CAS 56-86-0|CAS 617-65-2|CAS 25513-46-6|(S)-2-氨基戊二酸|L-谷氨酸|L-glutamic acid|(2S)-2-aminopentanedioic acid|Glu|L-Glutamic acid|L-GLUTAMIC ACID FREE ACID|L-2-Aminopentanedioic acid|L-(+)-Glutami...

General Information

Structure

Molecular Formula

C₅H₉NO₄

Molecular Mass

147.12926

Exact Mass

147.05315777

Charge

InChI

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

InChIKey

WHUUTDBJXJRKMK-VKHMYHEASA-N

Canonic Smiles

OC(=O)CC[C@@H](C(=O)O)N

Isomeric Smiles

OC(=O)[C@@H](N)CCC(=O)O

Calculated Properties

JChem

Lipinski's Rule of Five

false

Data Source

Academic Data

Data Source

Names and Identifiers

Synonyms

(S)-2-氨基戊二酸L-谷氨酸L-Glutamic acidGluL-GLUTAMIC ACID FREE ACIDL-2-Aminopentanedioic acid(2S)-2-Aminopentanedioic acidL-(+)-Glutamic acid(S)-2-Aminopentanedioic acidAcidum glutamicum谷氨酸(S)-(+)-Glutamic acidGlutaminolL-(+)-Glutamic acidGlutaton1-Aminopropane-1,3-dicarboxylic acidL-a-Aminoglutaric acidGlutaminic acid(S)-Glutamic acida-Aminoglutaric acidGlutamic acida-Glutamic acid2-Aminoglutaric acidGlutamicol(S)-2-Amino-1,5-pentanedioic Acidα-Glutamic AcidGlutamidexGlusateL-α-Aminoglutaric AcidGlutacidL-Glutamic Acid2-Aminopentanedioic acidL-GlutamateL-Glutaminic acid2-AMinopentanedioic acidL-2-Aminoglutaric acidH-Glu-OH(S)-2-AMinopentanedioic acidL-Glutamic acidGLUTAMIC ACID(S)-2-aminopentanedioic acidGluL-Glutaminic acid(S)-glutamic acidL-GluL-GlutaminsaeureL-glutamic acidEGlutamatePLGAGlutamic acid polymerPoly-L-glutamatePolyglutamic acidPoly(alpha-L-glutamic acid)poly(L-glutamicacid)gamma-poly(L-glutamic acid)alpha-L-Glutamic acid polymergamma-poly(L-glutamic acid) macromoleculepoly(L-glutamic acid)

IUPAC name

(2S)-2-aminopentanedioic acid

IUPAC Traditional name

L-glutamic acid

Brand Name

AciglutGlutatonGlutamidexGlutaminolGlutamicolGlusateGlutacid

International Nonproprietary Name (INN)

acido glutamicoglutamic acidacidum glutamicumacide glutamique

Names and Identifiers

Registration numbers

EC Number

Merck Index

MDL Number

Beilstein Number

CAS Number

56-86-0617-65-225513-46-6

E Number

E620

PubChem SID

24895340248729082490160946505816160963491248463582489505224895223814373785305506

FEMA ID

3285

PubChem CID

33032

PubMed Citation Links

19581495227353341671981916892196159304652221930115739367

BRENDA Database

1.5.99.52.4.2.142.6.1.286.3.1.62.6.1.861.4.3.113.4.11.63.5.3.61.14.18.12.6.1.23.4.11.232.6.1.1072.6.1.876.3.5.6

MetaboLights Database

MTBLS763MTBLS106MTBLS16MTBLS642MTBLS412MTBLS5405MTBLS615MTBLS680MTBLS1495MTBLS883MTBLS2878MTBLS601MTBLS1541MTBLS3322MTBLS4579

Protein Data Bank

1gul3g3g1lzq3fas3ik63lsw7tno4x485h8q5weo6hch1ewk2aoe2yep3uzo6dhd

UniProt Database

Q7RTP6Q69YN4Q8N594A4JB91P01505Q9Z1S0Q99542P0A1A5P48318A5DSU5Q0SNK7Q821S0B9MFR5B0BRH4O00555

SABIO-RK Database

72077216862348351038172138942788973751791032070767204389313793

BRENDA Ligand Database

116332051450251726781554613431459382295754122957312407120256579145029

BKMS React Database

1459381163565791450291459412295731554613205145025124071229575

MetaCyc Database

CHEMBL

ACToR Database

KNApSAcK Database

KEGG ID

SureChEMBL Database

Reaxys Registry

CompTox Database

LINCS Database

Golm Database

677a2165-15f8-4756-bb1f-8209cb73537165bfd68d-73fe-4290-9496-36eca7fce1dc4359b3dc-10a1-4084-9a7e-fe351a8496b2c6df6178-40a5-4312-819b-561d37d495da85b97974-b179-4d2a-8edd-8ea9d13b7e5e58a3e485-8f71-46f2-9365-000be7a5a00c0c80d752-78ac-465c-b90e-6beaafe2a3733d091503-3702-4e68-8a71-6754c084f0f93de25525-7de6-43ab-9bd1-d79513f57bc55f5282d8-cd44-416a-8c38-e54cc21172c8c3a10b44-2d29-453c-849b-c8c44dc0b201433e8f18-6ddf-4bb1-adc6-d0c5047082bc27442b65-6648-4f51-a180-4d5570e87acb845caa82-5651-4753-845f-a13d5aec599d55bbc44b-1f85-4f0e-b486-796a851b62b690f88071-9181-495b-a373-516bd70fa1fadab18c8e-e316-435e-b539-d030a6ad3891

BioModels Database

BIOMD0000001061BIOMD0000000627BIOMD0000000239BIOMD0000000579

Patent number

EP1291342US2003049284US2006223760US2007197430US2004101523EP1632233US2005130881WO2008131368EP1958965WO2005010160EP1616963US2005085547US2007238669EP1541585

Gmelin ID

3502

CHEBI ID

CHEBI:42825CHEBI:6224CHEBI:16015CHEBI:21304CHEBI:53374

Wikipedia Title

L-Glutamic_Acid

Drug Central Database

KEGG DRUG Database

NMRShiftDB Database

DrugBank ID

PDBeChem Database

HMDB Database

BindingDB Database

BPDB Database

Registration numbers

Properties

Physical Property

Properties

Related Proteins

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00142

Drug Groups

approved; nutraceutical

Description

A peptide that is a homopolymer of glutamic acid. [PubChem]

Indication

Considered to be nature's "Brain food" by improving mental capacities; helps speed the healing of ulcers; gives a "lift" from fatigue; helps control alcoholism, schizophrenia and the craving for sugar.

Pharmacology

In addition to being one of the building blocks in protein synthesis, it is the most widespread neurotransmitter in brain function, as an excitatory neurotransmitter and as a precursor for the synthesis of GABA in GABAergic neurons.

Toxicity

Glutamate causes neuronal damage and eventual cell death, particularly when NMDA receptors are activated, High dosages of glutamic acid may include symptoms such as headaches and neurological problems.

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic

Absorption

Absorbed from the lumen of the small intestine into the enterocytes.Absorption is efficient and occurs by an active transport mechanism.

References

• Smith QR: Transport of glutamate and other amino acids at the blood-brain barrier. J Nutr. 2000 Apr;130(4S Suppl):1016S-22S. [Pubmed]

• Okumoto S, Looger LL, Micheva KD, Reimer RJ, Smith SJ, Frommer WB: Detection of glutamate release from neurons by genetically encoded surface-displayed FRET nanosensors. Proc Natl Acad Sci U S A. 2005 Jun 14;102(24):8740-5. Epub 2005 Jun 6. [Pubmed]

• Reeds PJ, Burrin DG, Stoll B, Jahoor F: Intestinal glutamate metabolism. J Nutr. 2000 Apr;130(4S Suppl):978S-82S. [Pubmed]

• Corrie JE, DeSantis A, Katayama Y, Khodakhah K, Messenger JB, Ogden DC, Trentham DR: Postsynaptic activation at the squid giant synapse by photolytic release of L-glutamate from a 'caged' L-glutamate. J Physiol. 1993 Jun;465:1-8. [Pubmed]

• Augustin H, Grosjean Y, Chen K, Sheng Q, Featherstone DE: Nonvesicular release of glutamate by glial xCT transporters suppresses glutamate receptor clustering in vivo. J Neurosci. 2007 Jan 3;27(1):111-23. [Pubmed]

External Links

• [Wikipedia]

MP Biomedicals

02101793

Free Acid
Purity: 99-100%
Crystalline

02194676

Free Acid
Cell Culture Reagent
Purity: 99-100%
Crystalline

Sigma Aldrich

G1251

Biochem/physiol Actions
一种兴奋性氨基酸神经递质，为谷氨酸盐受体所有亚型(代谢型红藻氨酸、NMDA 和 AMPA)的激动剂。
包装
1 kg in poly bottle
100, 500 g in poly bottle
5 kg in poly drum
法律信息
ReagentPlus 注册商标 Sigma-Aldrich Co. LLC

G8415

Biochem/physiol Actions
Glutamic acid, or glutamate, the salt form of glutamic acid, functions as a neurotransmitter. Glutamic acid also plays a key role in many metabolic pathways. It is converted to α-ketoglutarate, a key component of the TCA cycle, and a precursor for the biosynthesis of nucleic acids and certain amino acids. In cells, glutamine is converted to glutamate by the enzyme glutaminase.
一种兴奋性氨基酸神经递质，为谷氨酸盐受体所有亚型(代谢型红藻氨酸、NMDA 和 AMPA)的激动剂。
包装
10 mg in autosmp vl

128430

Biochem/physiol Actions
An excitatory amino acid neurotransmitter that is an agonist at all subtypes of glutamate receptors (metabotropic, kainate, NMDA, and AMPA).
Packaging
1 kg in poly bottle
100 g in poly bottle

W328502

49449

Biochem/physiol Actions
An excitatory amino acid neurotransmitter that is an agonist at all subtypes of glutamate receptors (metabotropic, kainate, NMDA, and AMPA).
Other Notes
Lesion-sparing agent, has excitotoxic properties1; May function as precipitating agent in protein crystallization2; Growth requirement of various microorganisms3

TRC

G596960

A non-essential amino acid. Its salt form (glutamate) is an important neurotransmitter that plays a key role in long-term potentiation and is important for learning and memory. It is also a key molecule in cellular metabolism.

ChEBI

CHEBI:16015

An optically active form of glutamic acid having L-configuration.

CHEBI:53374

A macromolecule composed of repeating gamma-linked L-glutamyl units.

Molecule Details

References

PubChem Literature

From Data Sources

• Smith QR: Transport of glutamate and other amino acids at the blood-brain barrier. J Nutr. 2000 Apr;130(4S Suppl):1016S-22S. Pubmed

• Reeds PJ, Burrin DG, Stoll B, Jahoor F: Intestinal glutamate metabolism. J Nutr. 2000 Apr;130(4S Suppl):978S-82S. Pubmed

• McEntee, W., et al.: Psychopharmacology, 111, 391 (1993)

• Manev, H., et al.: Mol. Pharmacol., 36, 106 (1993)

• For use as a chiral building-block in the synthesis of the (S)-isomer of -butyrolactone-4-carboxylic acid, see: Org. Synth. Coll., 7, 99 (1990):

• For the differential protection of the ɑ-carboxyl group of N-protected glutamic acid by reaction with formaldehyde to form the cyclic 5-oxazolidinone, see: Synthesis, 542 (1989).

