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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:06 UTC
HMDB IDHMDB0000795
Secondary Accession Numbers
  • HMDB00795
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.
Structure
Data?1582752157
Synonyms
ValueSource
2,6,10,14-Tetramethyl-pentadecansaeureChEBI
2,6,10,14-Tetramethylpentadecylic acidChEBI
Acide pristaniqueChEBI
Acido pristanicoChEBI
PristaninsaeureChEBI
2,6,10,14-TetramethylpentadecylateGenerator
PristanateGenerator
(2S)-Pristanic acidHMDB
(2S,6R,10R)-2,6,10,14-TetramethylpentadecanoateHMDB
(2S,6R,10R)-2,6,10,14-Tetramethylpentadecanoic acidHMDB
(2S,6R,10R)-Pristanic acidHMDB
2,6,10,14-TetramethylpentadecanoateHMDB
2,6,10,14-Tetramethylpentadecanoic acidHMDB
Pristanate:(2S,6R,10R)-pristanateHMDB
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
SMILES
CC(C)CCCC(C)CCCC(C)CCCC(C)C(O)=O
InChI Identifier
InChI=1S/C19H38O2/c1-15(2)9-6-10-16(3)11-7-12-17(4)13-8-14-18(5)19(20)21/h15-18H,6-14H2,1-5H3,(H,20,21)
InChI KeyPAHGJZDQXIOYTH-UHFFFAOYSA-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 Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0035 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg178.78830932474
[M-H]-Not Available178.788http://allccs.zhulab.cn/database/detail?ID=AllCCS00000216
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00014 g/LALOGPS
logP6.9ALOGPS
logP7.22ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity90.7 m³·mol⁻¹ChemAxon
Polarizability38.82 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]+174.68331661259
DarkChem[M-H]-173.01931661259
AllCCS[M+H]+186.51232859911
AllCCS[M-H]-183.05132859911
DeepCCS[M+H]+180.83830932474
DeepCCS[M-H]-178.38830932474
DeepCCS[M-2H]-212.3930932474
DeepCCS[M+Na]+188.54830932474
AllCCS[M+H]+186.532859911
AllCCS[M+H-H2O]+183.732859911
AllCCS[M+NH4]+189.132859911
AllCCS[M+Na]+189.832859911
AllCCS[M-H]-183.132859911
AllCCS[M+Na-2H]-184.832859911
AllCCS[M+HCOO]-186.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Pristanic acidCC(C)CCCC(C)CCCC(C)CCCC(C)C(O)=O3003.4Standard polar33892256
Pristanic acidCC(C)CCCC(C)CCCC(C)CCCC(C)C(O)=O1993.1Standard non polar33892256
Pristanic acidCC(C)CCCC(C)CCCC(C)CCCC(C)C(O)=O2056.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Pristanic acid,1TMS,isomer #1CC(C)CCCC(C)CCCC(C)CCCC(C)C(=O)O[Si](C)(C)C2066.4Semi standard non polar33892256
Pristanic acid,1TBDMS,isomer #1CC(C)CCCC(C)CCCC(C)CCCC(C)C(=O)O[Si](C)(C)C(C)(C)C2302.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Pristanic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9870000000-f2a1fccf594927bf26582017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pristanic acid GC-MS (1 TMS) - 70eV, Positivesplash10-05g0-9432000000-dff09e9ff5d30894796a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pristanic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pristanic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Pristanic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-06si-4940000000-03beff6ee7e5712b0be32012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pristanic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-052r-2900000000-257d1f0711d1a7f283382012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pristanic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-00xr-5932000000-d9475b731502d4745a322012-07-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pristanic acid 10V, Positive-QTOFsplash10-0002-0190000000-9f7f32c22384a93f6bdb2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pristanic acid 20V, Positive-QTOFsplash10-0kdj-6960000000-7187029bd8b4d1886bf62017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pristanic acid 40V, Positive-QTOFsplash10-0a6s-9810000000-051a9ebc7e20e03dd4882017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pristanic acid 10V, Negative-QTOFsplash10-0002-0090000000-2e296a53a5e430402f602017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pristanic acid 20V, Negative-QTOFsplash10-0f6t-0090000000-ae75aba02491d467a13d2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pristanic acid 40V, Negative-QTOFsplash10-059i-9480000000-ef08cae03dc3995f91f52017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pristanic acid 10V, Positive-QTOFsplash10-0002-2290000000-23db43d16b6195905dda2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pristanic acid 20V, Positive-QTOFsplash10-07li-9620000000-5c45c02dd25695e1c91b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pristanic acid 40V, Positive-QTOFsplash10-0a4i-9000000000-be260050b449f341bc602021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pristanic acid 10V, Negative-QTOFsplash10-0002-0090000000-d78513c03955a860495d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pristanic acid 20V, Negative-QTOFsplash10-0002-0090000000-b72f0143bca09dec99f92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pristanic acid 40V, Negative-QTOFsplash10-0007-7690000000-4162e1382b3a0cd647362021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Peroxisome
Biospecimen Locations
  • Blood
  • Feces
Tissue Locations
  • Fibroblasts
  • Neuron
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified<3.000 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0-3.350 uMChildren (1-13 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.5 (0.0-3.0) uMNewborn (0-30 days old)BothAdrenoleukodystrophy, neonatal
    • MetaGene: Metabol...
