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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-12 19:07:11 UTC

Update Date

2022-03-07 02:49:18 UTC

HMDB ID

HMDB0003339

Secondary Accession Numbers

HMDB03339

Metabolite Identification

Common Name

D-Glutamic acid

Description

There are two forms of glutamic acid found in nature: L-glutamic acid and D-glutamic acid. D-glutamic acid, is not endogenously produced in higher mammals. It is found naturally primarily in the cell walls of certain bacteria. D-glutamate is also present in certain foods e.g., soybeans and also arises from the turnover of the intestinal tract microflora, whose cell walls contain significant D-glutamate. Unlike other D-amino acids, D-glutamate is not oxidized by the D-amino acid oxidases, and therefore this detoxification pathway is not available for handling D-glutamate. Likewise, D-glutamic acid, when ingested, largely escapes most deamination reactions (unlike the L-counterpart). Free D-glutamate is found in mammalian tissue at surprisingly high levels, with D-glutamate accounting for 9% of the total glutamate present in liver. D-glutamate is the most potent natural inhibitor of glutathione synthesis identified to date and this may account for its localization to the liver, since circulating D-glutamate may alter redox stabiity (PMID 11158923 ). Certain eels are known to use D-glutamic acid as a phermone for chemical communication. D-Glutamic acid has been found to be a metabolite of Lactobacillus (PMID: 22754309 ).

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

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

Not Available

Physical Properties

State

Solid

Experimental Molecular 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

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	13.19 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]+	132.664	31661259
DarkChem	[M-H]-	125.328	31661259
DeepCCS	[M+H]+	126.815	30932474
DeepCCS	[M-H]-	122.95	30932474
DeepCCS	[M-2H]-	160.541	30932474
DeepCCS	[M+Na]+	135.925	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. 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
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	400.3 seconds	40023050
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
D-Glutamic acid	N[C@H](CCC(O)=O)C(O)=O	2199.6	Standard polar	33892256
D-Glutamic acid	N[C@H](CCC(O)=O)C(O)=O	1237.6	Standard non polar	33892256
D-Glutamic acid	N[C@H](CCC(O)=O)C(O)=O	1815.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
D-Glutamic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CC[C@@H](N)C(=O)O	1507.5	Semi standard non polar	33892256
D-Glutamic acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](N)CCC(=O)O	1472.0	Semi standard non polar	33892256
D-Glutamic acid,1TMS,isomer #3	C[Si](C)(C)N[C@H](CCC(=O)O)C(=O)O	1533.4	Semi standard non polar	33892256
D-Glutamic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CC[C@@H](N)C(=O)O[Si](C)(C)C	1518.9	Semi standard non polar	33892256
D-Glutamic acid,2TMS,isomer #2	C[Si](C)(C)N[C@H](CCC(=O)O[Si](C)(C)C)C(=O)O	1617.6	Semi standard non polar	33892256
D-Glutamic acid,2TMS,isomer #3	C[Si](C)(C)N[C@H](CCC(=O)O)C(=O)O[Si](C)(C)C	1589.3	Semi standard non polar	33892256
D-Glutamic acid,2TMS,isomer #4	C[Si](C)(C)N([C@H](CCC(=O)O)C(=O)O)[Si](C)(C)C	1729.5	Semi standard non polar	33892256
D-Glutamic acid,3TMS,isomer #1	C[Si](C)(C)N[C@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1625.8	Semi standard non polar	33892256
D-Glutamic acid,3TMS,isomer #1	C[Si](C)(C)N[C@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1664.7	Standard non polar	33892256
D-Glutamic acid,3TMS,isomer #1	C[Si](C)(C)N[C@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1807.9	Standard polar	33892256
D-Glutamic acid,3TMS,isomer #2	C[Si](C)(C)OC(=O)CC[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1779.5	Semi standard non polar	33892256
D-Glutamic acid,3TMS,isomer #2	C[Si](C)(C)OC(=O)CC[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1718.7	Standard non polar	33892256
D-Glutamic acid,3TMS,isomer #2	C[Si](C)(C)OC(=O)CC[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1969.6	Standard polar	33892256
D-Glutamic acid,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@@H](CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1765.0	Semi standard non polar	33892256
D-Glutamic acid,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@@H](CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1708.5	Standard non polar	33892256
D-Glutamic acid,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@@H](CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1949.2	Standard polar	33892256
D-Glutamic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)CC[C@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1804.2	Semi standard non polar	33892256
D-Glutamic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)CC[C@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1776.6	Standard non polar	33892256
D-Glutamic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)CC[C@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1746.4	Standard polar	33892256
D-Glutamic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H](N)C(=O)O	1765.9	Semi standard non polar	33892256
D-Glutamic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](N)CCC(=O)O	1743.3	Semi standard non polar	33892256
D-Glutamic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@H](CCC(=O)O)C(=O)O	1797.0	Semi standard non polar	33892256
D-Glutamic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H](N)C(=O)O[Si](C)(C)C(C)(C)C	1982.4	Semi standard non polar	33892256
D-Glutamic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	2094.9	Semi standard non polar	33892256
D-Glutamic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@H](CCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	2043.8	Semi standard non polar	33892256
D-Glutamic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N([C@H](CCC(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C	2168.8	Semi standard non polar	33892256
D-Glutamic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2272.6	Semi standard non polar	33892256
D-Glutamic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2259.4	Standard non polar	33892256
D-Glutamic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2195.4	Standard polar	33892256
D-Glutamic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CC[C@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2433.4	Semi standard non polar	33892256
D-Glutamic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CC[C@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2321.6	Standard non polar	33892256
D-Glutamic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CC[C@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2263.8	Standard polar	33892256
D-Glutamic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2427.8	Semi standard non polar	33892256
D-Glutamic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2289.5	Standard non polar	33892256
D-Glutamic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2256.1	Standard polar	33892256
D-Glutamic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC[C@H](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	2668.5	Semi standard non polar	33892256
D-Glutamic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC[C@H](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	2533.6	Standard non polar	33892256
D-Glutamic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC[C@H](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	2243.6	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Breast Milk
Feces
Saliva
Urine

Tissue Locations

Epidermis
Fibroblasts
Intestine
Neuron
Placenta
Spleen
Testis

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0140-0.200 uM	Adult (>18 years old)	Not Specified	Normal	238530	details
Breast Milk	Detected and Quantified	1600 +/- 320 uM	Adult (>18 years old)	Female	Normal	24027187	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	17269711	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	18052033	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	19006102	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	19573517	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21330412	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21761941	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Both	Normal	22411374	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25670064	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Normal	27609529	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	25985090	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27107423	details
Feces	Detected and Quantified	880 +/- 680 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected and Quantified	490 +/- 390 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected and Quantified	11382 nmol/g wet feces	Adult (>18 years old)	Not Specified	Normal	26416813	details
Feces	Detected and Quantified	8923 nmol/g wet feces	Adult (>18 years old)	Not Specified	Normal	26416813	details
Feces	Detected and Quantified	11117 nmol/g wet feces	Adult (>18 years old)	Not Specified	Normal	26416813	details
Saliva	Detected and Quantified	43.4 +/- 55.1 uM	Adult (>18 years old)	Male	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	8.91 +/- 3.90 uM	Adult (>18 years old)	Both	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	123.84 +/- 110.2 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected and Quantified	67.51 +/- 75.14 uM	Adult (>18 years old)	Female	Normal	23857558	details
Saliva	Detected and Quantified	13.5 +/- 8.75 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	14.5 +/- 19.8 uM	Adult (>18 years old)	Not Specified	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	14.5 +/- 6.75 uM	Adult (>18 years old)	Both	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	14.9 +/- 7.60 uM	Adult (>18 years old)	Not Specified	Normal	Sugimoto et al. (...	details
Urine	Detected and Quantified	7.9 +/- 3.9 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	15992788	details
Urine	Detected and Quantified	<2.0 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	3168222	details
Urine	Detected and Quantified	<2.0 umol/mmol creatinine	Infant (1 - 6 months old)	Both	Normal	3168222	details
Urine	Detected and Quantified	<2.0 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	3168222	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	16939360	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	16939360	details
Urine	Detected and Quantified	8.5 (3.3-18.4) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	2.6 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	21388201	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	156.0 +/- 90.0 uM	Adult (>18 years old)	Both	Schizophrenia	17276036	details
Blood	Detected and Quantified	82.0 +/- 8.0 uM	Infant (0-1 year old)	Both	Premature	17622957	details
Blood	Detected and Quantified	0.429 uM	Adult (>18 years old)	Not Specified	Gamma-glutamyltransferase deficiency	238530	details
Blood	Detected and Quantified	56.4 (12.69) uM	Adult (>18 years old)	Female	Pregnancy	24704061	details
Blood	Detected and Quantified	52.21 (14.83) uM	Adult (>18 years old)	Female	Pregnancy with fetus having congenital heart defect	24704061	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27107423	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Unclassified IBD	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Ulcerative colitis	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Crohns disease	27609529	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative colitis	21761941	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Irritable bowel syndrome	21761941	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Irritable bowel syndrome	21330412	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	19006102	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative Colitis	17269711	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Crohn’s Disease	17269711	details
Saliva	Detected and Quantified	47.82 +/- 18.36 uM	Adult (>18 years old)	Both	Lewy body disease	23857558	details
Saliva	Detected and Quantified	43.79 +/- 10.57 uM	Adult (>18 years old)	Male	Frontotemporal lobe dementia	23857558	details
Saliva	Detected and Quantified	38.26 +/- 29.05 uM	Adult (>18 years old)	Male	Alzheimer's disease	23857558	details
Urine	Detected and Quantified	0.0064 umol/mmol creatinine	Adult (>18 years old)	Both	ADPKD	21389975	details

