Human Metabolome Database Version 3.5

Showing metabocard for Succinyl-CoA (HMDB01022)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:30:03 -0600
HMDB ID HMDB01022
Secondary Accession Numbers None
Metabolite Identification
Common Name Succinyl-CoA
Description Succinyl-CoA is an important intermediate in the citric acid cycle, where it is synthesized from α-Ketoglutarate by α-ketoglutarate dehydrogenase (EC 1.2.4.2) through decarboxylation, and is converted into succinate through the hydrolytic release of coenzyme A by succinyl-CoA synthetase (EC 6.2.1.5). Succinyl-CoA may be an end product of peroxisomal beta-oxidation of dicarboxylic fatty acids; the identification of an apparently specific succinyl-CoA thioesterase (ACOT4, EC 3.1.2.3, hydrolyzes succinyl-CoA) in peroxisomes strongly suggests that succinyl-CoA is formed in peroxisomes. Acyl-CoA thioesterases (ACOTs) are a family of enzymes that catalyze the hydrolysis of the CoA esters of various lipids to the free acids and coenzyme A, thereby regulating levels of these compounds. (PMID: 16141203 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. CoA S-(hydrogen succinate)
  2. CoA S-succinate
  3. Coenzyme A S-(hydrogen succinate)
  4. Coenzyme A S-succinate
  5. S-(Hydrogen butanedioate
  6. S-(Hydrogen butanedioate) CoA
  7. S-(Hydrogen butanedioate) Coenzyme A
  8. S-(Hydrogen butanedioic acid
  9. S-Succinoylcoenzyme A
  10. Suc-co-A
  11. Suc-coa
  12. Succ-CoA
  13. Succ-Coenzyme A
  14. Succ-coenzyme-A
  15. Succ-S-CoA
  16. Succ-S-Coenzyme A
  17. Succ-S-coenzyme-A
  18. Succino-1-yl-coenzyme a
  19. Succinyl CoA
  20. Succinyl coenzyme A
  21. Succinyl-S-CoA
  22. Succinyl-S-Coenzyme A
  23. Succinyl-S-coenzyme-A
  24. Succinylcoenzyme-A
Chemical Formula C25H40N7O19P3S
Average Molecular Weight 867.607
Monoisotopic Molecular Weight 867.131252359
IUPAC Name 4-{[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 IUPAC Name 4-({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 Number 604-98-8
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 Key VNOYUJKHFWYWIR-FZEDXVDRSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acid Esters
Sub Class Acyl CoAs
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
Substituents
  • 1 Phosphoribosyl Imidazole
  • Aminopyrimidine
  • Carboxamide Group
  • Carboxylic Acid
  • Carboxylic Thioester
  • Coenzyme A
  • Glycosyl Compound
  • Imidazole
  • Imidazopyrimidine
  • Monosaccharide Phosphate
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxolane
  • Pentose Monosaccharide
  • Phosphoric Acid Ester
  • Purine
  • Purine Ribonucleoside 3',5' Bisphosphate
  • Pyrimidine
  • Saccharide
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
  • Thiocarboxylic Acid Ester
Direct Parent Acyl CoAs
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Component of Butanoate metabolism
  • Component of C5-Branched dibasic acid metabolism
  • Component of Glycine, serine and threonine metabolism
  • Component of Propanoate metabolism
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
  • Mitochondria
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 3.84 g/L ALOGPS
LogP -0.61 ALOGPS
LogP -7.2 ChemAxon
LogS -2.35 ALOGPS
pKa (strongest acidic) 0.82 ChemAxon
pKa (strongest basic) 4.98 ChemAxon
Hydrogen Acceptor Count 19 ChemAxon
Hydrogen Donor Count 10 ChemAxon
Polar Surface Area 400.93 A2 ChemAxon
Rotatable Bond Count 23 ChemAxon
Refractivity 183.1 ChemAxon
Polarizability 74.96 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -5 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Mitochondria
Biofluid Locations Not Available
Tissue Location
  • Muscle
  • Testes
Pathways
Name SMPDB Link KEGG Link
Valine, Leucine and Isoleucine Degradation SMP00032 map00280 Link_out
Citric Acid Cycle SMP00057 map00020 Link_out
Propanoate Metabolism SMP00016 map00640 Link_out
Threonine and 2-Oxobutanoate Degradation SMP00452 Not Available
Glycine and Serine Metabolism SMP00004 map00260 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022375
KNApSAcK ID Not Available
Chemspider ID 388307 Link_out
KEGG Compound ID C00091 Link_out
BioCyc ID 3-METHYLBENZYLSUCCINYL-COA Link_out
BiGG ID 33820 Link_out
Wikipedia Link Succinyl-CoA Link_out
NuGOwiki Link HMDB01022 Link_out
Metagene Link HMDB01022 Link_out
METLIN ID 5951 Link_out
PubChem Compound 439161 Link_out
PDB ID Not Available
ChEBI ID 15380 Link_out
References
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
General References
  1. Elpeleg O, Miller C, Hershkovitz E, Bitner-Glindzicz M, Bondi-Rubinstein G, Rahman S, Pagnamenta A, Eshhar S, Saada A: Deficiency of the ADP-forming succinyl-CoA synthase activity is associated with encephalomyopathy and mitochondrial DNA depletion. Am J Hum Genet. 2005 Jun;76(6):1081-6. Epub 2005 Apr 22. Pubmed: 15877282 Link_out
  2. Tanaka H, Kohroki J, Iguchi N, Onishi M, Nishimune Y: Cloning and characterization of a human orthologue of testis-specific succinyl CoA: 3-oxo acid CoA transferase (Scot-t) cDNA. Mol Hum Reprod. 2002 Jan;8(1):16-23. Pubmed: 11756565 Link_out
  3. Westin MA, Hunt MC, Alexson SE: The identification of a succinyl-CoA thioesterase suggests a novel pathway for succinate production in peroxisomes. J Biol Chem. 2005 Nov 18;280(46):38125-32. Epub 2005 Aug 31. Pubmed: 16141203 Link_out

Enzymes
Name: 5-aminolevulinate synthase, erythroid-specific, mitochondrial
Reactions:
Succinyl-CoA + Glycine unknown 5-Aminolevulinic acid + Coenzyme A + CO(2) details
Succinyl-CoA + Glycine unknown 5-Aminolevulinic acid + Coenzyme A + Carbon dioxide details
Gene Name: ALAS2
Uniprot ID: P22557 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 5-aminolevulinate synthase, nonspecific, mitochondrial
Reactions:
Succinyl-CoA + Glycine unknown 5-Aminolevulinic acid + Coenzyme A + CO(2) details
Succinyl-CoA + Glycine unknown 5-Aminolevulinic acid + Coenzyme A + Carbon dioxide details
Gene Name: ALAS1
Uniprot ID: P13196 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 3-ketoacyl-CoA thiolase, mitochondrial
Reactions:
Succinyl-CoA + Acetyl-CoA unknown Coenzyme A + 3-Oxoadipyl-CoA details
Gene Name: ACAA2
Uniprot ID: P42765 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 3-ketoacyl-CoA thiolase, peroxisomal
Reactions:
Succinyl-CoA + Acetyl-CoA unknown Coenzyme A + 3-Oxoadipyl-CoA details
Gene Name: ACAA1
Uniprot ID: P09110 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Trifunctional enzyme subunit beta, mitochondrial
Reactions:
Succinyl-CoA + Acetyl-CoA unknown Coenzyme A + 3-Oxoadipyl-CoA details
Gene Name: HADHB
Uniprot ID: P55084 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Dihydrolipoyl dehydrogenase, mitochondrial
Reactions: Not Available
Gene Name: DLD
Uniprot ID: P09622 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Methylmalonyl-CoA mutase, mitochondrial
Reactions:
Methylmalonyl-CoA unknown Succinyl-CoA details
Gene Name: MUT
Uniprot ID: P22033 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 2-oxoglutarate dehydrogenase, mitochondrial
Reactions: Not Available
Gene Name: OGDH
Uniprot ID: Q02218 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Succinyl-CoA:3-ketoacid coenzyme A transferase 1, mitochondrial
Reactions:
Succinyl-CoA + a 3-oxo acid unknown Succinic acid + a 3-oxoacyl-CoA details
Succinyl-CoA + Acetoacetic acid unknown Succinic acid + Acetoacetyl-CoA details
Gene Name: OXCT1
Uniprot ID: P55809 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Succinyl-CoA:3-ketoacid coenzyme A transferase 2, mitochondrial
Reactions:
Succinyl-CoA + a 3-oxo acid unknown Succinic acid + a 3-oxoacyl-CoA details
Succinyl-CoA + Acetoacetic acid unknown Succinic acid + Acetoacetyl-CoA details
Gene Name: OXCT2
Uniprot ID: Q9BYC2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Succinyl-CoA ligase [ADP/GDP-forming] subunit alpha, mitochondrial
Reactions:
Guanosine triphosphate + Succinic acid + Coenzyme A unknown Guanosine diphosphate + Phosphoric acid + Succinyl-CoA details
Adenosine triphosphate + Succinic acid + Coenzyme A unknown ADP + Phosphoric acid + Succinyl-CoA details
Inosine triphosphate + Succinic acid + Coenzyme A unknown IDP + Phosphoric acid + Succinyl-CoA details
Gene Name: SUCLG1
Uniprot ID: P53597 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Succinyl-CoA ligase [GDP-forming] subunit beta, mitochondrial
Reactions:
Guanosine triphosphate + Succinic acid + Coenzyme A unknown Guanosine diphosphate + Phosphoric acid + Succinyl-CoA details
Inosine triphosphate + Succinic acid + Coenzyme A unknown IDP + Phosphoric acid + Succinyl-CoA details
Gene Name: SUCLG2
Uniprot ID: Q96I99 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Dihydrolipoyllysine-residue succinyltransferase component of 2-oxoglutarate dehydrogenase complex, mitochondrial
Reactions:
Succinyl-CoA + enzyme N(6)-(dihydrolipoyl)lysine unknown Coenzyme A + enzyme N(6)-(S-succinyldihydrolipoyl)lysine details
Succinyl-CoA + Enzyme N6-(dihydrolipoyl)lysine unknown Coenzyme A + [Dihydrolipoyllysine-residue succinyltransferase] S-succinyldihydrolipoyllysine details
Gene Name: DLST
Uniprot ID: P36957 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Succinyl-CoA ligase [ADP-forming] subunit beta, mitochondrial
Reactions:
Adenosine triphosphate + Succinic acid + Coenzyme A unknown ADP + Phosphoric acid + Succinyl-CoA details
Guanosine triphosphate + Succinic acid + Coenzyme A unknown Guanosine diphosphate + Phosphoric acid + Succinyl-CoA details
Inosine triphosphate + Succinic acid + Coenzyme A unknown IDP + Phosphoric acid + Succinyl-CoA details
Gene Name: SUCLA2
Uniprot ID: Q9P2R7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 2-oxoglutarate dehydrogenase-like, mitochondrial
Reactions: Not Available
Gene Name: OGDHL
Uniprot ID: Q9ULD0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA