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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

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:47 UTC

HMDB ID

HMDB0001552

Secondary Accession Numbers

HMDB01552

Metabolite Identification

Common Name

2-Keto-glutaramic acid

Description

2-Keto-glutaramic acid, also known as 2-ketoglutaramate, belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms. 2-Keto-glutaramic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Keto-glutaramic acid exists in all living species, ranging from bacteria to humans. Outside of the human body, 2-Keto-glutaramic acid has been detected, but not quantified in, milk (cow). This could make 2-keto-glutaramic acid a potential biomarker for the consumption of these foods. deaminated metabolite of glutamine in csf of patients with hepatic coma; intermediate in the detoxification of ammonia in brain; structure.

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-Ketoglutaramate	ChEBI
alpha-Ketoglutaramate	ChEBI
2-Ketoglutaramic acid	Generator
2-keto-Glutaramate	Generator, HMDB
a-Ketoglutaramate	Generator
a-Ketoglutaramic acid	Generator
alpha-Ketoglutaramic acid	Generator
α-Ketoglutaramate	Generator
α-Ketoglutaramic acid	Generator
2-Oxoglutaramate	HMDB, Generator
2-Oxoglutaramic acid	KEGG
4-Oxoglutaramic acid	HMDB
5-Amino-2,5-dioxopentanoic acid	HMDB

Chemical Formula

C₅H₇NO₄

Average Molecular Weight

145.1134

Monoisotopic Molecular Weight

145.037507717

IUPAC Name

4-carbamoyl-2-oxobutanoic acid

Traditional Name

2-keto-glutaramate

CAS Registry Number

18465-19-5

SMILES

NC(=O)CCC(=O)C(O)=O

InChI Identifier

InChI=1S/C5H7NO4/c6-4(8)2-1-3(7)5(9)10/h1-2H2,(H2,6,8)(H,9,10)

InChI Key

COJBGNAUUSNXHX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Short-chain keto acids and derivatives

Direct Parent

Short-chain keto acids and derivatives

Alternative Parents

Substituents

Short-chain keto acid
Alpha-keto acid
Fatty acyl
Fatty amide
Alpha-hydroxy ketone
Carboxamide group
Primary carboxylic acid amide
Ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-oxo monocarboxylic acid (CHEBI:30882 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Source

Endogenous

Endogenous (HMDB: HMDB0001552)

Exogenous

Food

Food (HMDB: HMDB0001552)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Exogenous (HMDB: HMDB0001552)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0001552)

Role

Biological role

Energy source (HMDB: HMDB0001552)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0001552)

Physical Properties

State

Solid

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	26.7 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-0.92	ChemAxon
logS	-0.74	ALOGPS
pKa (Strongest Acidic)	2.97	ChemAxon
pKa (Strongest Basic)	-1.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	97.46 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	30.71 m³·mol⁻¹	ChemAxon
Polarizability	12.56 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]+	131.798	31661259
DarkChem	[M-H]-	126.113	31661259
AllCCS	[M+H]+	132.558	32859911
AllCCS	[M-H]-	126.156	32859911
DeepCCS	[M+H]+	126.584	30932474
DeepCCS	[M-H]-	123.355	30932474
DeepCCS	[M-2H]-	160.27	30932474
DeepCCS	[M+Na]+	135.23	30932474
AllCCS	[M+H]+	132.6	32859911
AllCCS	[M+H-H2O]+	128.5	32859911
AllCCS	[M+NH4]+	136.3	32859911
AllCCS	[M+Na]+	137.4	32859911
AllCCS	[M-H]-	126.2	32859911
AllCCS	[M+Na-2H]-	128.3	32859911
AllCCS	[M+HCOO]-	130.7	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.	1.59 minutes	32390414
Predicted by Siyang on May 30, 2022	8.8871 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.96 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	226.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	738.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	304.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	68.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	185.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	59.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	244.5 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	256.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	698.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	579.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	54.2 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	747.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	197.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	189.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	609.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	393.4 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	304.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Keto-glutaramic acid	NC(=O)CCC(=O)C(O)=O	2031.0	Standard polar	33892256
2-Keto-glutaramic acid	NC(=O)CCC(=O)C(O)=O	1454.4	Standard non polar	33892256
2-Keto-glutaramic acid	NC(=O)CCC(=O)C(O)=O	1494.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Keto-glutaramic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C(=O)CCC(N)=O	1537.2	Semi standard non polar	33892256
2-Keto-glutaramic acid,1TMS,isomer #2	C[Si](C)(C)OC(=CCC(N)=O)C(=O)O	1602.5	Semi standard non polar	33892256
2-Keto-glutaramic acid,1TMS,isomer #3	C[Si](C)(C)NC(=O)CCC(=O)C(=O)O	1584.0	Semi standard non polar	33892256
2-Keto-glutaramic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(=CCC(N)=O)O[Si](C)(C)C	1661.9	Semi standard non polar	33892256
2-Keto-glutaramic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(=CCC(N)=O)O[Si](C)(C)C	1596.2	Standard non polar	33892256
2-Keto-glutaramic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(=CCC(N)=O)O[Si](C)(C)C	2412.7	Standard polar	33892256
2-Keto-glutaramic acid,2TMS,isomer #2	C[Si](C)(C)NC(=O)CCC(=O)C(=O)O[Si](C)(C)C	1630.7	Semi standard non polar	33892256
2-Keto-glutaramic acid,2TMS,isomer #2	C[Si](C)(C)NC(=O)CCC(=O)C(=O)O[Si](C)(C)C	1638.7	Standard non polar	33892256
2-Keto-glutaramic acid,2TMS,isomer #2	C[Si](C)(C)NC(=O)CCC(=O)C(=O)O[Si](C)(C)C	1977.0	Standard polar	33892256
2-Keto-glutaramic acid,2TMS,isomer #3	C[Si](C)(C)NC(=O)CC=C(O[Si](C)(C)C)C(=O)O	1728.0	Semi standard non polar	33892256
2-Keto-glutaramic acid,2TMS,isomer #3	C[Si](C)(C)NC(=O)CC=C(O[Si](C)(C)C)C(=O)O	1805.4	Standard non polar	33892256
2-Keto-glutaramic acid,2TMS,isomer #3	C[Si](C)(C)NC(=O)CC=C(O[Si](C)(C)C)C(=O)O	2148.8	Standard polar	33892256
2-Keto-glutaramic acid,2TMS,isomer #4	C[Si](C)(C)N(C(=O)CCC(=O)C(=O)O)[Si](C)(C)C	1769.5	Semi standard non polar	33892256
2-Keto-glutaramic acid,2TMS,isomer #4	C[Si](C)(C)N(C(=O)CCC(=O)C(=O)O)[Si](C)(C)C	1686.6	Standard non polar	33892256
2-Keto-glutaramic acid,2TMS,isomer #4	C[Si](C)(C)N(C(=O)CCC(=O)C(=O)O)[Si](C)(C)C	2219.7	Standard polar	33892256
2-Keto-glutaramic acid,3TMS,isomer #1	C[Si](C)(C)NC(=O)CC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1751.3	Semi standard non polar	33892256
2-Keto-glutaramic acid,3TMS,isomer #1	C[Si](C)(C)NC(=O)CC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1728.2	Standard non polar	33892256
2-Keto-glutaramic acid,3TMS,isomer #1	C[Si](C)(C)NC(=O)CC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1857.5	Standard polar	33892256
2-Keto-glutaramic acid,3TMS,isomer #2	C[Si](C)(C)OC(=O)C(=O)CCC(=O)N([Si](C)(C)C)[Si](C)(C)C	1740.9	Semi standard non polar	33892256
2-Keto-glutaramic acid,3TMS,isomer #2	C[Si](C)(C)OC(=O)C(=O)CCC(=O)N([Si](C)(C)C)[Si](C)(C)C	1685.2	Standard non polar	33892256
2-Keto-glutaramic acid,3TMS,isomer #2	C[Si](C)(C)OC(=O)C(=O)CCC(=O)N([Si](C)(C)C)[Si](C)(C)C	1823.0	Standard polar	33892256
2-Keto-glutaramic acid,3TMS,isomer #3	C[Si](C)(C)OC(=CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	1835.1	Semi standard non polar	33892256
2-Keto-glutaramic acid,3TMS,isomer #3	C[Si](C)(C)OC(=CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	1896.0	Standard non polar	33892256
2-Keto-glutaramic acid,3TMS,isomer #3	C[Si](C)(C)OC(=CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	1993.7	Standard polar	33892256
2-Keto-glutaramic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(=CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	1816.9	Semi standard non polar	33892256
2-Keto-glutaramic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(=CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	1817.6	Standard non polar	33892256
2-Keto-glutaramic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(=CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	1752.0	Standard polar	33892256
