Record Information
Version1.0
Creation Date2016-09-30 23:03:49 UTC
Update Date2020-06-04 20:27:49 UTC
BMDB IDBMDB0003339
Secondary Accession Numbers
  • BMDB03339
Metabolite Identification
Common NameD-Glutamic acid
DescriptionD-Glutamic acid, also known as glutamate D-form or D-glutamate, 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. D-Glutamic acid exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. D-Glutamic acid exists in all living organisms, ranging from bacteria to humans.
Structure
Thumb
Synonyms
ValueSource
(R)-2-Aminopentanedioic acidChEBI
D-2-Aminoglutaric acidChEBI
D-Glutaminic acidChEBI
D-GlutaminsaeureChEBI
DGLChEBI
Glutamic acid D-formChEBI
(R)-2-AminopentanedioateGenerator
D-2-AminoglutarateGenerator
D-GlutaminateGenerator
Glutamate D-formGenerator
D-GlutamateGenerator
(2R)-2-AminopentanedioateHMDB
(2R)-2-Aminopentanedioic acidHMDB
D-2-AminopentanedioateHMDB
D-2-Aminopentanedioic acidHMDB
delta-2-AminoglutarateHMDB
delta-2-Aminoglutaric acidHMDB
delta-2-AminopentanedioateHMDB
delta-2-Aminopentanedioic acidHMDB
delta-GlutamateHMDB
delta-Glutamic acidHMDB
delta-GlutaminateHMDB
delta-Glutaminic acidHMDB
delta-GlutaminsaeureHMDB
GlutamateHMDB
Lopac-g-2128HMDB
Lopac-gamma-2128HMDB
R-(-)-GlutamateHMDB
R-(-)-Glutamic acidHMDB
Tocris-0217HMDB
Glutamic acid, (D)-isomerHMDB
L Glutamic acidHMDB
L-GlutamateHMDB
L-Glutamic acidHMDB
D GlutamateHMDB
Glutamate, potassiumHMDB
L-Glutamate, aluminumHMDB
Aluminum L glutamateHMDB
Glutamic acidHMDB
L GlutamateHMDB
Aluminum L-glutamateHMDB
Potassium glutamateHMDB
Chemical FormulaC5H9NO4
Average Molecular Weight147.1293
Monoisotopic Molecular Weight147.053157781
IUPAC Name(2R)-2-aminopentanedioic acid
Traditional NameD-glutamic acid
CAS Registry Number6893-26-1
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-/m1/s1
InChI KeyWHUUTDBJXJRKMK-GSVOUGTGSA-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
  • D-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
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point201 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility8.88 mg/mL at 25 °CNot 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
Polarizability13.19 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0k9x-9300000000-a43e0122a45b9abf09d6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dl-9240000000-53c8c708191dfcd550d0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0900000000-ad4a2989e599a67182c0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-c449cfd2231fe941d44fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-1900000000-f71458032a132069f94fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-7900000000-810570c8cfcea8da64f5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-d5167570d11d77fd541eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-0900000000-c7d42b011a328bb7991dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9300000000-9fd882f84339f600b5ebView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-407a30a35de9c1cceb3aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-8610ea89d52ef116caf5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9000000000-331b7ed6ea33880c306eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-3900000000-58248bb2a0c7ddc905cfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zgi-9600000000-076b628a6858a60a475fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-bd3823a5fab8a2d9b62cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1900000000-11233b5887638266e512View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fba-4900000000-1e8ea62e3fbd8467396fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-9100000000-6c956e122b59de69a472View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-4900000000-c467fa409affedc9ab85View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9100000000-ddda6500978ea1670dcfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-4c6639c8639f077b57a0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-4900000000-503f6a47bc72662de09cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ugi-3900000000-ec06b29308ff068bf7a2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-e06c31345e8a86e71de1View in MoNA
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Epidermis
  • Fibroblasts
  • Intestine
  • Liver
  • Mammary Gland
  • Neuron
  • Placenta
  • Ruminal Fluid
  • Semen
  • Spleen
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Ruminal FluidDetected and Quantified361.35 +/- 47.53 uMNot SpecifiedNot SpecifiedNormal
    • Fozia Saleem, Sou...
details
SemenDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
SpleenExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
TestisDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Ruminal FluidDetected and Quantified516.48 +/- 110.81 uMNot SpecifiedNot SpecifiedRumen acidosis
    • Fozia Saleem, Sou...
details
HMDB IDHMDB0003339
DrugBank IDDB02517
Phenol Explorer Compound IDNot Available
FooDB IDFDB023148
KNApSAcK IDC00019577
Chemspider ID21814
KEGG Compound IDC00217
BioCyc IDD-GLT
BiGG IDNot Available
Wikipedia LinkGlutamic acid
METLIN ID6895
PubChem Compound23327
PDB IDNot Available
ChEBI ID15966
References
Synthesis ReferenceOzaki, Akio; Yagasaki, Makoto; Takada, Hideyoshi; Hashimoto, Yukio. Manufacture of D-glutamic acid with Lactobacillus. Jpn. Kokai Tokkyo Koho (1990), 4 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Enzymes

General function:
Amino acid transport and metabolism
Specific function:
Aminopeptidase with specificity towards an acidic amino acid at the N-terminus. Likely to play an important role in intracellular protein and peptide metabolism (By similarity).
Gene Name:
DNPEP
Uniprot ID:
Q2HJH1
Molecular weight:
51828.0
General function:
Amino acid transport and metabolism
Specific function:
Regulates central hypertension through its calcium-modulated preference to cleave N-terminal acidic residues from peptides such as angiotensin II.
Gene Name:
ENPEP
Uniprot ID:
Q32LQ0
Molecular weight:
109801.0
General function:
Inorganic ion transport and metabolism
Specific function:
Not Available
Gene Name:
atp1A3
Uniprot ID:
Q8HYW6
Molecular weight:
19015.0
General function:
Involved in cadherin binding
Specific function:
p35 is a neuron specific activator of CDK5. The complex p35/CDK5 is required for neurite outgrowth and cortical lamination. Involved in dendritic spine morphogenesis by mediating the EFNA1-EPHA4 signaling. Activator of TPKII. The complex p35/CDK5 participates in the regulation of the circadian clock by modulating the function of CLOCK protein: phosphorylates CLOCK at 'Thr-451' and 'Thr-461' and regulates the transcriptional activity of the CLOCK-ARNTL/BMAL1 heterodimer in association with altered stability and subcellular distribution (By similarity).
Gene Name:
CDK5R1
Uniprot ID:
Q28199
Molecular weight:
34088.0
General function:
Involved in protein binding
Specific function:
Probable adapter protein that bind to and organize the subcellular localization of a variety of membrane proteins containing some PDZ recognition sequence. Involved in the clustering of various receptors, possibly by acting at the receptor internalization level. Plays a role in synaptic plasticity by regulating the trafficking and internalization of AMPA receptors. May be regulated upon PRKCA activation. May regulate ASIC1/ASIC3 channel. Regulates actin polymerization by inhibiting the actin-nucleating activity of the Arp2/3 complex; the function is competetive with nucleation promoting factors and is linked to neuronal morphology regulation and AMPA receptor (AMPAR) endocytosis. Via interaction with the Arp2/3 complex involved in regulation of synaptic plasicity of excitatory synapses and required for spine shrinkage during long-term depression (LTD). Involved in regulation of astrocyte morphology, antagonistic to Arp2/3 complex activator WASL/N-WASP function (By similarity).
Gene Name:
PICK1
Uniprot ID:
Q2T9M1
Molecular weight:
46729.0
General function:
Involved in ATP binding
Specific function:
Not Available
Gene Name:
CAMK2A
Uniprot ID:
Q08E45
Molecular weight:
54115.0
General function:
Involved in protein binding
Specific function:
Regulates intracellular concentrations of taurine and glutamate. Negatively modulates SLC1A1/EAAC1 glutamate transport activity by decreasing its affinity for glutamate in a PKC activity-dependent manner. May be involved in membrane traffic.
Gene Name:
ARL6IP5
Uniprot ID:
Q5E9M1
Molecular weight:
21666.0
General function:
Energy production and conversion
Specific function:
Not Available
Gene Name:
SLC1A6
Uniprot ID:
A6H774
Molecular weight:
61424.0
General function:
Involved in glutamate:sodium symporter activity
Specific function:
Not Available
Gene Name:
SLC1A2
Uniprot ID:
A5HSH1
Molecular weight:
2798.0
General function:
Not Available
Specific function:
Potential apoptotic regulator.
Gene Name:
GRINA
Uniprot ID:
Q32L53
Molecular weight:
40232.0
General function:
Energy production and conversion
Specific function:
Sodium-dependent, high-affinity amino acid transporter that mediates the uptake of L-glutamate and also L-aspartate and D-aspartate. Can also transport L-cysteine (By similarity). Functions as a symporter that transports one amino acid molecule together with two or three Na(+) ions and one proton, in parallel with the counter-transport of one K(+) ion. Mediates Cl(-) flux that is not coupled to amino acid transport; this avoids the accumulation of negative charges due to aspartate and Na(+) symport (By similarity). Plays an important role in L-glutamate and L-aspartate reabsorption in renal tubuli. Plays a redundant role in the rapid removal of released glutamate from the synaptic cleft, which is essential for terminating the postsynaptic action of glutamate (By similarity). Contributes to glutathione biosynthesis and protection against oxidative stress via its role in L-glutamate and L-cysteine transport. Negatively regulated by ARL6IP5 (By similarity).
Gene Name:
SLC1A1
Uniprot ID:
Q95135
Molecular weight:
57297.0
General function:
Involved in extracellular-glutamate-gated ion channel a
Specific function:
Not Available
Gene Name:
GRIK1
Uniprot ID:
A4FV91
Molecular weight:
90384.0
General function:
Amino acid transport and metabolism
Specific function:
Not Available
Gene Name:
GRM3
Uniprot ID:
A5D7D8
Molecular weight:
98871.0
General function:
Amino acid transport and metabolism
Specific function:
Not Available
Gene Name:
GRIA2
Uniprot ID:
Q0III4
Molecular weight:
71694.0
General function:
Involved in extracellular-glutamate-gated ion channel a
Specific function:
Not Available
Gene Name:
GRIK1
Uniprot ID:
A2VE57
Molecular weight:
102597.0
General function:
Involved in DNA binding
Specific function:
Not Available
Gene Name:
APP
Uniprot ID:
O97917
Molecular weight:
5183.0
General function:
Involved in calcium-dependent protein binding
Specific function:
Not Available
Gene Name:
CLN3
Uniprot ID:
Q17QK0
Molecular weight:
34337.0
General function:
Involved in protein binding
Specific function:
Not Available
Gene Name:
LOC518313
Uniprot ID:
Q2KI33
Molecular weight:
26387.0
General function:
Involved in protein binding
Specific function:
Regulates voltage-gated potassium channels assembled from KCNA1, KCNA4 and KCNAB1. It slows down channel inactivation by precluding channel closure mediated by the KCNAB1 subunit. Ligand for ADAM22 that positively regulates synaptic transmission mediated by AMPA-type glutamate receptors. Plays a role in suppressing the production of MMP1/3 through the phosphatidylinositol 3-kinase/ERK pathway (By similarity).
Gene Name:
LGI1
Uniprot ID:
Q5E9T6
Molecular weight:
61161.0
General function:
Involved in calcium channel regulator activity
Specific function:
Not Available
Gene Name:
GRM3
Uniprot ID:
A6QNZ6
Molecular weight:
82738.0
General function:
Amino acid transport and metabolism
Specific function:
Not Available
Gene Name:
GRIK5
Uniprot ID:
Q2HJD2
Molecular weight:
77502.0
General function:
Involved in DNA-directed RNA polymerase activity
Specific function:
Appears to be a stable component of the Pol II(G) complex form of RNA polymerase II (Pol II). Pol II synthesizes mRNA precursors and many functional non-coding RNAs and is the central component of the basal RNA polymerase II transcription machinery. May play a role in Mediator complex-dependent regulation of transcription activation. Acts in vitro as a negative regulator of transcriptional activation; this repression is relieved by the Mediator complex, which restores Pol II(G) activator-dependent transcription to a level equivalent to that of Pol II.
Gene Name:
POLR2M
Uniprot ID:
Q17QE3
Molecular weight:
41312.0
General function:
Involved in binding
Specific function:
Involved in the transport of glutamate across the inner mitochondrial membrane. Glutamate is cotransported with H(+) (By similarity).
Gene Name:
SLC25A22
Uniprot ID:
Q08DK4
Molecular weight:
34531.0
General function:
Involved in ion channel activity
Specific function:
Not Available
Gene Name:
GRIA4
Uniprot ID:
A0JN75
Molecular weight:
49050.0