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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:02 UTC
HMDB IDHMDB0000417
Secondary Accession Numbers
  • HMDB00417
Metabolite Identification
Common Name3D,7D,11D-Phytanic acid
Description3D,7D,11D-Phytanic acid is an isomer of Phytanic acid, an unusual 20-carbon branched-chain fatty acid; Phytanic acid accumulates in blood and tissues of patients with Refsum disease (RD, an inborn error of lipid metabolism inherited as an autosomal recessive trait (OMIM 266500 )), and is a reliable identifier of RD from a large number of other neurological disorders. Phytanic acid also accumulates in a number of other disorders with a very different clinical course: disorders of peroxisome biogenesis (Zellweger syndrome (OMIM 214100 ), neonatal adrenoleukodystrophy (OMIM 202370 ), infantile Refsum disease (OMIM 266510 )) and rhizomelic chondrodysplasia punctata, type 1 (OMIM 215100 ). Phytanic acid is a 3-methyl fatty acid that cannot be beta-oxidized directly, and first undergoes an alpha-oxidation a reaction catalyzed by the enzyme phytanoyl-CoA hydroxylase, which is deficient in RD, the only true disorder of phytanic acid alpha-oxidation. (The Metabolic and Molecular Bases of Inherited Disease).
Structure
Data?1582752130
Synonyms
ValueSource
3D,7D,11D-PhytanateGenerator
((3R,7R,11R)-)3,7,11,15-TetramethylhexadecanoateHMDB
((3R,7R,11R)-)3,7,11,15-Tetramethylhexadecanoic acidHMDB
3,7,11,15-Tetramethyl-D,D,D-hexadecanoateHMDB
3,7,11,15-Tetramethyl-D,D,D-hexadecanoic acidHMDB
3,7,11,15-Tetramethyl-[3R-(3R*,7R*,11R*)]-hexadecanoateHMDB
3,7,11,15-Tetramethyl-[3R-(3R*,7R*,11R*)]-hexadecanoic acidHMDB
D,D,D-PhytanateHMDB
D,D,D-Phytanic acidHMDB
(3R,7R,11R)-1-PhytanoateHMDB
Chemical FormulaC20H40O2
Average Molecular Weight312.5304
Monoisotopic Molecular Weight312.302830524
IUPAC Name(3R,7R,11R)-3,7,11,15-tetramethylhexadecanoic acid
Traditional Namephytanoic acid
CAS Registry Number18654-64-3
SMILES
CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@@H](C)CC(O)=O
InChI Identifier
InChI=1S/C20H40O2/c1-16(2)9-6-10-17(3)11-7-12-18(4)13-8-14-19(5)15-20(21)22/h16-19H,6-15H2,1-5H3,(H,21,22)/t17-,18-,19-/m1/s1
InChI KeyRLCKHJSFHOZMDR-GUDVDZBRSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentAcyclic diterpenoids
Alternative Parents
Substituents
  • Acyclic diterpenoid
  • Long-chain fatty acid
  • Methyl-branched fatty acid
  • Branched fatty acid
  • Fatty acyl
  • Fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility8.2e-05 g/LALOGPS
logP7.28ALOGPS
logP7.4ChemAxon
logS-6.6ALOGPS
pKa (Strongest Acidic)5.04ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity95.28 m³·mol⁻¹ChemAxon
Polarizability40.96 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+177.03931661259
DarkChem[M-H]-176.48731661259
AllCCS[M+H]+191.79432859911
AllCCS[M-H]-186.41332859911
DeepCCS[M+H]+194.58230932474
DeepCCS[M-H]-192.22430932474
DeepCCS[M-2H]-225.70530932474
DeepCCS[M+Na]+200.93230932474
AllCCS[M+H]+191.832859911
AllCCS[M+H-H2O]+189.132859911
AllCCS[M+NH4]+194.332859911
AllCCS[M+Na]+195.032859911
AllCCS[M-H]-186.432859911
AllCCS[M+Na-2H]-188.432859911
AllCCS[M+HCOO]-190.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3D,7D,11D-Phytanic acidCC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@@H](C)CC(O)=O3150.8Standard polar33892256
3D,7D,11D-Phytanic acidCC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@@H](C)CC(O)=O2108.5Standard non polar33892256
3D,7D,11D-Phytanic acidCC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@@H](C)CC(O)=O2174.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3D,7D,11D-Phytanic acid,1TMS,isomer #1CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@@H](C)CC(=O)O[Si](C)(C)C2194.7Semi standard non polar33892256
3D,7D,11D-Phytanic acid,1TBDMS,isomer #1CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@@H](C)CC(=O)O[Si](C)(C)C(C)(C)C2411.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3D,7D,11D-Phytanic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9780000000-d08f456f5acb304b7ea22017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3D,7D,11D-Phytanic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00y0-9443000000-5bbc79ddca11ee15c3462017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3D,7D,11D-Phytanic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3D,7D,11D-Phytanic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3D,7D,11D-Phytanic acid 10V, Positive-QTOFsplash10-03dj-0194000000-076273f1edebfb1f71632016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3D,7D,11D-Phytanic acid 20V, Positive-QTOFsplash10-014j-4890000000-ced9d745a9185ff0418f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3D,7D,11D-Phytanic acid 40V, Positive-QTOFsplash10-0a4i-9820000000-a5081751e548b4df90ab2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3D,7D,11D-Phytanic acid 10V, Negative-QTOFsplash10-03xr-0059000000-ad0c503c6bf877381cf42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3D,7D,11D-Phytanic acid 20V, Negative-QTOFsplash10-03xr-1096000000-41b47d7194262d8befce2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3D,7D,11D-Phytanic acid 40V, Negative-QTOFsplash10-0a4i-9470000000-4f142588383dd12f544f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3D,7D,11D-Phytanic acid 10V, Positive-QTOFsplash10-03di-4569000000-0ae84af33d4a6cee15632021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3D,7D,11D-Phytanic acid 20V, Positive-QTOFsplash10-06y9-9720000000-8d0e05ef1818d392c4fb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3D,7D,11D-Phytanic acid 40V, Positive-QTOFsplash10-0a4l-9000000000-19bc307031b7da7b34142021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3D,7D,11D-Phytanic acid 10V, Negative-QTOFsplash10-03di-0009000000-849ba1e33116074451822021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3D,7D,11D-Phytanic acid 20V, Negative-QTOFsplash10-03di-0029000000-1d86a3df25ae3d6f62b52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3D,7D,11D-Phytanic acid 40V, Negative-QTOFsplash10-06r6-8393000000-8564c0781362b5ca2da42021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013514
KNApSAcK IDNot Available
Chemspider ID8556273
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5406
PubChem Compound10380830
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceSita, Lawrence R. Convenient highly stereoselective syntheses of (3R,7R,11R)- and (3S,7R,11R)-3,7,11,15-tetramethylhexadecanoic acid (phytanic acid) and the corresponding 3,7,11,15-tetramethylhexadecan-1-ols. Journal of Organic Chemistry (1993), 58(19), 5285-7.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available