Metabolite page

Showing information for HMDB0000208 ('2-oxoglutarate', '2-ketoglutaric acid', 'alpha-ketoglutarate', 'alpha-ketoglutaric acid')

Metabolite information
HMDB ID	HMDB0000208
Synonyms	2-Ketoglutarate 2-Ketoglutaric acid 2-Oxoglutarate 2-Oxoglutaric acid 2-Oxopentanedioate 2-Oxopentanedioic acid 2-oxo-1,5-Pentanedioate 2-oxo-1,5-Pentanedioic acid Aerobic glycolysis Calcium alpha-ketoglutarate Calcium ketoglutarate Csf Cucurbits Cytoplasma Digestion Er Extracellular region Faecal Faeces Fauna Fecal Flora Gourds Gramineae Legume Oxoglutarate Papilionoideae Peroxisomal Peroxisome vesicle Soy Soya Soya bean Soybean Stool a-Ketoglutarate a-Ketoglutaric acid alpha-Ketoglutarate alpha-Ketoglutaric acid alpha-Ketoglutaric acid, calcium salt [2:1] alpha-Ketoglutaric acid, diammonium salt alpha-Ketoglutaric acid, dipotassium salt alpha-Ketoglutaric acid, disodium salt alpha-Ketoglutaric acid, monopotassium salt alpha-Ketoglutaric acid, monosodium salt alpha-Ketoglutaric acid, potassium salt alpha-Ketoglutaric acid, sodium salt alpha-Oxoglutarate α-ketoglutarate α-ketoglutaric acid
Chemical formula	C5H6O5
IUPAC name	2-oxopentanedioic acid
CAS registry number	328-50-7
Monisotopic molecular weight	146.021523302
Chemical taxonomy
Super class	Organic acids and derivatives
Class	Keto acids and derivatives
Sub class	Gamma-keto acids and derivatives
Biological properties
Pahtways	2-Hydroxyglutric Aciduria [D And L Form] 2-Methyl-3-Hydroxybutryl CoA Dehydrogenase Deficiency 2-aminoadipic 2-oxoadipic aciduria 2-ketoglutarate dehydrogenase complex deficiency 3-Hydroxy-3-Methylglutaryl-CoA Lyase Deficiency 3-Methylcrotonyl Coa Carboxylase Deficiency Type I 3-Methylglutaconic Aciduria Type I 3-Methylglutaconic Aciduria Type III 3-Methylglutaconic Aciduria Type IV 3-Phosphoglycerate dehydrogenase deficiency 3-hydroxyisobutyric acid dehydrogenase deficiency 3-hydroxyisobutyric aciduria 4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase Deficiency Alanine Metabolism Alkaptonuria Ammonia Recycling Arginine and Proline Metabolism Arginine: Glycine Amidinotransferase Deficiency [AGAT Deficiency] Argininemia Argininosuccinic Aciduria Aspartate Metabolism Beta-Alanine Metabolism Beta-Ketothiolase Deficiency Beta-mercaptolactate-cysteine disulfiduria Canavan Disease Carbamoyl Phosphate Synthetase Deficiency Carnitine Synthesis Carnosinuria, carnosinemia Citric Acid Cycle Citrullinemia Type I Congenital lactic acidosis Creatine deficiency, guanidinoacetate methyltransferase deficiency Cysteine Metabolism Cystinosis, ocular nonnephropathic Dihydropyrimidine Dehydrogenase Deficiency [DHPD] Dimethylglycine Dehydrogenase Deficiency Dimethylglycine Dehydrogenase Deficiency Disulfiram Action Pathway Dopamine beta-hydroxylase deficiency Fructose-1,6-diphosphatase deficiency Fumarase deficiency GABA-Transaminase Deficiency Gluconeogenesis Glucose-Alanine Cycle Glutamate Metabolism Glutaminolysis and Cancer Glutaric Aciduria Type I Glycine and Serine Metabolism Glycogen Storage Disease Type 1A [GSD1A] or Von Gierke Disease Glycogenosis, Type IA. Von gierke disease Glycogenosis, Type IB Glycogenosis, Type IC Guanidinoacetate Methyltransferase Deficiency [GAMT Deficiency] Hawkinsinuria Homocarnosinosis Hyperglycinemia, non-ketotic Hyperinsulinism-Hyperammonemia Syndrome Hyperlysinemia I, Familial Hyperlysinemia II or Saccharopinuria Hyperornithinemia with gyrate atrophy [HOGA] Hyperornithinemia-hyperammonemia-homocitrullinuria [HHH-syndrome] Hyperprolinemia Type I Hyperprolinemia Type II Hypoacetylaspartia Isobutyryl-coa dehydrogenase deficiency Isovaleric Aciduria Isovaleric acidemia L-arginine:glycine amidinotransferase deficiency Lactic Acidemia Lysine Degradation Malate-Aspartate Shuttle Malonic Aciduria Malonyl-coa decarboxylase deficiency Maple Syrup Urine Disease Methylmalonate Semialdehyde Dehydrogenase Deficiency Methylmalonic Aciduria Methylmalonic Aciduria Due to Cobalamin-Related Disorders Mitochondrial complex II deficiency Monoamine oxidase-a deficiency [MAO-A] Non Ketotic Hyperglycinemia Ornithine Aminotransferase Deficiency [OAT Deficiency] Ornithine Transcarbamylase Deficiency [OTC Deficiency] Oxidation of Branched Chain Fatty Acids Phenylalanine and Tyrosine Metabolism Phenylketonuria Phosphoenolpyruvate carboxykinase deficiency 1 [PEPCK1] Phytanic Acid Peroxisomal Oxidation Primary Hyperoxaluria Type I Prolidase Deficiency [PD] Prolinemia Type II Propanoate Metabolism Propionic Acidemia Pyridoxine dependency with seizures Pyruvate Carboxylase Deficiency Pyruvate dehydrogenase deficiency [E2] Pyruvate dehydrogenase deficiency [E3] Refsum Disease Saccharopinuria/Hyperlysinemia II Sarcosinemia Succinic semialdehyde dehydrogenase deficiency The Oncogenic Action of Fumarate The Oncogenic Action of Succinate The oncogenic action of 2-hydroxyglutarate The oncogenic action of D-2-hydroxyglutarate in Hydroxygluaricaciduria The oncogenic action of L-2-hydroxyglutarate in Hydroxygluaricaciduria Triosephosphate isomerase Tryptophan Metabolism Tyrosine Metabolism Tyrosinemia Type 2 [or Richner-Hanhart syndrome] Tyrosinemia Type 3 [TYRO3] Tyrosinemia Type I Tyrosinemia, transient, of the newborn Urea Cycle Ureidopropionase Deficiency Valine, Leucine and Isoleucine Degradation Warburg Effect
Author-emphasized biomarker in the paper(s)

Lung cancer metabolomics studies that identify HMDB0000208 ('2-oxoglutarate', '2-ketoglutaric acid', 'alpha-ketoglutarate', 'alpha-ketoglutaric acid')

Reference	Country	Specimen	Marker function	Participants (Case)						Participants (Control)
Reference	Country	Specimen	Marker function	Cancer type	Stage	Number	Gender (M,F)	Age mean (range) (M/F)	Smoking status	Type	Number	Gender (M,F)	Age mean (range) (M/F)	Smoking status
Mazzone et al. 2016	–	serum	–	adenocarcinoma, squamous cell carcinoma	I, II, III	94	55.3%, 44.7%	68.7	–	at-risk controls	190	50.5%, 49.5%	66.2	–
Moreno et al. 2018	–	tissue	therapy, diagnosis	squamous cell carcinoma	I, II, III	35	35, 0	68.71 ± 7.46	–	tumor vs. adjacent normal tissue	35	35, 0	68.71 ± 7.46	–
Hori et al. 2011	–	tissue	diagnosis	adenocarcinoma, squamous cell carcinoma, SCLC	–	7	6, 1	median: 61 (53-82)	smoker, non-smoker	tumor vs. adjacent normal tissue	7	6, 1	median: 61 (53-82)	smoker, non-smoker
Miyamoto et al. 2015	–	blood	diagnosis	NSCLC, SCLC, mesothelioma, secondary metastasis to lung	I, II, III, IV	11	4, 7	67 (61-73) / 67 (47-76)	smoker, non-smoker	healthy	11	5, 6	69 (61-83) / 54 (44-61)	unknown
Hao et al. 2016	–	serum	diagnosis	lung cancer	I, II, III, IV	25	15, 10	64 (42–77)	smoker, non-smoker	before vs. after treatment (radiation treatment)	–	–	–	smoker, non-smoker
Wikoff et al. 2015b	–	tissue	diagnosis	adenocarcinoma	I	39	15, 24	72.33 ± 8.78	smoker, non-smoker	tumor vs. adjacent normal tissue	39	15, 24	72.33 ± 8.78	smoker, non-smoker

Reference	Chromatography	Ion source	Positive/Negative mode	Mass analyzer	Identification level
Mazzone et al. 2016	GC	EI	–	quadrupole	MS/MS
Moreno et al. 2018	LC, GC	ESI, EI	positive, negative	LC: linear ion‐trap, GC: single‐quadrupole	LC: MS/MS
Hori et al. 2011	GC	–	–	–	–
Miyamoto et al. 2015	GC	EI	–	TOF	MS/MS
Hao et al. 2016	–	–	–	NMR	–
Wikoff et al. 2015b	GC	EI	–	TOF	–

Reference	Data processing software	Database search
Mazzone et al. 2016	Metabolon LIMS system	Metabolon LIMS system
Moreno et al. 2018	–	KEGG, HMDB
Hori et al. 2011	Shimadzu GCMSsolution software	commercially available GC/MS Metabolite Mass Spectral Database (Shimadzu Co.), NIST Mass Spectral Library (NIST 08)
Miyamoto et al. 2015	ChromaTOF software (Leco)	UC Davis Metabolomics BinBase database
Hao et al. 2016	Chenomx NMR Suite 7.1, Metabolite Detector	–
Wikoff et al. 2015b	BinBase	NIST11, BinBase

Differential analysis
Classification analysis

Reference	Difference method	Mean concentration (case)	Mean concentration (control)	Fold change (case/control)	P-value	FDR	VIP
Mazzone et al. 2016	two- sample independent t test	0.9707989± 0.6326111	0.9231879± 0.5633581	1.05157238304358	0.5202245	0.586078412	–
Moreno et al. 2018	paired two‐sample t‐test, PLS-DA	–	–	1.06858899501538	0.363377465100949	0.403865204945065	–
Hori et al. 2011	student’s t-test, PLS-DA	–	–	0.84	0.324	–	–
Miyamoto et al. 2015	Analysis of Covariance	564.090909090909	653.545454545455	0.863124217554597	0.304053298911539	–	–
Hao et al. 2016	OPLS-DA, CV-ANOVA	–	–	–	–	–	–
Wikoff et al. 2015b	OPLS-DA	–	–	1	–	0.845	–

Reference	Classification method	Cutoff value	AUROC 95%CI	Sensitivity (%)	Specificity (%)	Accuracy (%)
Mazzone et al. 2016	–	–	–	–	–	–
Moreno et al. 2018	–	–	–	–	–	–
Hori et al. 2011	–	–	–	–	–	–
Miyamoto et al. 2015	–	–	–	–	–	–
Hao et al. 2016	–	–	–	–	–	–
Wikoff et al. 2015b	–	–	–	–	–	–