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Record Information
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:09 UTC
Secondary Accession Numbers
  • HMDB0006504
  • HMDB01359
  • HMDB06504
Metabolite Identification
Common NamePhytanoyl-CoA
DescriptionPhytanoyl CoA is a coenzyme A derivative of phytanic acid. Phytanic acid is present in human diet or in animal tissues where it may be derived from chlorophyll in plant extracts. Specifically it is an epimeric metabolite of the isoprenoid side chain of chlorophyll. Owing to the presence of its epimeric beta-methyl group, phytanic acid cannot be metabolized by beta-oxidation. Instead, it is metabolized in peroxisomes via alpha-oxidation to give pristanic acid, which is then oxidized by beta-oxidation. PhyH (phytanoyl-CoA 2-hydroxylase) catalyses hydroxylation of phytanoyl-CoA. Mutations of PhyH can lead to phytanic acid accumulation. High levels of phytanic acid are found in patients suffering from Refsum's syndrome. This inherited neurological disorder is characterized by an accumulation of phytanic acid in blood and tissues. Clinically it is characterized by adult onset retinitis pigmentosa, anosmia, sensory neuropathy, and phytanic acidaemia. This disorder has been found to be related to deficiency in the α-oxidation pathway in the liver. (PMID: 17956235 ). Phytanoyl CoA and other branched-chain fatty acid CoA products are potent inducers of the peroxisome proliferator-activated receptor PPARalpha, a nuclear receptor that enhances transcription of peroxisomal enzymes mediating beta-oxidation of these potentially toxic fatty acids (PMID: 16768463 ). Pyruvate dehydrogenase and 2-oxoglutarate dehydrogenase are strongly inhibited by phytanoyl-CoA. Decreased activity of these important mitochondrial metabolism complexes might therefore contribute to neurological symptoms upon accumulation of phytanic acid in Refsum disease (PMID: 16737698 ).
3,7,11,15-Tetramethyl hexadecanoyl CoAHMDB
3,7,11,15-Tetramethyl hexadecanoyl coenzyme AHMDB
Phytanoyl CoAHMDB
Phytanoyl coenzyme AHMDB
Phytanoyl-coenzyme AHMDB
Phytanyl CoAHMDB
Phytanyl coenzyme AHMDB
Chemical FormulaC41H74N7O17P3S
Average Molecular Weight1062.049
Monoisotopic Molecular Weight1061.407474203
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-{[(3S,7R,11R)-3,7,11,15-tetramethylhexadecanoyl]sulfanyl}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-{[(3S,7R,11R)-3,7,11,15-tetramethylhexadecanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid
CAS Registry Number146622-45-9
InChI Identifier
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
  • Coenzyme a or derivatives
  • Purine ribonucleoside 3',5'-bisphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside diphosphate
  • Diterpenoid
  • Pentose phosphate
  • Ribonucleoside 3'-phosphate
  • Pentose-5-phosphate
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • Pentose monosaccharide
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Monosaccharide
  • Fatty amide
  • N-substituted imidazole
  • N-acyl-amine
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Thiocarboxylic acid ester
  • Amino acid or derivatives
  • Carbothioic s-ester
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Oxacycle
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic oxide
  • Carbonyl group
  • Primary amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Alcohol
  • Amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Not AvailableNot Available
Physical Properties
Experimental Molecular Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Water Solubility0.77 g/LALOGPS
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 Count34ChemAxon
Refractivity254.84 m³·mol⁻¹ChemAxon
Polarizability106.07 ųChemAxon
Number of Rings3ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference

Predicted Kovats Retention Indices

Not Available

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytanoyl-CoA 10V, Positive-QTOFsplash10-000i-4901110200-c8e2fb3674f9f0da45d72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytanoyl-CoA 20V, Positive-QTOFsplash10-000i-1912130000-09f25ff6c40daa790a9c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytanoyl-CoA 40V, Positive-QTOFsplash10-000i-1900010000-5ec62b87df52230c45402017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytanoyl-CoA 10V, Negative-QTOFsplash10-01rx-9652431500-04d5c22d9e4fc31c0be82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytanoyl-CoA 20V, Negative-QTOFsplash10-001l-5920210100-9766416a475cedb2730d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytanoyl-CoA 40V, Negative-QTOFsplash10-057i-5900100000-b16bf5536d8209fb8b472017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytanoyl-CoA 10V, Positive-QTOFsplash10-03di-9000000003-ffbd4b8db32357807b8f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytanoyl-CoA 20V, Positive-QTOFsplash10-000i-9400000028-f96e20f26253411b40602021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytanoyl-CoA 40V, Positive-QTOFsplash10-0a4i-0100390000-3eea46ca9905d83557892021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytanoyl-CoA 10V, Negative-QTOFsplash10-03di-9000000100-482574b4d2f10c2535c12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytanoyl-CoA 20V, Negative-QTOFsplash10-03fu-9100101200-f50e099d92a0038c6df02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytanoyl-CoA 40V, Negative-QTOFsplash10-056u-9204400301-256ca3412920b74581222021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Peroxisome
Biospecimen LocationsNot Available
Tissue LocationsNot Available
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
FooDB IDFDB022577
KNApSAcK IDNot Available
Chemspider ID388712
KEGG Compound IDC02060
BioCyc IDNot Available
BiGG ID2364522
Wikipedia LinkPhytanoyl-CoA
PubChem Compound439640
PDB IDNot Available
ChEBI ID15538
Food Biomarker OntologyNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
Synthesis ReferenceKershaw, N. J.; Mukherji, M.; MacKinnon, C. H.; Claridge, T. D. W.; Odell, B.; Wierzbicki, A. S.; Lloyd, M. D.; Schofield, C. J. Studies on phytanoyl-CoA 2-hydroxylase and synthesis of phytanoyl-Coenzyme A. Bioorganic & Medicinal Chemistry Letters (2001) 11(18), 17 September 2001, p.2545-2548
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Bunik VI, Raddatz G, Wanders RJ, Reiser G: Brain pyruvate and 2-oxoglutarate dehydrogenase complexes are mitochondrial targets of the CoA ester of the Refsum disease marker phytanic acid. FEBS Lett. 2006 Jun 12;580(14):3551-7. Epub 2006 May 24. [PubMed:16737698 ]
  2. Schofield CJ, McDonough MA: Structural and mechanistic studies on the peroxisomal oxygenase phytanoyl-CoA 2-hydroxylase (PhyH). Biochem Soc Trans. 2007 Nov;35(Pt 5):870-5. [PubMed:17956235 ]
  3. Hostetler HA, Kier AB, Schroeder F: Very-long-chain and branched-chain fatty acyl-CoAs are high affinity ligands for the peroxisome proliferator-activated receptor alpha (PPARalpha). Biochemistry. 2006 Jun 20;45(24):7669-81. [PubMed:16768463 ]


General function:
Involved in acyltransferase activity
Specific function:
Carnitine acetylase is specific for short chain fatty acids. Carnitine acetylase seems to affect the flux through the pyruvate dehydrogenase complex. It may be involved as well in the transport of acetyl-CoA into mitochondria.
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in electron carrier activity
Specific function:
Converts phytanoyl-CoA to 2-hydroxyphytanoyl-CoA.
Gene Name:
Uniprot ID:
Molecular weight:
Phytanoyl-CoA + Oxoglutaric acid + Oxygen → 2-Hydroxyphytanoyl-CoA + Succinic acid + CO(2)details
General function:
Involved in catalytic activity
Specific function:
Activation of long-chain fatty acids for both synthesis of cellular lipids, and degradation via beta-oxidation. Preferentially uses palmitoleate, oleate and linoleate.
Gene Name:
Uniprot ID:
Molecular weight: