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Record Information
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-03-02 21:26:11 UTC
Secondary Accession NumbersNone
Metabolite Identification
Common NamePristanic acid
DescriptionPristanic acid (2,6,10,14-tetramethylpentadecanoic acid) is a terpenoid acid present at micromolar concentrations in the plasma of healthy individuals. It is also found in the lipids from many sources such as freshwater sponges, krill, earthworms, whales, human milk fat, bovine depot fat, butterfat or Californian petroleum. It is usually present in combination with phytanic acid. In humans, pristanic acid is obtained from two sources: either directly from the diet or as the alpha oxidation product of phytanic acid. At physiological concentrations pristanic acid is a natural ligand for PPARalpha. In liver, pristanic acid is degraded by peroxisomal beta oxidation to propionyl-CoA. Together with phytanic acid, pristanic acid accumulates in several inherited disorders such as Zellweger syndrome. Pristanic acid is a branched chain fatty acid that arises from the breakdown of phytanic acid. It is present at micromolar concentrations in the plasma of healthy individuals. Pristanic acid is normally degraded by peroxisomal beta-oxidation. In patients affected with generalized peroxisomal disorders, degradation of both phytanic acid and pristanic acid is impaired owing to absence of functional peroxisomes. Pristanic acid has been found to activate the peroxisome proliferator-activated receptor {alpha} (PPAR{alpha}) in a concentration dependent manner.
2,6,10,14-Tetramethylpentadecylic acidChEBI
Acide pristaniqueChEBI
acido PristanicoChEBI
(2S)-Pristanic acidHMDB
(2S,6R,10R)-2,6,10,14-Tetramethylpentadecanoic acidHMDB
(2S,6R,10R)-Pristanic acidHMDB
2,6,10,14-Tetramethylpentadecanoic acidHMDB
Chemical FormulaC19H38O2
Average Molecular Weight298.511
Monoisotopic Molecular Weight298.287180464
IUPAC Name2,6,10,14-tetramethylpentadecanoic acid
Traditional Namepristanic acid
CAS Registry Number1189-37-3
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassPrenol lipids
Direct ParentAcyclic diterpenoids
Alternative Parents
  • 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 Descriptors
StatusDetected and Quantified
  • Endogenous
  • Food
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Peroxisome
Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.000136 mg/mLALOGPS
pKa (Strongest Acidic)5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity90.7 m3·mol-1ChemAxon
Polarizability38.82 Å3ChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-06si-4940000000-03beff6ee7e5712b0be3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-052r-2900000000-257d1f0711d1a7f28338View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00xr-5932000000-d9475b731502d4745a32View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Peroxisome
Biofluid Locations
  • Blood
Tissue Location
  • Fibroblasts
  • Myelin
  • Prostate
Oxidation of Branched Chain Fatty AcidsSMP00030Not Available
Phytanic Acid Peroxisomal OxidationSMP00450Not Available
Refsum DiseaseSMP00451Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
BloodDetected and Quantified1.5 (0.0-3.0) uMNewborn (0-30 days old)BothAdrenoleukodystrophy, neonatal details
BloodDetected and Quantified21.0 uMNewborn (0-30 days old)BothNeonatal adrenoleukodystrophy details
Associated Disorders and Diseases
Disease References
  1. MetaGene [Link]
Adrenoleukodystrophy, neonatal
  1. MetaGene [Link]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012993
KNApSAcK IDNot Available
Chemspider ID110458
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID2364527
Wikipedia LinkPristanic acid
NuGOwiki LinkHMDB00795
Metagene LinkHMDB00795
PubChem Compound123929
PDB IDNot Available
ChEBI ID51340
Synthesis ReferenceNakajima, Kenji; Sato, Akio. Microbial oxidation of isoprenoid hydrocarbons. Part II. Production of pristanol and pristanic acid from pristane by Nocardia sp. BPM 1613. Nippon Nogei Kagaku Kaishi (1981), 55(9), 825-8.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Wanders RJ, Barth PG, Schutgens RB, Tager JM: Clinical and biochemical characteristics of peroxisomal disorders: an update. Eur J Pediatr. 1994;153(7 Suppl 1):S44-8. [7957386 ]
  2. Mobley JA, Leav I, Zielie P, Wotkowitz C, Evans J, Lam YW, L'Esperance BS, Jiang Z, Ho SM: Branched fatty acids in dairy and beef products markedly enhance alpha-methylacyl-CoA racemase expression in prostate cancer cells in vitro. Cancer Epidemiol Biomarkers Prev. 2003 Aug;12(8):775-83. [12917210 ]
  3. Ferdinandusse S, Denis S, IJlst L, Dacremont G, Waterham HR, Wanders RJ: Subcellular localization and physiological role of alpha-methylacyl-CoA racemase. J Lipid Res. 2000 Nov;41(11):1890-6. [11060359 ]
  4. Straube R, Gackler D, Thiele A, Muselmann L, Kingreen H, Klingel R: Membrane differential filtration is safe and effective for the long-term treatment of Refsum syndrome--an update of treatment modalities and pathophysiological cognition. Transfus Apher Sci. 2003 Aug;29(1):85-91. [12877898 ]
  5. Verhoeven NM, Kulik W, van den Heuvel CM, Jakobs C: Pre- and postnatal diagnosis of peroxisomal disorders using stable-isotope dilution gas chromatography--mass spectrometry. J Inherit Metab Dis. 1995;18 Suppl 1:45-60. [9053555 ]
  6. Ferdinandusse S, Kostopoulos P, Denis S, Rusch H, Overmars H, Dillmann U, Reith W, Haas D, Wanders RJ, Duran M, Marziniak M: Mutations in the gene encoding peroxisomal sterol carrier protein X (SCPx) cause leukencephalopathy with dystonia and motor neuropathy. Am J Hum Genet. 2006 Jun;78(6):1046-52. Epub 2006 Mar 29. [16685654 ]
  7. Gootjes J, Mooijer PA, Dekker C, Barth PG, Poll-The BT, Waterham HR, Wanders RJ: Biochemical markers predicting survival in peroxisome biogenesis disorders. Neurology. 2002 Dec 10;59(11):1746-9. [12473763 ]
  8. Zomer AW, van Der Burg B, Jansen GA, Wanders RJ, Poll-The BT, van Der Saag PT: Pristanic acid and phytanic acid: naturally occurring ligands for the nuclear receptor peroxisome proliferator-activated receptor alpha. J Lipid Res. 2000 Nov;41(11):1801-7. [11060349 ]


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: