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Showing NP-Card for Oxoglutaric acid (NP0000103)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2022-02-04 03:13:46 UTC
NP-MRD IDNP0000103
Secondary Accession NumbersNone
Natural Product Identification
Common NameOxoglutaric acid
DescriptionOxoglutaric acid, also known as alpha-ketoglutarate, alpha-ketoglutaric acid, AKG, or 2-oxoglutaric acid, is classified as a gamma-keto acid or a gamma-keto acid derivative. Gamma-Keto acids are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. Alpha-Ketoglutarate is considered to be soluble (in water) and acidic. Alpha-Ketoglutarate is a key molecule in the TCA cycle, playing a fundamental role in determining the overall rate of this important metabolic process (PMID: 26759695 ). In the TCA cycle, AKG is decarboxylated to succinyl-CoA and carbon dioxide by AKG dehydrogenase, which functions as a key control point of the TCA cycle. Additionally, AKG can be generated from isocitrate by oxidative decarboxylation catalyzed by the enzyme known as isocitrate dehydrogenase (IDH). In addition to these routes of production, AKG can be produced from glutamate by oxidative deamination via glutamate dehydrogenase, and as a product of pyridoxal phosphate-dependent transamination reactions (mediated by branched-chain amino acid transaminases) in which glutamate is a common amino donor. AKG is a nitrogen scavenger and a source of glutamate and glutamine that stimulates protein synthesis and inhibits protein degradation in muscles. In particular, AKG can decrease protein catabolism and increase protein synthesis to enhance bone tissue formation in skeletal muscles (PMID: 26759695 ). Interestingly, enteric feeding of AKG supplements can significantly increase circulating plasma levels of hormones such as insulin, growth hormone, and insulin-like growth factor-1 (PMID: 26759695 ). It has recently been shown that AKG can extend the lifespan of adult C. Elegans by inhibiting ATP synthase and TOR (PMID: 24828042 ). In combination with molecular oxygen, alpha-ketoglutarate is required for the hydroxylation of proline to hydroxyproline in the production of type I collagen. A recent study has shown that alpha-ketoglutarate promotes TH1 differentiation along with the depletion of glutamine thereby favouring Treg (regulatory T-cell) differentiation (PMID: 26420908 ). Alpha-Ketoglutarate has been found to be associated with fumarase deficiency, 2-ketoglutarate dehydrogenase complex deficiency, and D-2-hydroxyglutaric aciduria, which are all inborn errors of metabolism (PMID: 8338207 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000103 (Oxoglutaric acid)

HMDB01645_MOL.mol
  Mrv1652309032023562D          

 10  9  0  0  0  0            999 V2000
    1.4289   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  6  2  0  0  0  0
  1  7  1  0  0  0  0
  5  8  2  0  0  0  0
  5  9  1  0  0  0  0
  2 10  2  0  0  0  0
M  END
Download

3D MOL for NP0000103 (Oxoglutaric acid)

HMDB0000208
     RDKit          3D
Oxoglutaric acid
 16 15  0  0  0  0  0  0  0  0999 V2000
   -2.9855   -0.2226    1.1813 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5012    0.0535    0.0637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1185    0.9272   -0.8063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2199   -0.5925   -0.3163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0888    0.1232    0.3883 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2046   -0.4940    0.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2213   -1.4633   -0.7479 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4181    0.0426    0.6062 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3955    1.0238    1.3995 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6800   -0.5008    0.3073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8048    1.8750   -0.9766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1165   -0.5163   -1.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1795   -1.6521    0.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0949    1.1980    0.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1801    0.0991    1.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3703    0.0992   -0.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  3 11  1  0
  4 12  1  0
  4 13  1  0
  5 14  1  0
  5 15  1  0
 10 16  1  0
M  END
Download

3D SDF for NP0000103 (Oxoglutaric acid)

HMDB01645_MOL.mol
  Mrv1652309032023562D          

 10  9  0  0  0  0            999 V2000
    1.4289   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  6  2  0  0  0  0
  1  7  1  0  0  0  0
  5  8  2  0  0  0  0
  5  9  1  0  0  0  0
  2 10  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0000103

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C5H6O5

> <MOLECULAR_WEIGHT>
146.0981

> <EXACT_MASS>
146.021523302

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
12.166536450524555

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-oxopentanedioic acid

> <ALOGPS_LOGP>
-0.60

> <JCHEM_LOGP>
-0.1092632996666667

> <ALOGPS_LOGS>
-0.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.866108156790311

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.663960637840809

> <JCHEM_PKA_STRONGEST_BASIC>
-9.667717541536742

> <JCHEM_POLAR_SURFACE_AREA>
91.66999999999999

> <JCHEM_REFRACTIVITY>
28.883000000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.31e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
oxoglutarate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000103 (Oxoglutaric acid)

HMDB0000208
     RDKit          3D
Oxoglutaric acid
 16 15  0  0  0  0  0  0  0  0999 V2000
   -2.9855   -0.2226    1.1813 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5012    0.0535    0.0637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1185    0.9272   -0.8063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2199   -0.5925   -0.3163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0888    0.1232    0.3883 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2046   -0.4940    0.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2213   -1.4633   -0.7479 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4181    0.0426    0.6062 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3955    1.0238    1.3995 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6800   -0.5008    0.3073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8048    1.8750   -0.9766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1165   -0.5163   -1.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1795   -1.6521    0.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0949    1.1980    0.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1801    0.0991    1.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3703    0.0992   -0.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  3 11  1  0
  4 12  1  0
  4 13  1  0
  5 14  1  0
  5 15  1  0
 10 16  1  0
M  END
Download

PDB for NP0000103 (Oxoglutaric acid)

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: HMDB01645_MOL.mol                                 
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  C   UNK     0       2.667  -0.385   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   0.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -0.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -0.385   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.667  -1.925   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       4.001   0.385   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -2.667  -1.925   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -4.001   0.385   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.334   1.925   0.000  0.00  0.00           O+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    8    9                                                  
CONECT    6    1                                                            
CONECT    7    1                                                            
CONECT    8    5                                                            
CONECT    9    5                                                            
CONECT   10    2                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for NP0000103 (Oxoglutaric acid)

COMPND    HMDB0000208
HETATM    1  O1  UNL     1      -2.986  -0.223   1.181  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.501   0.054   0.064  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.118   0.927  -0.806  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.220  -0.592  -0.316  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.089   0.123   0.388  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.205  -0.494   0.035  1.00  0.00           C  
HETATM    7  O3  UNL     1       1.221  -1.463  -0.748  1.00  0.00           O  
HETATM    8  C5  UNL     1       2.418   0.043   0.606  1.00  0.00           C  
HETATM    9  O4  UNL     1       2.395   1.024   1.400  1.00  0.00           O  
HETATM   10  O5  UNL     1       3.680  -0.501   0.307  1.00  0.00           O  
HETATM   11  H1  UNL     1      -2.805   1.875  -0.977  1.00  0.00           H  
HETATM   12  H2  UNL     1      -1.117  -0.516  -1.408  1.00  0.00           H  
HETATM   13  H3  UNL     1      -1.179  -1.652   0.025  1.00  0.00           H  
HETATM   14  H4  UNL     1      -0.095   1.198   0.088  1.00  0.00           H  
HETATM   15  H5  UNL     1      -0.180   0.099   1.477  1.00  0.00           H  
HETATM   16  H6  UNL     1       4.370   0.099  -0.122  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   11
CONECT    4    5   12   13
CONECT    5    6   14   15
CONECT    6    7    7    8
CONECT    8    9    9   10
CONECT   10   16
END
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SMILES for NP0000103 (Oxoglutaric acid)

OC(=O)CCC(=O)C(O)=O
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INCHI for NP0000103 (Oxoglutaric acid)

InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)
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View in JSmol
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 Mass146.0981 Da
Monoisotopic Mass146.02152 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-02-04View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)v.dorna83@yahoo.comNot AvailableNot Available2021-07-25View Spectrum
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Actinidia chinensisFooDB
Agaricus bisporusFooDB
AgaveFooDB
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosumFooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Aloysia triphyllaFooDB
AmaranthusFooDB
Amelanchier alnifoliaFooDB
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anethum graveolensFooDB
Angelica keiskeiFooDB
Annona cherimolaFooDB
Annona muricataFooDB
Annona reticulataFooDB
Annona squamosaFooDB
Anser anserFooDB
Anthriscus cerefoliumFooDB
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arabidopsis thalianaPlant
Arachis hypogaeaFooDB
Arctium lappaFooDB
Armoracia rusticanaFooDB
Artemisia dracunculusFooDB
Artemisia vulgarisFooDB
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Asparagus officinalisFooDB
Attalea speciosaFooDB
Auricularia auricula-judaeFooDB
Auricularia polytrichaFooDB
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Basella albaFooDB
Benincasa hispidaFooDB
Bertholletia excelsaFooDB
Beta vulgarisFooDB
Beta vulgaris ssp. ciclaFooDB
Bison bisonFooDB
Borago officinalisFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica alboglabraFooDB
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridisFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensisFooDB
Brassica rapa var. rapaFooDB
Brassica ruvoFooDB
Brosimum alicastrumFooDB
Bubalus bubalisFooDB
Byrsonima crassifoliaFooDB
Cajanus cajanFooDB
Canarium ovatumFooDB
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Capsicum annuum L.FooDB
Capsicum annuum var. annuumFooDB
Capsicum chinenseFooDB
Capsicum pubescensFooDB
Carica papaya L.FooDB
Carissa macrocarpaFooDB
Carthamus tinctoriusFooDB
Carum carviFooDB
CaryaFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Castanea crenataFooDB
Castanea mollissimaFooDB
Castanea sativaFooDB
Ceratonia siliquaFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chamaemelum nobileFooDB
Chamerion angustifoliumFooDB
Chenopodium albumFooDB
Chenopodium quinoaFooDB
Chlamydomonas reinhardtiiLOTUS Database
Chrysanthemum coronariumFooDB
Cicer arietinumFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
Cinnamomum aromaticumFooDB
Cinnamomum verumFooDB
CirsiumFooDB
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus latifoliaFooDB
Citrus limonFooDB
Citrus maximaFooDB
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colocasia esculentaFooDB
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ColumbidaeFooDB
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Salvia elegansFooDB
Salvia hispanicaFooDB
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Sambucus nigraFooDB
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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
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
Water Solubility53.1 g/LALOGPS
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
HMDB IDHMDB0000208
DrugBank IDDB08845
Phenol Explorer Compound IDNot Available
FoodDB IDFDB007242
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
Good Scents IDrw1048551
References
General References
  1. Stromme JH, Borud O, Moe PJ: Fatal lactic acidosis in a newborn attributable to a congenital defect of pyruvate dehydrogenase. Pediatr Res. 1976 Jan;10(1):62-6. [PubMed:813176 ]
  2. Rocchiccioli F, Leroux JP, Cartier PH: Microdetermination of 2-ketoglutaric acid in plasma and cerebrospinal fluid by capillary gas chromatography mass spectrometry; application to pediatrics. Biomed Mass Spectrom. 1984 Jan;11(1):24-8. [PubMed:6704500 ]
  3. Kitaura J, Miki Y, Kato H, Sakakihara Y, Yanagisawa M: Hyperinsulinaemic hypoglycaemia associated with persistent hyperammonaemia. Eur J Pediatr. 1999 May;158(5):410-3. [PubMed:10333126 ]
  4. Kelley RI: Octenylsuccinic aciduria in children fed protein-hydrolysate formulas containing modified cornstarch. Pediatr Res. 1991 Dec;30(6):564-9. [PubMed:1805153 ]
  5. Wu N, Yang M, Gaur U, Xu H, Yao Y, Li D: Alpha-Ketoglutarate: Physiological Functions and Applications. Biomol Ther (Seoul). 2016 Jan;24(1):1-8. doi: 10.4062/biomolther.2015.078. Epub 2016 Jan 1. [PubMed:26759695 ]
  6. Chin RM, Fu X, Pai MY, Vergnes L, Hwang H, Deng G, Diep S, Lomenick B, Meli VS, Monsalve GC, Hu E, Whelan SA, Wang JX, Jung G, Solis GM, Fazlollahi F, Kaweeteerawat C, Quach A, Nili M, Krall AS, Godwin HA, Chang HR, Faull KF, Guo F, Jiang M, Trauger SA, Saghatelian A, Braas D, Christofk HR, Clarke CF, Teitell MA, Petrascheck M, Reue K, Jung ME, Frand AR, Huang J: The metabolite alpha-ketoglutarate extends lifespan by inhibiting ATP synthase and TOR. Nature. 2014 Jun 19;510(7505):397-401. doi: 10.1038/nature13264. Epub 2014 May 14. [PubMed:24828042 ]
  7. Klysz D, Tai X, Robert PA, Craveiro M, Cretenet G, Oburoglu L, Mongellaz C, Floess S, Fritz V, Matias MI, Yong C, Surh N, Marie JC, Huehn J, Zimmermann V, Kinet S, Dardalhon V, Taylor N: Glutamine-dependent alpha-ketoglutarate production regulates the balance between T helper 1 cell and regulatory T cell generation. Sci Signal. 2015 Sep 29;8(396):ra97. doi: 10.1126/scisignal.aab2610. [PubMed:26420908 ]
  8. De Vivo DC: The expanding clinical spectrum of mitochondrial diseases. Brain Dev. 1993 Jan-Feb;15(1):1-22. [PubMed:8338207 ]
  9. Celaya-Padilla JM, Villagrana-Banuelos KE, Oropeza-Valdez JJ, Monarrez-Espino J, Castaneda-Delgado JE, Oostdam ASH, Fernandez-Ruiz JC, Ochoa-Gonzalez F, Borrego JC, Enciso-Moreno JA, Lopez JA, Lopez-Hernandez Y, Galvan-Tejada CE: Kynurenine and Hemoglobin as Sex-Specific Variables in COVID-19 Patients: A Machine Learning and Genetic Algorithms Approach. Diagnostics (Basel). 2021 Nov 25;11(12). pii: diagnostics11122197. doi: 10.3390/diagnostics11122197. [PubMed:34943434 ]