KEGG   COMPOUND: C00026
Entry
C00026                      Compound                               
Name
2-Oxoglutarate;
Oxoglutaric acid;
2-Ketoglutaric acid;
alpha-Ketoglutaric acid
Formula
C5H6O5
Exact mass
146.0215
Mol weight
146.10
Structure
Reaction
R00021 R00093 R00114 R00243 R00248 R00250 R00258 R00264
R00265 R00267 R00268 R00269 R00270 R00271 R00272 R00279
R00298 R00355 R00372 R00457 R00474 R00563 R00621 R00667
R00668 R00684 R00694 R00709 R00715 R00716 R00734 R00895
R00896 R00908 R01090 R01148 R01155 R01161 R01197 R01214
R01252 R01339 R01412 R01580 R01582 R01587 R01648 R01684
R01700 R01879 R01939 R01956 R02077 R02160 R02199 R02274
R02283 R02397 R02433 R02444 R02445 R02486 R02619 R02700
R02772 R02773 R03008 R03009 R03053 R03063 R03120 R03126
R03207 R03218 R03219 R03225 R03243 R03266 R03376 R03451
R03534 R03590 R03640 R03698 R03737 R03806 R03807 R03809
R03812 R03859 R03952 R04028 R04029 R04051 R04073 R04171
R04173 R04188 R04217 R04234 R04269 R04276 R04338 R04438
R04467 R04475 R04529 R05036 R05037 R05039 R05052 R05085
R05097 R05126 R05127 R05228 R05229 R05301 R05302 R05320
R05419 R05466 R05468 R05469 R05493 R05507 R05722 R05723
R05839 R05857 R06322 R06323 R06335 R06336 R06337 R06338
R06423 R06426 R06539 R06540 R06551 R06586 R06631 R06634
R06977 R07184 R07185 R07186 R07187 R07275 R07276 R07277
R07329 R07366 R07367 R07368 R07396 R07613 R07659 R07712
R07993 R07996 R07997 R08050 R08081 R08082 R08165 R08198
R08201 R08213 R08254 R08549 R08610 R08611 R08897 R08903
R08931 R08972 R09363 R09402 R09510 R09511 R09572 R09778
R09784 R09785 R09824 R09825 R10056 R10081 R10086 R10094
R10141 R10143 R10144 R10145 R10157 R10210 R10312 R10413
R10415 R10445 R10446 R10460 R10487 R10522 R10527 R10539
R10542 R10575 R10698 R10723 R10724 R10735 R10740 R10741
R10742 R10845 R10920 R10932 R10991 R11030 R11053 R11118
R11210 R11269 R11270 R11285 R11291 R11297 R11298 R11299
R11337 R11340 R11345 R11395 R11409 R11475 R11549 R11593
R11594 R11607 R11655 R11768 R11948 R11960 R11963 R11991
R11993 R12024 R12076 R12081 R12082 R12083 R12165 R12166
R12176 R12210 R12214 R12216 R12217 R12222 R12306 R12312
R12315 R12407 R12411 R12452 R12459 R12460 R12461 R12501
R12509 R12510 R12606 R12615 R12645 R12650 R12651 R12663
R12688 R12706 R12778 R12826 R12848 R12906 R12936 R13012
R13013 R13014 R13015 R13036 R13108 R13109 R13110 R13111
R13122 R13305 R13401 R13442 R13443
 » show all
Pathway
map00020  Citrate cycle (TCA cycle)
map00040  Pentose and glucuronate interconversions
map00053  Ascorbate and aldarate metabolism
map00220  Arginine biosynthesis
map00250  Alanine, aspartate and glutamate metabolism
map00300  Lysine biosynthesis
map00310  Lysine degradation
map00340  Histidine metabolism
map00365  Furfural degradation
map00430  Taurine and hypotaurine metabolism
map00470  D-Amino acid metabolism
map00630  Glyoxylate and dicarboxylate metabolism
map00650  Butanoate metabolism
map00660  C5-Branched dibasic acid metabolism
map00720  Other carbon fixation pathways
map00785  Lipoic acid metabolism
map00997  Biosynthesis of various other secondary metabolites
map00998  Biosynthesis of various antibiotics
map01060  Biosynthesis of plant secondary metabolites
map01061  Biosynthesis of phenylpropanoids
map01062  Biosynthesis of terpenoids and steroids
map01063  Biosynthesis of alkaloids derived from shikimate pathway
map01064  Biosynthesis of alkaloids derived from ornithine, lysine and nicotinic acid
map01065  Biosynthesis of alkaloids derived from histidine and purine
map01066  Biosynthesis of alkaloids derived from terpenoid and polyketide
map01070  Biosynthesis of plant hormones
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
map01120  Microbial metabolism in diverse environments
map01200  Carbon metabolism
map01210  2-Oxocarboxylic acid metabolism
map01230  Biosynthesis of amino acids
map01240  Biosynthesis of cofactors
map04066  HIF-1 signaling pathway
map04727  GABAergic synapse
map04922  Glucagon signaling pathway
map04964  Proximal tubule bicarbonate reclamation
map04976  Bile secretion
map05230  Central carbon metabolism in cancer
Module
M00009  Citrate cycle (TCA cycle, Krebs cycle)
M00010  Citrate cycle, first carbon oxidation, oxaloacetate => 2-oxoglutarate
M00011  Citrate cycle, second carbon oxidation, 2-oxoglutarate => oxaloacetate
