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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
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MetaCyc Compound: succinyl-CoA

Systematic Name: Coenzyme A, S-(hydrogen butanedioate)

Synonyms: suc-coa, succ-coenzyme-A, succ-S-coenzyme-A, succinyl-S-coenzyme-A, succ-S-CoA, succinylcoenzyme-A, succ-CoA, suc-co-A, succinyl-S-CoA, succinyl-coenzyme A

Superclasses: an ester a thioester a coenzyme A-activated compound

Chemical Formula: C25H35N7O19P3S

Molecular Weight: 862.57 Daltons

Monoisotopic Molecular Weight: 867.1312523603 Daltons

SMILES: CC(C)(C(O)C(=O)NCCC(=O)NCCSC(=O)CCC(=O)[O-])COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-]

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)/p-5/t13-,18-,19-,20+,24-/m1/s1

InChIKey: InChIKey=VNOYUJKHFWYWIR-ITIYDSSPSA-I

Unification Links: CAS:604-98-8 , ChEBI:57292 , HMDB:HMDB01022 , IAF1260:33820 , KEGG:C00091 , MetaboLights:MTBLC57292 , PubChem:25245777

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -575.61127 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

2-amino-3-hydroxycyclopent-2-enone biosynthesis , tetrapyrrole biosynthesis II (from glycine) :
glycine + succinyl-CoA + H+ → CO2 + 5-aminolevulinate + coenzyme A

3-hydroxypropanoate/4-hydroxybutanate cycle , succinate fermentation to butyrate :
succinate semialdehyde + coenzyme A + NADP+succinyl-CoA + NADPH + H+

3-oxoadipate degradation :
3-oxoadipate + succinyl-CoA → 3-oxoadipyl-CoA + succinate

4-methylcatechol degradation (ortho cleavage) :
4-methyl-3-oxoadipate + succinyl-CoA → 4-methyl-3-oxoadipyl-CoA + succinate

alcaligin biosynthesis , putrebactin biosynthesis :
N-hydroxyputrescine + succinyl-CoA + H+N-hydroxy-N-succinyl-putrescine + coenzyme A

arginine degradation II (AST pathway) :
L-arginine + succinyl-CoA → N2-succinyl-L-arginine + coenzyme A + H+

bisucaberin biosynthesis , desferrioxamine B biosynthesis , desferrioxamine E biosynthesis :
N-hydroxycadaverine + succinyl-CoAN-hydroxy-N-succinylcadaverine + coenzyme A

itaconate degradation :
succinyl-CoA + itaconate → succinate + itaconyl-CoA

lysine biosynthesis I :
(S)-2,3,4,5-tetrahydrodipicolinate + succinyl-CoA + H2O → N-succinyl-2-amino-6-ketopimelate + coenzyme A

lysine degradation IV , lysine degradation V , lysine degradation X :
glutarate + succinyl-CoA → glutaryl-CoA + succinate

m-xylene degradation (anaerobic) :
(3-methylbenzyl)succinate + succinyl-CoA → (3-methylbenzyl)succinyl-CoA + succinate

methionine biosynthesis I :
L-homoserine + succinyl-CoA → O-succinyl-L-homoserine + coenzyme A

methylaspartate cycle :
mesaconate + succinyl-CoA → 2-methylfumaryl-CoA + succinate

oxalate degradation II , oxalate degradation III :
oxalate + succinyl-CoA → oxalyl-CoA + succinate

Not in pathways:
succinyl-CoA + H2O → succinate + coenzyme A + H+

Reactions known to produce the compound:

3-oxoadipate degradation , benzoyl-CoA degradation I (aerobic) , phenylacetate degradation I (aerobic) :
succinyl-CoA + acetyl-CoA ← 3-oxoadipyl-CoA + coenzyme A

m-xylene degradation (anaerobic) :
(3-methylphenyl)itaconyl-CoA + coenzyme A + an oxidized electron acceptor + H2O → 3-methylbenzoyl-CoA + succinyl-CoA + a reduced electron acceptor

TCA cycle I (prokaryotic) , TCA cycle II (plants and fungi) , TCA cycle III (animals) , TCA cycle VII (acetate-producers) :
2-oxoglutarate + coenzyme A + NAD+succinyl-CoA + CO2 + NADH

toluene degradation to benzoyl-CoA (anaerobic) :
benzoylsuccinyl-CoA + coenzyme A → benzoyl-CoA + succinyl-CoA

Reactions known to both consume and produce the compound:

2-oxoglutarate decarboxylation to succinyl-CoA :
succinyl-CoA + a [2-oxoglutarate dehydrogenase E2 protein] N6-dihydrolipoyl-L-lysine → a [2-oxoglutarate dehydrogenase E2 protein] N6-S-succinyldihydrolipoyl-L-lysine + coenzyme A

3-hydroxypropanoate cycle :
(R)-methylmalonyl-CoA ↔ succinyl-CoA
succinyl-CoA + (S)-malate ↔ succinate + (S)-malyl-CoA

3-hydroxypropanoate/4-hydroxybutanate cycle , propionyl CoA degradation :
(R)-methylmalonyl-CoA ↔ succinyl-CoA

acetate formation from acetyl-CoA III (succinate) , succinate fermentation to butyrate , TCA cycle VII (acetate-producers) :
acetate + succinyl-CoA ↔ acetyl-CoA + succinate

anaerobic energy metabolism (invertebrates, mitochondrial) :
(R)-methylmalonyl-CoA ↔ succinyl-CoA
propanoyl-CoA + succinate ↔ propanoate + succinyl-CoA
succinate[mitochondrial lumen] + ATP[mitochondrial lumen] + coenzyme A[mitochondrial lumen]succinyl-CoA[mitochondrial lumen] + ADP[mitochondrial lumen] + phosphate[mitochondrial lumen]
acetate + succinyl-CoA ↔ acetyl-CoA + succinate

conversion of succinate to propionate :
(R)-methylmalonyl-CoA ↔ succinyl-CoA
propanoyl-CoA + succinate ↔ propanoate + succinyl-CoA

incomplete reductive TCA cycle :
2-oxoglutarate + 2 an oxidized ferredoxin + coenzyme A ↔ succinyl-CoA + CO2 + 2 a reduced ferredoxin + H+
succinate[mitochondrial lumen] + ATP[mitochondrial lumen] + coenzyme A[mitochondrial lumen]succinyl-CoA[mitochondrial lumen] + ADP[mitochondrial lumen] + phosphate[mitochondrial lumen]

ketolysis :
succinyl-CoA + acetoacetate ↔ succinate + acetoacetyl-CoA

methylaspartate cycle :
(R)-methylmalonyl-CoA ↔ succinyl-CoA
succinate[mitochondrial lumen] + ATP[mitochondrial lumen] + coenzyme A[mitochondrial lumen]succinyl-CoA[mitochondrial lumen] + ADP[mitochondrial lumen] + phosphate[mitochondrial lumen]

pyruvate fermentation to acetate V , pyruvate fermentation to acetate VI , TCA cycle I (prokaryotic) , TCA cycle II (plants and fungi) , TCA cycle VI (obligate autotrophs) :
succinate[mitochondrial lumen] + ATP[mitochondrial lumen] + coenzyme A[mitochondrial lumen]succinyl-CoA[mitochondrial lumen] + ADP[mitochondrial lumen] + phosphate[mitochondrial lumen]

pyruvate fermentation to propionate I :
(R)-methylmalonyl-CoA ↔ succinyl-CoA
propanoyl-CoA + succinate ↔ propanoate + succinyl-CoA

reductive TCA cycle I :
2-oxoglutarate + 2 an oxidized ferredoxin + coenzyme A ↔ succinyl-CoA + CO2 + 2 a reduced ferredoxin + H+
succinate[mitochondrial lumen] + ATP[mitochondrial lumen] + coenzyme A[mitochondrial lumen]succinyl-CoA[mitochondrial lumen] + ADP[mitochondrial lumen] + phosphate[mitochondrial lumen]

reductive TCA cycle II :
2-oxoglutarate + 2 an oxidized ferredoxin + coenzyme A ↔ succinyl-CoA + CO2 + 2 a reduced ferredoxin + H+
succinate[mitochondrial lumen] + ATP[mitochondrial lumen] + coenzyme A[mitochondrial lumen]succinyl-CoA[mitochondrial lumen] + ADP[mitochondrial lumen] + phosphate[mitochondrial lumen]

