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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:04:12 UTC
HMDB IDHMDB01295
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-Hydroxyphytanoyl-CoA
Description2-Hydroxyphytanoyl-CoA is a substrate for Phytanoyl-CoA dioxygenase (peroxisomal).
Structure
Thumb
Synonyms
ValueSource
(3S)-2-Hydroxyphytanoyl-CoAHMDB
(3S)-2-Hydroxyphytanoyl-coenzyme AHMDB
(3S,7R,11R)-2-Hydroxy-3,7,11,15-tetramethylhexadecanoyl-CoAHMDB
(3S,7R,11R)-2-Hydroxy-3,7,11,15-tetramethylhexadecanoyl-coenzyme AHMDB
2-Hydroxyphytanoyl-coenzyme AHMDB
3(S)-2-Hydroxyphytanoyl-CoAHMDB
3(S)-2-Hydroxyphytanoyl-coenzyme AHMDB
3S2hPhy-CoAHMDB
3S2hPhy-coenzyme AHMDB
Chemical FormulaC41H74N7O18P3S
Average Molecular Weight1078.049
Monoisotopic Molecular Weight1077.402388825
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[3-hydroxy-3-({2-[(2-{[(3S,7R,11R)-2-hydroxy-3,7,11,15-tetramethylhexadecanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]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-3-({2-[(2-{[(3S,7R,11R)-2-hydroxy-3,7,11,15-tetramethylhexadecanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid
CAS Registry Number172787-73-4
SMILES
CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@H](C)C(O)C(=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/C41H74N7O18P3S/c1-25(2)11-8-12-26(3)13-9-14-27(4)15-10-16-28(5)32(50)40(54)70-20-19-43-30(49)17-18-44-38(53)35(52)41(6,7)22-63-69(60,61)66-68(58,59)62-21-29-34(65-67(55,56)57)33(51)39(64-29)48-24-47-31-36(42)45-23-46-37(31)48/h23-29,32-35,39,50-52H,8-22H2,1-7H3,(H,43,49)(H,44,53)(H,58,59)(H,60,61)(H2,42,45,46)(H2,55,56,57)/t26-,27-,28+,29-,32?,33-,34-,35?,39-/m1/s1
InChI KeyInChIKey=WNVFJMYPVBOLKV-PJDIVXIPSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
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
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • 6-aminopurine
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Fatty amide
  • Alkyl phosphate
  • Monosaccharide
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Imidolactam
  • Phosphoric acid ester
  • Primary aromatic amine
  • Pyrimidine
  • Oxolane
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Thiocarboxylic acid ester
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carbothioic s-ester
  • Secondary alcohol
  • Thiocarboxylic acid or derivatives
  • Sulfenyl compound
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Amine
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Organopnictogen compound
  • Organic oxide
  • Primary amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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
  • 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
Water Solubility1.43 mg/mLALOGPS
logP2.41ALOGPS
logP-0.14ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area383.86 Å2ChemAxon
Rotatable Bond Count34ChemAxon
Refractivity256.26 m3·mol-1ChemAxon
Polarizability108.2 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Peroxisome
Biofluid LocationsNot Available
Tissue Location
  • Fibroblasts
Pathways
NameSMPDB LinkKEGG Link
Oxidation of Branched Chain Fatty AcidsSMP00030Not Available
Phytanic Acid Peroxisomal OxidationSMP00450Not Available
Refsum DiseaseSMP00451Not 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 IDFDB022539
KNApSAcK IDNot Available
Chemspider ID390032
KEGG Compound IDC07343
BioCyc ID2-HYDROXYPHYTANOYL-COA
BiGG ID2364545
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01295
Metagene LinkHMDB01295
METLIN ID6140
PubChem Compound441263
PDB IDNot Available
ChEBI ID15475
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Foulon V, Sniekers M, Huysmans E, Asselberghs S, Mahieu V, Mannaerts GP, Van Veldhoven PP, Casteels M: Breakdown of 2-hydroxylated straight chain fatty acids via peroxisomal 2-hydroxyphytanoyl-CoA lyase: a revised pathway for the alpha-oxidation of straight chain fatty acids. J Biol Chem. 2005 Mar 18;280(11):9802-12. Epub 2005 Jan 11. [15644336 ]

Enzymes

General function:
Involved in electron carrier activity
Specific function:
Converts phytanoyl-CoA to 2-hydroxyphytanoyl-CoA.
Gene Name:
PHYH
Uniprot ID:
O14832
Molecular weight:
38538.065
Reactions
Phytanoyl-CoA + Oxoglutaric acid + Oxygen → 2-Hydroxyphytanoyl-CoA + Succinic acid + CO(2)details
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes a carbon-carbon cleavage reaction; cleaves a 2-hydroxy-3-methylacyl-CoA into formyl-CoA and a 2-methyl-branched fatty aldehyde.
Gene Name:
HACL1
Uniprot ID:
Q9UJ83
Molecular weight:
63728.095
Reactions
2-Hydroxyphytanoyl-CoA → Pristanal + Formyl-CoAdetails