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Record Information
Version1.0
Creation Date2016-09-30 22:40:01 UTC
Update Date2020-05-21 16:28:30 UTC
BMDB IDBMDB0001022
Secondary Accession Numbers
  • BMDB01022
Metabolite Identification
Common NameSuccinyl-CoA
DescriptionSuccinyl-CoA, also known as CoA S-succinate or suc-CO-a, 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. Succinyl-CoA is a strong basic compound (based on its pKa). Succinyl-CoA is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
CoA S-(Hydrogen succinate)HMDB
CoA S-SuccinateHMDB
coenzyme A S-(Hydrogen succinate)HMDB
coenzyme A S-SuccinateHMDB
S-(Hydrogen butanedioateHMDB
S-(Hydrogen butanedioate) CoAHMDB
S-(Hydrogen butanedioate) coenzyme AHMDB
S-(Hydrogen butanedioic acidHMDB
S-Succinoylcoenzyme AHMDB
Suc-CO-aHMDB
Suc-CoAHMDB
Succ-CoAHMDB
Succ-coenzyme AHMDB
Succ-S-CoAHMDB
Succ-S-coenzyme AHMDB
Succino-1-yl-coenzyme AHMDB
Succinyl CoAHMDB
Succinyl coenzyme AHMDB
Succinyl-S-CoAHMDB
Succinyl-S-coenzyme AHMDB
Succinylcoenzyme AHMDB
Succinyl-coenzyme AHMDB
Chemical FormulaC25H40N7O19P3S
Average Molecular Weight867.607
Monoisotopic Molecular Weight867.131252359
IUPAC Name4-{[2-(3-{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 Name4-({2-[3-(3-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-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
CAS Registry Number604-98-8
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
InChI Identifier
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
InChI KeyVNOYUJKHFWYWIR-FZEDXVDRSA-N
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentAcyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside 3',5'-bisphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside diphosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Ribonucleoside 3'-phosphate
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Hydroxy fatty acid
  • Monoalkyl phosphate
  • Thia fatty acid
  • Aminopyrimidine
  • Monosaccharide
  • Fatty amide
  • Alkyl phosphate
  • Phosphoric acid ester
  • N-acyl-amine
  • N-substituted imidazole
  • Pyrimidine
  • Organic phosphoric acid derivative
  • Imidolactam
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Tetrahydrofuran
  • Carboxamide group
  • Amino acid
  • Carbothioic s-ester
  • Amino acid or derivatives
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Thiocarboxylic acid ester
  • Thiocarboxylic acid or derivatives
  • Sulfenyl compound
  • Azacycle
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organic oxide
  • Primary amine
  • Carbonyl group
  • Organopnictogen compound
  • Alcohol
  • Amine
  • Organic oxygen compound
  • Organosulfur compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.44ALOGPS
logP-6.1ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.24ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area400.93 ŲChemAxon
Rotatable Bond Count23ChemAxon
Refractivity183.1 m³·mol⁻¹ChemAxon
Polarizability76.26 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0921000120-1e5e7bd80daf7c7bb340View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002r-0911000000-c39ff72dec199bc2f3beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1910000000-6ff9a08f5f37f45325aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00nb-8911142570-e798aa8a621c254da5daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-4911110010-55034115d2f086587073View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-7900100000-e9c5dedea80def47642dView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Mitochondria
Biospecimen Locations
  • Skeletal Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Skeletal MuscleExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
TestisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001022
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022375
KNApSAcK IDNot Available
Chemspider ID388307
KEGG Compound IDC00091
BioCyc IDNot Available
BiGG ID33820
Wikipedia LinkSuccinyl-CoA
METLIN ID5951
PubChem Compound439161
PDB IDNot Available
ChEBI ID15380
References
Synthesis ReferenceWollemann, 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
General ReferencesNot Available

Enzymes

General function:
Lipid transport and metabolism
Specific function:
Involved in the degradation of several amino acids, odd-chain fatty acids and cholesterol via propionyl-CoA to the tricarboxylic acid cycle.
Gene Name:
MMUT
Uniprot ID:
Q9GK13
Molecular weight:
83235.0
Reactions
R-Methylmalonyl-CoA → Succinyl-CoAdetails
General function:
Coenzyme transport and metabolism
Specific function:
Not Available
Gene Name:
ALAS1
Uniprot ID:
A6QLI6
Molecular weight:
71062.0
Reactions
Glycine + Succinyl-CoA → 5-Aminolevulinic acid + Carbon dioxidedetails
Glycine + Succinyl-CoA → 5-Aminolevulinic acid + Coenzyme Adetails
General function:
Energy production and conversion
Specific function:
ATP-specific succinyl-CoA synthetase functions in the citric acid cycle (TCA), coupling the hydrolysis of succinyl-CoA to the synthesis of ATP and thus represents the only step of substrate-level phosphorylation in the TCA. The beta subunit provides nucleotide specificity of the enzyme and binds the substrate succinate, while the binding sites for coenzyme A and phosphate are found in the alpha subunit.
Gene Name:
SUCLA2
Uniprot ID:
Q148D5
Molecular weight:
50130.0
General function:
Energy production and conversion
Specific function:
Succinyl-CoA synthetase functions in the citric acid cycle (TCA), coupling the hydrolysis of succinyl-CoA to the synthesis of either ATP or GTP and thus represents the only step of substrate-level phosphorylation in the TCA. The alpha subunit of the enzyme binds the substrates coenzyme A and phosphate, while succinate binding and specificity for either ATP or GTP is provided by different beta subunits.
Gene Name:
SUCLG1
Uniprot ID:
Q58DR8
Molecular weight:
36167.0
Reactions
Succinyl-CoA + Hydrogen phosphate + Guanosine diphosphate → Succinic acid + Coenzyme A + Guanosine triphosphatedetails
General function:
Energy production and conversion
Specific function:
GTP-specific succinyl-CoA synthetase functions in the citric acid cycle (TCA), coupling the hydrolysis of succinyl-CoA to the synthesis of GTP and thus represents the only step of substrate-level phosphorylation in the TCA. The beta subunit provides nucleotide specificity of the enzyme and binds the substrate succinate, while the binding sites for coenzyme A and phosphate are found in the alpha subunit.
Gene Name:
SUCLG2
Uniprot ID:
Q3MHX5
Molecular weight:
46691.0
Reactions
Succinyl-CoA + Hydrogen phosphate + Guanosine diphosphate → Succinic acid + Coenzyme A + Guanosine triphosphatedetails
General function:
Energy production and conversion
Specific function:
Dihydrolipoamide succinyltransferase (E2) component of the 2-oxoglutarate dehydrogenase complex (By similarity). The 2-oxoglutarate dehydrogenase complex catalyzes the overall conversion of 2-oxoglutarate to succinyl-CoA and CO(2) (By similarity). The 2-oxoglutarate dehydrogenase complex is mainly active in the mitochondrion. A fraction of the 2-oxoglutarate dehydrogenase complex also localizes in the nucleus and is required for lysine succinylation of histones: associates with KAT2A on chromatin and provides succinyl-CoA to histone succinyltransferase KAT2A (By similarity).
Gene Name:
DLST
Uniprot ID:
P11179
Molecular weight:
48973.0
General function:
Coenzyme transport and metabolism
Specific function:
Not Available
Gene Name:
ALAS2
Uniprot ID:
Q3ZC31
Molecular weight:
65137.0
General function:
Not Available
Specific function:
Key enzyme for ketone body catabolism. Transfers the CoA moiety from succinate to acetoacetate. Formation of the enzyme-CoA intermediate proceeds via an unstable anhydride species formed between the carboxylate groups of the enzyme and substrate.
Gene Name:
OXCT1
Uniprot ID:
Q24JZ7
Molecular weight:
56453.0
Reactions
Acetoacetic acid + Succinyl-CoA → Succinic acid + Acetoacetyl-CoAdetails
Acetoacetic acid + Succinyl-CoA → Acetoacetyl-CoA + Succinic aciddetails