Livestock Metabolome Database: Showing metabocard for Oxoglutaric acid (LMDB00094)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:42:13 UTC

Update Date

2021-04-30 20:57:58 UTC

Lmdb

LMDB00094

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Oxoglutaric acid

Description

Oxoglutaric acid, also known as oxoglutarate or alpha-ketoglutarate, 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. Oxoglutaric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Oxoglutaric acid exists in all living species, ranging from bacteria to humans. Within humans, oxoglutaric acid participates in a number of enzymatic reactions. In particular, oxoglutaric acid can be biosynthesized from isocitric acid; which is mediated by the enzyme isocitrate dehydrogenase. In addition, oxoglutaric acid can be converted into succinyl-CoA; which is mediated by the enzyme oxoglutarate dehydrogenase complex. In humans, oxoglutaric acid is involved in the oncogenic action of fumarate. Oxoglutaric acid is an odorless tasting compound. Outside of the human body, Oxoglutaric acid is found, on average, in the highest concentration within star fruits and milk (cow). Oxoglutaric acid has also been detected, but not quantified in, several different foods, such as common chokecherries, red beetroots, adzuki beans, buffalo currants, and grapefruit/pummelo hybrids. This could make oxoglutaric acid a potential biomarker for the consumption of these foods. Oxoglutaric acid is a potentially toxic compound. An oxo dicarboxylic acid that consists of glutaric acid bearing an oxo substituent at position 2.

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 Weight

146.0981

Monoisotopic Molecular Weight

146.021523302

IUPAC Name

2-oxopentanedioic acid

Traditional Name

oxoglutarate

CAS Registry Number

328-50-7

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 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	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

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Feces
Milk
Plasma
Serum
Urine

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Feces	Detected but not Quantified	Not Applicable	Not Available	Ovine	17249687	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23497994	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23438684	details
Milk	Detected and Quantified	37-156 uM	Not Available	Bovine	22098372	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	22370585	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Ovine	17249687	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	24070026	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Ovine	22242129	details
Serum	Detected and Quantified	15.2158 +/- 6.7722 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	13.1833 +/- 5.2814 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details
Serum	Detected and Quantified	12.3209 +/- 3.2099 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	14.3828 +/- 6.4828 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	18.9586 +/- 7.9021 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	12.3833 +/- 3.6169 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	15.3714 +/- 4.3241 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	18.56 +/- 8.65 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	16.4933 +/- 8.3871 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	16.3726 +/- 10.2938 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	14.7028 +/- 7.73 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.00855 +/- 0.000904 uM	Not Available	Porcine	19847666	details
Serum	Detected and Quantified	0.00544 +/- 0.000794 uM	Not Available	Porcine	19847666	details
Serum	Detected and Quantified	13.4769 +/- 6.5454 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	16.368 +/- 7.4112 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	12.8349 +/- 4.3834 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	13.0107 +/- 4.1298 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	13.6629 +/- 5.4605 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	14.6829 +/- 5.9676 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	13.0499 +/- 4.1092 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	16.6518 +/- 8.3562 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	15.3235 +/- 3.6967 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	14.9915 +/- 6.2442 uM	Normal	Ovine	Goldansaz et al.,...	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details
Urine	Detected and Quantified	265 umol/mmol creatinine	Not Available	Porcine	23741447	details
Urine	Detected and Quantified	465 umol/mmol creatinine	Not Available	Porcine	23741447	details