Showing Compound Card for alpha-Ketoglutaric acid (CDB006340)

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Record Information
Version1.0
Created at2020-09-11 15:49:40 UTC
Updated at2022-12-13 23:36:29 UTC
CannabisDB IDCDB006340
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namealpha-Ketoglutaric 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.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-Ketoglutaric acidChEBI
alpha-Ketoglutaric acidChEBI
2-KetoglutarateGenerator
a-KetoglutarateGenerator
a-Ketoglutaric acidGenerator
alpha-KetoglutarateGenerator
Α-ketoglutarateGenerator
Α-ketoglutaric acidGenerator
OxoglutarateGenerator
2-oxo-1,5-PentanedioateHMDB
2-oxo-1,5-Pentanedioic acidHMDB
2-OxoglutarateHMDB
2-Oxoglutaric acidHMDB
2-OxopentanedioateHMDB
2-Oxopentanedioic acidHMDB
alpha-OxoglutarateHMDB
Oxogluric acidHMDB
2 Oxoglutaric acidHMDB
Ketoglutaric acidHMDB
alpha Ketoglutaric acidHMDB
2 Ketoglutaric acidHMDB
alpha KetoglutarateHMDB
alpha OxoglutarateHMDB
2 KetoglutarateHMDB
2 OxoglutarateHMDB
alpha-Oxoglutaric acidHMDB
alpha-Oxopentanedioic acidHMDB
alpha-Keto-glutaric acidHMDB
Α-oxoglutaric acidHMDB
Α-oxopentanedioic acidHMDB
Α-keto-glutaric acidHMDB
Chemical FormulaC5H6O5
Average Molecular Weight146.0981
Monoisotopic Molecular Weight146.021523302
IUPAC Name2-oxopentanedioic acid
Traditional Nameoxoglutarate
CAS Registry NumberNot Available
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
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot 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
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0fba-9200000000-4e367c66e94c51eb1a1b2014-09-20View Spectrum
GC-MSOxoglutaric acid, 2 TMS, GC-MS Spectrumsplash10-000b-3910000000-4097b7eb52c2910a4277Spectrum
GC-MSOxoglutaric acid, non-derivatized, GC-MS Spectrumsplash10-0002-1910000000-3277227b9c4da4baa1f7Spectrum
GC-MSOxoglutaric acid, 2 TMS; 1 MEOX, GC-MS Spectrumsplash10-00di-9300000000-974bce546caa4fbe6b0fSpectrum
GC-MSOxoglutaric acid, 1 MEOX; 2 TMS, GC-MS Spectrumsplash10-000i-9710000000-d0aea11e947b042571f9Spectrum
GC-MSOxoglutaric acid, 1 MEOX; 2 TMS, GC-MS Spectrumsplash10-052s-4920000000-bf7ed92c68fd4c8dbb6bSpectrum
GC-MSOxoglutaric acid, non-derivatized, GC-MS Spectrumsplash10-000b-3910000000-4097b7eb52c2910a4277Spectrum
GC-MSOxoglutaric acid, non-derivatized, GC-MS Spectrumsplash10-0002-1910000000-3277227b9c4da4baa1f7Spectrum
GC-MSOxoglutaric acid, non-derivatized, GC-MS Spectrumsplash10-00di-9300000000-974bce546caa4fbe6b0fSpectrum
GC-MSOxoglutaric acid, non-derivatized, GC-MS Spectrumsplash10-000i-9710000000-d0aea11e947b042571f9Spectrum
GC-MSOxoglutaric acid, non-derivatized, GC-MS Spectrumsplash10-052s-4920000000-bf7ed92c68fd4c8dbb6bSpectrum
GC-MSOxoglutaric acid, non-derivatized, GC-MS Spectrumsplash10-000b-2900000000-e514f7afea2490bbe9edSpectrum
Predicted GC-MSOxoglutaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0kfx-9200000000-0ee77a39e9862659f8a7Spectrum
Predicted GC-MSOxoglutaric acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9730000000-5e17bd8cfd944963c79fSpectrum
Predicted GC-MSOxoglutaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSOxoglutaric acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSOxoglutaric acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSOxoglutaric acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSOxoglutaric acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSOxoglutaric acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSOxoglutaric acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSOxoglutaric acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSOxoglutaric acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSOxoglutaric acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSOxoglutaric acid, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSOxoglutaric acid, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0zfr-6900000000-7fc343a243ce5d2a4f392012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-9200000000-1a7af9946604baa8b3d22012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0a4l-9800000000-30495b2afdd3526854e72012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-0925200000-af33449c9638276466c22012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-9000000000-6e43f767847790112b652012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0900000000-4cacc41705b7b385e91e2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0900000000-1367eeeb6ad64c67a0aa2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-000t-0915051100-91cda631ee54800322b82012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-9000000000-4f842c3673925d29c4022012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0900000000-5e751351656f6eb62de32012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0910000000-7729faa24733fbad77b72012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-c3c62f83bff99f44f7ab2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0zfr-6900000000-b6d8379db3e3f1480b142012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9300000000-4fde39bb93cde5a27f232012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00i0-9000000000-4343832f3a55842423a92012-08-31View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-2900000000-5aa3d6d620db1d733a652015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0m30-7900000000-fc77f69ad43f915bf23e2015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9000000000-c597f1f5e416037aa82d2015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-2900000000-5aa3d6d620db1d733a652015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0m30-7900000000-fc77f69ad43f915bf23e2015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9000000000-c597f1f5e416037aa82d2015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1900000000-f2b463076a150a514f0c2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f9t-8900000000-b2d3fa8d7ab01a220d9a2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-9100000000-554bfbd6839bc376cba02015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1900000000-f2b463076a150a514f0c2015-05-27View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100.54 MHz, DMSO-d6, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.00132 mg/g dry wt
    • David S. Wishart,...
 details
GabriolaDetected and Quantified0.00126 mg/g dry wt
    • David S. Wishart,...
 details
Island HoneyDetected and Quantified0.00191 mg/g dry wt
    • David S. Wishart,...
 details
QuadraDetected and Quantified0.000539 mg/g dry wt
    • David S. Wishart,...
 details
Sensi StarDetected and Quantified0.00253 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine DreamDetected and Quantified0.00364 mg/g dry wt
    • David S. Wishart,...
 details
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