details
BloodDetected and Quantified105 uMAdult (>18 years old)Male
Alpha-Methylacyl-CoA racemase deficiency
details
BloodDetected and Quantified0.61 uMNewborn (0-30 days old)Female
Rhizomelic chondrodysplasia punctata
details
BloodDetected and Quantified4.24 uMInfant (0-1 year old)Male
Peroxisomal biogenesis disorder
details
BloodDetected and Quantified27.6 uMNewborn (0-30 days old)Not Specified
Zellweger syndrome
details
BloodDetected and Quantified68.6 uMNewborn (0-30 days old)Not Specified
Neonatal adrenoleukodystrophy
details
BloodDetected and Quantified1.0100-51.960 uMChildren (1-13 years old)Female
Peroxisomal biogenesis disorder
details
BloodDetected and Quantified16.100-24.800 uMNewborn (0-30 days old)Female
Peroxisomal biogenesis disorder
details
Associated Disorders and Diseases
Disease References
Adrenoleukodystrophy, neonatal
  1. G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
Rhizomelic chondrodysplasia punctata
  1. Baumgartner MR, Poll-The BT, Verhoeven NM, Jakobs C, Espeel M, Roels F, Rabier D, Levade T, Rolland MO, Martinez M, Wanders RJ, Saudubray JM: Clinical approach to inherited peroxisomal disorders: a series of 27 patients. Ann Neurol. 1998 Nov;44(5):720-30. [PubMed:9818927 ]
Peroxisomal biogenesis defect
  1. Baumgartner MR, Poll-The BT, Verhoeven NM, Jakobs C, Espeel M, Roels F, Rabier D, Levade T, Rolland MO, Martinez M, Wanders RJ, Saudubray JM: Clinical approach to inherited peroxisomal disorders: a series of 27 patients. Ann Neurol. 1998 Nov;44(5):720-30. [PubMed:9818927 ]
Alpha-Methylacyl-CoA racemase deficiency
  1. McLean BN, Allen J, Ferdinandusse S, Wanders RJ: A new defect of peroxisomal function involving pristanic acid: a case report. J Neurol Neurosurg Psychiatry. 2002 Mar;72(3):396-9. [PubMed:11861706 ]
Associated OMIM IDs
  • 215100 (Rhizomelic chondrodysplasia punctata)
  • 214100 (Peroxisomal biogenesis defect)
  • 614307 (Alpha-Methylacyl-CoA racemase deficiency)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012993
KNApSAcK IDNot Available
Chemspider ID110458
KEGG Compound IDNot Available
BioCyc IDPRISTANATE
BiGG ID2364527
Wikipedia LinkPristanic acid
METLIN ID5760
PubChem Compound123929
PDB IDNot Available
ChEBI ID51340
Food Biomarker OntologyNot Available
VMH IDPRIST
MarkerDB IDMDB00000255
Good Scents IDrw1489071
References
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:11060349 ]

Enzymes

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:
ACSL1
Uniprot ID:
P33121
Molecular weight:
77942.685