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myristoyl-CoA (YMDB00528)

Identification
YMDB IDYMDB00528
Namemyristoyl-CoA
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionMyristoyl-Coa, also known as N-C14:0-CoA or tetradecanoyl-CoA, belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms. Thus, myristoyl-CoA is considered to be a fatty ester lipid molecule. Myristoyl-Coa is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • Myristoyl-CoA
  • Myristoyl-coenzyme A
  • n-C14:0-CoA
  • n-C14:0-coenzyme A
  • n-C14:0CoA
  • n-C14:0Coenzyme A
  • S-Tetradecanoyl-coenzyme A
  • Tetradecanoyl CoA
  • Tetradecanoyl Coenzyme A
  • Tetradecanoyl-CoA
  • Tetradecanoyl-coenzyme A
CAS number3130-72-1
WeightAverage: 977.89
Monoisotopic: 977.313573819
InChI KeyDUAFKXOFBZQTQE-QSGBVPJFSA-N
InChIInChI=1S/C35H62N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-26(44)63-19-18-37-25(43)16-17-38-33(47)30(46)35(2,3)21-56-62(53,54)59-61(51,52)55-20-24-29(58-60(48,49)50)28(45)34(57-24)42-23-41-27-31(36)39-22-40-32(27)42/h22-24,28-30,34,45-46H,4-21H2,1-3H3,(H,37,43)(H,38,47)(H,51,52)(H,53,54)(H2,36,39,40)(H2,48,49,50)/t24-,28-,29-,30+,34-/m1/s1
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-(tetradecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional IUPAC NameS-tetradecanoyl-coenzyme A
Chemical FormulaC35H62N7O17P3S
SMILESCCCCCCCCCCCCCC(=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
Chemical Taxonomy
Description belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a 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 fatty acyl 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
  • Imidolactam
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Pyrimidine
  • Alkyl phosphate
  • Fatty amide
  • Phosphoric acid ester
  • Tetrahydrofuran
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Carbothioic s-ester
  • Secondary alcohol
  • 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
  • Alcohol
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility2.21 g/LALOGPS
logP1.84ALOGPS
logP-0.29ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area363.63 ŲChemAxon
Rotatable Bond Count32ChemAxon
Refractivity227.45 m³·mol⁻¹ChemAxon
Polarizability97.97 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm, Endoplasmic Reticulum, Lipid Particle, Peroxisome
Organoleptic PropertiesNot Available
SMPDB Pathways
Cholesterol biosynthesis and metabolism CE(14:0)PW002544 ThumbThumb?image type=greyscaleThumb?image type=simple
Fatty acid elongation in mitochondriaPW002467 ThumbThumb?image type=greyscaleThumb?image type=simple
Fatty acid metabolismPW002460 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Fatty acid elongation in mitochondriaec00062 Map00062
Fatty acid metabolismec00071 Map00071
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1955000202-492920eecd7306497c0fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1973200000-1cbb294df62724605b18JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2931000000-c0fe3c1a0997b03e03c5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-057i-4951233406-cf208cd5fd7a420f18a6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0560-2910201001-2f881d14a81696fceb34JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-7900100000-e664035807d8a9423b0eJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Jones, J. M., Nau, K., Geraghty, M. T., Erdmann, R., Gould, S. J. (1999). "Identification of peroxisomal acyl-CoA thioesterases in yeast and humans." J Biol Chem 274:9216-9223.10092594
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID15532
HMDB IDHMDB01521
Pubchem Compound ID1126
Kegg IDC02593
ChemSpider IDNot Available
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDTETRADECANOYL-COA

Enzymes

Protein Details
1. Long-chain-fatty-acid--CoA ligase 4
General function:
Involved in catalytic activity
Specific function:
Esterification, concomitant with transport, of exogenous long-chain fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids. Contributes, with FAA1, to the activation of imported myristate
Gene Name:
FAA4
Uniprot ID:
P47912
Molecular weight:
77266.5
Reactions
ATP + a long-chain carboxylic acid + CoA → AMP + diphosphate + an acyl-CoA.
Protein Details
2. Acyl-coenzyme A oxidase
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Acyl-CoA + O(2) = trans-2,3-dehydroacyl-CoA + H(2)O(2)
Gene Name:
POX1
Uniprot ID:
P13711
Molecular weight:
84041.39844
Reactions
Acyl-CoA + O(2) → trans-2,3-dehydroacyl-CoA + H(2)O(2).
Protein Details
3. Long-chain-fatty-acid--CoA ligase 1
General function:
Involved in catalytic activity
Specific function:
Esterification, concomitant with transport, of exogenous long-chain fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids. It may supplement intracellular myristoyl-CoA pools from exogenous myristate. Preferentially acts on C12:0-C16:0 fatty acids with myristic and pentadecanic acid (C15:0) having the highest activities
Gene Name:
FAA1
Uniprot ID:
P30624
Molecular weight:
77865.79688
Reactions
ATP + a long-chain carboxylic acid + CoA → AMP + diphosphate + an acyl-CoA.
Protein Details
4. Long-chain-fatty-acid--CoA ligase 3
General function:
Involved in catalytic activity
Specific function:
Esterification, concomitant with transport, of endogenous long-chain fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids. This enzyme acts preferentially on C16 and C18 fatty acids with a cis-double bond at C-9-C-10
Gene Name:
FAA3
Uniprot ID:
P39002
Molecular weight:
77946.0
Reactions
ATP + a long-chain carboxylic acid + CoA → AMP + diphosphate + an acyl-CoA.
Protein Details
5. Long-chain-fatty-acid--CoA ligase 2
General function:
Involved in catalytic activity
Specific function:
Esterification, concomitant with transport, of endogenous long-chain fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids. Preferentially acts on C9:0-C13:0 fatty acids although C7:0-C17:0 fatty acids are tolerated
Gene Name:
FAA2
Uniprot ID:
P39518
Molecular weight:
83437.10156
Reactions
ATP + a long-chain carboxylic acid + CoA → AMP + diphosphate + an acyl-CoA.
Protein Details
6. 3-ketoacyl-CoA thiolase, peroxisomal
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Acyl-CoA + acetyl-CoA = CoA + 3-oxoacyl-CoA
Gene Name:
POT1
Uniprot ID:
P27796
Molecular weight:
44729.89844
Reactions
Acyl-CoA + acetyl-CoA → CoA + 3-oxoacyl-CoA.
Protein Details
7. Fatty acid synthase subunit beta
General function:
Involved in transferase activity
Specific function:
Fatty acid synthetase catalyzes the formation of long- chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. The beta subunit contains domains for:[acyl-carrier-protein] acetyltransferase and malonyltransferase, S-acyl fatty acid synthase thioesterase, enoyl-[acyl-carrier-protein] reductase, and 3-hydroxypalmitoyl-[acyl-carrier-protein] dehydratase
Gene Name:
FAS1
Uniprot ID:
P07149
Molecular weight:
228689.0
Reactions
Acetyl-CoA + n malonyl-CoA + 2n NADH + 2n NADPH → long-chain-acyl-CoA + n CoA + n CO(2) + 2n NAD(+) + 2n NADP(+).
Acetyl-CoA + [acyl-carrier-protein] → CoA + acetyl-[acyl-carrier-protein].
Malonyl-CoA + [acyl-carrier-protein] → CoA + malonyl-[acyl-carrier-protein].
(3R)-3-hydroxypalmitoyl-[acyl-carrier-protein] → hexadec-2-enoyl-[acyl-carrier-protein] + H(2)O.
Acyl-[acyl-carrier-protein] + NAD(+) → trans-2,3-dehydroacyl-[acyl-carrier-protein] + NADH.
Oleoyl-[acyl-carrier-protein] + H(2)O → [acyl-carrier-protein] + oleate.
Protein Details
8. Peroxisomal acyl-coenzyme A thioester hydrolase 1
General function:
Involved in acyl-CoA thioesterase activity
Specific function:
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH
Gene Name:
TES1
Uniprot ID:
P41903
Molecular weight:
40259.39844
Reactions
Palmitoyl-CoA + H(2)O → CoA + palmitate.
Protein Details
9. Glycylpeptide N-tetradecanoyltransferase
General function:
Involved in glycylpeptide N-tetradecanoyltransferase activity
Specific function:
Adds a myristoyl group to the N-terminal glycine residue of certain cellular proteins. Substrate specificity requires an N- terminal glycine in the nascent polypeptide substrates. Uncharged amino acids are preferred at position 2 while neutral residues are favored at positions 3 and 4. Ser is present at position 5 in almost all known N-myristoyl proteins and Lys is commonly encountered at postion 6
Gene Name:
NMT1
Uniprot ID:
P14743
Molecular weight:
52837.10156
Reactions
Tetradecanoyl-CoA + glycylpeptide → CoA + N-tetradecanoylglycylpeptide.

Transporters

Protein Details
1. Peroxisomal long-chain fatty acid import protein 1
General function:
Involved in transport
Specific function:
Involved in the import of activated long-chain fatty acids from the cytosol to the peroxisomal matrix
Gene Name:
PXA2
Uniprot ID:
P34230
Molecular weight:
97125.29688