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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-10-23 19:03:49 UTC
HMDB IDHMDB0001295
Secondary Accession Numbers
  • HMDB01295
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 KeyWNVFJMYPVBOLKV-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
Disposition

Biological Location:

  Subcellular:

  Cell and elements:

    Cell:

  Biofluid and excreta:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

    Biochemical process:

    Chemical reaction:

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 Solubility1.43 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count34ChemAxon
Refractivity256.26 m³·mol⁻¹ChemAxon
Polarizability108.2 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-4901110200-170aee27b4e79c002131View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1913130000-f3f3a31b1f2f1eadfa1bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900010000-8676dc6b110ef7b1cd90View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05rr-8732251900-bda6cb0d556520fc587cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0560-5932220200-8cfcacf29ba06547d671View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a7i-5900100000-5c05acebab4cee45d967View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Peroxisome
Biofluid LocationsNot Available
Tissue Location
  • Fibroblasts
Pathways
NameSMPDB/PathwhizKEGG
Oxidation of Branched Chain Fatty AcidsPw000155Pw000155 greyscalePw000155 simpleNot Available
Phytanic Acid Peroxisomal OxidationPw000041Pw000041 greyscalePw000041 simpleNot Available
Refsum DiseasePw000122Pw000122 greyscalePw000122 simpleNot Available
Displaying all 3 entries
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
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. [PubMed: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