TCA cycle III (animals) :
succinate[mitochondrial lumen] + GTP[mitochondrial lumen] + coenzyme A[mitochondrial lumen]succinyl-CoA[mitochondrial lumen] + GDP[mitochondrial lumen] + phosphate[mitochondrial lumen]
succinate[mitochondrial lumen] + ATP[mitochondrial lumen] + coenzyme A[mitochondrial lumen]succinyl-CoA[mitochondrial lumen] + ADP[mitochondrial lumen] + phosphate[mitochondrial lumen]

TCA cycle V (2-oxoglutarate:ferredoxin oxidoreductase) :
2-oxoglutarate + 2 an oxidized ferredoxin + coenzyme A ↔ succinyl-CoA + CO2 + 2 a reduced ferredoxin + H+
succinate[mitochondrial lumen] + ATP[mitochondrial lumen] + coenzyme A[mitochondrial lumen]succinyl-CoA[mitochondrial lumen] + ADP[mitochondrial lumen] + phosphate[mitochondrial lumen]

TCA cycle VIII (helicobacter) :
2-oxoglutarate + 2 an oxidized ferredoxin + coenzyme A ↔ succinyl-CoA + CO2 + 2 a reduced ferredoxin + H+
succinyl-CoA + acetoacetate ↔ succinate + acetoacetyl-CoA

toluene degradation to benzoyl-CoA (anaerobic) :
(R)-2-benzylsuccinate + succinyl-CoA ↔ (R)-benzylsuccinyl-CoA + succinate

Not in pathways:
succinyl-CoA + (S)-citramalate ↔ (3S)-citramalyl-CoA + succinate

In Reactions of unknown directionality:

Not in pathways:
succinate + ITP + coenzyme A = succinyl-CoA + IDP + phosphate
2-oxoglutarate + coenzyme A + NADP+ = succinyl-CoA + CO2 + NADPH
succinyl-CoA + citramalate = citramalyl-CoA + succinate
succinyl-CoA + (R)-malate = succinate + (R)-malyl-CoA
succinyl-CoA + (R)-citramalate = succinate + (3R)-citramalyl-CoA
3-hydroxy-3-methylglutarate + succinyl-CoA = (S)-3-hydroxy-3-methylglutaryl-CoA + succinate
a 3-oxo acid + succinyl-CoA = a 3-oxoacyl-CoA + succinate
L-ornithine + succinyl-CoA = N2-succinyl-L-ornithine + coenzyme A + H+

Enzymes activated by succinyl-CoA, sorted by the type of activation, are:

Activator (Allosteric) of: DL-methylmalonyl-CoA racemase [Stabler85]

Enzymes inhibited by succinyl-CoA, sorted by the type of inhibition, are:

Inhibitor (Mechanism unknown) of: pyruvate kinase [Comment 1] , propionyl CoA carboxylase [Hugler03a] , acetyl CoA carboxylase [Chuakrut03]


References

Chuakrut03: Chuakrut S, Arai H, Ishii M, Igarashi Y (2003). "Characterization of a bifunctional archaeal acyl coenzyme A carboxylase." J Bacteriol 185(3);938-47. PMID: 12533469

Hugler03a: Hugler M, Krieger RS, Jahn M, Fuchs G (2003). "Characterization of acetyl-CoA/propionyl-CoA carboxylase in Metallosphaera sedula. Carboxylating enzyme in the 3-hydroxypropionate cycle for autotrophic carbon fixation." Eur J Biochem 270(4);736-44. PMID: 12581213

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Speranza89: Speranza ML, Valentini G, Iadarola P, Stoppini M, Malcovati M, Ferri G (1989). "Primary structure of three peptides at the catalytic and allosteric sites of the fructose-1,6-bisphosphate-activated pyruvate kinase from Escherichia coli." Biol Chem Hoppe Seyler 1989;370(3);211-6. PMID: 2653362

Stabler85: Stabler SP, Marcell PD, Allen RH (1985). "Isolation and characterization of DL-methylmalonyl-coenzyme A racemase from rat liver." Arch Biochem Biophys 241(1);252-64. PMID: 2862845


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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Mon Dec 22, 2014, biocyc11.