Associated Disorders and Diseases

Disease References

Schizophrenia
Heresco-Levy U, Bar G, Levin R, Ermilov M, Ebstein RP, Javitt DC: High glycine levels are associated with prepulse inhibition deficits in chronic schizophrenia patients. Schizophr Res. 2007 Mar;91(1-3):14-21. Epub 2007 Feb 2. [PubMed:17276036 ]
Pregnancy
Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
Gamma-glutamyltransferase deficiency
Schulman JD, Goodman SI, Mace JW, Patrick AD, Tietze F, Butler EJ: Glutathionuria: inborn error of metabolism due to tissue deficiency of gamma-glutamyl transpeptidase. Biochem Biophys Res Commun. 1975 Jul 8;65(1):68-74. [PubMed:238530 ]
Crohn's disease
Marchesi JR, Holmes E, Khan F, Kochhar S, Scanlan P, Shanahan F, Wilson ID, Wang Y: Rapid and noninvasive metabonomic characterization of inflammatory bowel disease. J Proteome Res. 2007 Feb;6(2):546-51. [PubMed:17269711 ] Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Ulcerative colitis
Marchesi JR, Holmes E, Khan F, Kochhar S, Scanlan P, Shanahan F, Wilson ID, Wang Y: Rapid and noninvasive metabonomic characterization of inflammatory bowel disease. J Proteome Res. 2007 Feb;6(2):546-51. [PubMed:17269711 ] Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ] Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Colorectal cancer
Monleon D, Morales JM, Barrasa A, Lopez JA, Vazquez C, Celda B: Metabolite profiling of fecal water extracts from human colorectal cancer. NMR Biomed. 2009 Apr;22(3):342-8. doi: 10.1002/nbm.1345. [PubMed:19006102 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ] Lin Y, Ma C, Liu C, Wang Z, Yang J, Liu X, Shen Z, Wu R: NMR-based fecal metabolomics fingerprinting as predictors of earlier diagnosis in patients with colorectal cancer. Oncotarget. 2016 May 17;7(20):29454-64. doi: 10.18632/oncotarget.8762. [PubMed:27107423 ]
Irritable bowel syndrome
Ponnusamy K, Choi JN, Kim J, Lee SY, Lee CH: Microbial community and metabolomic comparison of irritable bowel syndrome faeces. J Med Microbiol. 2011 Jun;60(Pt 6):817-27. doi: 10.1099/jmm.0.028126-0. Epub 2011 Feb 17. [PubMed:21330412 ] Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
Alzheimer's disease
Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Frontotemporal dementia
Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Lewy body disease
Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Autosomal dominant polycystic kidney disease
Gronwald W, Klein MS, Zeltner R, Schulze BD, Reinhold SW, Deutschmann M, Immervoll AK, Boger CA, Banas B, Eckardt KU, Oefner PJ: Detection of autosomal dominant polycystic kidney disease by NMR spectroscopic fingerprinting of urine. Kidney Int. 2011 Jun;79(11):1244-53. doi: 10.1038/ki.2011.30. Epub 2011 Mar 9. [PubMed:21389975 ]

Associated OMIM IDs

181500 (Schizophrenia)
266600 (Crohn's disease)
114500 (Colorectal cancer)
104300 (Alzheimer's disease)
600274 (Frontotemporal dementia)
601313 (Autosomal dominant polycystic kidney disease)

External Links

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

Food Biomarker Ontology

Not Available

VMH ID

GLU_D

MarkerDB ID

MDB00000422

Good Scents ID

Not Available

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)

Download (PDF)

General References

Emi M, Wilson DE, Iverius PH, Wu L, Hata A, Hegele R, Williams RR, Lalouel JM: Missense mutation (Gly----Glu188) of human lipoprotein lipase imparting functional deficiency. J Biol Chem. 1990 Apr 5;265(10):5910-6. [PubMed:1969408 ]
Persson H, Pelto-Huikko M, Metsis M, Soder O, Brene S, Skog S, Hokfelt T, Ritzen EM: Expression of the neurotransmitter-synthesizing enzyme glutamic acid decarboxylase in male germ cells. Mol Cell Biol. 1990 Sep;10(9):4701-11. [PubMed:1697032 ]
Ahlman B, Andersson K, Leijonmarck CE, Ljungqvist O, Hedenborg L, Wernerman J: Short-term starvation alters the free amino acid content of the human intestinal mucosa. Clin Sci (Lond). 1994 Jun;86(6):653-62. [PubMed:7914846 ]
Wang M, Meng Z, Fu J: Synthesis and biodistribution of six novel 99mTc complexes of 2-hydroxybenzaldehyde-amino acid Schiff bases. Appl Radiat Isot. 2006 Feb;64(2):235-40. [PubMed:16309915 ]
Majid SM, Liss AS, You M, Bose HR: The suppression of SH3BGRL is important for v-Rel-mediated transformation. Oncogene. 2006 Feb 2;25(5):756-68. [PubMed:16186799 ]
Canal N, Nemni R: Autoimmunity and diabetic neuropathy. Clin Neurosci. 1997;4(6):371-3. [PubMed:9358982 ]
Danke NA, Koelle DM, Yee C, Beheray S, Kwok WW: Autoreactive T cells in healthy individuals. J Immunol. 2004 May 15;172(10):5967-72. [PubMed:15128778 ]
Guariso G, Brotto F, Basso D, Alaggio R, Betterle C: Organ-specific autoantibodies in children with Helicobacter pylori infection. Helicobacter. 2004 Dec;9(6):622-8. [PubMed:15610075 ]
Nagai A, Suzuki Y, Baek SY, Lee KS, Lee MC, McLarnon JG, Kim SU: Generation and characterization of human hybrid neurons produced between embryonic CNS neurons and neuroblastoma cells. Neurobiol Dis. 2002 Oct;11(1):184-98. [PubMed:12460557 ]
Mally MI, Cirulli V, Hayek A, Otonkoski T: ICA69 is expressed equally in the human endocrine and exocrine pancreas. Diabetologia. 1996 Apr;39(4):474-80. [PubMed:8777998 ]
Maechler P, Gjinovci A, Wollheim CB: Implication of glutamate in the kinetics of insulin secretion in rat and mouse perfused pancreas. Diabetes. 2002 Feb;51 Suppl 1:S99-102. [PubMed:11815466 ]
Nielsen C, Hansen D, Husby S, Jacobsen BB, Lillevang ST: No allelic variation in genes with high gliadin homology in patients with celiac disease and type 1 diabetes. Immunogenetics. 2004 Aug;56(5):375-8. Epub 2004 Aug 7. [PubMed:15309343 ]
Luo J, Kaplitt MG, Fitzsimons HL, Zuzga DS, Liu Y, Oshinsky ML, During MJ: Subthalamic GAD gene therapy in a Parkinson's disease rat model. Science. 2002 Oct 11;298(5592):425-9. [PubMed:12376704 ]
Meyer W, Poehling HM, Neurand K: Intraepidermal distribution of free amino acids in porcine skin. J Dermatol Sci. 1991 Sep;2(5):383-92. [PubMed:1742249 ]
Cuervo JH, Rodriguez B, Houghten RA: The Magainins: sequence factors relevant to increased antimicrobial activity and decreased hemolytic activity. Pept Res. 1988 Nov-Dec;1(2):81-6. [PubMed:2980783 ]
Roll U, Scheeser J, Standl E, Ziegler AG: Alterations of lymphocyte subsets in children of diabetic mothers. Diabetologia. 1994 Nov;37(11):1132-41. [PubMed:7867885 ]
Bill JR, Mack DG, Falta MT, Maier LA, Sullivan AK, Joslin FG, Martin AK, Freed BM, Kotzin BL, Fontenot AP: Beryllium presentation to CD4+ T cells is dependent on a single amino acid residue of the MHC class II beta-chain. J Immunol. 2005 Nov 15;175(10):7029-37. [PubMed:16272364 ]
Raj D, Langford M, Krueger S, Shelton M, Welbourne T: Regulatory responses to an oral D-glutamate load: formation of D-pyrrolidone carboxylic acid in humans. Am J Physiol Endocrinol Metab. 2001 Feb;280(2):E214-20. [PubMed:11158923 ]
Zareian M, Ebrahimpour A, Bakar FA, Mohamed AK, Forghani B, Ab-Kadir MS, Saari N: A glutamic acid-producing lactic acid bacteria isolated from Malaysian fermented foods. Int J Mol Sci. 2012;13(5):5482-97. doi: 10.3390/ijms13055482. Epub 2012 May 7. [PubMed:22754309 ]

Enzymes

Enzyme Details

1. Glutaminase liver isoform, mitochondrial

General function:: Involved in glutaminase activity
Specific function:: Plays an important role in the regulation of glutamine catabolism. Promotes mitochondrial respiration and increases ATP generation in cells by catalyzing the synthesis of glutamate and alpha-ketoglutarate. Increases cellular anti-oxidant function via NADH and glutathione production. May play a role in preventing tumor proliferation.
Gene Name:: GLS2
Uniprot ID:: Q9UI32
Molecular weight:: 66322.225

Reactions

D-Glutamine + Water → D-Glutamic acid + Ammonia	details

Enzyme Details

2. Glutaminase kidney isoform, mitochondrial

General function:: Involved in glutaminase activity
Specific function:: Catalyzes the first reaction in the primary pathway for the renal catabolism of glutamine. Plays a role in maintaining acid-base homeostasis. Regulates the levels of the neurotransmitter glutamate in the brain. Isoform 2 lacks catalytic activity.
Gene Name:: GLS
Uniprot ID:: O94925
Molecular weight:: 65459.525

Reactions

D-Glutamine + Water → D-Glutamic acid + Ammonia	details

Showing metabocard for D-Glutamic acid (HMDB0003339)

MOL for HMDB0003339 (D-Glutamic acid)

3D MOL for HMDB0003339 (D-Glutamic acid)

3D SDF for HMDB0003339 (D-Glutamic acid)

3D-SDF for HMDB0003339 (D-Glutamic acid)

PDB for HMDB0003339 (D-Glutamic acid)

3D PDB for HMDB0003339 (D-Glutamic acid)

SMILES for HMDB0003339 (D-Glutamic acid)

INCHI for HMDB0003339 (D-Glutamic acid)

Structure for HMDB0003339 (D-Glutamic acid)

3D Structure for HMDB0003339 (D-Glutamic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

Reactions

Reactions