2-Keto-glutaramic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=O)CCC(N)=O	1794.2	Semi standard non polar	33892256
2-Keto-glutaramic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=CCC(N)=O)C(=O)O	1865.0	Semi standard non polar	33892256
2-Keto-glutaramic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(=O)CCC(=O)C(=O)O	1849.7	Semi standard non polar	33892256
2-Keto-glutaramic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=CCC(N)=O)O[Si](C)(C)C(C)(C)C	2126.6	Semi standard non polar	33892256
2-Keto-glutaramic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=CCC(N)=O)O[Si](C)(C)C(C)(C)C	1981.8	Standard non polar	33892256
2-Keto-glutaramic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=CCC(N)=O)O[Si](C)(C)C(C)(C)C	2455.7	Standard polar	33892256
2-Keto-glutaramic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)CCC(=O)C(=O)O[Si](C)(C)C(C)(C)C	2094.5	Semi standard non polar	33892256
2-Keto-glutaramic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)CCC(=O)C(=O)O[Si](C)(C)C(C)(C)C	2027.3	Standard non polar	33892256
2-Keto-glutaramic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)CCC(=O)C(=O)O[Si](C)(C)C(C)(C)C	2148.1	Standard polar	33892256
2-Keto-glutaramic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(=O)CC=C(O[Si](C)(C)C(C)(C)C)C(=O)O	2185.7	Semi standard non polar	33892256
2-Keto-glutaramic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(=O)CC=C(O[Si](C)(C)C(C)(C)C)C(=O)O	2169.9	Standard non polar	33892256
2-Keto-glutaramic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(=O)CC=C(O[Si](C)(C)C(C)(C)C)C(=O)O	2257.7	Standard polar	33892256
2-Keto-glutaramic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C(=O)CCC(=O)C(=O)O)[Si](C)(C)C(C)(C)C	2220.1	Semi standard non polar	33892256
2-Keto-glutaramic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C(=O)CCC(=O)C(=O)O)[Si](C)(C)C(C)(C)C	2106.6	Standard non polar	33892256
2-Keto-glutaramic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C(=O)CCC(=O)C(=O)O)[Si](C)(C)C(C)(C)C	2236.2	Standard polar	33892256
2-Keto-glutaramic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)CC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2391.3	Semi standard non polar	33892256
2-Keto-glutaramic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)CC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2250.1	Standard non polar	33892256
2-Keto-glutaramic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)CC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2215.0	Standard polar	33892256
2-Keto-glutaramic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(=O)CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2420.3	Semi standard non polar	33892256
2-Keto-glutaramic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(=O)CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2312.6	Standard non polar	33892256
2-Keto-glutaramic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(=O)CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2187.4	Standard polar	33892256
2-Keto-glutaramic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	2489.7	Semi standard non polar	33892256
2-Keto-glutaramic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	2416.6	Standard non polar	33892256
2-Keto-glutaramic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	2280.1	Standard polar	33892256
2-Keto-glutaramic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2668.8	Semi standard non polar	33892256
2-Keto-glutaramic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2508.7	Standard non polar	33892256
2-Keto-glutaramic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2225.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Keto-glutaramic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6x-9300000000-364f00f83f2890864bf3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Keto-glutaramic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0uk9-9600000000-f15721df49885ecdf65e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Keto-glutaramic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Keto-glutaramic acid 10V, Positive-QTOF	splash10-004i-1900000000-2eb098e06d8301b0bce6	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Keto-glutaramic acid 20V, Positive-QTOF	splash10-06w9-6900000000-d802d6bf63187e0b9714	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Keto-glutaramic acid 40V, Positive-QTOF	splash10-0ab9-9000000000-0aaaa6f3f4d3183b6b21	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Keto-glutaramic acid 10V, Negative-QTOF	splash10-0006-2900000000-c4ab5bdf984680f19900	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Keto-glutaramic acid 20V, Negative-QTOF	splash10-0f96-9800000000-6a2a8c2f9da457c041c2	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Keto-glutaramic acid 40V, Negative-QTOF	splash10-0006-9000000000-76ca31bd526f5a4086c8	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Keto-glutaramic acid 10V, Negative-QTOF	splash10-0udl-5900000000-bfedace6bca6e0663444	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Keto-glutaramic acid 20V, Negative-QTOF	splash10-0006-9100000000-0a497925699a66249231	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Keto-glutaramic acid 40V, Negative-QTOF	splash10-0006-9000000000-90726b17dc36e29c5299	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Keto-glutaramic acid 10V, Positive-QTOF	splash10-0fbc-6900000000-a420c6f7f5db4cb58165	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Keto-glutaramic acid 20V, Positive-QTOF	splash10-0ac3-9100000000-e9bdcc615e9a7032177c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Keto-glutaramic acid 40V, Positive-QTOF	splash10-0k97-9000000000-02445ea4ef20f8ea72fb	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

