Showing metabocard for Phytanoyl-CoA (BMDB0001359)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:44:41 UTC
Update Date2020-05-21 16:28:37 UTC
BMDB IDBMDB0001359
Secondary Accession Numbers
  • BMDB01359
Metabolite Identification
Common NamePhytanoyl-CoA
DescriptionPhytanoyl-CoA, also known as phytanoyl CoA, 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. Phytanoyl-CoA is a strong basic compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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
SMILES
CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@H](C)CC(=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/C41H74N7O17P3S/c1-26(2)11-8-12-27(3)13-9-14-28(4)15-10-16-29(5)21-32(50)69-20-19-43-31(49)17-18-44-39(53)36(52)41(6,7)23-62-68(59,60)65-67(57,58)61-22-30-35(64-66(54,55)56)34(51)40(63-30)48-25-47-33-37(42)45-24-46-38(33)48/h24-30,34-36,40,51-52H,8-23H2,1-7H3,(H,43,49)(H,44,53)(H,57,58)(H,59,60)(H2,42,45,46)(H2,54,55,56)/t27-,28-,29+,30-,34-,35-,36?,40-/m1/s1
InChI KeyNRJQGHHZMSOUEN-IYJVDCLDSA-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
  • 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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Mitochondria
  • Peroxisome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3ALOGPS
logP0.65ChemAxon
logS-3.1ALOGPS
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
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-4901110200-c8e2fb3674f9f0da45d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1912130000-09f25ff6c40daa790a9cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900010000-5ec62b87df52230c4540View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01rx-9652431500-04d5c22d9e4fc31c0be8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001l-5920210100-9766416a475cedb2730dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-5900100000-b16bf5536d8209fb8b47View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-9000000003-ffbd4b8db32357807b8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9400000028-f96e20f26253411b4060View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0100390000-3eea46ca9905d8355789View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-9000000100-482574b4d2f10c2535c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03fu-9100101200-f50e099d92a0038c6df0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056u-9204400301-256ca3412920b7458122View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Mitochondria
  • Peroxisome
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001359
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
METLIN ID6189
PubChem Compound439640
PDB IDNot Available
ChEBI ID15538
References
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 ReferencesNot Available

Enzymes

Enzyme Details
1. Phytanoyl-CoA dioxygenase, peroxisomal
General function:
Involved in iron ion binding
Specific function:
Converts phytanoyl-CoA to 2-hydroxyphytanoyl-CoA.
Gene Name:
PHYH
Uniprot ID:
O18778
Molecular weight:
38770.0
Reactions
Phytanoyl-CoA + Oxoglutaric acid + Oxygen → 2-Hydroxyphytanoyl-CoA + Succinic acid + Carbon dioxidedetails
Enzyme Details
2. Long-chain-fatty-acid--CoA ligase ACSBG1
General function:
Lipid transport and metabolism
Specific function:
Catalyzes the conversion of fatty acids such as long-chain and very long-chain fatty acids to their active form acyl-CoAs for both synthesis of cellular lipids, and degradation via beta-oxidation. Can activate diverse saturated, monosaturated and polyunsaturated fatty acids.
Gene Name:
ACSBG1
Uniprot ID:
Q2KHW5
Molecular weight:
80585.0
Reactions
Phytanic acid + Adenosine triphosphate + Coenzyme A → Phytanoyl-CoA + ADP + Pyrophosphatedetails
Enzyme Details
3. Long-chain fatty acid transport protein 1
General function:
Not Available
Specific function:
Mediates the ATP-dependent import of long-chain fatty acids (LCFA) into the cell by mediating their translocation at the plasma membrane. Has also an acyl-CoA ligase activity for long-chain and very-long-chain fatty acids. May act directly as a bona fide transporter, or alternatively, in a cytoplasmic or membrane-associated multimeric protein complex to trap and draw fatty acids towards accumulation. Plays a pivotal role in regulating available LCFA substrates from exogenous sources in tissues undergoing high levels of beta-oxidation or triglyceride synthesis. May be involved in regulation of cholesterol metabolism.
Gene Name:
SLC27A1
Uniprot ID:
Q3ZKN0
Molecular weight:
71123.0
Reactions
Phytanic acid + Adenosine triphosphate + Coenzyme A → Phytanoyl-CoA + ADP + Pyrophosphatedetails