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3-Oxotetradecanoyl-CoA (M2MDB000531)

Record Information
Version2.0
Creation Date2012-05-31 14:00:42 -0600
Update Date2015-06-03 15:54:33 -0600
Secondary Accession Numbers
  • ECMDB03935
Identification
Name:3-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)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 3-Oxomyristoyl-CoA
  • 3-Oxomyristoyl-Coenzyme A
  • 3-Oxotetradecanoyl-CoA
  • 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'-phosphoadenosine
  • 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-{[3-oxo-3-({2-[(3-oxotetradecanoyl)sulfanyl]ethyl}amino)propyl]amino}butyl] dihydrogen diphosphoric acid}3'-phosphoadenosine
  • 5'-{3-[(3R)-3-Hydroxy-2,2-dimethyl-4-oxo-4-{[3-oxo-3-({2-[(3-oxotetradecanoyl)sulphanyl]ethyl}amino)propyl]amino}butyl] dihydrogen diphosphate}3'-phosphoadenosine
  • 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-{[3-oxo-3-({2-[(3-oxotetradecanoyl)sulphanyl]ethyl}amino)propyl]amino}butyl] dihydrogen diphosphoric acid}3'-phosphoadenosine
  • S-(3-oxotetradecanoate
  • S-(3-Oxotetradecanoate)
  • S-(3-Oxotetradecanoate) CoA
  • S-(3-Oxotetradecanoate) Coenzyme A
  • S-(3-oxotetradecanoic acid
  • S-(3-Oxotetradecanoic acid)
  • S-(3-Oxotetradecanoic acid) CoA
  • S-(3-Oxotetradecanoic acid) coenzyme A
Chemical Formula:C35H60N7O18P3S
Weight:Average: 991.873
Monoisotopic: 991.292838377
InChI Key:IQNFBGHLIVBNOU-QSGBVPJFSA-N
InChI:InChI=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
CAS number:122364-86-7
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
Traditional IUPAC Name:3-oxotetradecanoyl-coa
SMILES:CCCCCCCCCCCC(=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
Chemical Taxonomy
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
Physical Properties
State:Solid
Charge:-4
Melting point:Not Available
Experimental Properties:
PropertyValueSource
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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Acetyl-CoA + Lauroyl-CoA <> 3-Oxotetradecanoyl-CoA + Coenzyme A
3-Oxotetradecanoyl-CoA + Hydrogen ion + NADH <> (S)-3-Hydroxytetradecanoyl-CoA + NAD
(S)-3-Hydroxytetradecanoyl-CoA + NAD <> 3-Oxotetradecanoyl-CoA + NADH
(S)-3-Hydroxytetradecanoyl-CoA + NAD > NADH + Hydrogen ion + 3-Oxotetradecanoyl-CoA
3-Oxotetradecanoyl-CoA + Coenzyme A > Acetyl-CoA + Palmityl-CoA
(S)-3-Hydroxytetradecanoyl-CoA + NAD <> 3-Oxotetradecanoyl-CoA + NADH + Hydrogen ion
Lauroyl-CoA + Acetyl-CoA > 3-Oxotetradecanoyl-CoA + Coenzyme A
SMPDB Pathways:
Fatty acid metabolismPW000796 ThumbThumb?image type=greyscaleThumb?image type=simple
fatty acid oxidation (myristate)PW001021 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1902100203-37e47fa131f279d1ccdbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0922300000-89842e38a36b7c108b45View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900101000-4f1b2969f929942e67b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00al-3951231305-e64e775b7655f9988bfeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3921200001-fab03116b2cfb433bbaeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900100000-457e07aa65d0f83247fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000009-342646973b6a3f3d5bf3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00g3-4200201329-23aa6cf502f4d804fa11View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02jc-2101301309-a62c66b8cd13c607e063View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0000000009-01e6acdaa109155ae7aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0600100189-f65f6ff48a5a3738933cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0001900000-d1155a9305d5c03af39aView in MoNA
MSMass Spectrum (Electron Ionization)Not AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • 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
  • Kishore NS, Wood DC, Mehta PP, Wade AC, Lu T, Gokel GW, Gordon JI: Comparison of the acyl chain specificities of human myristoyl-CoA synthetase and human myristoyl-CoA:protein N-myristoyltransferase. J Biol Chem. 1993 Mar 5;268(7):4889-902. Pubmed: 8444867
  • Nagi MN, Cook L, Suneja SK, Osei P, Cinti DL: Spectrophotometric assay for the condensing enzyme activity of the microsomal fatty acid chain elongation system. Anal Biochem. 1989 Jun;179(2):251-61. Pubmed: 2774174
  • Sleboda, J., Pourfarzam, M., Bartlett, K., Osmundsen, H. (1995). "Effects of added l-carnitine, acetyl-CoA and CoA on peroxisomal beta-oxidation of [U-14C]hexadecanoate by isolated peroxisomal fractions." Biochim Biophys Acta 1258:309-318. Pubmed: 7548202
  • Watmough NJ, Turnbull DM, Sherratt HS, Bartlett K: Measurement of the acyl-CoA intermediates of beta-oxidation by h.p.l.c. with on-line radiochemical and photodiode-array detection. Application to the study of [U-14C]hexadecanoate oxidation by intact rat liver mitochondria. Biochem J. 1989 Aug 15;262(1):261-9. Pubmed: 2818568
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID28726
HMDB IDHMDB03935
Pubchem Compound ID11966197
Kegg IDC05261
ChemSpider ID10140190
Wikipedia IDNot Available
BioCyc IDCPD-10284
EcoCyc IDCPD-10284

