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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:04:53 UTC
HMDB IDHMDB01521
Secondary Accession Numbers
  • HMDB06517
Metabolite Identification
Common NameTetradecanoyl-CoA
DescriptionTetradecanoyl-CoA (or myristoyl-CoA) is an intermediate in fatty acid biosynthesis, fatty acid elongation and the beta oxidation of fatty acids. It is also used in the myristoylation of proteins. The first pass through the beta-oxidation process starts with the saturated fatty acid palmitoyl-CoA and produces myristoyl-CoA. A total of four enzymatic steps are required, starting with VLCAD CoA dehydrogenase (Very Long Chain) activity, followed by three enzymatic steps catalyzed by enoyl-CoA hydratase, 3-hydroxyacyl-CoA dehydrogenase, and ketoacyl-CoA thiolase, all present in the mitochondria. Myristoylation of proteins is also catalyzed by the presence of myristoyl-CoA along with Myristoyl-CoA:protein N-myristoyltransferase (NMT). Myristoylation is an irreversible, co-translational (during translation) protein modification found in animals, plants, fungi and viruses. In this protein modification a myristoyl group (derived from myristioyl CoA) is covalently attached via an amide bond to the alpha-amino group of an N-terminal amino acid of a nascent polypeptide. It is more common on glycine residues but also occurs on other amino acids. Myristoylation also occurs post-translationally, for example when previously internal glycine residues become exposed by caspase cleavage during apoptosis. Myristoylation plays a vital role in membrane targeting and signal transduction in plant responses to environmental stress. Compared to other species that possess a single functional myristoyl-CoA: protein N-myristoyltransferase (NMT) gene copy, human, mouse and cow possess 2 NMT genes, and more than 2 protein isoforms.
Structure
Thumb
Synonyms
ValueSource
Myristoyl-CoAHMDB
Myristoyl-coenzyme AHMDB
N-C14:0CoAHMDB
N-C14:0coenzyme AHMDB
S-Tetradecanoyl-coenzyme AHMDB
Tetradecanoyl CoAHMDB
Tetradecanoyl coenzyme AHMDB
Tetradecanoyl-coenzyme AHMDB
Chemical FormulaC35H62N7O17P3S
Average Molecular Weight977.89
Monoisotopic Molecular Weight977.313573819
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 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
CAS Registry Number3130-72-1
SMILES
CCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)C(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/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
InChI KeyInChIKey=DUAFKXOFBZQTQE-XVDJLSDJSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 2,3,4-saturated fatty acyl coas. These are acyl-CoAs carrying a 2,3,4-saturated fatty acyl chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct Parent2,3,4-saturated fatty acyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside diphosphate
  • Purine ribonucleoside 3',5'-bisphosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Beta amino acid or derivatives
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • N-acyl-amine
  • Monosaccharide
  • Fatty amide
  • Saccharide
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Thiocarboxylic acid ester
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Thioether
  • Thiocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Lipid biosynthesis, Fatty acid transport
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
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 Solubility2.21 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count32ChemAxon
Refractivity227.45 m3·mol-1ChemAxon
Polarizability96.43 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1911101102-349a13615858f61c2639View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0941300000-9797f6c398276f5d5e98View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2900102000-cc4f9c8978927acec695View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a7i-4971342506-ab177bf279e0e32e2b12View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0560-3921201001-624d08d1bbb66df93c2eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900000000-d973a8b2d469b04161ebView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue Location
  • Fibroblasts
Pathways
NameSMPDB LinkKEGG Link
Adrenoleukodystrophy, X-linkedSMP00516Not Available
Beta Oxidation of Very Long Chain Fatty AcidsSMP00052map01040
Carnitine palmitoyl transferase deficiency (I)SMP00538Not Available
Carnitine palmitoyl transferase deficiency (II)SMP00541Not Available
Carnitine-acylcarnitine translocase deficiencySMP00517Not Available
Ethylmalonic EncephalopathySMP00181Not Available
Fatty Acid Elongation In MitochondriaSMP00054map00062
Fatty acid MetabolismSMP00051map00071
Glutaric Aciduria Type ISMP00185Not Available
Long chain acyl-CoA dehydrogenase deficiency (LCAD)SMP00539Not Available
Long-chain-3-hydroxyacyl-coa dehydrogenase deficiency (LCHAD)SMP00544Not Available
Medium chain acyl-coa dehydrogenase deficiency (MCAD)SMP00542Not Available
Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty AcidsSMP00482Not Available
Short Chain Acyl CoA Dehydrogenase Deficiency (SCAD Deficiency)SMP00235Not Available
Trifunctional protein deficiencySMP00545Not Available
Very-long-chain acyl coa dehydrogenase deficiency (VLCAD)SMP00540Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022670
KNApSAcK IDNot Available
Chemspider ID58623
KEGG Compound IDC02593
BioCyc IDTETRADECANOYL-COA
BiGG ID40154
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01521
Metagene LinkHMDB01521
METLIN ID3707
PubChem Compound65113
PDB ID1IIC
ChEBI ID15532
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hunt MC, Ruiter J, Mooyer P, van Roermond CW, Ofman R, Ijlst L, Wanders RJ: Identification of fatty acid oxidation disorder patients with lowered acyl-CoA thioesterase activity in human skin fibroblasts. Eur J Clin Invest. 2005 Jan;35(1):38-46. [15638818 ]

Enzymes

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
Tetradecanoyl-CoA + Acetyl-CoA → Coenzyme A + 3-Oxohexadecanoyl-CoAdetails
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
Tetradecanoyl-CoA + Acetyl-CoA → Coenzyme A + 3-Oxohexadecanoyl-CoAdetails
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
Tetradecanoyl-CoA + Acetyl-CoA → Coenzyme A + 3-Oxohexadecanoyl-CoAdetails
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Not Available
Gene Name:
ACADL
Uniprot ID:
P28330
Molecular weight:
47655.275
Reactions
Tetradecanoyl-CoA + FAD → (2E)-Tetradecenoyl-CoA + FADHdetails
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
This enzyme is specific for acyl chain lengths of 4 to 16.
Gene Name:
ACADM
Uniprot ID:
P11310
Molecular weight:
46587.98
Reactions
Tetradecanoyl-CoA + FAD → (2E)-Tetradecenoyl-CoA + FADHdetails
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Catalyzes the desaturation of acyl-CoAs to 2-trans-enoyl-CoAs. Isoform 1 shows highest activity against medium-chain fatty acyl-CoAs and activity decreases with increasing chain length. Isoform 2 is active against a much broader range of substrates and shows activity towards very long-chain acyl-CoAs. Isoform 2 is twice as active as isoform 1 against 16-hydroxy-palmitoyl-CoA and is 25% more active against 1,16-hexadecanodioyl-CoA.
Gene Name:
ACOX1
Uniprot ID:
Q15067
Molecular weight:
70135.205
Reactions
Tetradecanoyl-CoA + FAD → (2E)-Tetradecenoyl-CoA + FADHdetails
General function:
Involved in oxidoreductase activity, acting on the CH-CH group of donors
Specific function:
Oxidizes the CoA-esters of 2-methyl-branched fatty acids (By similarity).
Gene Name:
ACOX3
Uniprot ID:
O15254
Molecular weight:
69574.075
Reactions
Tetradecanoyl-CoA + FAD → (2E)-Tetradecenoyl-CoA + FADHdetails
General function:
Involved in zinc ion binding
Specific function:
Catalyzes the reduction of trans-2-enoyl-CoA to acyl-CoA with chain length from C6 to C16 in an NADPH-dependent manner with preference to medium chain length substrate. May have a role in the mitochondrial synthesis of fatty acids.
Gene Name:
MECR
Uniprot ID:
Q9BV79
Molecular weight:
32228.0
Reactions
Tetradecanoyl-CoA + NADP → (2E)-Tetradecenoyl-CoA + NADPH + Hydrogen Iondetails
General function:
Involved in regulation of apoptosis
Specific function:
Participates in chain elongation of fatty acids. Has no 2,4-dienoyl-CoA reductase activity.
Gene Name:
PECR
Uniprot ID:
Q9BY49
Molecular weight:
32544.11
General function:
Involved in glycylpeptide N-tetradecanoyltransferase activity
Specific function:
Adds a myristoyl group to the N-terminal glycine residue of certain cellular and viral proteins.
Gene Name:
NMT1
Uniprot ID:
P30419
Molecular weight:
56805.865
Reactions
Tetradecanoyl-CoA + glycylpeptide → Coenzyme A + N-tetradecanoylglycylpeptidedetails
General function:
Involved in glycylpeptide N-tetradecanoyltransferase activity
Specific function:
Adds a myristoyl group to the N-terminal glycine residue of certain cellular and viral proteins.
Gene Name:
NMT2
Uniprot ID:
O60551
Molecular weight:
56979.755
Reactions
Tetradecanoyl-CoA + glycylpeptide → Coenzyme A + N-tetradecanoylglycylpeptidedetails
General function:
Involved in glycylpeptide N-tetradecanoyltransferase activity
Specific function:
Adds a myristoyl group to the N-terminal glycine residue of certain cellular proteins
Gene Name:
NMT1
Uniprot ID:
Q96HI4
Molecular weight:
56603.6
General function:
Involved in glycylpeptide N-tetradecanoyltransferase activity
Specific function:
Adds a myristoyl group to the N-terminal glycine residue of certain cellular proteins
Gene Name:
NMT2
Uniprot ID:
Q5VUC7
Molecular weight:
60378.5
General function:
Involved in glycylpeptide N-tetradecanoyltransferase activity
Specific function:
Adds a myristoyl group to the N-terminal glycine residue of certain cellular proteins
Gene Name:
NMT2
Uniprot ID:
Q5VUC6
Molecular weight:
56716.1
General function:
Involved in glycylpeptide N-tetradecanoyltransferase activity
Specific function:
Adds a myristoyl group to the N-terminal glycine residue of certain cellular proteins
Gene Name:
NMT1
Uniprot ID:
A4FU65
Molecular weight:
20763.6