Showing metabocard for alpha-Ketoglutarate (MMDBc0029698)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:38:01 UTC
Update Date2022-08-31 17:12:45 UTC
Metabolite IDMMDBc0029698
Metabolite Identification
Common Namealpha-Ketoglutarate
DescriptionAlpha-ketoglutarate 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. Alpha-ketoglutarate is invovled in pentose and glucuronate interconversions, C5-Branched dibasic acid metabolism, Vitamin B6 metabolism, alanine, aspartate and glutamate metabolism, Butanoate metabolism, Glyoxylate and dicarboxylate metabolism, Carbon fixation pathways in prokaryotes, Lysine biosynthesis, Biosynthesis of terpenoids and steroids, and the Citrate cycle (TCA cycle). Alpha-Ketoglutaric acid is one of two ketone derivatives of glutaric acid. (The term ketoglutaric acid, when not further qualified, almost always refers to the alpha variant. Alpha-Ketoglutaric acid varies only by the position of the ketone functional group, and is much less common. Its anion, alpha-ketoglutarate (alpha-KG, also called oxo-glutarate) is an important biological compound. It is the keto acid produced by de-amination of glutamate, and is an intermediate in the Krebs cycle. (WikiPedia)
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007fdb58eb7838>

Structure #1
  Mrv0541 02241206242D          

 10  9  0  0  0  0            999 V2000
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.6039    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  2  0  0  0  0
  4  7  2  0  0  0  0
  4  8  1  0  0  0  0
  5  9  2  0  0  0  0
  5 10  1  0  0  0  0
M  CHG  2   8  -1  10  -1
M  END
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3D MOL for #<Metabolite:0x00007fdb58eb7838>

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3D SDF for #<Metabolite:0x00007fdb58eb7838>
Structure #1
  Mrv0541 02241206242D          

 10  9  0  0  0  0            999 V2000
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.6039    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  2  0  0  0  0
  4  7  2  0  0  0  0
  4  8  1  0  0  0  0
  5  9  2  0  0  0  0
  5 10  1  0  0  0  0
M  CHG  2   8  -1  10  -1
M  END
> <DATABASE_ID>
MMDBc0029698

> <DATABASE_NAME>
MIME

> <SMILES>
[O-]C(=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)/p-2

> <INCHI_KEY>
KPGXRSRHYNQIFN-UHFFFAOYSA-L

> <FORMULA>
C5H4O5

> <MOLECULAR_WEIGHT>
144.0823

> <EXACT_MASS>
144.005873238

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
11.32289821308254

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-oxopentanedioate

> <ALOGPS_LOGP>
-0.45

> <JCHEM_LOGP>
-0.1092632996666667

> <ALOGPS_LOGS>
-0.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.866108156790311

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.663960637840807

> <JCHEM_PKA_STRONGEST_BASIC>
-9.667717541536742

> <JCHEM_POLAR_SURFACE_AREA>
97.33000000000001

> <JCHEM_REFRACTIVITY>
50.5572

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.65e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α ketoglutarate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00007fdb58eb7838>
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PDB for #<Metabolite:0x00007fdb58eb7838>
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.621   4.977   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       3.286   3.437   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       4.620   1.127   0.000  0.00  0.00           O-1
HETATM    9  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       9.955   1.127   0.000  0.00  0.00           O-1
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5    6                                                  
CONECT    4    2    7    8                                                  
CONECT    5    3    9   10                                                  
CONECT    6    3                                                            
CONECT    7    4                                                            
CONECT    8    4                                                            
CONECT    9    5                                                            
CONECT   10    5                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END

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3D PDB for #<Metabolite:0x00007fdb58eb7838>
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SMILES for #<Metabolite:0x00007fdb58eb7838>
[O-]C(=O)CCC(=O)C([O-])=O
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INCHI for #<Metabolite:0x00007fdb58eb7838>
InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)/p-2
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Synonyms
ValueSource
2-KetoglutarateChEBI
2-OxoglutarateChEBI
2-Oxopentanedioic acid, ion(2-)ChEBI
2-Ketoglutaric acidGenerator
2-Oxoglutaric acidGenerator
2-Oxopentanedioate, ion(2-)Generator
a-KetoglutarateGenerator
a-Ketoglutaric acidGenerator
alpha-Ketoglutaric acidGenerator
Α-ketoglutarateGenerator
Α-ketoglutaric acidGenerator
Ketoglutaric acidMeSH
alpha Ketoglutaric acid, monosodium saltMeSH
alpha-Ketoglutaric acid, dipotassium saltMeSH
alpha Ketoglutaric acid, diammonium saltMeSH
OxoglutaratesMeSH
Calcium ketoglutarateMeSH
2 Ketoglutaric acidMeSH
alpha-OxoglutarateMeSH
Ketoglutaric acidsMeSH
2 KetoglutarateMeSH
alpha Ketoglutaric acidMeSH
2 Oxoglutaric acidMeSH
alpha-Ketoglutaric acid, diammonium saltMeSH
alpha-Ketoglutaric acid, calcium salt (2:1)MeSH
2 OxoglutarateMeSH
alpha-Ketoglutaric acid, disodium saltMeSH
alpha Ketoglutaric acid, disodium saltMeSH
alpha Ketoglutaric acid, potassium saltMeSH
alpha Ketoglutaric acid, sodium saltMeSH
alpha OxoglutarateMeSH
alpha-Ketoglutaric acid, monosodium saltMeSH
alpha-Ketoglutaric acid, potassium saltMeSH
Oxogluric acidMeSH
alpha-Ketoglutaric acid, sodium saltMeSH
alpha Ketoglutaric acid, monopotassium saltMeSH
Calcium alpha ketoglutarateMeSH
alpha KetoglutarateMeSH
alpha Ketoglutaric acid, dipotassium saltMeSH
Calcium alpha-ketoglutarateMeSH
alpha-Ketoglutarate, calciumMeSH
alpha-Ketoglutaric acid, monopotassium saltMeSH
Molecular FormulaC5H4O5
Average Mass144.0823
Monoisotopic Mass144.005873238
IUPAC Name2-oxopentanedioate
Traditional Nameα ketoglutarate
CAS Registry NumberNot Available
SMILES
[O-]C(=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)/p-2
InChI KeyKPGXRSRHYNQIFN-UHFFFAOYSA-L