M00030  Lysine biosynthesis, AAA pathway, 2-oxoglutarate => 2-aminoadipate => lysine
M00173  Reductive citrate cycle (Arnon-Buchanan cycle)
M00433  Lysine biosynthesis, 2-oxoglutarate => 2-oxoadipate
M00532  Photorespiration
M00608  2-Oxocarboxylic acid chain extension, 2-oxoglutarate => 2-oxoadipate => 2-oxopimelate => 2-oxosuberate
M00620  Incomplete reductive citrate cycle, acetyl-CoA => oxoglutarate
M00740  Methylaspartate cycle
M00948  Hydroxyproline degradation, trans-4-hydroxy-L-proline => 2-oxoglutarate
M00956  Lysine degradation, bacteria, L-lysine => succinate
M00957  Lysine degradation, bacteria, L-lysine => glutarate => succinate/acetyl-CoA
M00960  Lysine degradation, bacteria, L-lysine => D-lysine => succinate
Network
nt06031  Citrate cycle and pyruvate metabolism
nt06032  Lipoic acid metabolism
Enzyme
1.1.1.41        1.1.1.42        1.1.1.95        1.1.1.286       
1.1.1.399       1.1.5.13        1.1.99.2        1.1.99.24       
1.1.99.39       1.1.99.40       1.1.-.-         1.2.1.3         
1.2.1.26        1.2.1.52        1.2.1.105       1.2.1.-         
1.2.4.2         1.2.7.3         1.2.7.11        1.4.1.2         
1.4.1.3         1.4.1.4         1.4.1.13        1.4.1.14        
1.4.3.7         1.4.3.11        1.4.3.15        1.4.7.1         
1.5.1.7         1.5.1.8         1.5.1.19        1.5.1.51        
1.13.12.19      1.14.11.1       1.14.11.2       1.14.11.3       
1.14.11.4       1.14.11.6       1.14.11.7       1.14.11.8       
1.14.11.9       1.14.11.10      1.14.11.11      1.14.11.12      
1.14.11.13      1.14.11.15      1.14.11.16      1.14.11.17      
1.14.11.18      1.14.11.20      1.14.11.21      1.14.11.24      
1.14.11.25      1.14.11.26      1.14.11.27      1.14.11.28      
1.14.11.31      1.14.11.32      1.14.11.35      1.14.11.36      
1.14.11.37      1.14.11.38      1.14.11.39      1.14.11.40      
1.14.11.41      1.14.11.42      1.14.11.43      1.14.11.44      
1.14.11.45      1.14.11.46      1.14.11.48      1.14.11.49      
1.14.11.51      1.14.11.52      1.14.11.55      1.14.11.56      
1.14.11.57      1.14.11.58      1.14.11.59      1.14.11.60      
1.14.11.61      1.14.11.62      1.14.11.63      1.14.11.64      
1.14.11.65      1.14.11.66      1.14.11.67      1.14.11.68      
1.14.11.69      1.14.11.70      1.14.11.71      1.14.11.72      
1.14.11.73      1.14.11.74      1.14.11.75      1.14.11.76      
1.14.11.77      1.14.11.78      1.14.11.79      1.14.11.80      
1.14.11.81      1.14.11.82      1.14.11.-       1.14.20.1       
1.14.20.3       1.14.20.4       1.14.20.5       1.14.20.6       
1.14.20.7       1.14.20.8       1.14.20.9       1.14.20.10      
1.14.20.11      1.14.20.12      1.14.20.13      1.14.20.14      
1.14.20.15      1.14.20.16      1.14.20.-       2.2.1.5         
2.2.1.9         2.3.3.4         2.3.3.14        2.6.1.1         
2.6.1.2         2.6.1.3         2.6.1.4         2.6.1.5         
2.6.1.6         2.6.1.7         2.6.1.9         2.6.1.11        
2.6.1.13        2.6.1.17        2.6.1.19        2.6.1.21        
2.6.1.22        2.6.1.23        2.6.1.24        2.6.1.26        
2.6.1.27        2.6.1.29        2.6.1.33        2.6.1.34        
2.6.1.36        2.6.1.38        2.6.1.39        2.6.1.42        
2.6.1.44        2.6.1.48        2.6.1.49        2.6.1.52        
2.6.1.54        2.6.1.55        2.6.1.57        2.6.1.59        
2.6.1.65        2.6.1.67        2.6.1.72        2.6.1.74        
2.6.1.75        2.6.1.76        2.6.1.79        2.6.1.80        
2.6.1.81        2.6.1.82        2.6.1.83        2.6.1.87        
2.6.1.89        2.6.1.90        2.6.1.92        2.6.1.93        
2.6.1.94        2.6.1.95        2.6.1.98        2.6.1.102       
2.6.1.103       2.6.1.104       2.6.1.106       2.6.1.107       
2.6.1.109       2.6.1.110       2.6.1.111       2.6.1.114       
2.6.1.116       2.6.1.118       2.6.1.120       2.6.1.122       
2.6.1.125       2.6.1.-         3.5.1.3         3.5.1.36        
3.5.1.111       3.5.1.128       4.1.1.71        4.2.1.168       
6.3.2.56        6.3.2.65        6.4.1.7
 » show all
Brite
Compounds with biological roles [BR:br08001]
 Organic acids
  Carboxylic acids
   2-Oxocarboxylic acids
    C00026  2-Oxoglutarate
Other DBs
CAS: 328-50-7
PubChem: 3328
ChEBI: 16810 30915
KNApSAcK: C00000769
PDB-CCD: AKG[PDBj]
NIKKAJI: J11.847H
LinkDB
KCF data

ATOM        10
            1   C5a C    27.7045  -20.9076
            2   C1b C    26.4954  -20.2102
            3   C6a C    28.9072  -20.2102
            4   O5a O    27.7045  -22.3718
            5   C1b C    25.2927  -20.9076
            6   O6a O    30.1100  -20.9139
            7   O6a O    28.9007  -18.8219
            8   C6a C    24.0836  -20.2102
            9   O6a O    24.0899  -18.8219
            10  O6a O    22.8808  -20.9139
BOND        9
            1     1   2 1
            2     1   3 1
            3     1   4 2
            4     2   5 1
            5     3   6 1
            6     3   7 2
            7     5   8 1
            8     8   9 2
            9     8  10 1

» Japanese version

KEGG   COMPOUND: C15972
Entry
C15972                      Compound                               
Name
Enzyme N6-(lipoyl)lysine;
Lipoamide-E;
[E2 protein]-N6-lipoyl-L-lysine;
[Lipoyl-carrier protein E2]-N6-lipoyl-L-lysine
Formula
C8H14NOS2R
Structure
Comment
Generic compound in reaction hierarchy
The oxidized lipoyllysine residue in EC 2.3.1.12, dihydrolipoyllysine-residue acetyltransferase ( EC 2.3.1.61, dihydrolipoyllysine-residue succinyltransferase or EC 2.3.1.168, dihydrolipoyllysine-residue (2-methylpropanoyl)transferase ).
Reaction
R01699 R01700 R01701 R01702 R01940 R03270 R03316 R04225
R07600 R07602 R07604 R07618 R10997 R12426 R12435 R12449
R12450 R12603 R13167 R13186
Pathway
map00010  Glycolysis / Gluconeogenesis
map00020  Citrate cycle (TCA cycle)
map00280  Valine, leucine and isoleucine degradation
map00310  Lysine degradation
map00620  Pyruvate metabolism
map00640  Propanoate metabolism
map00785  Lipoic acid metabolism
map01100  Metabolic pathways
map01240  Biosynthesis of cofactors
Module
M00009  Citrate cycle (TCA cycle, Krebs cycle)
M00011  Citrate cycle, second carbon oxidation, 2-oxoglutarate => oxaloacetate
M00032  Lysine degradation, lysine => saccharopine => acetoacetyl-CoA
M00036  Leucine degradation, leucine => acetoacetate + acetyl-CoA
M00307  Pyruvate oxidation, pyruvate => acetyl-CoA
Network
nt06024  Valine, leucine and isoleucine degradation
nt06031  Citrate cycle and pyruvate metabolism
nt06032  Lipoic acid metabolism
nt06036  Lysine degradation
Enzyme
1.2.4.1         1.2.4.2         1.2.4.4         1.2.4.-         
1.8.1.4         1.11.1.28       2.3.1.200       2.3.1.313       
6.3.1.20
Other DBs
PubChem: 47205285
ChEBI: 80218
LinkDB
KCF data

ATOM        13
            1   S3x S    14.9894  -14.4968
            2   S3x S    13.5885  -14.4968
            3   C1x C    13.1557  -15.8291
            4   C1x C    14.2890  -16.6526
            5   C1y C    15.4223  -15.8291
            6   C1b C    16.6229  -16.5281
            7   C1b C    17.8362  -15.8276
            8   C1b C    19.0493  -16.5281
            9   C1b C    20.2625  -15.8276
            10  C5a C    21.4758  -16.5281
            11  N1b N    22.6890  -15.8276
            12  O5a O    21.4758  -17.9290
            13  R   R    24.0899  -15.8276
BOND        13
            1     1   2 1
            2     2   3 1
            3     3   4 1
            4     4   5 1
            5     1   5 1
            6     5   6 1 #Down
            7     6   7 1
            8     7   8 1
            9     8   9 1
            10    9  10 1
            11   10  11 1
            12   10  12 2
            13   11  13 1

» Japanese version

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