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Record Information
Version1.0
Creation Date2016-07-13 19:41:33 UTC
Update Date2016-09-23 18:44:35 UTC
LmdbLMDB00063
Secondary Accession NumbersNone
Metabolite Identification
Common NameL-Glutamic acid
DescriptionGlutamic acid (Glu), also referred to as glutamate (the anion), is one of the 20 proteinogenic amino acids. It is not among the essential amino acids. Glutamate is a key molecule in cellular metabolism. In animals, dietary proteins are broken down by digestion into amino acids, which serves as metabolic fuel or other functional roles in the body. 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 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, they can work in reverse and excess glutamate can accumulate outside cells. This process causes calcium ions to enter cells via NMDA receptor channels, leading to neuronal damage and eventual cell death, and is called excitotoxicity. The mechanisms of cell death include: * Damage to mitochondria from excessively high intracellular Ca2+. * Glu/Ca2+-mediated promotion of transcription factors for pro-apoptotic genes, or downregulation of transcription factors for anti-apoptotic genes. Excitotoxicity due to glutamate occurs as part of the ischemic cascade and is associated with stroke and diseases like amyotrophic lateral sclerosis, lathyrism, and Alzheimer's disease. glutamic acid has been implicated in epileptic seizures. Microinjection of glutamic acid into neurons produces spontaneous depolarization around one second apart, and this firing pattern is similar to what is known as paroxysmal depolarizing shift 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. (http://en.wikipedia.org/wiki/Glutamic_acid).
Structure
Thumb
Synonyms
ValueSource
(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
Chemical FormulaC5H9NO4
Average Molecular Weight147.1293
Monoisotopic Molecular Weight147.053157781
IUPAC Name(2S)-2-aminopentanedioic acid
Traditional NameL-glutamic acid
CAS Registry Number56-86-0
SMILES
N[C@@H](CCC(O)=O)C(O)=O
InChI Identifier
InChI=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
Chemical Taxonomy
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
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
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
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Brain
  • Cerebrospinal Fluid (CSF)
  • Colostrum
  • Embryo culture media
  • Feces
  • Jejunum
  • Kidney
  • Kidney perfusate
  • Liver
  • Meat
  • Milk
  • Plasma
  • Ruminal Fluid
  • Serum
  • Urine
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
BrainDetected but not QuantifiedNot ApplicableNot AvailableOvine details
Cerebrospinal Fluid (CSF)Detected but not QuantifiedNot ApplicableNot AvailableOvine details
Cerebrospinal Fluid (CSF)Detected but not QuantifiedNot ApplicableNot AvailableOvine details
ColostrumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
ColostrumDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • S. F. Graham, T. ...
details
Embryo culture mediaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
Embryo culture mediaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
FecesDetected but not QuantifiedNot ApplicableNot AvailableOvine details
FecesDetected but not QuantifiedNot ApplicableNot AvailableEquine
    • E. E. Escalona, J...
details
JejunumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
KidneyDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
Kidney perfusateDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
LiverDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
MeatDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MeatDetected and Quantified1.69+/-0.21 umol/gNot AvailableBovine
    • S. F. Graham, T. ...
details
MeatDetected and Quantified8.38+/-0.64 umol/gNot AvailableBovine
    • S. F. Graham, T. ...
details
MeatDetected and Quantified9.21+/-0.74 umol/gNot AvailableBovine
    • S. F. Graham, T. ...
details
MeatDetected and Quantified9.83+/-1.55 umol/gNot AvailableBovine
    • S. F. Graham, T. ...
details
MeatDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • S. F. Graham, T. ...
details
MeatDetected and Quantified229.91 +/- 25.7 uMNot AvailableBovine details
MeatDetected and Quantified241.62 +/- 45.32 uMNot AvailableBovine details
MeatDetected and Quantified393.05 +/- 31.17 uMNot AvailableBovine details
MeatDetected and Quantified489.03 +/- 20.47 uMNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected and Quantified270-740 uMNot AvailableBovine details
MilkDetected and Quantified44-693 uMNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableOvine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
PlasmaDetected and Quantified76.6 uMNot AvailableBovine details
PlasmaDetected and Quantified80.2 uMNot AvailableBovine details
PlasmaDetected and Quantified85.1 uMNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableOvine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableOvine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
PlasmaDetected and Quantified1056 +/- 381 uMNot AvailableBovine
    • Abdullah BAŞOĞLU,...
details
PlasmaDetected and Quantified1909 +/- 659 uMNot AvailableBovine
    • Abdullah BAŞOĞLU,...
details
PlasmaDetected and Quantified2348 +/- 312 uMNot AvailableBovine
    • Abdullah BAŞOĞLU,...
details
PlasmaDetected and Quantified1342 +/- 416 uMNot AvailableBovine
    • Abdullah BAŞOĞLU,...
details
PlasmaDetected and Quantified2050 +/- 692 uMNot AvailableBovine
    • Abdullah BAŞOĞLU,...
details
PlasmaDetected and Quantified2978 +/- 411 uMNot AvailableBovine
    • Abdullah BAŞOĞLU,...
details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableEquine
    • E. E. Escalona, J...
details
Ruminal FluidDetected and Quantified317 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected but not QuantifiedNot ApplicableNot AvailableBovine details
Ruminal FluidDetected and Quantified342 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified425 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified442 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected but not QuantifiedNot ApplicableNot AvailableBovine details
Ruminal FluidDetected and Quantified361.4 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified379.4 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified490.1 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified516.5 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified330 +/- 18 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified333 +/- 12 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified333 +/- 12 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified380 +/- 59 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified490 +/- 92 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified517 +/- 115 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified256 +/- 18 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified341 +/- 46 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified479 +/- 45 uMNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected and Quantified75.036 uMNot AvailablePorcine details
SerumDetected and Quantified54.85 uMNot AvailablePorcine details
SerumDetected and Quantified56.345 uMNot AvailablePorcine details
SerumDetected and Quantified72.453 uMNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableEquine
    • Lucia Pappalardo,...
details
UrineDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
DrugBank IDDB00142
HMDB IDHMDB0000148
FooDB IDFDB012535
Phenol Explorer IDNot Available
KNApSAcK IDC00001358
BiGG ID33561
BioCyc IDGLT
METLIN ID5174
PDB IDNot Available
Wikipedia LinkL-Glutamic_Acid
Chemspider ID30572
ChEBI ID16015
PubChem Compound ID33032
Kegg Compound IDC00025
YMDB IDYMDB00271
ECMDB IDECMDB00148
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available