC-MSL-Glutamic acid, non-derivatized, GC-MS Spectrumsplash10-0002-2950000000-2d6edc93ec5f8dee2223Spectrum
GC-MSL-Glutamic acid, non-derivatized, GC-MS Spectrumsplash10-002b-0940000000-4e285988bc537825d94dSpectrum
GC-MSL-Glutamic acid, non-derivatized, GC-MS Spectrumsplash10-00ea-6932100000-30d3f5dcc198a5971e96Spectrum
GC-MSL-Glutamic acid, non-derivatized, GC-MS Spectrumsplash10-00dj-9630000000-1ecc76aab86283892139Spectrum
GC-MSL-Glutamic acid, non-derivatized, GC-MS Spectrumsplash10-001i-8910000000-00f65ced0c55aa4ad169Spectrum
GC-MSL-Glutamic acid, non-derivatized, GC-MS Spectrumsplash10-0032-3980000000-3069de5b6c49e4176968Spectrum
Predicted GC-MSL-Glutamic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0znc-9300000000-f88e86b78a4cee99a2d4Spectrum
Predicted GC-MSL-Glutamic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-8290000000-f99e03763f636e557887Spectrum
Predicted GC-MSL-Glutamic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Glutamic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Glutamic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Glutamic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Glutamic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Glutamic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Glutamic acid, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Glutamic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Glutamic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Glutamic acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Glutamic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-003r-6900000000-95b0a084dc076f9c7b912012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9000000000-c37d4c80a14ec029ef632012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a59-9000000000-6f1888aa71bcb0adf76c2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004j-0900000000-5fa8a338dcd2f2a6bdd22012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004i-0900000000-16763200aa07f7629ad42012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-03di-3900000000-d9cfc5187aa799f6f9782012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0900000000-10ee9a593e13550bec1c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-0900000000-4d045a3c1fc6e56f801b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-9000000000-c3c7f8f3754109a0c25b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004i-0900000000-48bfae26c69408b7f0ae2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-0900000000-82c2a681e7522a7bb1d12012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-0905010000-af1c9ec4d0062fa6960e2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-01q9-9700000000-2b967b896a6e489145122012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0900000000-1434321646181ea894a02012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0900000000-11fadb2530828eedad8a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-006t-0941100000-07d051890cb1d9e5c8562012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-9200000000-f8619d11f1f54d836bb12012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0900000000-ea2dd00e79ef06e8dc042012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0900000000-3e239d4014c95a2ef8732012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-b548959edce39d319cf42012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0udi-0900000000-40d901f655797db2cd0f2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0udi-1900000000-f997527a39900ac431c72012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0udi-7900000000-60816f0601a4e6d25ffb2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0007-9000000000-6ee821f657c604d1afca2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-000t-0900000000-7c02624abe56da9247a22012-08-31View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
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
Processing...
Biological Effects and Interactions
Health Effects / Bioactivities
Enzymes
Pathways
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
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.