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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-24 18:48:02 UTC
HMDB IDHMDB0001521
Secondary Accession Numbers
  • HMDB0006517
  • HMDB01521
  • 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
Tetradecanoyl-CoAMeSH
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 KeyDUAFKXOFBZQTQE-XVDJLSDJSA-N
Chemical Taxonomy
DescriptionThis compound 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
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 Solubility2.21 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
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
Biospecimen LocationsNot Available
Tissue Location
  • Fibroblasts
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 IDFDB022670
KNApSAcK IDNot Available
Chemspider ID58623
KEGG Compound IDC02593
BioCyc IDTETRADECANOYL-COA
BiGG ID40154
Wikipedia LinkNot Available
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. [PubMed:15638818 ]

Only showing the first 10 proteins. There are 15 proteins in total.

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

Only showing the first 10 proteins. There are 15 proteins in total.