MiMeDB: Showing metabocard for 4-Hydroxy-2-oxoglutaric acid (MMDBc0029681)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:37:19 UTC

Update Date

2022-08-31 17:11:57 UTC

Metabolite ID

MMDBc0029681

Metabolite Identification

Common Name

4-Hydroxy-2-oxoglutaric acid

Description

4-hydroxy-2-oxoglutaric acid is a member of the chemical class known as Gamma Keto-Acids and Derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. 4-hydroxy-2-oxoglutaric acid is invovled in Glyoxylate and dicarboxylate metabolism. 2-Keto-4-hydroxyglutarate aldolase also plays a role in respiratory metabolic pathways, which suggests a mechanism for respiration resumption during the termination of the SOS response. (PMID 8524853 )

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

Synonyms

Value	Source
4-Hydroxy-2-oxoglutarate	Generator
2-Keto-4-hydroxyglutarate	MeSH
2-Keto-4-hydroxyglutarate, (+-)-isomer	MeSH
(+/-)-2-hydroxy-4-oxopentanedioate	HMDB
(+/-)-2-hydroxy-4-oxopentanedioic acid	HMDB
2-Hydroxy-4-oxopentanedioate	HMDB
2-Hydroxy-4-oxopentanedioic acid	HMDB
2-oxo-4-Hydroxyglutarate	HMDB
4-Hydroxy-2-ketoglutarate	HMDB
D-4-Hydroxy-2-ketoglutarate	HMDB

Molecular Formula

C₅H₆O₆

Average Mass

162.0975

Monoisotopic Mass

162.016437924

IUPAC Name

2-hydroxy-4-oxopentanedioic acid

Traditional Name

4-hydroxy-2-oxoglutaric acid

CAS Registry Number

Not Available

SMILES

OC(CC(=O)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C5H6O6/c6-2(4(8)9)1-3(7)5(10)11/h2,6H,1H2,(H,8,9)(H,10,11)

InChI Key

WXSKVKPSMAHCSG-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
Alpha-hydroxy acid
Alpha-keto acid
Beta-hydroxy ketone
Dicarboxylic acid or derivatives
Hydroxy acid
Alpha-hydroxy ketone
Secondary alcohol
Ketone
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organic oxide
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

oxo dicarboxylic acid (CHEBI:30923 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	69.8 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-0.82	ChemAxon
logS	-0.37	ALOGPS
pKa (Strongest Acidic)	2.45	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.9 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	30.22 m³·mol⁻¹	ChemAxon
Polarizability	12.76 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9100000000-86646efd7b91f9c2b26e	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-03ki-5194000000-f0675d41da8301324b83	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01ot-2900000000-fd2a634c0c83321df9f8	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002b-6900000000-13f2fbc268a7b1bfe885	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05i4-9100000000-ca03fcf215517c709245	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-2900000000-7b0bd810c920b58daa79	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00xs-9600000000-6734be382dda3c66592a	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dm-9000000000-ff1b08ca89e9629f0912	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kb-6900000000-661f455fd4b6e8da0c82	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dm-9100000000-b9bce861b26dd8001332	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-a0587223ecf12202531f	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014j-5900000000-30fe0301167b3cea2c0b	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006t-9000000000-5bbf6f8b15e9a3af889b	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-e7768f77ba36e7e3743b	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum

Biological Properties

Cellular Locations

Mitochondria

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191953	Aspartate aminotransferase, cytoplasmic	Enzyme	P17174	Homo sapiens
MMDBp0196843	Probable 4-hydroxy-2-oxoglutarate aldolase, mitochondrial	Unknown	Q86XE5

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0000641	4-Hydroxy-2-oxoglutaric acid	Glyoxylic acid	Not Available	VMH; KEGG	12660328 14193832 15849464 9783918
MMDBr0000854	L-Glutamyl-tRNA(Glu)	4-Hydroxy-2-oxoglutaric acid	glutamic-oxaloacetic transaminase 2, mitochondrial	VMH	12660328 15849464
MMDBr0000855	Oxoglutaric acid	4-Hydroxy-2-oxoglutaric acid	glutamic-oxaloacetic transaminase 2, mitochondrial	VMH	15849464
MMDBr0007305	4-Hydroxy-2-oxoglutaric acid	Glyoxylic acid	Not Available	VMH	30371894
MMDBr0007328	Oxoglutaric acid	4-Hydroxy-2-oxoglutaric acid	Not Available	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	181	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	387	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle ; Human stool	Metabolic reconstruction
Bacteria	Actinobacteria	126	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	116	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human supragingival plaque; Human subgingival plaque	Metabolic reconstruction
Bacteria	Synergistetes	4	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0002070

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022830

KNApSAcK ID

Not Available

Chemspider ID

579

KEGG Compound ID

C01127

BioCyc ID

Not Available

BiGG ID

36868

Wikipedia Link

Not Available

METLIN ID

6471

PubChem Compound

599

PDB ID

Not Available

ChEBI ID

30923

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]

Showing metabocard for 4-Hydroxy-2-oxoglutaric acid (MMDBc0029681)

MOL for #<Metabolite:0x00007fdb2d2f8220>

3D MOL for #<Metabolite:0x00007fdb2d2f8220>

3D SDF for #<Metabolite:0x00007fdb2d2f8220>

3D-SDF for #<Metabolite:0x00007fdb2d2f8220>

PDB for #<Metabolite:0x00007fdb2d2f8220>

3D PDB for #<Metabolite:0x00007fdb2d2f8220>

SMILES for #<Metabolite:0x00007fdb2d2f8220>

INCHI for #<Metabolite:0x00007fdb2d2f8220>

Structure for #<Metabolite:0x00007fdb2d2f8220>

3D Structure for #<Metabolite:0x00007fdb2d2f8220>