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- Name help_outline hexadecanedioyl-CoA Identifier CHEBI:77085 Charge -5 Formula C37H59N7O19P3S InChIKeyhelp_outline GTCSHNMTNCXODY-CCAJQFMUSA-I SMILEShelp_outline CC(C)(COP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP([O-])([O-])=O)n1cnc2c(N)ncnc12)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CCCCCCCCCCCCCCC([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 4 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline (R)-carnitine Identifier CHEBI:16347 (Beilstein: 4292315,5732837; CAS: 541-15-1) help_outline Charge 0 Formula C7H15NO3 InChIKeyhelp_outline PHIQHXFUZVPYII-ZCFIWIBFSA-N SMILEShelp_outline C[N+](C)(C)C[C@H](O)CC([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 48 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline O-hexadecanedioyl-L-carnitine Identifier CHEBI:77087 Charge -1 Formula C23H42NO6 InChIKeyhelp_outline UNHCPLSWMNPZTD-HXUWFJFHSA-M SMILEShelp_outline C[N+](C)(C)C[C@@H](CC([O-])=O)OC(=O)CCCCCCCCCCCCCCC([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 1 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline CoA Identifier CHEBI:57287 (Beilstein: 11604429) help_outline Charge -4 Formula C21H32N7O16P3S InChIKeyhelp_outline RGJOEKWQDUBAIZ-IBOSZNHHSA-J SMILEShelp_outline CC(C)(COP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP([O-])([O-])=O)n1cnc2c(N)ncnc12)[C@@H](O)C(=O)NCCC(=O)NCCS 2D coordinates Mol file for the small molecule Search links Involved in 1,511 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:40283 | RHEA:40284 | RHEA:40285 | RHEA:40286 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Related reactions help_outline
More general form(s) of this reaction
Publications
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Rat liver metabolism of dicarboxylic acids.
Vamecq J., Draye J.P., Brison J.
Recently, we demonstrated in rat liver that dicarboxylic acids containing more than five carbons can be activated by a microsomal dicarboxylyl-CoA synthetase (J. Vamecq, E. de Hoffmann, and F. Van Hoof. Biochem. J. 230: 683-693, 1985). The products of this reaction, dicarboxylyl-CoA esters, were f ... >> More
Recently, we demonstrated in rat liver that dicarboxylic acids containing more than five carbons can be activated by a microsomal dicarboxylyl-CoA synthetase (J. Vamecq, E. de Hoffmann, and F. Van Hoof. Biochem. J. 230: 683-693, 1985). The products of this reaction, dicarboxylyl-CoA esters, were found to be substrates for an H2O2-generating dicarboxylyl-CoA oxidase. In the present work we report that 1) the catalytic center or the essential domains of dicarboxylyl-CoA synthetase are located at the cytosolic aspect of the endoplasmic reticulum membrane; 2) dicarboxylyl-CoA oxidase is optimally active on dodecanedioyl-CoA and is a peroxisomal enzyme; 3) cyanide-insensitive dodecanedioyl-CoA oxidation (NADH production) is catalyzed by rat liver homogenates. Cell fractionation studies disclose that, similar to dodecanedioyl-CoA oxidase (H2O2 production), the cyanide-insensitive dodecanedioyl-CoA oxidizing activity also belongs to peroxisomes; 4) a dodecanedioyl-CoA oxidoreductase reaction can be assayed by the dichlorphenolindophenol procedure in rat liver homogenates, and the activity is abundant in peroxisomal, mitochondrial, and soluble fractions; 5) by contrast with monocarboxylyl-CoA esters, the dicarboxylyl-CoAs are apparently not substrates for mitochondrial fatty acid oxidation; however, the use of dicarboxylylcarnitine esters as direct substrate for mitochondria suggests the existence of an active beta-oxidation of dicarboxylates in these organelles, which is further confirmed by experiments in which mitochondria are permeabilized with digitonin; 6) the in vivo oxidation of infused dodecanedioic acid results in a rapid appearance in urine of medium-chain dicarboxylic acids, with only 30-50% of the infused dose recovered in urine. << Less
Am J Physiol 256:G680-8(1989) [PubMed] [EuropePMC]
This publication is cited by 6 other entries.