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Showing metabocard for 3-Oxotetradecanoyl-CoA (HMDB0003935)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (8) Show 8 proteinsXML
enzymes (8) Show 8 proteins
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-13 07:44:28 UTC
Update Date2020-02-26 21:24:50 UTC
HMDB IDHMDB0003935
Secondary Accession Numbers
  • HMDB0006527
  • HMDB03935
  • HMDB06527
Metabolite Identification
Common 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 ).
Structure
Data?1582752290
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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
Chemical FormulaC35H60N7O18P3S
Average Molecular Weight991.873
Monoisotopic Molecular Weight991.292838377
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 Name3-oxotetradecanoyl-coa
CAS Registry Number122364-86-7
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=C1N=CN=C2N
InChI Identifier
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
InChI KeyIQNFBGHLIVBNOU-QSGBVPJFSA-N
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1902100203-37e47fa131f279d1ccdbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0922300000-89842e38a36b7c108b45Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900101000-4f1b2969f929942e67b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00al-3951231305-e64e775b7655f9988bfeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3921200001-fab03116b2cfb433bbaeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900100000-457e07aa65d0f83247fbSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023254
KNApSAcK IDNot Available
Chemspider ID10140190
KEGG Compound IDC05261
BioCyc IDNot Available
BiGG ID45449
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11966197
PDB IDNot Available
ChEBI ID28726
Food Biomarker OntologyNot Available
VMH ID3OTDCOA
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sleboda J, Pourfarzam M, Bartlett K, Osmundsen H: Effects of added l-carnitine, acetyl-CoA and CoA on peroxisomal beta-oxidation of [U-14C]hexadecanoate by isolated peroxisomal fractions. Biochim Biophys Acta. 1995 Oct 5;1258(3):309-18. [PubMed:7548202 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]

Enzymes

Enzyme Details
1. 3-ketoacyl-CoA thiolase, mitochondrial
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Abolishes BNIP3-mediated apoptosis and mitochondrial damage.
Gene Name:
ACAA2
Uniprot ID:
P42765
Molecular weight:
41923.82
Reactions
Lauroyl-CoA + Acetyl-CoA → Coenzyme A + 3-Oxotetradecanoyl-CoAdetails
Enzyme Details
2. 3-ketoacyl-CoA thiolase, peroxisomal
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Not Available
Gene Name:
ACAA1
Uniprot ID:
P09110
Molecular weight:
34664.46
Reactions
Lauroyl-CoA + Acetyl-CoA → Coenzyme A + 3-Oxotetradecanoyl-CoAdetails
Enzyme Details
3. Trifunctional enzyme subunit beta, mitochondrial
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Not Available
Gene Name:
HADHB
Uniprot ID:
P55084
Molecular weight:
51293.955
Reactions
Lauroyl-CoA + Acetyl-CoA → Coenzyme A + 3-Oxotetradecanoyl-CoAdetails
Enzyme Details
4. 3-hydroxyacyl-CoA dehydrogenase type-2
General function:
Involved in oxidoreductase activity
Specific function:
Functions in mitochondrial tRNA maturation. Part of mitochondrial ribonuclease P, an enzyme composed of MRPP1/TRMT10C, MRPP2/HSD17B10 and MRPP3/KIAA0391, which cleaves tRNA molecules in their 5'-ends. By interacting with intracellular amyloid-beta, it may contribute to the neuronal dysfunction associated with Alzheimer disease (AD).
Gene Name:
HSD17B10
Uniprot ID:
Q99714
Molecular weight:
25983.695
Enzyme Details
5. Peroxisomal bifunctional enzyme
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
EHHADH
Uniprot ID:
Q08426
Molecular weight:
69153.26
Reactions
(S)-3-Hydroxytetradecanoyl-CoA + NAD → 3-Oxotetradecanoyl-CoA + NADHdetails
Enzyme Details
6. Hydroxyacyl-coenzyme A dehydrogenase, mitochondrial
General function:
Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:
Plays an essential role in the mitochondrial beta-oxidation of short chain fatty acids. Exerts it highest activity toward 3-hydroxybutyryl-CoA.
Gene Name:
HADH
Uniprot ID:
Q16836
Molecular weight:
36035.11
Reactions
(S)-3-Hydroxytetradecanoyl-CoA + NAD → 3-Oxotetradecanoyl-CoA + NADHdetails
Enzyme Details
7. Trifunctional enzyme subunit alpha, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Bifunctional subunit.
Gene Name:
HADHA
Uniprot ID:
P40939
Molecular weight:
82998.97
Reactions
(S)-3-Hydroxytetradecanoyl-CoA + NAD → 3-Oxotetradecanoyl-CoA + NADHdetails
Enzyme Details
8. Peroxisomal multifunctional enzyme type 2
General function:
Involved in oxidoreductase activity
Specific function:
Bifunctional enzyme acting on the peroxisomal beta-oxidation pathway for fatty acids. Catalyzes the formation of 3-ketoacyl-CoA intermediates from both straight-chain and 2-methyl-branched-chain fatty acids.
Gene Name:
HSD17B4
Uniprot ID:
P51659
Molecular weight:
79685.715