References

Bioactivity

PubChem BioAssay

Bioactivity

Navigation

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Calculated Properties

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• JChem

Data Source

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Names and Identifiers

• Synonyms

• IUPAC name

• IUPAC Traditional name

• Brand Name

• International Nonproprietary Name (INN)

Names and Identifiers

Registration numbers

• EC Number

• Merck Index

• MDL Number

• Beilstein Number

• CAS Number

• E Number

• PubChem SID

• FEMA ID

• PubChem CID

• PubMed Citation Links

• BRENDA Database

• MetaboLights Database

• Protein Data Bank

• UniProt Database

• SABIO-RK Database

• BRENDA Ligand Database

• BKMS React Database

• MetaCyc Database

• CHEMBL

• ACToR Database

• KNApSAcK Database

• KEGG ID

• SureChEMBL Database

• Reaxys Registry

• CompTox Database

• LINCS Database

• Golm Database

• BioModels Database

• Patent number

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Properties

• Physical Property

• Product Information

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• ChEBI

Molecule Details

References

• PubChem Literature

• From Data Sources

Bioactivity

• PubChem BioAssay

Synonyms

IUPAC name

(2S)-2-aminopentanedioic acid

IUPAC Traditional name

L-glutamic acid

Brand Name

AciglutGlutatonGlutamidexGlutaminolGlutamicolGlusateGlutacid

International Nonproprietary Name (INN)

acido glutamicoglutamic acidacidum glutamicumacide glutamique

From Data Sources

• Smith QR: Transport of glutamate and other amino acids at the blood-brain barrier. J Nutr. 2000 Apr;130(4S Suppl):1016S-22S. Pubmed

• Reeds PJ, Burrin DG, Stoll B, Jahoor F: Intestinal glutamate metabolism. J Nutr. 2000 Apr;130(4S Suppl):978S-82S. Pubmed

• McEntee, W., et al.: Psychopharmacology, 111, 391 (1993)

• Manev, H., et al.: Mol. Pharmacol., 36, 106 (1993)

• For use as a chiral building-block in the synthesis of the (S)-isomer of -butyrolactone-4-carboxylic acid, see: Org. Synth. Coll., 7, 99 (1990):

• For the differential protection of the ɑ-carboxyl group of N-protected glutamic acid by reaction with formaldehyde to form the cyclic 5-oxazolidinone, see: Synthesis, 542 (1989).

Physical Property

Melting Point

224-225°C

205 °C (dec.)(lit.)

199-201°C

189-192°C dec.

Apperance

powder

White Solid

Optical Rotation

[α]20/D +31.5°, c = 2 in 5 M HCl

[α]20/D +32°, c = 10 in 2 M HCl

[α]20/D +31.5±1.0°, c = 5% in 5 M HCl

+31 (c=5 in 5N HCl)

Absorption Wavelength

λ: 280 nm Amax: 0.1

λ: 260 nm Amax: 0.1

Product Information

Safety Information

Pharmacology Properties

Gene Information

human ... CCR2(1231), GRIA1(2890), GRIA2(2891), GRIA4(2893), GRIK1(2897), GRIK2(2898), GRIK3(2899), GRIK5(2901), GRIN2B(2904), GRM2(2912), SLC1A1(6505), SLC1A2(6506)rat ... Gria1(50592), Grik1(29559), Grik2(54257), Grik4(24406), Grin2a(24409), Grm1(24414), Grm2(24415), Grm3(24416), Grm4(24417), Grm5(24418), Grm6(24419), Grm7(81672), Slc1a2(29482)

human ... CCR2(1231), GRIA1(2890), GRIA2(2891), GRIA4(2893), GRIK2(2898), GRIK3(2899), GRIK5(2901), GRIN2B(2904), GRM2(2912), SLC1A1(6505), SLC1A2(6506)rat ... Gria1(50592), Grik1(29559), Grik2(54257), Grik4(24406), Grin2a(24409), Grm1(24414), Grm2(24415), Grm3(24416), Grm4(24417), Grm5(24418), Grm6(24419), Grm7(81672), Slc1a2(29482)