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	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022686

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

C00940

BioCyc ID

2-KETO-GLUTARAMATE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6318

PubChem Compound

PDB ID

Not Available

ChEBI ID

30882

Food Biomarker Ontology

Not Available

VMH ID

HC00591

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Lalonde, James J. Synthesis of 2-oxoglutaramate from L-glutamine. U.S. Pat. Appl. Publ. (2003), 7 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Kynurenine--oxoglutarate transaminase 1

General function:: Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:: Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Metabolizes the cysteine conjugates of certain halogenated alkenes and alkanes to form reactive metabolites. Catalyzes the beta-elimination of S-conjugates and Se-conjugates of L-(seleno)cysteine, resulting in the cleavage of the C-S or C-Se bond.
Gene Name:: CCBL1
Uniprot ID:: Q16773
Molecular weight:: 47874.765

Reactions

Glutamine + Phenylpyruvic acid → 2-Keto-glutaramic acid + Phenylalanine	details

Enzyme Details

2. Omega-amidase NIT2

General function:: Not Available
Specific function:: Has a omega-amidase activity. The role of omega-amidase is to remove potentially toxic intermediates by converting alpha-ketoglutaramate and alpha-ketosuccinamate to biologically useful alpha-ketoglutarate and oxaloacetate, respectively. Overexpression decreases the colony-forming capacity of cultured cells by arresting cells in the G2 phase of the cell cycle.
Gene Name:: NIT2
Uniprot ID:: Q9NQR4
Molecular weight:: 30607.645

Reactions

2-Keto-glutaramic acid + Water → Oxoglutaric acid + Ammonia	details

Showing metabocard for 2-Keto-glutaramic acid (HMDB0001552)

MOL for HMDB0001552 (2-Keto-glutaramic acid)

3D MOL for HMDB0001552 (2-Keto-glutaramic acid)

3D SDF for HMDB0001552 (2-Keto-glutaramic acid)

3D-SDF for HMDB0001552 (2-Keto-glutaramic acid)

PDB for HMDB0001552 (2-Keto-glutaramic acid)

3D PDB for HMDB0001552 (2-Keto-glutaramic acid)

SMILES for HMDB0001552 (2-Keto-glutaramic acid)

INCHI for HMDB0001552 (2-Keto-glutaramic acid)

Structure for HMDB0001552 (2-Keto-glutaramic acid)

3D Structure for HMDB0001552 (2-Keto-glutaramic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions