Record Information
Version1.0
Creation date2011-09-21 00:27:00 UTC
Update date2015-07-21 06:57:36 UTC
Primary IDFDB023254
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3-Oxotetradecanoyl-CoA
Description3-Oxotetradecanoyl-CoA is a product of the peroxisomal beta oxidation of hexadenoic acid by the enzyme acyl-CoA oxidase which results in long-chain 3-oxoacyl-CoA-esters. (PMID: 7548202) Myristoyl-CoA:protein N-myristoyltransferase (E.C. 2.3.1.97) is a eukaryotic enzyme that catalyzes the transfer of myristate (C14:O) from myristoyl-CoA to the amino nitrogen of glycine. This covalent protein modification occurs cotranslationally, is apparently irreversible, and affects proteins with diverse functions. (PMID: 2818568) [HMDB]
CAS Number122364-86-7
Structure
Thumb
Synonyms
SynonymSource
3-Oxomyristoyl-CoAChEBI
3-Oxomyristoyl-coenzyme AHMDB
5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-{[3-oxo-3-({2-[(3-oxotetradecanoyl)sulfanyl]ethyl}amino)propyl]amino}butyl] dihydrogen diphosphate}3'-phosphoadenosineHMDB
S-(3-OxotetradecanoateHMDB
S-(3-Oxotetradecanoate) CoAHMDB
S-(3-Oxotetradecanoate) coenzyme AHMDB
S-(3-Oxotetradecanoic acidHMDB
3-oxomyristoyl-CoAhmdb
3-oxomyristoyl-Coenzyme Ahmdb
5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-{[3-oxo-3-({2-[(3-oxotetradecanoyl)sulfanyl]ethyl}amino)propyl]amino}butyl] dihydrogen diate}3'-oadenosineHMDB
S-(3-oxotetradecanoatehmdb
S-(3-oxotetradecanoate) CoAhmdb
S-(3-oxotetradecanoate) Coenzyme Ahmdb
S-(3-oxotetradecanoic acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility2.38 g/LALOGPS
logP1.48ALOGPS
logP-0.96ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area380.7 ŲChemAxon
Rotatable Bond Count32ChemAxon
Refractivity228.14 m³·mol⁻¹ChemAxon
Polarizability95.71 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC35H60N7O18P3S
IUPAC name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-oxotetradecanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
InChI IdentifierInChI=1S/C35H60N7O18P3S/c1-4-5-6-7-8-9-10-11-12-13-23(43)18-26(45)64-17-16-37-25(44)14-15-38-33(48)30(47)35(2,3)20-57-63(54,55)60-62(52,53)56-19-24-29(59-61(49,50)51)28(46)34(58-24)42-22-41-27-31(36)39-21-40-32(27)42/h21-22,24,28-30,34,46-47H,4-20H2,1-3H3,(H,37,44)(H,38,48)(H,52,53)(H,54,55)(H2,36,39,40)(H2,49,50,51)/t24-,28-,29-,30+,34-/m1/s1
InChI KeyIQNFBGHLIVBNOU-QSGBVPJFSA-N
Isomeric SMILESCCCCCCCCCCCC(=O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](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
Average Molecular Weight991.873
Monoisotopic Molecular Weight991.292838377
Classification
Description Belongs to the class of organic compounds known as long-chain 3-oxoacyl coas. These are organic compounds containing a coenzyme A derivative, which is 3-oxo acylated long aliphatic chain of 13 to 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentLong-chain 3-oxoacyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside 3',5'-bisphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside diphosphate
  • Ribonucleoside 3'-phosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • 1,3-dicarbonyl compound
  • Imidolactam
  • Monosaccharide
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Pyrimidine
  • Alkyl phosphate
  • Fatty amide
  • Phosphoric acid ester
  • Tetrahydrofuran
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Carbothioic s-ester
  • Secondary alcohol
  • Ketone
  • Thiocarboxylic acid ester
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Organosulfur compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic nitrogen compound
  • Primary amine
  • Organopnictogen compound
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)Not AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00al-3951231305-e64e775b7655f9988bfeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3921200001-fab03116b2cfb433bbaeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900100000-457e07aa65d0f83247fbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000009-342646973b6a3f3d5bf3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00g3-4200201329-23aa6cf502f4d804fa11Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02jc-2101301309-a62c66b8cd13c607e063Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1902100203-37e47fa131f279d1ccdbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0922300000-89842e38a36b7c108b45Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900101000-4f1b2969f929942e67b3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0000000009-01e6acdaa109155ae7aaSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0600100189-f65f6ff48a5a3738933cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0001900000-d1155a9305d5c03af39aSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
ChemSpider ID10140190
ChEMBL IDNot Available
KEGG Compound IDC05261
Pubchem Compound ID11966197
Pubchem Substance IDNot Available
ChEBI ID28726
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03935
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID45449
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
3-ketoacyl-CoA thiolase, mitochondrialACAA2P42765
3-ketoacyl-CoA thiolase, peroxisomalACAA1P09110
Trifunctional enzyme subunit beta, mitochondrialHADHBP55084
Pathways
NameSMPDB LinkKEGG Link
Fatty Acid Elongation In MitochondriaSMP00054 map00062
Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty AcidsSMP00482 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference