ContaminantDB: Oxoglutaric acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (1)XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:03:30 UTC

Update Date

2026-04-14 17:32:46 UTC

Accession Number

CHEM003209

Identification

Common Name

Oxoglutaric acid

Class

Small Molecule

Description

Alpha-ketoglutaric acid is an important biological compound and is a key intermediate in the Krebs cycle. Alpha-ketoglutaric acid occurs naturally within cells. One of its functions is to combine with ammonia to form glutamic acid and then glutamine. Another function is to combine with nitrogen released in the cell, therefore preventing nitrogen overload. .

Contaminant Sources

EAFUS Chemicals
FooDB Chemicals
HMDB Contaminants - Feces
HMDB Contaminants - Urine
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Animal Toxin
Food Toxin
Metabolite
Natural Compound
Organic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
2-Ketoglutaric acid	ChEBI
alpha-Ketoglutaric acid	ChEBI
2-Ketoglutarate	Generator
a-Ketoglutarate	Generator
a-Ketoglutaric acid	Generator
alpha-Ketoglutarate	Generator
Α-ketoglutarate	Generator
Α-ketoglutaric acid	Generator
Oxoglutarate	Generator
2-oxo-1,5-Pentanedioate	HMDB
2-oxo-1,5-Pentanedioic acid	HMDB
2-Oxoglutarate	HMDB
2-Oxoglutaric acid	HMDB
2-Oxopentanedioate	HMDB
2-Oxopentanedioic acid	HMDB
alpha-Oxoglutarate	HMDB
Oxogluric acid	HMDB
2 Oxoglutaric acid	HMDB
Ketoglutaric acid	HMDB
alpha Ketoglutaric acid	HMDB
2 Ketoglutaric acid	HMDB
alpha Ketoglutarate	HMDB
alpha Oxoglutarate	HMDB
2 Ketoglutarate	HMDB
2 Oxoglutarate	HMDB
alpha-Oxoglutaric acid	HMDB
alpha-Oxopentanedioic acid	HMDB
alpha-Keto-glutaric acid	HMDB
Α-oxoglutaric acid	HMDB
Α-oxopentanedioic acid	HMDB
Α-keto-glutaric acid	HMDB

Chemical Formula

C₅H₆O₅

Average Molecular Mass

146.098 g/mol

Monoisotopic Mass

146.022 g/mol

CAS Registry Number

328-50-7

IUPAC Name

2-oxopentanedioic acid

Traditional Name

oxoglutarate

SMILES

OC(=O)CCC(=O)C(O)=O

InChI Identifier

InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)

InChI Key

KPGXRSRHYNQIFN-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Gamma-keto acids and derivatives

Direct Parent

Gamma-keto acids and derivatives

Alternative Parents

Substituents

Gamma-keto acid
Short-chain keto acid
Dicarboxylic acid or derivatives
Alpha-keto acid
Alpha-hydroxy ketone
Ketone
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

oxo dicarboxylic acid (CHEBI:30915 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Endoplasmic reticulum
Extracellular
Mitochondria
Peroxisome

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Alanine Metabolism	SMP00055	map00250
Ammonia Recycling	SMP00009	map00910
Carnitine Synthesis	SMP00465	Not Available
Citric Acid Cycle	SMP00057	map00020
Gluconeogenesis	SMP00128	Not Available
Glucose-Alanine Cycle	SMP00127	Not Available
Glutamate Metabolism	SMP00072	map00250
Glycine and Serine Metabolism	SMP00004	map00260
Malate-Aspartate Shuttle	SMP00129	Not Available
Phytanic Acid Peroxisomal Oxidation	SMP00450	Not Available
Urea Cycle	SMP00059	Not Available
2-Hydroxyglutric Aciduria (D And L Form)	SMP00136	Not Available
2-ketoglutarate dehydrogenase complex deficiency	SMP00549	Not Available
Fumarase deficiency	SMP00547	Not Available
Pyruvate Carboxylase Deficiency	SMP00350	Not Available
Pyruvate dehydrogenase deficiency (E3)	SMP00550	Not Available

Applications

Not Available

Biological Roles

metabolite

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	115.5°C
Boiling Point	Not Available
Solubility	541.5 mg/mL

Predicted Properties

Property	Value	Source
Water Solubility	53.1 g/L	ALOGPS
logP	-0.6	ALOGPS
logP	-0.11	ChemAxon
logS	-0.44	ALOGPS
pKa (Strongest Acidic)	2.66	ChemAxon
pKa (Strongest Basic)	-9.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.67 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	28.88 m³·mol⁻¹	ChemAxon
Polarizability	12.17 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-000b-3910000000-4097b7eb52c2910a4277	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0002-1910000000-3277227b9c4da4baa1f7	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS; 1 MEOX)	splash10-00di-9300000000-974bce546caa4fbe6b0f	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)	splash10-000i-9710000000-d0aea11e947b042571f9	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)	splash10-052s-4920000000-bf7ed92c68fd4c8dbb6b	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000b-3910000000-4097b7eb52c2910a4277	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-1910000000-3277227b9c4da4baa1f7	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9300000000-974bce546caa4fbe6b0f	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-000i-9710000000-d0aea11e947b042571f9	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-052s-4920000000-bf7ed92c68fd4c8dbb6b	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000b-2900000000-e514f7afea2490bbe9ed	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kfx-9200000000-0ee77a39e9862659f8a7	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00di-9730000000-5e17bd8cfd944963c79f	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0zfr-6900000000-7fc343a243ce5d2a4f39	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0a4i-9200000000-1a7af9946604baa8b3d2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0a4l-9800000000-30495b2afdd3526854e7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0002-0925200000-af33449c9638276466c2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4i-9000000000-6e43f767847790112b65	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03di-0900000000-4cacc41705b7b385e91e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0udi-0900000000-1367eeeb6ad64c67a0aa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-000t-0915051100-91cda631ee54800322b8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4i-9000000000-4f842c3673925d29c402	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0udi-0900000000-5e751351656f6eb62de3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0910000000-7729faa24733fbad77b7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0002-0900000000-c3c62f83bff99f44f7ab	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0zfr-6900000000-b6d8379db3e3f1480b14	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0a4i-9300000000-4fde39bb93cde5a27f23	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-00i0-9000000000-4343832f3a55842423a9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-2900000000-5aa3d6d620db1d733a65	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0m30-7900000000-fc77f69ad43f915bf23e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9000000000-c597f1f5e416037aa82d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-2900000000-5aa3d6d620db1d733a65	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0m30-7900000000-fc77f69ad43f915bf23e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9000000000-c597f1f5e416037aa82d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-1900000000-f2b463076a150a514f0c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f9t-8900000000-b2d3fa8d7ab01a220d9a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-053r-9100000000-554bfbd6839bc376cba0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-1900000000-f2b463076a150a514f0c	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0fba-9200000000-4e367c66e94c51eb1a1b	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum