Showing metabocard for Tetradecanoyl-CoA (BMDB0001521)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (6) Show 6 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:47:08 UTC
Update Date2020-05-11 20:02:12 UTC
BMDB IDBMDB0001521
Secondary Accession Numbers
  • BMDB01521
Metabolite Identification
Common NameTetradecanoyl-CoA
DescriptionTetradecanoyl-CoA , also known as myristoyl-CoA or N-C14:0CoA, 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. Tetradecanoyl-CoA is possibly soluble (in water) and a strong basic compound (based on its pKa). Tetradecanoyl-CoA exists in all living species, ranging from bacteria to humans. Tetradecanoyl-CoA participates in a number of enzymatic reactions, within cattle. In particular, Tetradecanoyl-CoA and glycerol 3-phosphate can be converted into lpa(14:0/0:0) through the action of the enzyme glycerol-3-phosphate acyltransferase. In addition, Lpa(14:0/0:0) and tetradecanoyl-CoA can be converted into PA(14:0/14:0) through its interaction with the enzyme 1-acyl-sn-glycerol-3-phosphate acyltransferase. In cattle, tetradecanoyl-CoA is involved in the metabolic pathway called de novo triacylglycerol biosynthesis TG(14:0/14:0/14:0) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
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, HMDB
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
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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • 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
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
BioavailabilityYesChemAxon
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000000009-3239f04ec07dfb05c844View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-4120302409-5222d96c1a16a7c2a7dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0570-2102301209-fd8e6272e04594f37eaaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000000009-7a4d637e9994bab811ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0800100449-955bc85312168f96efe1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0101900000-c9607999f9d61657c1fbView in MoNA
MSMass Spectrum (Electron Ionization)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Fibroblasts
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001521
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB031010
KNApSAcK IDNot Available
Chemspider ID58623
KEGG Compound IDC02593
BioCyc IDNot Available
BiGG ID40154
Wikipedia LinkNot Available
METLIN ID3707
PubChem Compound65113
PDB IDNot Available
ChEBI ID15532
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Glycylpeptide N-tetradecanoyltransferase
General function:
Involved in glycylpeptide N-tetradecanoyltransferase ac
Specific function:
Adds a myristoyl group to the N-terminal glycine residue of certain cellular proteins.
Gene Name:
NMT1
Uniprot ID:
Q32LK5
Molecular weight:
56714.0
Enzyme Details
2. Glycylpeptide N-tetradecanoyltransferase 1
General function:
Involved in glycylpeptide N-tetradecanoyltransferase ac
Specific function:
Adds a myristoyl group to the N-terminal glycine residue of certain cellular and viral proteins.
Gene Name:
NMT1
Uniprot ID:
P31717
Molecular weight:
56919.0
Enzyme Details
3. Glycylpeptide N-tetradecanoyltransferase
General function:
Involved in glycylpeptide N-tetradecanoyltransferase ac
Specific function:
Adds a myristoyl group to the N-terminal glycine residue of certain cellular proteins.
Gene Name:
Not Available
Uniprot ID:
Q8MKE3
Molecular weight:
48141.0
Enzyme Details
4. Glycylpeptide N-tetradecanoyltransferase
General function:
Involved in glycylpeptide N-tetradecanoyltransferase ac
Specific function:
Adds a myristoyl group to the N-terminal glycine residue of certain cellular proteins.
Gene Name:
NMT2
Uniprot ID:
Q2KIZ5
Molecular weight:
47702.0
Enzyme Details
5. Glycylpeptide N-tetradecanoyltransferase
General function:
Involved in glycylpeptide N-tetradecanoyltransferase ac
Specific function:
Adds a myristoyl group to the N-terminal glycine residue of certain cellular proteins.
Gene Name:
Not Available
Uniprot ID:
Q9GL39
Molecular weight:
51185.0
Enzyme Details
6. Glycylpeptide N-tetradecanoyltransferase 2
General function:
Involved in glycylpeptide N-tetradecanoyltransferase ac
Specific function:
Adds a myristoyl group to the N-terminal glycine residue of certain cellular and viral proteins.
Gene Name:
NMT2
Uniprot ID:
Q9N181
Molecular weight:
56803.0