succinyl-CoA (PAMDB110378)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB110378
Identification
Name: succinyl-CoA
Description:An acyl-CoA oxoanion that is the pentaanion of succinyl-CoA, arising from deprotonation of the phosphate, diphosphate and carboxylic acid OH groups.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
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
Chemical Formula: C25H35N7O19P3S
Average Molecular Weight: 862.57
Monoisotopic Molecular Weight: 867.1312523603
InChI Key: VNOYUJKHFWYWIR-ITIYDSSPSA-I
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
CAS number: 604-98-8
IUPAC Name:3'-phosphonatoadenosine 5'-{3-[(3R)-4-{[3-({2-[(3-carboxylatopropanoyl)sulfanyl]ethyl}amino)-3-oxopropyl]amino}-3-hydroxy-2,2-dimethyl-4-oxobutyl]diphosphate}
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
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-]
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Lipids and lipid-like molecules
Sub ClassFatty Acyls
Direct Parent Acyl 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
  • Aminopyrimidine
  • Hydroxy fatty acid
  • Monoalkyl phosphate
  • Thia fatty acid
  • Imidolactam
  • Fatty amide
  • Alkyl phosphate
  • Monosaccharide
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Primary aromatic amine
  • Pyrimidine
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Oxolane
  • Amino acid
  • Secondary alcohol
  • Thiocarboxylic acid ester
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Carbothioic s-ester
  • Thiocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Organopnictogen compound
  • Organic nitrogen compound
  • Alcohol
  • Amine
  • Organonitrogen compound
  • Primary amine
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Organosulfur compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:-5
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.84 mg/mLALOGPS
logP-0.61ALOGPS
logP-7.2ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.98ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area400.93 Å2ChemAxon
Rotatable Bond Count23ChemAxon
Refractivity183.1 m3·mol-1ChemAxon
Polarizability74.96 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Hydrogen ion + Glycine + succinyl-CoA → Carbon dioxide + coenzyme A + 5-Aminolevulinic acid
succinyl-CoA + acetyl-CoA → 3-oxoadipyl-CoA + coenzyme A
succinyl-CoA + acetoacetate → succinate + acetoacetyl-CoA
L-ornithine + succinyl-CoA → Hydrogen ion + N2-succinyl-L-ornithine + coenzyme A
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
References:
  • 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. [11756565 ]
  • 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. [15877282 ]
  • 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. [16141203 ]
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
External Links:
ResourceLink
CAS604-98-8
ChEBI57292
HMDBHMDB01022
IAF126033820
KEGGC00091
MetaboLightsMTBLC57292
PubChem25245777