3-Oxooctanoyl-CoA (PAMDB000537)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000537
Identification
Name: 3-Oxooctanoyl-CoA
Description:3-Oxooctanoyl-CoA is the substrate of the acetyl-CoA C-acyltransferase/oxoacyl-CoA thiolase A (EC 2.3.1.16, SCP2/3-oxoacyl-CoA thiolase).
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 3-Ketooctanoyl-CoA
  • 3-Ketooctanoyl-Coenzyme A
  • 3-Oxooctanoyl coenzyme A
  • 3-Oxooctanoyl-coenzyme A
  • S-(3-oxooctanoate
  • S-(3-Oxooctanoate)
  • S-(3-Oxooctanoate) CoA
  • S-(3-Oxooctanoate) Coenzyme A
  • S-(3-oxooctanoic acid
  • S-(3-Oxooctanoic acid)
  • S-(3-Oxooctanoic acid) CoA
  • S-(3-Oxooctanoic acid) coenzyme A
Chemical Formula: C29H48N7O18P3S
Average Molecular Weight: 907.714
Monoisotopic Molecular Weight: 907.198937993
InChI Key: WPIVBCGRGVNDDT-FFJUWABQSA-N
InChI:InChI=1S/C29H48N7O18P3S/c1-4-5-6-7-17(37)12-20(39)58-11-10-31-19(38)8-9-32-27(42)24(41)29(2,3)14-51-57(48,49)54-56(46,47)50-13-18-23(53-55(43,44)45)22(40)28(52-18)36-16-35-21-25(30)33-15-34-26(21)36/h15-16,18,22-24,28,40-41H,4-14H2,1-3H3,(H,31,38)(H,32,42)(H,46,47)(H,48,49)(H2,30,33,34)(H2,43,44,45)/t18-,22-,23-,24?,28-/m1/s1
CAS number: 54684-64-9
IUPAC Name:{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-oxooctanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional IUPAC Name: [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-oxooctanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid
SMILES:CCCCCC(=O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as 3-oxo-acyl coas. These are organic compounds containing a 3-oxo acylated coenzyme A derivative.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Fatty Acyls
Sub ClassFatty acyl thioesters
Direct Parent 3-oxo-acyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside diphosphate
  • Purine ribonucleoside 3',5'-bisphosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Beta amino acid or derivatives
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • Alkyl phosphate
  • 1,3-dicarbonyl compound
  • Pyrimidine
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • N-acyl-amine
  • Monosaccharide
  • Fatty amide
  • Saccharide
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Thiocarboxylic acid ester
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Ketone
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Thioether
  • Thiocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-4
Melting point: Not Available
Experimental Properties:
PropertyValueSource
LogP:-2.164PhysProp
Predicted Properties
PropertyValueSource
Water Solubility3.07 mg/mLALOGPS
logP0.23ALOGPS
logP-4.7ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area380.7 Å2ChemAxon
Rotatable Bond Count26ChemAxon
Refractivity200.53 m3·mol-1ChemAxon
Polarizability81.88 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Acetyl-CoA + Hexanoyl-CoA <> 3-Oxooctanoyl-CoA + Coenzyme A
3-Oxooctanoyl-CoA + Hydrogen ion + NADH <> (S)-Hydroxyoctanoyl-CoA + NAD
(S)-Hydroxyoctanoyl-CoA + NAD + (S)-Hydroxyoctanoyl-CoA NADH + Hydrogen ion + 3-Oxooctanoyl-CoA
3-Oxooctanoyl-CoA + Coenzyme A > Acetyl-CoA + Decanoyl-CoA (n-C10:0CoA) + Decanoyl-CoA (N-C10:0CoA)
Acetyl-CoA + Hexanyl-CoA <> 3-Oxooctanoyl-CoA + Coenzyme A
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1920100120-cd410d4a53d934763ea7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0941200000-7cb4acb73a370d1909bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2920000000-eba79c033775684afd01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-055r-2911020222-0c38a22725feacf64342View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-2910110010-a4bf55bed0c3fdbf24bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900100000-c125ac237096994d43daView in MoNA
References
References:
  • Antonenkov VD, Van Veldhoven PP, Waelkens E, Mannaerts GP: Substrate specificities of 3-oxoacyl-CoA thiolase A and sterol carrier protein 2/3-oxoacyl-CoA thiolase purified from normal rat liver peroxisomes. Sterol carrier protein 2/3-oxoacyl-CoA thiolase is involved in the metabolism of 2-methyl-branched fatty acids and bile acid intermediates. J Biol Chem. 1997 Oct 10;272(41):26023-31. Pubmed: 9325339
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference: Thorpe, Colin. A method for the preparation of 3-ketoacyl-CoA derivatives. Analytical Biochemistry (1986), 155(2), 391-4.
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID28264
HMDB IDHMDB03941
Pubchem Compound ID440608
Kegg IDC05267
ChemSpider ID389506
Wikipedia IDNot Available
BioCyc IDCPD0-2106
EcoCyc IDCPD0-2106