3-oxooctanoyl-CoA (PAMDB120027)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120027
Identification
Name: 3-oxooctanoyl-CoA
Description:An acyl-CoA(4−) oxoanion arising from deprotonation of the phosphate and diphosphate OH groups of 3-oxooctanoyl-CoA; major species at pH 7.3.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 3-ketooctanoyl-CoA(4−)
  • 3-oxooctanoyl-CoA
Chemical Formula: C29H44N7O18P3S
Average Molecular Weight: 903.684
Monoisotopic Molecular Weight: 907.1989
InChI Key: WPIVBCGRGVNDDT-CECATXLMSA-J
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)/p-4/t18-,22-,23-,24+,28-/m1/s1
CAS number: 54684-64-9
IUPAC Name:3'-phosphonatoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-{[3-oxo-3-({2-[(3-oxooctanoyl)sulfanyl]ethyl}amino)propyl]amino}butyl] diphosphate}
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(C(O)C(C)(C)COP([O-])(=O)OP([O-])(=O)OCC1(C(OP(=O)([O-])[O-])C(O)C(O1)N3(C=NC2(C(N)=NC=NC=23))))=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as 3-oxo-acyl coas. These are organic compounds containing a 3-oxo acylated coenzyme A derivative.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Lipids and lipid-like molecules
Sub ClassFatty Acyls
Direct Parent 3-oxo-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
  • Pentose monosaccharide
  • Organic pyrophosphate
  • 6-aminopurine
  • Monosaccharide phosphate
  • Purine
  • Imidazopyrimidine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Fatty amide
  • Monosaccharide
  • Pyrimidine
  • 1,3-dicarbonyl compound
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Primary aromatic amine
  • Alkyl phosphate
  • Phosphoric acid ester
  • Imidolactam
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Oxolane
  • Amino acid or derivatives
  • Carbothioic s-ester
  • Carboxamide group
  • Thiocarboxylic acid ester
  • Ketone
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Oxacycle
  • Sulfenyl compound
  • Carboxylic acid derivative
  • Azacycle
  • Thiocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Organic oxide
  • Organic nitrogen compound
  • Organooxygen compound
  • Primary amine
  • Carbonyl group
  • Organic oxygen compound
  • Organopnictogen compound
  • Alcohol
  • Amine
  • Organosulfur compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-4
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-2.164Not Available
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: Not Available
Reactions:
(S)-3-hydroxyoctanoyl-CoA + NAD+ → 3-oxooctanoyl-CoA + NADH + Hydrogen ion
hexanoyl-CoA + acetyl-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. [9325339 ]
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
HMDBHMDB03941
BIGG45463
CHEBI62619
PUBCHEM46173417
LIGAND-CPDC05267