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Identification
YMDB IDYMDB00099
NameTetradecanoyl-CoA
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionTetradecanoyl-CoA , also known as myristoyl-CoA or N-C14:0CoA, belongs to the class of organic compounds known as 1-ribosyl-imidazolecarboxamides. These are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond. Tetradecanoyl-CoA is a strong basic compound (based on its pKa). Tetradecanoyl-CoA exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
  • 2-Hydroxybutane-1,2,4-tricarboxylate
  • 3-hydroxy-3-carboxyadipate
  • Homocitrate
  • Myristoyl-CoA
  • Myristoyl-coenzyme A
  • n-C14:0CoA
  • n-C14:0Coenzyme A
  • S-Tetradecanoyl-coenzyme A
  • Tetradecanoyl CoA
  • Tetradecanoyl Coenzyme A
  • Tetradecanoyl-coenzyme A
  • Tetradecanoyl-CoA
CAS number3130-72-1
WeightAverage: 977.89
Monoisotopic: 977.313573819
InChI KeyDUAFKXOFBZQTQE-XVDJLSDJSA-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({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 Name[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-2,2-dimethyl-3-[(2-{[2-(tetradecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid
Chemical FormulaC35H62N7O17P3S
SMILES[H]OC([H])(C(=O)N([H])C([H])([H])C([H])([H])C(=O)N([H])C([H])([H])C([H])([H])SC(=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])OP(=O)(O[H])OP(=O)(O[H])OC([H])([H])[C@@]1([H])O[C@@]([H])(N2C([H])=NC3=C2N=C([H])N=C3N([H])[H])[C@]([H])(O[H])[C@]1([H])OP(=O)(O[H])O[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-ribosyl-imidazolecarboxamides. These are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassImidazole ribonucleosides and ribonucleotides
Sub Class1-ribosyl-imidazolecarboxamides
Direct Parent1-ribosyl-imidazolecarboxamides
Alternative Parents
Substituents
  • 1-ribosyl-imidazolecarboxamide
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • 2-heteroaryl carboxamide
  • Imidazole-4-carbonyl group
  • Monoalkyl phosphate
  • Aminoimidazole
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Phosphoric acid ester
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Tetrahydrofuran
  • Primary carboxylic acid amide
  • Secondary alcohol
  • Amino acid or derivatives
  • 1,2-diol
  • Carboxamide group
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Primary amine
  • Organonitrogen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Amine
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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-1.4ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area363.63 ŲChemAxon
Rotatable Bond Count32ChemAxon
Refractivity227.45 m³·mol⁻¹ChemAxon
Polarizability96.43 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • lipid particle
  • endoplasmic reticulum
  • peroxisome
  • cytoplasm
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 Reactions
Tetradecanoyl-CoA + Acetyl-CoA3-Oxohexadecanoyl-CoA + Coenzyme A
Tetradecanoyl-CoA + electron-transfer flavoprotein → (2E)-Tetradecenoyl-CoA + Reduced electron-transfer flavoprotein
(2E)-Tetradecenoyl-CoA + NADPHTetradecanoyl-CoA + NADP
KEGG Reactions
Tetradecanoyl-CoA but-1-ene-1,2,4-tricarboxylic acid + water
Coenzyme A + 3-oxopalmitoyl-CoAAcetyl-CoA + Tetradecanoyl-CoA
Tetradecanoyl-CoA + oxygenHydrogen peroxide + trans-tetradec-2-enoyl-CoA
Adenosine triphosphate + myristic acid + Coenzyme AAdenosine monophosphate + Pyrophosphate + Tetradecanoyl-CoA
malonyl-CoA + lauroyl-CoA + hydron + NADPHCarbon dioxide + NADP + water + Tetradecanoyl-CoA + Coenzyme A
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Rudnick, D. A., Rocque, W. J., McWherter, C. A., Toth, M. V., Jackson-Machelski, E., Gordon, J. I. (1993). "Use of photoactivatable peptide substrates of Saccharomyces cerevisiae myristoyl-CoA:protein N-myristoyltransferase (Nmt1p) to characterize a myristoyl-CoA-Nmt1p-peptide ternary complex and to provide evidence for an ordered reaction mechanism." Proc Natl Acad Sci U S A 90:1087-1091.8430078
  • Farazi, T. A., Waksman, G., Gordon, J. I. (2001). "Structures of Saccharomyces cerevisiae N-myristoyltransferase with bound myristoylCoA and peptide provide insights about substrate recognition and catalysis." Biochemistry 40:6335-6343.11371195
  • Duronio, R. J., Knoll, L. J., Gordon, J. I. (1992). "Isolation of a Saccharomyces cerevisiae long chain fatty acyl:CoA synthetase gene (FAA1) and assessment of its role in protein N-myristoylation." J Cell Biol 117:515-529.1572893
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID15532
HMDB IDHMDB01521
Pubchem Compound ID1126
Kegg IDC02593
ChemSpider ID58623
FOODB IDFDB022670
Wikipedia IDNot Available
BioCyc IDTETRADECANOYL-COA

Enzymes

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.
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.