Pristanic acid (CHEM028523)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:31:08 UTC
Update Date2016-11-09 01:18:42 UTC
Accession NumberCHEM028523
Identification
Common NamePristanic acid
ClassSmall Molecule
DescriptionA branched, long-chain saturated fatty acid composed of pentadecanoic acid having methyl substituents at the 2-, 6-, 10- and 14-positions.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass298.511 g/mol
Monoisotopic Mass298.287 g/mol
CAS Registry Number1189-37-3
IUPAC Name2,6,10,14-tetramethylpentadecanoic acid
Traditional Namepristanic acid
SMILESCC(C)CCCC(C)CCCC(C)CCCC(C)C(O)=O
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted 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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9870000000-f2a1fccf594927bf2658Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05g0-9432000000-dff09e9ff5d30894796aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-06si-4940000000-03beff6ee7e5712b0be3Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-052r-2900000000-257d1f0711d1a7f28338Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00xr-5932000000-d9475b731502d4745a32Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0190000000-9f7f32c22384a93f6bdbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kdj-6960000000-7187029bd8b4d1886bf6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6s-9810000000-051a9ebc7e20e03dd488Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-2e296a53a5e430402f60Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6t-0090000000-ae75aba02491d467a13dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-059i-9480000000-ef08cae03dc3995f91f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-2290000000-23db43d16b6195905ddaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-07li-9620000000-5c45c02dd25695e1c91bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-be260050b449f341bc60Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-d78513c03955a860495dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-b72f0143bca09dec99f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-7690000000-4162e1382b3a0cd64736Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000795
FooDB IDFDB012993
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID2364527
BioCyc IDPRISTANATE
METLIN ID5760
PDB IDNot Available
Wikipedia LinkPristanic acid
Chemspider ID110458
ChEBI ID51340
PubChem Compound ID123929
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11861706
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=9819701
3. Nakajima, 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.
4. 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.
5. 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.
6. 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.
7. 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.
8. 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.
9. 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.
10. 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.
11. 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.