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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2013-05-17 01:23:31 UTC

Update Date

2022-03-07 03:17:45 UTC

HMDB ID

HMDB0060475

Secondary Accession Numbers

HMDB60475

Metabolite Identification

Common Name

DL-Glutamate

Description

DL-Glutamate, also known as E or DL-glutamic acid, 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. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). DL-Glutamate exists in all living organisms, ranging from bacteria to humans. DL-Glutamate is found, on average, in the highest concentration within a few different foods, such as red bell peppers, milk (cow), and wheats and in a lower concentration in eggplants, romaine lettuces, and nanking cherries. DL-Glutamate has also been detected, but not quantified, in a few different foods, such as apples, broccoli, and lettuces.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Aminoglutaric acid	ChEBI
DL-Glutamic acid	ChEBI
DL-Glutaminic acid	ChEBI
E	ChEBI
Glu	ChEBI
Glutamate	ChEBI
Glutaminic acid	ChEBI
Glutaminsaeure	ChEBI
2-Aminoglutarate	Generator
DL-Glutaminate	Generator
Glutamic acid	Generator
Glutaminate	Generator
D-Glutamate	HMDB
L Glutamate	HMDB
L Glutamic acid	HMDB
D Glutamate	HMDB
Glutamate, potassium	HMDB
Glutamic acid, (D)-isomer	HMDB
L-Glutamate	HMDB
L-Glutamic acid	HMDB
Aluminum L glutamate	HMDB
Aluminum L-glutamate	HMDB
L-Glutamate, aluminum	HMDB
Potassium glutamate	HMDB
DL-Glutamate	Generator

Chemical Formula

C₅H₉NO₄

Average Molecular Weight

147.1293

Monoisotopic Molecular Weight

147.053157781

IUPAC Name

2-aminopentanedioic acid

Traditional Name

glutaminsaeure

CAS Registry Number

Not Available

SMILES

NC(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)

InChI Key

WHUUTDBJXJRKMK-UHFFFAOYSA-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
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

alpha-amino acid (CHEBI:18237 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 22613268)

Source

Exogenous

Exogenous (HMDB: HMDB0060475)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	80.6 g/L	ALOGPS
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	13.49 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	131.952	31661259
DarkChem	[M-H]-	125.492	31661259
DeepCCS	[M+H]+	125.129	30932474
DeepCCS	[M-H]-	122.142	30932474
DeepCCS	[M-2H]-	158.982	30932474
DeepCCS	[M+Na]+	133.789	30932474
AllCCS	[M+H]+	133.8	32859911
AllCCS	[M+H-H2O]+	129.8	32859911
AllCCS	[M+NH4]+	137.6	32859911
AllCCS	[M+Na]+	138.6	32859911
AllCCS	[M-H]-	126.6	32859911
AllCCS	[M+Na-2H]-	128.8	32859911
AllCCS	[M+HCOO]-	131.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter)). Predicted by Afia on May 17, 2022.	1.0 minutes	32390414
Predicted by Siyang on May 30, 2022	9.2343 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	7.62 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	484.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	318.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	40.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	195.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	67.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	287.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	220.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	836.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	584.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	39.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	677.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	198.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	277.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	725.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	480.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	478.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
DL-Glutamate	NC(CCC(O)=O)C(O)=O	2209.7	Standard polar	33892256
DL-Glutamate	NC(CCC(O)=O)C(O)=O	1219.0	Standard non polar	33892256
DL-Glutamate	NC(CCC(O)=O)C(O)=O	1854.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
DL-Glutamate,1TMS,isomer #1	C[Si](C)(C)OC(=O)CCC(N)C(=O)O	1497.9	Semi standard non polar	33892256
DL-Glutamate,1TMS,isomer #2	C[Si](C)(C)OC(=O)C(N)CCC(=O)O	1496.8	Semi standard non polar	33892256
DL-Glutamate,1TMS,isomer #3	C[Si](C)(C)NC(CCC(=O)O)C(=O)O	1554.6	Semi standard non polar	33892256
DL-Glutamate,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCC(N)C(=O)O[Si](C)(C)C	1518.1	Semi standard non polar	33892256
DL-Glutamate,2TMS,isomer #2	C[Si](C)(C)NC(CCC(=O)O[Si](C)(C)C)C(=O)O	1623.3	Semi standard non polar	33892256
DL-Glutamate,2TMS,isomer #3	C[Si](C)(C)NC(CCC(=O)O)C(=O)O[Si](C)(C)C	1592.6	Semi standard non polar	33892256
DL-Glutamate,2TMS,isomer #4	C[Si](C)(C)N(C(CCC(=O)O)C(=O)O)[Si](C)(C)C	1772.3	Semi standard non polar	33892256
DL-Glutamate,3TMS,isomer #1	C[Si](C)(C)NC(CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1621.4	Semi standard non polar	33892256
DL-Glutamate,3TMS,isomer #1	C[Si](C)(C)NC(CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1659.0	Standard non polar	33892256
DL-Glutamate,3TMS,isomer #1	C[Si](C)(C)NC(CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1785.5	Standard polar	33892256
DL-Glutamate,3TMS,isomer #2	C[Si](C)(C)OC(=O)CCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1814.5	Semi standard non polar	33892256
DL-Glutamate,3TMS,isomer #2	C[Si](C)(C)OC(=O)CCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1713.5	Standard non polar	33892256
DL-Glutamate,3TMS,isomer #2	C[Si](C)(C)OC(=O)CCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1971.9	Standard polar	33892256
DL-Glutamate,3TMS,isomer #3	C[Si](C)(C)OC(=O)C(CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1778.6	Semi standard non polar	33892256
DL-Glutamate,3TMS,isomer #3	C[Si](C)(C)OC(=O)C(CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1697.5	Standard non polar	33892256
DL-Glutamate,3TMS,isomer #3	C[Si](C)(C)OC(=O)C(CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1942.0	Standard polar	33892256
DL-Glutamate,4TMS,isomer #1	C[Si](C)(C)OC(=O)CCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1819.7	Semi standard non polar	33892256
DL-Glutamate,4TMS,isomer #1	C[Si](C)(C)OC(=O)CCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1768.6	Standard non polar	33892256
DL-Glutamate,4TMS,isomer #1	C[Si](C)(C)OC(=O)CCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1751.4	Standard polar	33892256
DL-Glutamate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC(N)C(=O)O	1751.6	Semi standard non polar	33892256
DL-Glutamate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(N)CCC(=O)O	1749.6	Semi standard non polar	33892256
DL-Glutamate,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(CCC(=O)O)C(=O)O	1805.2	Semi standard non polar	33892256
DL-Glutamate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC(N)C(=O)O[Si](C)(C)C(C)(C)C	1972.1	Semi standard non polar	33892256
DL-Glutamate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	2089.8	Semi standard non polar	33892256
DL-Glutamate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(CCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	2049.8	Semi standard non polar	33892256
DL-Glutamate,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C(CCC(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C	2186.7	Semi standard non polar	33892256
DL-Glutamate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2263.6	Semi standard non polar	33892256
DL-Glutamate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2262.2	Standard non polar	33892256
DL-Glutamate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2181.8	Standard polar	33892256
DL-Glutamate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2437.1	Semi standard non polar	33892256
DL-Glutamate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2315.1	Standard non polar	33892256
DL-Glutamate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2266.7	Standard polar	33892256
DL-Glutamate,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(CCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2431.7	Semi standard non polar	33892256
DL-Glutamate,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(CCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2285.3	Standard non polar	33892256
DL-Glutamate,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(CCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2252.9	Standard polar	33892256
DL-Glutamate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2653.0	Semi standard non polar	33892256
DL-Glutamate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2531.1	Standard non polar	33892256
DL-Glutamate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2239.0	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Pancreatic cancer	22613268	details

Associated Disorders and Diseases

Disease References

Pancreatic cancer
Zhang L, Jin H, Guo X, Yang Z, Zhao L, Tang S, Mo P, Wu K, Nie Y, Pan Y, Fan D: Distinguishing pancreatic cancer from chronic pancreatitis and healthy individuals by (1)H nuclear magnetic resonance-based metabonomic profiles. Clin Biochem. 2012 Sep;45(13-14):1064-9. doi: 10.1016/j.clinbiochem.2012.05.012. Epub 2012 May 19. [PubMed:22613268 ]

Associated OMIM IDs

260350 (Pancreatic cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012536

KNApSAcK ID

C00019577

Chemspider ID

Not Available

KEGG Compound ID

C00302

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Glutamic_acid

METLIN ID

Not Available

PubChem Compound

611

PDB ID

Not Available

ChEBI ID

18237

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

Enzyme Details

1. Aspartate aminotransferase, cytoplasmic

General function:: Involved in transferase activity, transferring nitrogenous groups
Specific function:: Plays a key role in amino acid metabolism (By similarity).
Gene Name:: GOT1
Uniprot ID:: P17174
Molecular weight:: 46247.14

Reactions

L-Cysteine + Oxoglutaric acid → 3-Mercaptopyruvic acid + DL-Glutamate	details

Enzyme Details

2. Aspartate aminotransferase, mitochondrial

General function:: Involved in transferase activity, transferring nitrogenous groups
Specific function:: Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Plays a key role in amino acid metabolism. Important for metabolite exchange between mitochondria and cytosol. Facilitates cellular uptake of long-chain free fatty acids.
Gene Name:: GOT2
Uniprot ID:: P00505
Molecular weight:: 47517.285

Reactions

L-Cysteine + Oxoglutaric acid → 3-Mercaptopyruvic acid + DL-Glutamate	details

Showing metabocard for DL-Glutamate (HMDB0060475)

MOL for HMDB0060475 (DL-Glutamate)

3D MOL for HMDB0060475 (DL-Glutamate)

3D SDF for HMDB0060475 (DL-Glutamate)

3D-SDF for HMDB0060475 (DL-Glutamate)

PDB for HMDB0060475 (DL-Glutamate)

3D PDB for HMDB0060475 (DL-Glutamate)

SMILES for HMDB0060475 (DL-Glutamate)

INCHI for HMDB0060475 (DL-Glutamate)

Structure for HMDB0060475 (DL-Glutamate)

3D Structure for HMDB0060475 (DL-Glutamate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

Reactions

Reactions