Pathway Tools
Intro Tutorial
discounted registration ends Sept 5, 2015
Pathway Tools
Intro Tutorial
discounted registration ends Sept 5, 2015
Pathway Tools
Intro Tutorial
discounted registration ends Sept 5, 2015
Pathway Tools
Intro Tutorial
discounted registration ends Sept 5, 2015
Pathway Tools
Intro Tutorial
discounted registration ends Sept 5, 2015
twitter

MetaCyc Compound: succinate

Synonyms: succinic acid, suc, succ, butanedioic acid, ethylenesuccinic acid

Superclasses: an acid all carboxy acids a carboxylate a dicarboxylate a C4-dicarboxylate

Chemical Formula: C4H4O4

Molecular Weight: 116.07 Daltons

Monoisotopic Molecular Weight: 118.026608681 Daltons

succinate compound structure

SMILES: C(C([O-])=O)CC([O-])=O

InChI: InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)/p-2

InChIKey: InChIKey=KDYFGRWQOYBRFD-UHFFFAOYSA-L

Unification Links: CAS:110-15-6 , ChEBI:30031 , ChemSpider:140973 , HMDB:HMDB00254 , IAF1260:33633 , KEGG:C00042 , KNApSAcK:C00001205 , MetaboLights:MTBLC30031 , PubChem:160419

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -125.16375 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

aerobic respiration I (cytochrome c) , aerobic respiration II (cytochrome c) (yeast) , aerobic respiration III (alternative oxidase pathway) , methylaspartate cycle , succinate to cytochrome bd oxidase electron transfer , succinate to cytochrome bo oxidase electron transfer , superpathway of glyoxylate cycle and fatty acid degradation , TCA cycle I (prokaryotic) , TCA cycle II (plants and fungi) , TCA cycle III (animals) :
succinate[in] + a ubiquinone[membrane] → fumarate[in] + an ubiquinol[membrane]

TCA cycle IV (2-oxoglutarate decarboxylase) , TCA cycle V (2-oxoglutarate:ferredoxin oxidoreductase) , TCA cycle VII (acetate-producers) :
succinate[in] + an electron-transfer quinone[membrane] → fumarate[in] + an electron-transfer quinol[membrane]

Not in pathways:
caldariellaquinone[membrane] + succinate[in] → caldariellaquinol[membrane] + fumarate[in]

methyl ketone biosynthesis :
a carboxylate + ATP + coenzyme A → an acyl-CoA + AMP + diphosphate

Not in pathways:
an acyl-protein synthetase + a carboxylate + ATP → an acyl-protein thioester + AMP + diphosphate
a carboxylate + GTP + coenzyme A → an acyl-CoA + GDP + phosphate

Reactions known to produce the compound:

(5R)-carbapenem carboxylate biosynthesis :
(3S,5S)-carbapenam-3-carboxylate + 2-oxoglutarate + oxygen → (5R)-carbapen-2-em-3-carboxylate + succinate + CO2 + H2O

2,4-dichlorophenoxyacetate degradation :
2,4-dichlorophenoxyacetate + 2-oxoglutarate + oxygen → 2,4-dichlorophenol + glyoxylate + succinate + CO2

2-aminoethylphosphonate degradation III :
(2-aminoethyl)phosphonate + 2-oxoglutarate + oxygen → (2-amino-1-hydroxyethyl)phosphonate + succinate + CO2

3-hydroxy-L-homotyrosine biosynthesis :
L-homotyrosine + 2-oxoglutarate + oxygen → 3-hydroxy-L-homotyrosine + succinate + CO2

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

3-phenylpropanoate and 3-(3-hydroxyphenyl)propanoate degradation to 2-oxopent-4-enoate :
(2Z,4E)-2-hydroxy-6-oxonona-2,4-diene-1,9-dioate + H2O → (2Z)-2-hydroxypenta-2,4-dienoate + succinate + H+

4-aminobutanoate degradation I , 4-aminobutanoate degradation IV , GABA shunt , L-glutamate degradation IV :
succinate semialdehyde + NAD+ + H2O → succinate + NADH + 2 H+

4-aminobutanoate degradation II , 4-hydroxyphenylacetate degradation , nicotine degradation I (pyridine pathway) , nicotine degradation II (pyrrolidine pathway) , TCA cycle IV (2-oxoglutarate decarboxylase) :
succinate semialdehyde + NADP+ + H2O → succinate + NADPH + 2 H+

4-aminobutanoate degradation III :
succinate semialdehyde + NAD(P)+ + H2O → succinate + NAD(P)H + 2 H+

4-chloro-2-methylphenoxyacetate degradation :
4-chloro-2-methylphenoxyacetate + 2-oxoglutarate + oxygen → 2-methyl-4-chlorophenol + glyoxylate + succinate + CO2

4-methyl-proline biosynthesis :
L-leucine + 2-oxoglutarate + oxygen → 5-hydroxy-leucine + succinate + CO2
5-hydroxy-leucine + 2-oxoglutarate + oxygen → 5,5-dihydroxy-leucine + succinate + CO2

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

anaerobic energy metabolism (invertebrates, mitochondrial) :
fumarate[mitochondrial lumen] + a rhodoquinol[CCO-MIT-IM-SPC-CCO-MIT-LUM]succinate[mitochondrial lumen] + a rhodoquinone[CCO-MIT-IM-SPC-CCO-MIT-LUM]

anditomin biosynthesis :
preandiloid C + 2-oxoglutarate + an reduced unknown electron acceptor + oxygen → andiconin + succinate + CO2 + an oxidized unknown electron acceptor + H2O
andilesin C + 2-oxoglutarate + oxygen → anditomin + succinate + CO2 + H2O

anthocyanin biosynthesis (cyanidin 3-O-glucoside) :
leucocyanidin + 2-oxoglutarate + oxygen → a dihydroquercetin + succinate + CO2 + H2O
leucocyanidin + 2-oxoglutarate + oxygen → cyanidin + succinate + CO2 + H+ + 2 H2O

anthocyanin biosynthesis (delphinidin 3-O-glucoside) :
leucodelphinidin + 2-oxoglutarate + oxygen → delphinidin + CO2 + succinate + H+ + 2 H2O

anthocyanin biosynthesis (pelargonidin 3-O-glucoside) :
leucopelargonidin + 2-oxoglutarate + oxygen → pelargonidin + succinate + CO2 + H+ + 2 H2O

apigeninidin 5-O-glucoside biosynthesis :
apiforol + 2-oxoglutarate + oxygen → apigeninidin + succinate + CO2 + 2 H2O

brassicicene C biosynthesis :
fusicocca-2,10(14)-diene-8β,16-diol + 2-oxoglutarate + oxygen → fusicocca-1,10(14)-diene-3,8β,16-triol + succinate + CO2

chrysin biosynthesis :
(2S)-pinocembrin + 2-oxoglutarate + oxygen → chrysin + succinate + CO2 + H2O

clavulanate biosynthesis :
deoxyamidinoproclavaminate + 2-oxoglutarate + oxygen → amidinoproclavaminate + succinate + CO2
dihydroclavaminate + 2-oxoglutarate + oxygen → clavaminate + CO2 + succinate + H2O

Reactions known to both consume and produce the compound:

2-methylcitrate cycle I , 2-methylcitrate cycle II :
(2R,3S)-2-methylisocitrate ↔ succinate + pyruvate

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

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

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

conversion of succinate to propanoate :
propanoyl-CoA + succinate ↔ propanoate + succinyl-CoA

glycerol-3-phosphate to fumarate electron transfer , hydrogen to fumarate electron transfer , mixed acid fermentation , NADH to fumarate electron transfer :
fumarate[in] + a menaquinol[membrane]succinate[in] + a menaquinone[membrane]

glyoxylate cycle , TCA cycle IV (2-oxoglutarate decarboxylase) :
D-threo-isocitrate ↔ glyoxylate + succinate

incomplete reductive TCA cycle :
fumarate[in] + a menaquinol[membrane]succinate[in] + a menaquinone[membrane]
succinate + ATP + coenzyme A ↔ succinyl-CoA + ADP + phosphate

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

L-lysine biosynthesis I :
N-succinyl-L,L-2,6-diaminopimelate + H2O ↔ L,L-diaminopimelate + succinate

methylaspartate cycle , 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 + ATP + coenzyme A ↔ succinyl-CoA + ADP + phosphate

pyruvate fermentation to propanoate I :
fumarate[in] + a menaquinol[membrane]succinate[in] + a menaquinone[membrane]
propanoyl-CoA + succinate ↔ propanoate + succinyl-CoA

reductive TCA cycle I :
fumarate[in] + a menaquinol[membrane]succinate[in] + a menaquinone[membrane]
succinate + ATP + coenzyme A ↔ succinyl-CoA + ADP + phosphate

reductive TCA cycle II :
fumarate[in] + a menaquinol[membrane]succinate[in] + a menaquinone[membrane]
succinate + ATP + coenzyme A ↔ succinyl-CoA + ADP + phosphate

TCA cycle III (animals) :
succinate + GTP + coenzyme A ↔ succinyl-CoA + GDP + phosphate
succinate + ATP + coenzyme A ↔ succinyl-CoA + ADP + phosphate

TCA cycle V (2-oxoglutarate:ferredoxin oxidoreductase) :
D-threo-isocitrate ↔ glyoxylate + succinate
succinate + ATP + coenzyme A ↔ succinyl-CoA + ADP + phosphate

TCA cycle VIII (helicobacter) :
succinyl-CoA + acetoacetate ↔ succinate + acetoacetyl-CoA

In Reactions of unknown directionality:

glycolate degradation II :
6 glycolate + H+ = acetate + 2 succinate + 2 CO2 + 4 H2O

Not in pathways:
O-succinyl-L-homoserine + hydrogen sulfide = L-homocysteine + succinate + H+
a 3-oxo acid + succinyl-CoA = a 3-oxoacyl-CoA + succinate
3-hydroxy-3-methylglutarate + succinyl-CoA = (S)-3-hydroxy-3-methylglutaryl-CoA + succinate
succinyl-CoA + (R)-citramalate = succinate + (3R)-citramalyl-CoA
succinyl-CoA + (R)-malate = succinate + (R)-malyl-CoA
succinyl-CoA + citramalate = citramalyl-CoA + succinate
4-oxo-4-sulfanylbutanoate + H2O = succinate + hydrogen sulfide + H+
fumarate + coenzyme M + coenzyme B = succinate + CoB-CoM heterodisulfide
succinate + ITP + coenzyme A = succinyl-CoA + IDP + phosphate
succinate + NAD+ = fumarate + NADH + H+

Not in pathways:
a monoamide of a dicarboxylate + H2O = a dicarboxylate + ammonium

Not in pathways:
eugenol + a carboxylate + NADP+ = a coniferyl ester + NADPH
a 2-acyl 1-lyso-phosphatidylcholine[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + sn-glycero-3-phosphocholine[periplasmic space] + H+[periplasmic space]
an aldehyde + an electron-transfer quinone + H2O = a carboxylate + an electron-transfer quinol + H+
a triacyl-sn-glycerol + H2O = a 1,2-diacyl-sn-glycerol + a carboxylate + H+
a penicillin + H2O = 6-aminopenicillanate + a carboxylate
an aldehyde[periplasmic space] + FAD[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + FADH2[periplasmic space]
a nitrile + 2 H2O = a carboxylate + ammonium
an aliphatic nitrile + 2 H2O = a carboxylate + ammonium
an N-acyl-L-homoserine lactone + H2O = L-homoserine lactone + a carboxylate
an aldehyde + an oxidized unknown electron acceptor + H2O = a carboxylate + an reduced unknown electron acceptor + H+
an N-acylated aromatic-L-amino acid + H2O = a carboxylate + an aromatic L-amino acid
an N-acylated-D-amino acid + H2O = a D-amino acid + a carboxylate
an N-acylated aliphatic-L-amino acid + H2O = a carboxylate + an aliphatic L-amino acid

In Transport reactions:
succinate[cytosol] + fumarate[periplasmic space] → fumarate[cytosol] + succinate[periplasmic space] ,
succinate[periplasmic space] + 2 H+[periplasmic space]succinate[cytosol] + 2 H+[cytosol] ,
succinate[cytosol] + L-aspartate[periplasmic space] → L-aspartate[cytosol] + succinate[periplasmic space] ,
D-tartrate[periplasmic space] + succinate[cytosol]succinate[periplasmic space] + D-tartrate[cytosol] ,
succinate[cytosol] + citrate[periplasmic space] → citrate[cytosol] + succinate[periplasmic space] ,
succinate[cytosol] + (S)-malate[periplasmic space] → (S)-malate[cytosol] + succinate[periplasmic space] ,
L-tartrate[periplasmic space] + succinate[cytosol] → L-tartrate[cytosol] + succinate[periplasmic space] ,
succinate[periplasmic space]succinate[cytosol] ,
a C4-dicarboxylate[periplasmic space] + 2 H+[periplasmic space]a C4-dicarboxylate[cytosol] + 2 H+[cytosol] ,
a C4-dicarboxylate[periplasmic space] + 3 H+[periplasmic space]a C4-dicarboxylate[cytosol] + 3 H+[cytosol]

In Redox half-reactions:
fumarate[in] + 2 H+[in] + 2 e-[membrane]succinate[in]

Enzymes activated by succinate, sorted by the type of activation, are:

Activator (Mechanism unknown) of: isoflavone-7-O-glucoside-6''-O-malonate malonyltransferase [Hinderer86] , isoflavone-7-O-glucoside-6''-O-malonate malonylesterase [Hinderer86] , isoflavone-7-O-glucoside-6''-O-malonate malonylesterase [Hinderer86] , isoflavone-7-O-glucoside-6''-O-malonate malonylesterase [Hinderer86] , isoflavone-7-O-glucoside-6''-O-malonate malonylesterase [Hinderer86] , isoflavone-7-O-glucoside-6''-O-malonate malonylesterase [Hinderer86] , prolycopene isomerase [Isaacson04]

Enzymes inhibited by succinate, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: glutamate decarboxylase A [Fonda72] , glutamate decarboxylase B [Fonda72] , aspartate transcarbamylase [Changeux68, Comment 1] , 3-dehydroquinate dehydratase [Chaudhuri86] , citramalate hydrolyase , glutamate dehydrogenase (NADP-dependent) [Comment 2] , 2-methyleneglutarate mutase [Kung71] , urocanase [Hug68]

Inhibitor (Uncompetitive) of: isocitrate lyase [Hoyt88, Comment 3]

Inhibitor (Noncompetitive) of: glutamate dehydrogenase (NAD-dependent) [Bonete96, Comment 4]

Inhibitor (Mechanism unknown) of: triose phosphate isomerase [Tomlinson79] , desacetoxyvindoline 4-hydroxylase [De93] , aspartate aminotransferase [Michuda70]

This compound has been characterized as an alternative substrate of the following enzymes: succinyl-CoA-glutarate CoA-transferase , formyl-CoA transferase


References

Bonete90: Bonete MJ, Camacho ML, Cadenas E (1990). "Analysis of the kinetic mechanism of halophilic NADP-dependent glutamate dehydrogenase." Biochim Biophys Acta 1990;1041(3);305-10. PMID: 1980084

Bonete96: Bonete MJ, Perez-Pomares F, Ferrer J, Camacho ML (1996). "NAD-glutamate dehydrogenase from Halobacterium halobium: inhibition and activation by TCA intermediates and amino acids." Biochim Biophys Acta 1996;1289(1);14-24. PMID: 8605224

Changeux68: Changeux JP, Gerhart JC, Schachman HK (1968). "Allosteric interactions in aspartate transcarbamylase. I. Binding of specific ligands to the native enzyme and its isolated subunits." Biochemistry 7(2);531-8. PMID: 4868539

Chaudhuri86: Chaudhuri S, Lambert JM, McColl LA, Coggins JR (1986). "Purification and characterization of 3-dehydroquinase from Escherichia coli." Biochem J 1986;239(3);699-704. PMID: 2950851

De93: De Carolis E, De Luca V (1993). "Purification, characterization, and kinetic analysis of a 2-oxoglutarate-dependent dioxygenase involved in vindoline biosynthesis from Catharanthus roseus." J Biol Chem 268(8);5504-11. PMID: 8449913

Fonda72: Fonda ML (1972). "Glutamate decarboxylase. Substrate specificity and inhibition by carboxylic acids." Biochemistry 1972;11(7);1304-9. PMID: 4552052

Hinderer86: Hinderer W, Koster J, Barz W (1986). "Purfication and properties of a specific isoflavone 7-O-glucoside-6''-malonate malonyestrase from roots of chickpea (Cicer arietinum L.)." Arch Biochem Biophys 248(2);570-8. PMID: 3740841

Hoyt88: Hoyt JC, Robertson EF, Berlyn KA, Reeves HC (1988). "Escherichia coli isocitrate lyase: properties and comparisons." Biochim Biophys Acta 1988;966(1);30-5. PMID: 3291954

Hug68: Hug DH, Roth D, Hunter J (1968). "Regulation of histidine catabolism by succinate in Pseudomonas putida." J Bacteriol 96(2);396-402. PMID: 5674054

Isaacson04: Isaacson T, Ohad I, Beyer P, Hirschberg J (2004). "Analysis in vitro of the enzyme CRTISO establishes a poly-cis-carotenoid biosynthesis pathway in plants." Plant Physiol 136(4);4246-55. PMID: 15557094

Kung71: Kung HF, Stadtman TC (1971). "Nicotinic acid metabolism. VI. Purification and properties of alpha-methyleneglutarate mutase (B 12-dependent) and methylitaconate isomerase." J Biol Chem 246(10);3378-88. PMID: 5574401

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

Michuda70: Michuda CM, Martinez-Carrion M (1970). "The isozymes of glutamate-aspartate transaminase. Mechanism of inhibition of dicarboxylic acids." J Biol Chem 245(2);262-9. PMID: 4312670

Tomlinson79: Tomlinson J.D., Turner J.F. "Pea seed triose phosphate isomerase." Phytochemistry (1979) 18:1959-1962.

Tsuruta94: Tsuruta H, Vachette P, Sano T, Moody MF, Amemiya Y, Wakabayashi K, Kihara H (1994). "Kinetics of the quaternary structure change of aspartate transcarbamylase triggered by succinate, a competitive inhibitor." Biochemistry 1994;33(33);10007-12. PMID: 8060968


Report Errors or Provide Feedback
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 19.0 on Mon Aug 31, 2015, biocyc13.