Showing Compound Card for Oxoglutaric acid (CDB004819)

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Record Information
Version1.0
Created at2020-04-17 18:40:01 UTC
Updated at2020-12-07 19:11:01 UTC
CannabisDB IDCDB004819
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameOxoglutaric acid
DescriptionOxoglutaric 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. Oxoglutaric acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Chemical FormulaC5H6O5
Average Molecular Weight146.1
Monoisotopic Molecular Weight146.0215
IUPAC Name2-oxopentanedioic acid
Traditional Nameoxoglutarate
CAS Registry Number328-50-7
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 KeyKPGXRSRHYNQIFN-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassGamma-keto acids and derivatives
Direct ParentGamma-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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point115.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility541.5 mg/mLNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.6ALOGPS
logP-0.11ChemAxon
logS-0.44ALOGPS
pKa (Strongest Acidic)2.66ChemAxon
pKa (Strongest Basic)-9.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity28.88 m³·mol⁻¹ChemAxon
Polarizability12.17 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
MS/MS
NMR
Pathways
Pathways
Protein Targets
Enzymes
Transporters
Protein NameGene NameLocusUniprot IDDetails
Mitochondrial 2-oxoglutarate/malate carrier proteinSLC25A1117p13.3Q02978 details
Metal Bindings
Receptors
Protein NameGene NameLocusUniprot IDDetails
Egl nine homolog 2EGLN219q13.2Q96KS0 details
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
Aspartyl/asparaginyl beta-hydroxylaseASPH8q12.1Q12797 details
Hypoxia-inducible factor 1-alpha inhibitorHIF1AN10q24Q9NWT6 details
Lysine-specific demethylase 2AKDM2A11q13.2Q9Y2K7 details
Lysine-specific demethylase 2BKDM2B12q24.31Q8NHM5 details
Egl nine homolog 1EGLN11q42.1Q9GZT9 details
Egl nine homolog 2EGLN219q13.2Q96KS0 details
Egl nine homolog 3EGLN314q13.1Q9H6Z9 details
Lysine-specific demethylase 8KDM816p12.1Q8N371 details
Bifunctional lysine-specific demethylase and histidyl-hydroxylase NO66NO6614q24.3Q9H6W3 details
Histone lysine demethylase PHF8PHF8Xp11.22Q9UPP1 details
Methylcytosine dioxygenase TET1TET110q21Q8NFU7 details
Concentrations Data
Not Available
HMDB IDHMDB0000208
DrugBank IDDB08845
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003361
KNApSAcK IDC00000769
Chemspider ID50
KEGG Compound IDC00026
BioCyc ID2-KETOGLUTARATE
BiGG ID33565
Wikipedia LinkAlpha-Ketoglutaric_acid
METLIN ID5218
PubChem Compound51
PDB IDNot Available
ChEBI ID30915
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 106 proteins in total.

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Enzymes

Enzyme Details
1. Dihydrolipoyl dehydrogenase, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Lipoamide dehydrogenase is a component of the glycine cleavage system as well as of the alpha-ketoacid dehydrogenase complexes. Involved in the hyperactivation of spermatazoa during capacitation and in the spermatazoal acrosome reaction.
Gene Name:
DLD
Uniprot ID:
P09622
Molecular weight:
54176.91
Enzyme Details
2. 4-aminobutyrate aminotransferase, mitochondrial
General function:
Involved in 4-aminobutyrate transaminase activity
Specific function:
Catalyzes the conversion of gamma-aminobutyrate and L-beta-aminoisobutyrate to succinate semialdehyde and methylmalonate semialdehyde, respectively. Can also convert delta-aminovalerate and beta-alanine.
Gene Name:
ABAT
Uniprot ID:
P80404
Molecular weight:
56438.405
Enzyme Details
3. Phytanoyl-CoA dioxygenase, peroxisomal
General function:
Involved in electron carrier activity
Specific function:
Converts phytanoyl-CoA to 2-hydroxyphytanoyl-CoA.
Gene Name:
PHYH
Uniprot ID:
O14832
Molecular weight:
38538.065
Enzyme Details
4. Tyrosine aminotransferase
General function:
Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:
Transaminase involved in tyrosine breakdown. Converts tyrosine to p-hydroxyphenylpyruvate. Can catalyze the reverse reaction, using glutamic acid, with 2-oxoglutarate as cosubstrate (in vitro). Has much lower affinity and transaminase activity towards phenylalanine.
Gene Name:
TAT
Uniprot ID:
P17735
Molecular weight:
50398.895
Enzyme Details
5. Aspartate aminotransferase, cytoplasmic
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Plays a key role in amino acid metabolism (By similarity).
Gene Name:
GOT1
Uniprot ID:
P17174
Molecular weight:
46247.14
Enzyme Details
6. Aspartate aminotransferase, mitochondrial
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Plays a key role in amino acid metabolism. Important for metabolite exchange between mitochondria and cytosol. Facilitates cellular uptake of long-chain free fatty acids.
Gene Name:
GOT2
Uniprot ID:
P00505
Molecular weight:
47517.285
Enzyme Details
7. Aldehyde dehydrogenase, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
Enzyme Details
8. Fatty aldehyde dehydrogenase
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidation of long-chain aliphatic aldehydes to fatty acids. Active on a variety of saturated and unsaturated aliphatic aldehydes between 6 and 24 carbons in length. Responsible for conversion of the sphingosine 1-phosphate (S1P) degradation product hexadecenal to hexadecenoic acid.
Gene Name:
ALDH3A2
Uniprot ID:
P51648
Molecular weight:
54847.36
Enzyme Details
9. Aldehyde dehydrogenase X, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation.
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Molecular weight:
57248.96
Enzyme Details
10. Branched-chain-amino-acid aminotransferase, cytosolic
General function:
Involved in catalytic activity
Specific function:
Catalyzes the first reaction in the catabolism of the essential branched chain amino acids leucine, isoleucine, and valine.
Gene Name:
BCAT1
Uniprot ID:
P54687
Molecular weight:
38644.77

Transporters

Enzyme Details
1. Mitochondrial 2-oxoglutarate/malate carrier protein
General function:
Involved in transporter activity
Specific function:
Catalyzes the transport of 2-oxoglutarate across the inner mitochondrial membrane in an electroneutral exchange for malate or other dicarboxylic acids, and plays an important role in several metabolic processes, including the malate-aspartate shuttle, the oxoglutarate/isocitrate shuttle, in gluconeogenesis from lactate, and in nitrogen metabolism.
Gene Name:
SLC25A11
Uniprot ID:
Q02978
Molecular weight:
34061.405

Only showing the first 10 proteins. There are 106 proteins in total.

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