Succinyl-CoA (ECMDB01022) (M2MDB000228)
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Version | 2.0 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 13:03:35 -0600 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-09-17 15:41:07 -0600 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | Succinyl-CoA | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | Succinyl-CoA is a combination of succinic acid and coenzyme A. It is an important intermediate in the citric acid cycle, where it is synthesized from alpha-Ketoglutarate by alpha-ketoglutarate dehydrogenase through decarboxylation. During the process, coenzyme A is added. It is also synthesized from propionyl CoA, the odd-numbered fatty acid, which cannot undergo beta-oxidation. Propionyl-CoA is carboxylated to D-methylmalonyl-CoA, isomerized to L-methylmalonyl-CoA, and rearranged to yield succinyl-CoA via a vitamin B12-dependent enzyme. Succinyl-CoA is an intermediate of the citric acid cycle. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C25H40N7O19P3S | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 867.607 Monoisotopic: 867.131252359 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | VNOYUJKHFWYWIR-FZEDXVDRSA-N | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C25H40N7O19P3S/c1-25(2,20(38)23(39)28-6-5-14(33)27-7-8-55-16(36)4-3-15(34)35)10-48-54(45,46)51-53(43,44)47-9-13-19(50-52(40,41)42)18(37)24(49-13)32-12-31-17-21(26)29-11-30-22(17)32/h11-13,18-20,24,37-38H,3-10H2,1-2H3,(H,27,33)(H,28,39)(H,34,35)(H,43,44)(H,45,46)(H2,26,29,30)(H2,40,41,42)/t13-,18-,19-,20?,24-/m1/s1 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 604-98-8 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | 4-[(2-{3-[(2R)-3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido]propanamido}ethyl)sulfanyl]-4-oxobutanoic acid | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | succinyl-coa | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C(O)C(=O)NCCC(=O)NCCSC(=O)CCC(O)=O | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Taxonomy | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Lipids and lipid-like molecules | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Fatty Acyls | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Fatty acyl thioesters | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Acyl CoAs | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents |
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Substituents |
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Molecular Framework | Aromatic heteropolycyclic compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
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Physical Properties | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Solid | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | -5 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | alpha-Ketoglutarate + Coenzyme A + NAD > Carbon dioxide + NADH + Succinyl-CoA Adenosine triphosphate + Coenzyme A + Succinic acid <> ADP + Phosphate + Succinyl-CoA Water + Succinyl-CoA + Tetrahydrodipicolinate <> Coenzyme A + N-Succinyl-2-amino-6-ketopimelate Coenzyme A + 3-Oxoadipyl-CoA <> Acetyl-CoA + Succinyl-CoA L-Arginine + Succinyl-CoA <> Coenzyme A + Hydrogen ion + N2-Succinyl-L-arginine Succinyl-CoA > (S)-Methylmalonyl-CoA Propionyl-CoA + Succinic acid > Propionic acid + Succinyl-CoA L-Homoserine + Succinyl-CoA <> Coenzyme A + O-Succinyl-L-homoserine Succinyl-CoA + Acetyl-CoA <> Coenzyme A + 3-Oxoadipyl-CoA Succinyl-CoA + L-Arginine <> Coenzyme A + N2-Succinyl-L-arginine (R)-Methylmalonyl-CoA <> Succinyl-CoA Succinyl-CoA + Enzyme N6-(dihydrolipoyl)lysine + Enzyme N6-(dihydrolipoyl)lysine <> Coenzyme A + [Dihydrolipoyllysine-residue succinyltransferase] S-succinyldihydrolipoyllysine Oxoglutaric acid + Coenzyme A + NAD > Succinyl-CoA + Carbon dioxide + NADH L-Arginine + Succinyl-CoA > Hydrogen ion + N2-Succinyl-L-arginine + Coenzyme A L-Homoserine + Succinyl-CoA > O-Succinyl-L-homoserine + Coenzyme A R-Methylmalonyl-CoA <> Succinyl-CoA Succinyl-CoA + Acetyl-CoA < 3-Oxoadipyl-CoA + Coenzyme A Propionyl-CoA + Succinic acid <> Propionic acid + Succinyl-CoA Succinyl-CoA + L-Arginine > CoA + N2-Succinyl-L-arginine Succinyl-CoA + (S)-2,3,4,5-tetrahydropyridine-2,6-dicarboxylate + Water > CoA + N-Succinyl-2-amino-6-ketopimelate Succinyl-CoA + L-Homoserine > CoA + O-Succinyl-L-homoserine Succinyl-CoA + enzyme N(6)-(dihydrolipoyl)lysine > CoA + enzyme N(6)-(S-succinyldihydrolipoyl)lysine Succinyl-CoA + Acetyl-CoA > CoA + 3-Oxoadipyl-CoA R-Methylmalonyl-CoA > Succinyl-CoA Adenosine triphosphate + Succinic acid + CoA > ADP + Inorganic phosphate + Succinyl-CoA Acetoacetyl-CoA + Coenzyme A + Acetoacetyl-CoA > Acetyl-CoA + Succinyl-CoA + Succinyl-CoA More...(S)-2,3,4,5-tetrahydrodipicolinate + Succinyl-CoA + Water + Succinyl-CoA > Coenzyme A + N-Succinyl-2-amino-6-ketopimelate Oxoglutaric acid + NAD + Coenzyme A > Succinyl-CoA + NADH + Hydrogen ion + Carbon dioxide + Succinyl-CoA Succinyl-CoA + Phosphate + Guanosine diphosphate + Succinyl-CoA <> Succinic acid + Coenzyme A + Guanosine triphosphate Oxoglutaric acid + NAD + Coenzyme A > NADH + Carbon dioxide + Succinyl-CoA + Succinyl-CoA Succinyl-CoA + Adenosine diphosphate + Phosphate + Succinyl-CoA + ADP > Adenosine triphosphate + Coenzyme A + Succinic acid L-Arginine + Succinyl-CoA + Succinyl-CoA > Coenzyme A + Hydrogen ion + N2-succinyl-L-arginine + N2-succinyl-L-arginine L-Homoserine + Succinyl-CoA + L-Homoserine + Succinyl-CoA > Coenzyme A + O-Succinyl-L-homoserine Succinic acid + Propionyl-CoA + Propionyl-CoA > Propionic acid + Succinyl-CoA + Succinyl-CoA Succinyl-CoA + Succinyl-CoA > Methylmalonyl-CoA Succinyl-CoA + Dihydrolipoamide + Succinyl-CoA + Dihydrolipoamide > Coenzyme A + (S)-Succinyldihydrolipoamide 3-Oxoadipyl-CoA + Coenzyme A > Acetyl-CoA + Succinyl-CoA Succinyl-CoA <> R-Methylmalonyl-CoA a [2-oxoglutarate dehydrogenase E2 protein] N6-S-succinyldihydrolipoyl-L-lysine + Succinyl-CoA > a [2-oxoglutarate dehydrogenase E2 protein] N6-dihydrolipoyl-L-lysine + Coenzyme A L-Arginine + Succinyl-CoA <> Coenzyme A + Hydrogen ion + N2-Succinyl-L-arginine Adenosine triphosphate + Coenzyme A + Succinic acid <> ADP + Phosphate + Succinyl-CoA Water + Succinyl-CoA + Tetrahydrodipicolinate <> Coenzyme A + N-Succinyl-2-amino-6-ketopimelate L-Arginine + Succinyl-CoA <> Coenzyme A + Hydrogen ion + N2-Succinyl-L-arginine Succinyl-CoA + Enzyme N6-(dihydrolipoyl)lysine <> Coenzyme A + [Dihydrolipoyllysine-residue succinyltransferase] S-succinyldihydrolipoyllysine Adenosine triphosphate + Coenzyme A + Succinic acid <> ADP + Phosphate + Succinyl-CoA | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
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KEGG Pathways: |
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EcoCyc Pathways: |
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Concentrations | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Find out more about how we convert literature concentrations. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Wollemann, M. Mechanism of the succinyl-coenzyme A synthesis in brain extracts. Acta Physiologica Academiae Scientiarum Hungaricae (1959), 16 153-4. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Links | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Links: |
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Enzymes
- General function:
- Involved in transferase activity, transferring acyl groups
- Specific function:
- The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2). It contains multiple copies of three enzymatic components:pyruvate dehydrogenase (E1), dihydrolipoamide acetyltransferase (E2) and lipoamide dehydrogenase (E3)
- Gene Name:
- aceF
- Uniprot ID:
- P06959
- Molecular weight:
- 66096
Reactions
Acetyl-CoA + enzyme N(6)-(dihydrolipoyl)lysine = CoA + enzyme N(6)-(S-acetyldihydrolipoyl)lysine. |
- General function:
- Involved in transferase activity, transferring acyl groups
- Specific function:
- Succinyl-CoA + L-homoserine = CoA + O- succinyl-L-homoserine
- Gene Name:
- metA
- Uniprot ID:
- P07623
- Molecular weight:
- 35727
Reactions
Succinyl-CoA + L-homoserine = CoA + O-succinyl-L-homoserine. |
- General function:
- Involved in ATP binding
- Specific function:
- ATP + succinate + CoA = ADP + phosphate + succinyl-CoA
- Gene Name:
- sucC
- Uniprot ID:
- P0A836
- Molecular weight:
- 41392
Reactions
ATP + succinate + CoA = ADP + phosphate + succinyl-CoA. |
- General function:
- Involved in 2,3,4,5-tetrahydropyridine-2,6-dicarboxylate N-succinyltransferase activity
- Specific function:
- Succinyl-CoA + (S)-2,3,4,5-tetrahydropyridine- 2,6-dicarboxylate + H(2)O = CoA + N-succinyl-L-2-amino-6- oxoheptanedioate
- Gene Name:
- dapD
- Uniprot ID:
- P0A9D8
- Molecular weight:
- 29892
Reactions
Succinyl-CoA + (S)-2,3,4,5-tetrahydropyridine-2,6-dicarboxylate + H(2)O = CoA + N-succinyl-L-2-amino-6-oxoheptanedioate. |
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Lipoamide dehydrogenase is a component of the glycine cleavage system as well as of the alpha-ketoacid dehydrogenase complexes
- Gene Name:
- lpdA
- Uniprot ID:
- P0A9P0
- Molecular weight:
- 50688
Reactions
Protein N(6)-(dihydrolipoyl)lysine + NAD(+) = protein N(6)-(lipoyl)lysine + NADH. |
- General function:
- Involved in arginine N-succinyltransferase activity
- Specific function:
- Catalyzes the transfer of succinyl-CoA to arginine to produce N(2)-succinylarginine
- Gene Name:
- astA
- Uniprot ID:
- P0AE37
- Molecular weight:
- 38456
Reactions
Succinyl-CoA + L-arginine = CoA + N(2)-succinyl-L-arginine. |
- General function:
- Involved in oxoglutarate dehydrogenase (succinyl-transferring) activity
- Specific function:
- The 2-oxoglutarate dehydrogenase complex catalyzes the overall conversion of 2-oxoglutarate to succinyl-CoA and CO(2). It contains multiple copies of three enzymatic components:2- oxoglutarate dehydrogenase (E1), dihydrolipoamide succinyltransferase (E2) and lipoamide dehydrogenase (E3)
- Gene Name:
- sucA
- Uniprot ID:
- P0AFG3
- Molecular weight:
- 105061
Reactions
2-oxoglutarate + [dihydrolipoyllysine-residue succinyltransferase] lipoyllysine = [dihydrolipoyllysine-residue succinyltransferase] S-succinyldihydrolipoyllysine + CO(2). |
8. Dihydrolipoyllysine-residue succinyltransferase component of 2-oxoglutarate dehydrogenase complex
- General function:
- Involved in transferase activity, transferring acyl groups
- Specific function:
- The 2-oxoglutarate dehydrogenase complex catalyzes the overall conversion of 2-oxoglutarate to succinyl-CoA and CO(2). It contains multiple copies of three enzymatic components:2- oxoglutarate dehydrogenase (E1), dihydrolipoamide succinyltransferase (E2) and lipoamide dehydrogenase (E3)
- Gene Name:
- sucB
- Uniprot ID:
- P0AFG6
- Molecular weight:
- 44011
Reactions
Succinyl-CoA + enzyme N(6)-(dihydrolipoyl)lysine = CoA + enzyme N(6)-(S-succinyldihydrolipoyl)lysine. |
- General function:
- Involved in catalytic activity
- Specific function:
- ATP + succinate + CoA = ADP + phosphate + succinyl-CoA
- Gene Name:
- sucD
- Uniprot ID:
- P0AGE9
- Molecular weight:
- 29777
Reactions
ATP + succinate + CoA = ADP + phosphate + succinyl-CoA. |
- General function:
- Involved in transferase activity, transferring acyl groups other than amino-acyl groups
- Specific function:
- Catalyzes thiolytic cleavage of beta-ketoadipyl-CoA to succinyl-CoA and acetyl-CoA
- Gene Name:
- paaJ
- Uniprot ID:
- P0C7L2
- Molecular weight:
- 42276
Reactions
Succinyl-CoA + acetyl-CoA = CoA + 3-oxoadipyl-CoA. |
2,3-dehydroadipyl-CoA + acetyl-CoA = CoA + 3-oxo-5,6-dehydrosuberyl-CoA. |
- General function:
- Involved in acetyl-CoA C-acyltransferase activity
- Specific function:
- Catalyzes the final step of fatty acid oxidation in which acetyl-CoA is released and the CoA ester of a fatty acid two carbons shorter is formed. Involved in the aerobic and anaerobic degradation of long-chain fatty acids
- Gene Name:
- fadA
- Uniprot ID:
- P21151
- Molecular weight:
- 40876
Reactions
Acyl-CoA + acetyl-CoA = CoA + 3-oxoacyl-CoA. |
- General function:
- Involved in isomerase activity
- Specific function:
- Specific function unknown
- Gene Name:
- sbm
- Uniprot ID:
- P27253
- Molecular weight:
- 77871
Reactions
(R)-methylmalonyl-CoA = succinyl-CoA. |
- General function:
- Involved in transferase activity
- Specific function:
- Catalyzes the final step of fatty acid oxidation in which acetyl-CoA is released and the CoA ester of a fatty acid two carbons shorter is formed. Strongly involved in the anaerobic degradation of long and medium-chain fatty acids in the presence of nitrate and weakly involved in the aerobic degradation of long- chain fatty acids
- Gene Name:
- fadI
- Uniprot ID:
- P76503
- Molecular weight:
- 46530
Reactions
Acyl-CoA + acetyl-CoA = CoA + 3-oxoacyl-CoA. |
- General function:
- Involved in catalytic activity
- Specific function:
- Specific function unknown
- Gene Name:
- ygfH
- Uniprot ID:
- P52043
- Molecular weight:
- 53824
Reactions
Propanoyl-CoA + succinate = propionate + succinyl-CoA. |