3-oxo-myristoyl-CoA (PAMDB120281)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120281
Identification
Name: 3-oxo-myristoyl-CoA
Description:Tetraanion of 3-oxotetradecanoyl-CoA arising from deprotonation of the phosphate and diphosphate functions; principal microspecies at pH 7.3.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 3-oxo-myristoyl-CoA(4−)
  • 3-oxomyristoyl-CoA(4−)
  • 3-oxotetradecanoyl-CoA
Chemical Formula: C35H56N7O18P3S
Average Molecular Weight: 987.845
Monoisotopic Molecular Weight: 991.29285
InChI Key: IQNFBGHLIVBNOU-QSGBVPJFSA-J
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)/p-4/t24-,28-,29-,30+,34-/m1/s1
CAS number: 122364-86-7
IUPAC Name:3'-phosphonatoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-{[3-oxo-3-({2-[(3-oxotetradecanoyl)sulfanyl]ethyl}amino)propyl]amino}butyl] diphosphate}
Traditional IUPAC Name: 3-oxotetradecanoyl-coa
SMILES:CCCCCCCCCCCC(=O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-]
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities 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.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Lipids and lipid-like molecules
Sub ClassFatty Acyls
Direct Parent Long-chain 3-oxoacyl 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
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.38 mg/mLALOGPS
logP1.48ALOGPS
logP-2.1ChemAxon
logS-2.6ALOGPS
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 Count32ChemAxon
Refractivity228.14 m3·mol-1ChemAxon
Polarizability95.3 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
lauroyl-CoA + acetyl-CoA → 3-oxo-myristoyl-CoA + coenzyme-A-group
Pathways:
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
References
References:
  • 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. [7548202 ]
  • 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. [8444867 ]
  • 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. [2818568 ]
  • 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. [2774174 ]
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
HMDBHMDB03935
BIGG45449
CHEBI62543
PUBCHEM25245316
LIGAND-CPDC05261