Showing Compound Pristanic acid (FDB012993)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:28 UTC

Update date

2019-11-26 03:07:50 UTC

Primary ID

FDB012993

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Pristanic acid

Description

Component of butterfat and sheep perinephric fat Pristanic 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 (2,6,10,14-tetramethylpentadecanoic acid) is a terpenoid acid present at micromolar concentrations in the blood 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 PPAR?. 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 (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.

CAS Number

1189-37-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
2,6,10,14-Tetramethyl-pentadecansaeure	ChEBI
2,6,10,14-Tetramethylpentadecylic acid	ChEBI
Acide pristanique	ChEBI
Acido pristanico	ChEBI
Pristaninsaeure	ChEBI
2,6,10,14-Tetramethylpentadecylate	Generator
Pristanate	Generator
(2S)-Pristanic acid	HMDB
(2S,6R,10R)-2,6,10,14-Tetramethylpentadecanoate	HMDB
(2S,6R,10R)-2,6,10,14-Tetramethylpentadecanoic acid	HMDB
(2S,6R,10R)-Pristanic acid	HMDB
2,6,10,14-Tetramethylpentadecanoate	HMDB
2,6,10,14-Tetramethylpentadecanoic acid	HMDB
Pristanate:(2S,6R,10R)-pristanate	HMDB
(2S,6R,10R)-2,6,10,14-tetramethylpentadecanoate	biospider
(2S,6R,10R)-2,6,10,14-tetramethylpentadecanoic acid	biospider
(2S,6R,10R)-pristanic acid	biospider
(2S)-pristanic acid;	biospider
Pristanic acid	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.00014 g/L	ALOGPS
logP	6.9	ALOGPS
logP	7.22	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	90.7 m³·mol⁻¹	ChemAxon
Polarizability	38.82 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C19H38O2

IUPAC name

2,6,10,14-tetramethylpentadecanoic acid

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 Key

PAHGJZDQXIOYTH-UHFFFAOYSA-N

Isomeric SMILES

CC(C)CCCC(C)CCCC(C)CCCC(C)C(O)=O

Average Molecular Weight

298.511

Monoisotopic Molecular Weight

298.287180464

Classification

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Acyclic 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 Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:51340 )
branched-chain saturated fatty acid (CHEBI:51340 )
methyl-branched fatty acid (CHEBI:51340 )
Acyclic diterpenoids (LMPR0104010022 )

Ontology

Physiological effect

Health effect:

Health condition:

Adrenoleukodystrophy

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Organ and components:

Prostate

Cell and elements:

Extracellular

Cell:

Fibroblast

Subcellular:

Biofluid and excreta:

Blood

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 76.45%; H 12.83%; O 10.72%	DFC
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Pristanic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9870000000-f2a1fccf594927bf2658	Spectrum
Predicted GC-MS	Pristanic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05g0-9432000000-dff09e9ff5d30894796a	Spectrum
Predicted GC-MS	Pristanic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Pristanic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-06si-4940000000-03beff6ee7e5712b0be3	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-052r-2900000000-257d1f0711d1a7f28338	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00xr-5932000000-d9475b731502d4745a32	2012-07-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0190000000-9f7f32c22384a93f6bdb	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0kdj-6960000000-7187029bd8b4d1886bf6	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6s-9810000000-051a9ebc7e20e03dd488	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-2e296a53a5e430402f60	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f6t-0090000000-ae75aba02491d467a13d	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-059i-9480000000-ef08cae03dc3995f91f5	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-2290000000-23db43d16b6195905dda	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-07li-9620000000-5c45c02dd25695e1c91b	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-be260050b449f341bc60	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-d78513c03955a860495d	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0090000000-b72f0143bca09dec99f9	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0007-7690000000-4162e1382b3a0cd64736	2021-09-24	View Spectrum