AFCDB: 2-Oxopentanedioic acid (FDB003361)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:46 UTC

Update date

2024-11-29 22:27:55 UTC

Primary ID

FDB003361

Secondary Accession Numbers

FDB030357
FDB007242

Chemical Information

FooDB Name

2-Oxopentanedioic 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.

CAS Number

328-50-7

Structure

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

Synonyms

Synonym	Source
Not Available	Not Available

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C5H6O5

IUPAC name

2-oxopentanedioic acid

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

Isomeric SMILES

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

Average Molecular Weight

146.0981

Monoisotopic Molecular Weight

146.021523302

Classification

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

Ingestion

Source:

Biological:

Animal

Fungi:

Yeast

Microbe:

Corynebacterium:

Corynebacterium glutamicum

Plant:

Biological location:

Biofluid and excreta:

Cell and elements:

Extracellular

Subcellular:

Role

Biological role:

Metabolite

Industrial application:

Food and nutrition

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 41.11%; H 4.14%; O 54.76%	DFC
Melting Point	Mp 115°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0fba-9200000000-4e367c66e94c51eb1a1b	2014-09-20	View Spectrum
GC-MS	2-Oxopentanedioic acid, 2 TMS, GC-MS Spectrum	splash10-000b-3910000000-4097b7eb52c2910a4277	Spectrum
GC-MS	2-Oxopentanedioic acid, non-derivatized, GC-MS Spectrum	splash10-0002-1910000000-3277227b9c4da4baa1f7	Spectrum
GC-MS	2-Oxopentanedioic acid, 2 TMS; 1 MEOX, GC-MS Spectrum	splash10-00di-9300000000-974bce546caa4fbe6b0f	Spectrum
GC-MS	2-Oxopentanedioic acid, 1 MEOX; 2 TMS, GC-MS Spectrum	splash10-000i-9710000000-d0aea11e947b042571f9	Spectrum
GC-MS	2-Oxopentanedioic acid, 1 MEOX; 2 TMS, GC-MS Spectrum	splash10-052s-4920000000-bf7ed92c68fd4c8dbb6b	Spectrum
GC-MS	2-Oxopentanedioic acid, non-derivatized, GC-MS Spectrum	splash10-000b-3910000000-4097b7eb52c2910a4277	Spectrum
GC-MS	2-Oxopentanedioic acid, non-derivatized, GC-MS Spectrum	splash10-0002-1910000000-3277227b9c4da4baa1f7	Spectrum
GC-MS	2-Oxopentanedioic acid, non-derivatized, GC-MS Spectrum	splash10-00di-9300000000-974bce546caa4fbe6b0f	Spectrum
GC-MS	2-Oxopentanedioic acid, non-derivatized, GC-MS Spectrum	splash10-000i-9710000000-d0aea11e947b042571f9	Spectrum
GC-MS	2-Oxopentanedioic acid, non-derivatized, GC-MS Spectrum	splash10-052s-4920000000-bf7ed92c68fd4c8dbb6b	Spectrum
GC-MS	2-Oxopentanedioic acid, non-derivatized, GC-MS Spectrum	splash10-000b-2900000000-e514f7afea2490bbe9ed	Spectrum
Predicted GC-MS	2-Oxopentanedioic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0kfx-9200000000-0ee77a39e9862659f8a7	Spectrum
Predicted GC-MS	2-Oxopentanedioic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-9730000000-5e17bd8cfd944963c79f	Spectrum
Predicted GC-MS	2-Oxopentanedioic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Oxopentanedioic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Oxopentanedioic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Oxopentanedioic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Oxopentanedioic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Oxopentanedioic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Oxopentanedioic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Oxopentanedioic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Oxopentanedioic acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Oxopentanedioic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Oxopentanedioic acid, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Oxopentanedioic acid, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0zfr-6900000000-7fc343a243ce5d2a4f39	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0a4i-9200000000-1a7af9946604baa8b3d2	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0a4l-9800000000-30495b2afdd3526854e7	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0002-0925200000-af33449c9638276466c2	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4i-9000000000-6e43f767847790112b65	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03di-0900000000-4cacc41705b7b385e91e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0udi-0900000000-1367eeeb6ad64c67a0aa	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-000t-0915051100-91cda631ee54800322b8	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4i-9000000000-4f842c3673925d29c402	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0udi-0900000000-5e751351656f6eb62de3	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0910000000-7729faa24733fbad77b7	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0002-0900000000-c3c62f83bff99f44f7ab	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0zfr-6900000000-b6d8379db3e3f1480b14	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0a4i-9300000000-4fde39bb93cde5a27f23	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-00i0-9000000000-4343832f3a55842423a9	2012-08-31	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-2900000000-5aa3d6d620db1d733a65	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0m30-7900000000-fc77f69ad43f915bf23e	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9000000000-c597f1f5e416037aa82d	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-2900000000-5aa3d6d620db1d733a65	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0m30-7900000000-fc77f69ad43f915bf23e	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9000000000-c597f1f5e416037aa82d	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-1900000000-f2b463076a150a514f0c	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f9t-8900000000-b2d3fa8d7ab01a220d9a	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-053r-9100000000-554bfbd6839bc376cba0	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-1900000000-f2b463076a150a514f0c	2015-05-27	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100.54 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

CHEMBL1686

KEGG Compound ID

C00026

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

16810

Phenol-Explorer ID

Not Available

DrugBank ID

DB02926

HMDB ID

HMDB00208

CRC / DFC (Dictionary of Food Compounds) ID

CWH02-C:CWH02-C

EAFUS ID

2852

Dr. Duke ID

ALPHA-KETO-GLUTARIC-ACID

BIGG ID

33565

KNApSAcK ID

C00000769

HET ID

AKG

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1048551

SuperScent ID

Not Available

Wikipedia ID

Oxoglutarate

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Name	Gene Name	UniProt ID
Tyrosine aminotransferase	TAT	P17735
Aspartate aminotransferase, cytoplasmic	GOT1	P17174
Aspartate aminotransferase, mitochondrial	GOT2	P00505
Aminoadipate-semialdehyde synthase	AASS	A4D0W4
Branched-chain-amino-acid aminotransferase, cytosolic	BCAT1	P54687
Branched-chain-amino-acid aminotransferase, mitochondrial	BCAT2	O15382
Lysine-specific demethylase 2A	KDM2A	Q9Y2K7
Lysine-specific demethylase 2B	KDM2B	Q8NHM5
Alanine--glyoxylate aminotransferase 2, mitochondrial	AGXT2	Q9BYV1
Kynurenine--oxoglutarate transaminase 3	CCBL2	Q6YP21
Ornithine aminotransferase, mitochondrial	OAT	P04181
4-aminobutyrate aminotransferase, mitochondrial	ABAT	P80404
Alanine aminotransferase 1	GPT	P24298
Alanine aminotransferase 2	GPT2	Q8TD30
Prolyl 4-hydroxylase subunit alpha-2	P4HA2	O15460
Prolyl 4-hydroxylase subunit alpha-1	P4HA1	P13674
Prolyl 4-hydroxylase subunit alpha-3	P4HA3	Q7Z4N8
Egl nine homolog 1	EGLN1	Q9GZT9
Egl nine homolog 2	EGLN2	Q96KS0
Egl nine homolog 3	EGLN3	Q9H6Z9
Transmembrane prolyl 4-hydroxylase	P4HTM	Q9NXG6
Phosphoserine aminotransferase	PSAT1	Q9Y617
Putative aspartate aminotransferase, cytoplasmic 2	GOT1L1	Q8NHS2
2-oxoglutarate dehydrogenase, mitochondrial	OGDH	Q02218
2-oxoglutarate dehydrogenase-like, mitochondrial	OGDHL	Q9ULD0
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	AADAT	Q8N5Z0
Kynurenine--oxoglutarate transaminase 1	CCBL1	Q16773
Mitochondrial 2-oxoglutarate/malate carrier protein	SLC25A11	Q02978
Probable 2-oxoglutarate dehydrogenase E1 component DHKTD1, mitochondrial	DHTKD1	Q96HY7

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	map00010
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	map00330
Metabolism and Physiological Effects of Para-cresol	SMP0123214	Not Available
Metabolism and Physiological Effects of Oxalic acid	SMP0124875	Not Available
Metabolsim and Physiological Effects of Argininic acid	SMP0125504	Not Available
Metabolism and Physiological Effects of N-alpha-Acetyl-L-arginine	SMP0125530	Not Available
Metabolsim and Physiological Effects of 4-Ethylphenylsulfate	SMP0125541	Not Available
Metabolism and Physiological Effects of Tiglylglycine	SMP0126840	Not Available
Metabolism and Physiological Effects of p-Cresol sulphate	SMP0126850	Not Available
Metabolism and Physiological Effects of 4-Hydroxyphenylacetic acid	SMP0126879	Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
odorless	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

2-Oxopentanedioic acid (FDB003361)

Structure for FDB003361 (2-Oxopentanedioic acid)