2-Oxoglutaric acid (Compound)

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ID	1974
Name	2-Oxoglutaric acid
Synonyms	Oxoglutaric acid; 2-Oxopentanedioic acid; 2-Ketoglutaric acid; alpha-Ketoglutaric acid; alpha-Ketoglutarate
Structure	MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure Structure for EE001974 (2-Oxoglutaric acid) 3D Structure for EE001974 (2-Oxoglutaric acid) 51 -OEChem-03112021433D 16 15 0 0 0 0 0 0 0999 V2000 3.7402 -0.6979 0.0666 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2693 -1.6692 -0.0205 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7936 1.3637 -0.0282 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5037 -0.3863 0.0216 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3867 1.6090 0.0221 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1517 0.3062 -0.0298 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3699 -0.6143 -0.0356 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1592 -0.4522 -0.0114 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6775 0.1465 0.0018 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4140 0.3946 0.0134 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1833 0.9525 0.8551 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1668 0.9439 -0.9210 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3614 -1.2357 -0.9383 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3362 -1.2740 0.8393 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5921 -0.2119 0.0877 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3343 0.1353 0.0369 H 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 1 15 1 0 0 0 0 2 8 2 0 0 0 0 3 9 2 0 0 0 0 4 10 1 0 0 0 0 4 16 1 0 0 0 0 5 10 2 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 6 11 1 0 0 0 0 6 12 1 0 0 0 0 7 9 1 0 0 0 0 7 13 1 0 0 0 0 7 14 1 0 0 0 0 8 10 1 0 0 0 0 M END > <PUBCHEM_COMPOUND_CID> 51 > <PUBCHEM_CONFORMER_RMSD> 0.6 > <PUBCHEM_CONFORMER_DIVERSEORDER> 1 9 18 13 7 16 19 3 15 11 10 6 17 8 14 12 5 4 2 > <PUBCHEM_MMFF94_PARTIAL_CHARGES> 12 1 -0.65 10 0.72 15 0.5 16 0.5 2 -0.57 3 -0.57 4 -0.65 5 -0.57 6 0.06 7 0.06 8 0.51 9 0.66 > <PUBCHEM_EFFECTIVE_ROTOR_COUNT> 4 > <PUBCHEM_PHARMACOPHORE_FEATURES> 7 1 1 acceptor 1 2 acceptor 1 3 acceptor 1 4 acceptor 1 5 acceptor 3 1 3 9 anion 3 4 5 10 anion > <PUBCHEM_HEAVY_ATOM_COUNT> 10 > <PUBCHEM_ATOM_DEF_STEREO_COUNT> 0 > <PUBCHEM_ATOM_UDEF_STEREO_COUNT> 0 > <PUBCHEM_BOND_DEF_STEREO_COUNT> 0 > <PUBCHEM_BOND_UDEF_STEREO_COUNT> 0 > <PUBCHEM_ISOTOPIC_ATOM_COUNT> 0 > <PUBCHEM_COMPONENT_COUNT> 1 > <PUBCHEM_CACTVS_TAUTO_COUNT> 2 > <PUBCHEM_CONFORMER_ID> 0000003300000001 > <PUBCHEM_MMFF94_ENERGY> 10.0469 > <PUBCHEM_FEATURE_SELFOVERLAP> 35.65 > <PUBCHEM_SHAPE_FINGERPRINT> 11062470 55 12031785863932512347 12162725 195 18412263934665995044 12932764 1 17632010957122701742 14144814 61 18408321060288430098 14325111 11 18410856546760181925 14390081 3 18412261744116584088 19973954 147 18337955713472426368 20645464 45 18343308037175978879 20871998 184 18128543845669867871 21028194 46 18344146977306136704 23402539 116 18272358764054883685 3248919 1 18262789778693180934 > <PUBCHEM_SHAPE_MULTIPOLES> 176.45 5.91 1.32 0.57 1.69 0.11 0 0.46 0.1 -0.28 0 0.01 0 -0.03 > <PUBCHEM_SHAPE_SELFOVERLAP> 341.128 > <PUBCHEM_SHAPE_VOLUME> 105.7 > <PUBCHEM_COORDINATE_TYPE> 2 5 10 $$$$
Description	Intermediate in the Krebs cycle.
Classification	Compounds > Chemical entities > Organic compounds > Organic acids and derivatives > Keto acids and derivatives > Gamma-keto acids and derivatives
CAS number	328-50-7
PubChem ID	51
ChEBI ID	30915
FooDB ID	FDB003361
HMDB ID	HMDB0000208

Chemical data

MolDBi data

IUPAC Name	2-oxopentanedioic acid
Traditional IUPAC Name	oxoglutarate
Formula	C5H6O5
InChI	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
Molecular weight	146.0981
Exact mass	146.021523302
SMILES	OC(=O)CCC(=O)C(O)=O

ClassyFire 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	Short-chain keto acids and derivatives Dicarboxylic acids and derivatives Alpha-keto acids and derivatives Alpha-hydroxy ketones Carboxylic acids Organic oxides Hydrocarbon derivatives

Publications with 2-Oxoglutaric acid

ID	Title	First author	Authors	Year	Journal	Volume	Issue	Pages	PubMed ID	DOI	Study design	No. of Biomarkers	No. of Intake values	No. of Concentration values	No. of Reproducibility values	No. of Correlation values	No. of Metabolomic associations	No. of Microbiota associations	No. of Cancer associations

Biomarker data

Measurements of 2-Oxoglutaric acid in biospecimens

Concentration values

ID	Parent ID	Depth	Subject group	Population	Country	Cohort	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Measurement size	Detected (nb)	Detected (%)	Detected only?	Arithmethic mean	Arithmethic SD	Geometric mean	Geometric SD	Min	Min (detected)	Percentile_05	Percentile_10	Percentile_25	Median	Percentile_75	Percentile_90	Percentile_95	Max	Interquartile range	Mean 95% CI lower	Mean 95% CI upper	GMean 95% CI lower	GMean 95% CI upper	Unit	Converted arithmetic mean	Converted geometric mean	Converted median	Converted unit	Adjustment type	Adjusted on	Regressed on	Expressed as	Publication

Reproducibility values

ID	Excretion ID	Subject group	Population	Country	Cohort	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Arithmetic mean	Geometric mean	Median	Unit	Adjusted on	Reproducibility size	ICC	ICC 95% CI lower	ICC 95% CI upper	CV% WS	CV% BS	VAR WS	VAR BS	Publication

Associations of 2-Oxoglutaric acid with exposures

Correlation values

ID	Intake ID	Excretion ID	Subject group	Population	Country	Cohort	Intake Time definition	Intake Assessment method	Intake	Intake detail	Supplement intakes included?	Intake Arithmetic mean	Intake Geometric mean	Intake Median	Intake Unit	Intake Adjusted on	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Biomarker Arithmetic mean	Biomarker Geometric mean	Biomarker Median	Biomarker Unit	Biomarker Adjusted on	Correlation size	Correlation type	Correlation value	Correlation 95% CI lower	Correlation 95% CI upper	Correlation p-value	Significant?	Measurement adjustment	Deattenuated?	Covariates	Publication

Metabolomic associations

ID	Intake ID	Excretion ID	Subject group	Population	Country	Cohort	No. of subjects	Intake Assessment method	Intake	Intervention dose	Biospecimen	Analytical method	Biomarker	Structural identification	Feature selection	Area under curve	Sensitivity	Specificity	PLS-DA VIP	Beta coefficient	Beta coefficient p-value	ANOVA p-value	Publication

Microbiota associations

ID	Biomarker	Experimental evidence	Organism	Biospecimen	Antibiotic	Bacterial source	Substrate	Publication

Associations of 2-Oxoglutaric acid with cancer risk

Cancer associations

ID	Excretion ID	Subject group	Population	Country	Cohort	No. of subjects	No. of cases	No. of controls	Biospecimen	Analytical method	Biomarker	Biomarker detail	Cancer	Study design	Publication

Exposure data

Measurements of 2-Oxoglutaric acid exposures in populations

Intake values

ID	Parent ID	Depth	Subject group	Population	Country	Cohort	Intake Time definition	Intake assessment tool	Intake food coverage	Intake time coverage	Intake Assessment method	Intake	Intake detail	Food description	Supplement intakes included?	Measurement size	Detected (nb)	Detected (%)	Detected only?	Arithmethic mean	Arithmethic SD	Geometric mean	Geometric SD	Min	Min (detected)	Percentile_05	Percentile_10	Percentile_25	Median	Percentile_75	Percentile_90	Percentile_95	Max	Interquartile range	Mean 95% CI lower	Mean 95% CI upper	GMean 95% CI lower	GMean 95% CI upper	Unit	Converted arithmetic mean	Converted geometric mean	Converted median	Converted unit	Adjustment type	Adjusted on	Regressed on	Expressed as	Publication

Associations of 2-Oxoglutaric acid exposures with biomarkers

Correlation values

ID	Intake ID	Excretion ID	Subject group	Population	Country	Cohort	Intake Time definition	Intake Assessment method	Intake	Intake detail	Supplement intakes included?	Intake Arithmetic mean	Intake Geometric mean	Intake Median	Intake Unit	Intake Adjusted on	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Biomarker Arithmetic mean	Biomarker Geometric mean	Biomarker Median	Biomarker Unit	Biomarker Adjusted on	Correlation size	Correlation type	Correlation value	Correlation 95% CI lower	Correlation 95% CI upper	Correlation p-value	Significant?	Measurement adjustment	Deattenuated?	Covariates	Publication