Bovine Metabolome Database: Showing metabocard for D-Glutamic acid (BMDB0003339)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (24) Show 24 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:03:49 UTC

Update Date

2020-06-04 20:27:49 UTC

BMDB ID

BMDB0003339

Secondary Accession Numbers

BMDB03339

Metabolite Identification

Common Name

D-Glutamic acid

Description

D-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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(R)-2-Aminopentanedioic acid	ChEBI
D-2-Aminoglutaric acid	ChEBI
D-Glutaminic acid	ChEBI
D-Glutaminsaeure	ChEBI
DGL	ChEBI
Glutamic acid D-form	ChEBI
(R)-2-Aminopentanedioate	Generator
D-2-Aminoglutarate	Generator
D-Glutaminate	Generator
Glutamate D-form	Generator
D-Glutamate	Generator
(2R)-2-Aminopentanedioate	HMDB
(2R)-2-Aminopentanedioic acid	HMDB
D-2-Aminopentanedioate	HMDB
D-2-Aminopentanedioic acid	HMDB
delta-2-Aminoglutarate	HMDB
delta-2-Aminoglutaric acid	HMDB
delta-2-Aminopentanedioate	HMDB
delta-2-Aminopentanedioic acid	HMDB
delta-Glutamate	HMDB
delta-Glutamic acid	HMDB
delta-Glutaminate	HMDB
delta-Glutaminic acid	HMDB
delta-Glutaminsaeure	HMDB
Glutamate	HMDB
Lopac-g-2128	HMDB
Lopac-gamma-2128	HMDB
R-(-)-Glutamate	HMDB
R-(-)-Glutamic acid	HMDB
Tocris-0217	HMDB
Glutamic acid, (D)-isomer	HMDB
L Glutamic acid	HMDB
L-Glutamate	HMDB
L-Glutamic acid	HMDB
D Glutamate	HMDB
Glutamate, potassium	HMDB
L-Glutamate, aluminum	HMDB
Aluminum L glutamate	HMDB
Glutamic acid	HMDB
L Glutamate	HMDB
Aluminum L-glutamate	HMDB
Potassium glutamate	HMDB

Chemical Formula

C₅H₉NO₄

Average Molecular Weight

147.1293

Monoisotopic Molecular Weight

147.053157781

IUPAC Name

(2R)-2-aminopentanedioic acid

Traditional Name

D-glutamic acid

CAS Registry Number

6893-26-1

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 Key

WHUUTDBJXJRKMK-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glutamic 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 Framework

Aliphatic acyclic compounds

External Descriptors

D-alpha-amino acid (CHEBI:15966 )
glutamic acid (CHEBI:15966 )
Other amino acids (C00217 )

Ontology

Status

Detected and Quantified

Origin

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	201 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	8.88 mg/mL at 25 °C	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-3.5	ALOGPS
logP	-3.2	ChemAxon
logS	-0.26	ALOGPS
pKa (Strongest Acidic)	1.88	ChemAxon
pKa (Strongest Basic)	9.54	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	100.62 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	31.29 m³·mol⁻¹	ChemAxon
Polarizability	13.19 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Epidermis
Fibroblasts
Intestine
Liver
Mammary Gland
Neuron
Placenta
Ruminal Fluid
Semen
Spleen
Testis

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Epidermis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Intestine	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31867104	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Neuron	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Ruminal Fluid	Detected and Quantified	361.35 +/- 47.53 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Semen	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 5096119	details
Spleen	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Testis	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 5096119	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Ruminal Fluid	Detected and Quantified	516.48 +/- 110.81 uM	Not Specified	Not Specified	Rumen acidosis	Fozia Saleem, Sou...	details

External Links

HMDB ID

HMDB0003339

DrugBank ID

DB02517

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Glutamic acid

METLIN ID

6895

PubChem Compound

23327

PDB ID

Not Available

ChEBI ID

15966

References

Synthesis Reference

Ozaki, 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

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

Enzyme Details

1. Aspartyl aminopeptidase

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

Enzyme Details

2. Glutamyl aminopeptidase

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

Enzyme Details

3. Sodium/potassium-transporting ATPase alpha-3 chain

General function:: Inorganic ion transport and metabolism
Specific function:: Not Available
Gene Name:: atp1A3
Uniprot ID:: Q8HYW6
Molecular weight:: 19015.0

Enzyme Details

4. Cyclin-dependent kinase 5 activator 1

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

Enzyme Details

5. PRKCA-binding protein

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

Enzyme Details

6. Calcium/calmodulin-dependent protein kinase II alpha

General function:: Involved in ATP binding
Specific function:: Not Available
Gene Name:: CAMK2A
Uniprot ID:: Q08E45
Molecular weight:: 54115.0

Enzyme Details

7. PRA1 family protein 3

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

Enzyme Details

8. Amino acid transporter

General function:: Energy production and conversion
Specific function:: Not Available
Gene Name:: SLC1A6
Uniprot ID:: A6H774
Molecular weight:: 61424.0

Enzyme Details

9. Solute carrier family 1 member 2

General function:: Involved in glutamate:sodium symporter activity
Specific function:: Not Available
Gene Name:: SLC1A2
Uniprot ID:: A5HSH1
Molecular weight:: 2798.0

Enzyme Details

10. Protein lifeguard 1

General function:: Not Available
Specific function:: Potential apoptotic regulator.
Gene Name:: GRINA
Uniprot ID:: Q32L53
Molecular weight:: 40232.0

Enzyme Details

11. Excitatory amino acid transporter 3

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

Enzyme Details

12. GRIK1 protein

General function:: Involved in extracellular-glutamate-gated ion channel a
Specific function:: Not Available
Gene Name:: GRIK1
Uniprot ID:: A4FV91
Molecular weight:: 90384.0

Enzyme Details

13. GRM3 protein

General function:: Amino acid transport and metabolism
Specific function:: Not Available
Gene Name:: GRM3
Uniprot ID:: A5D7D8
Molecular weight:: 98871.0

Enzyme Details

14. Glutamate receptor, ionotropic, AMPA 2

General function:: Amino acid transport and metabolism
Specific function:: Not Available
Gene Name:: GRIA2
Uniprot ID:: Q0III4
Molecular weight:: 71694.0

Enzyme Details

15. GRIK1 protein

General function:: Involved in extracellular-glutamate-gated ion channel a
Specific function:: Not Available
Gene Name:: GRIK1
Uniprot ID:: A2VE57
Molecular weight:: 102597.0

Enzyme Details

16. Amyloid protein

General function:: Involved in DNA binding
Specific function:: Not Available
Gene Name:: APP
Uniprot ID:: O97917
Molecular weight:: 5183.0

Enzyme Details

17. Battenin

General function:: Involved in calcium-dependent protein binding
Specific function:: Not Available
Gene Name:: CLN3
Uniprot ID:: Q17QK0
Molecular weight:: 34337.0

Enzyme Details

18. Similar to glutamate receptor interacting protein 1

General function:: Involved in protein binding
Specific function:: Not Available
Gene Name:: LOC518313
Uniprot ID:: Q2KI33
Molecular weight:: 26387.0

Enzyme Details

19. Leucine-rich glioma-inactivated protein 1

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

Enzyme Details

20. GRM3 protein

General function:: Involved in calcium channel regulator activity
Specific function:: Not Available
Gene Name:: GRM3
Uniprot ID:: A6QNZ6
Molecular weight:: 82738.0

Enzyme Details

21. Glutamate ionotropic receptor kainate type subunit 5

General function:: Amino acid transport and metabolism
Specific function:: Not Available
Gene Name:: GRIK5
Uniprot ID:: Q2HJD2
Molecular weight:: 77502.0

Enzyme Details

22. DNA-directed RNA polymerase II subunit GRINL1A

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

Enzyme Details

23. Mitochondrial glutamate carrier 1

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

Enzyme Details

24. Glutamate receptor, ionotrophic, AMPA 4

General function:: Involved in ion channel activity
Specific function:: Not Available
Gene Name:: GRIA4
Uniprot ID:: A0JN75
Molecular weight:: 49050.0

Showing metabocard for D-Glutamic acid (BMDB0003339)

Structure for BMDB0003339 (D-Glutamic acid)

Enzymes