Enzymes

Protein Details
1. 3-ketoacyl-CoA thiolase
General function:
Involved in acetyl-CoA C-acyltransferase activity
Specific function:
Catalyzes the final step of fatty acid oxidation in which acetyl-CoA is released and the CoA ester of a fatty acid two carbons shorter is formed. Involved in the aerobic and anaerobic degradation of long-chain fatty acids
Gene Name:
fadA
Uniprot ID:
P21151
Molecular weight:
40876
Reactions
Acyl-CoA + acetyl-CoA = CoA + 3-oxoacyl-CoA.
Protein Details
2. Fatty acid oxidation complex subunit alpha
General function:
Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:
Catalyzes the formation of an hydroxyacyl-CoA by addition of water on enoyl-CoA. Also exhibits 3-hydroxyacyl-CoA epimerase and 3-hydroxyacyl-CoA dehydrogenase activities. Involved in the aerobic and anaerobic degradation of long-chain fatty acids
Gene Name:
fadB
Uniprot ID:
P21177
Molecular weight:
79593
Reactions
(S)-3-hydroxyacyl-CoA + NAD(+) = 3-oxoacyl-CoA + NADH.
(3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H(2)O.
(S)-3-hydroxybutanoyl-CoA = (R)-3-hydroxybutanoyl-CoA.
(3Z)-dodec-3-enoyl-CoA = (2E)-dodec-2-enoyl-CoA.
Protein Details
3. Probable enoyl-CoA hydratase paaF
General function:
Involved in catalytic activity
Specific function:
Could possibly oxidize fatty acids using specific components
Gene Name:
paaF
Uniprot ID:
P76082
Molecular weight:
27237
Reactions
(3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H(2)O.
Protein Details
4. 3-ketoacyl-CoA thiolase_
General function:
Involved in transferase activity
Specific function:
Catalyzes the final step of fatty acid oxidation in which acetyl-CoA is released and the CoA ester of a fatty acid two carbons shorter is formed. Strongly involved in the anaerobic degradation of long and medium-chain fatty acids in the presence of nitrate and weakly involved in the aerobic degradation of long- chain fatty acids
Gene Name:
fadI
Uniprot ID:
P76503
Molecular weight:
46530
Reactions
Acyl-CoA + acetyl-CoA = CoA + 3-oxoacyl-CoA.
Protein Details
5. Fatty acid oxidation complex subunit alpha_
General function:
Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:
Catalyzes the formation of an hydroxyacyl-CoA by addition of water on enoyl-CoA. Also exhibits 3-hydroxyacyl-CoA epimerase and 3-hydroxyacyl-CoA dehydrogenase activities. Strongly involved in the anaerobic degradation of long and medium-chain fatty acids in the presence of nitrate and weakly involved in the aerobic degradation of long-chain fatty acids
Gene Name:
fadJ
Uniprot ID:
P77399
Molecular weight:
77072
Reactions
(3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H(2)O.
(S)-3-hydroxyacyl-CoA + NAD(+) = 3-oxoacyl-CoA + NADH.
(S)-3-hydroxybutanoyl-CoA = (R)-3-hydroxybutanoyl-CoA.

Transporters

Protein Details
1. Fatty acid oxidation complex subunit alpha
General function:
Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:
Catalyzes the formation of an hydroxyacyl-CoA by addition of water on enoyl-CoA. Also exhibits 3-hydroxyacyl-CoA epimerase and 3-hydroxyacyl-CoA dehydrogenase activities. Involved in the aerobic and anaerobic degradation of long-chain fatty acids
Gene Name:
fadB
Uniprot ID:
P21177
Molecular weight:
79593
Reactions
(S)-3-hydroxyacyl-CoA + NAD(+) = 3-oxoacyl-CoA + NADH.
(3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H(2)O.
(S)-3-hydroxybutanoyl-CoA = (R)-3-hydroxybutanoyl-CoA.
(3Z)-dodec-3-enoyl-CoA = (2E)-dodec-2-enoyl-CoA.