Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110666
Identification
Name: L-glutamate
Description:An α-amino-acid anion that is the conjugate base of L-glutamic acid, having anionic carboxy groups and a cationic amino group
Structure
Thumb
Synonyms:
  • 1-amino-propane-1,3-dicarboxylic acid
  • glutacid
  • glutaminic acid
  • L-glutamic acid
  • α-aminoglutaric acid
  • E
  • glt
  • glu
  • glut
  • L-glu
  • 2-aminopentanedioic acid
Chemical Formula: C5H8NO4
Average Molecular Weight: 146.12
Monoisotopic Molecular Weight: 148.0609828146
InChI Key: WHUUTDBJXJRKMK-VKHMYHEASA-M
InChI: InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/p-1/t3-/m0/s1
CAS number: 56-86-0
IUPAC Name:(2S)-2-aminopentanedioic acid
Traditional IUPAC Name: L-glutamic acid
SMILES:C(CCC(C(=O)[O-])[N+])([O-])=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as glutamic acid and derivatives. These 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.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct Parent Glutamic 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 Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:Not Available
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility8.57 mg/mLNot Available
LogP-3.69HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility80.6 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.29 m3·mol-1ChemAxon
Polarizability13.32 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
L-glutamate + L-Tyrosine + L-2,4-diaminobutanoate + L-Serine + L-arginine + N5-formyl-N5-hydroxy-L-ornithine + L-lysine + L-Threonine → Hydrogen ion + ferribactin + Water
L-Phenylalanine + alpha-Ketoglutarate → 2-oxo-3-phenylpropanoate + L-glutamate
(S)-1-pyrroline-5-carboxylate + NAD+ + Water → Hydrogen ion + L-glutamate + NADH
S-Substituted-Glutathione + Water → CPD-6262 + L-glutamate
L-Glutamine + L-aspartate + ATP + Water → Hydrogen ion + L-glutamate + L-Asparagine + diphosphate + AMP
Aromatic-Amino-Acids + alpha-Ketoglutarate → Aromatic-Oxoacids + L-glutamate
alpha-Ketoglutarate + L-Alanine → L-glutamate + pyruvate
L-glutamate + Water + NAD+ → alpha-Ketoglutarate + Ammonium + NADH + Hydrogen ion
beta-Alanine + alpha-Ketoglutarate → 3-oxopropanoate + L-glutamate
METHYLENE-THF-GLU-N + L-glutamate + ATP → METHYLENE-THF-GLU-N + ADP + phosphate
5-oxoproline + Water + ATP → Hydrogen ion + L-glutamate + phosphate + ADP
alpha-N-Peptidyl-LGlutamate + L-glutamate + ATP → CPD0-2471 + ADP + phosphate + Hydrogen ion
N-acetylglutaminylglutamine + L-Glutamine → N-acetylglutaminylglutamine amide + L-glutamate
NAD-P-OR-NOP + Water + L-glutamate → NADH-P-OR-NOP + alpha-Ketoglutarate + Ammonium + Hydrogen ion
L-Methionine + alpha-Ketoglutarate → 2-oxo-4-methylthiobutanoate + L-glutamate
Uridine 5''-diphospho-{beta}-4-deoxy-4-amino-L-arabinose + alpha-Ketoglutarate → UDP-4-Keto-pyranose + L-glutamate
alpha-Ketoglutarate + Aminated-Amine-Donors → L-glutamate + Deaminated-Amine-Donors
Water + N-formyl-L-glutamate → L-glutamate + formate
Hydrogen ion + L-glutamate → Carbon dioxide + gamma-Aminobutyric acid

Pathways:
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)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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
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 Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
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Synthesis Reference: Horner, L.; Gross, A. Tertiary phosphines. IV. Use of phosphine imines in causing the introduction of primary amino groups. Ann. (1955), 591 117-34.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CAS56-86-0
ChEBI29985
ChemSpider4573882
HMDBHMDB00148
IAF126033561
KEGGC00025
KNApSAcKC00001358
MetaboLightsMTBLC29985
PubChem5460299