ChemFOnt: Showing chemical card for 13-Eicosenoic acid (CFc000335853)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:28:39 UTC

Chemfont ID

CFc000335853

Molecule Identification

Common Name

13-Eicosenoic acid

Definition

Paullinic acid, also known as (13z)-eicos-13-enoic acid or (Z)-13-eicosenoate, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, paullinic acid is considered to be a fatty acid lipid molecule. Paullinic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Paullinic acid can be found in fats and oils and fishes, which makes paullinic acid a potential biomarker for the consumption of these food products. Paullinic acid can be found primarily in blood. Paullinic acid is an omega-7 fatty acid find in a variety of plant sources, including guarana (Paullinia cupana) from which it gets its name. It is one of a number of eicosenoic acids .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(13Z)-Eicos-13-enoic acid	ChEBI
(Z)-13-Eicosenoic acid	ChEBI
(Z)-13-Icosenoic acid	ChEBI
(Z)-Eicos-13-enoic acid	ChEBI
13Z-Eicosenoic acid	ChEBI
C20:1N-7	ChEBI
cis-13-Eicosenoic acid	ChEBI
(13Z)-Eicos-13-enoate	Generator
(Z)-13-Eicosenoate	Generator
(Z)-13-Icosenoate	Generator
(Z)-Eicos-13-enoate	Generator
13Z-Eicosenoate	Generator
cis-13-Eicosenoate	Generator
Paullinate	Generator

Chemical Formula

C₂₀H₃₈O₂

Average Molecular Weight

310.5145

Monoisotopic Molecular Weight

310.28718046

IUPAC Name

(13Z)-icos-13-enoic acid

Traditional Name

paullinic acid

CAS Registry Number

14134-51-1

SMILES

CCCCCC\C=C/CCCCCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C20H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h7-8H,2-6,9-19H2,1H3,(H,21,22)/b8-7-

InChI Key

URXZXNYJPAJJOQ-FPLPWBNLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Unsaturated fatty acid
Straight chain 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

Unsaturated fatty acids (LMFA01030367 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0035159)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0035159)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0035159)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035159)

Source

Endogenous

Endogenous (HMDB: HMDB0035159)

Animal

Animal (HMDB: HMDB0035159)

Exogenous

Food

Food (HMDB: HMDB0035159)

Nut

Peanut (FooDB: FOOD00016)

Vegetable

Fruit vegetable

Italian sweet red pepper (FooDB: FOOD00881)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0035159)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0035159)

Lipid metabolism pathway (HMDB: HMDB0035159)

Cellular process

Cell signaling (HMDB: HMDB0035159)

Biochemical process

Lipid transport (HMDB: HMDB0035159)

Role

Biological role

Energy source (HMDB: HMDB0035159)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035159)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	5.0e-05 g/L	ALOGPS
logP	8.4	ALOGPS
logP	7.67	ChemAxon
logS	-6.8	ALOGPS
pKa (Strongest Acidic)	4.95	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	17	ChemAxon
Refractivity	96.6 m³·mol⁻¹	ChemAxon
Polarizability	41.34 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

External Links

HMDB ID

HMDB0035159

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB013796

KNApSAcK ID

Not Available

Chemspider ID

4471943

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Paullinic_acid

METLIN ID

Not Available

PubChem Compound

5312518

PDB ID

Not Available

ChEBI ID

134479

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 13-Eicosenoic acid (CFc000335853)

MOL for CFc000335853 (13-Eicosenoic acid)

3D MOL for CFc000335853 (13-Eicosenoic acid)

3D SDF for CFc000335853 (13-Eicosenoic acid)

3D-SDF for CFc000335853 (13-Eicosenoic acid)

PDB for CFc000335853 (13-Eicosenoic acid)

3D PDB for CFc000335853 (13-Eicosenoic acid)

SMILES for CFc000335853 (13-Eicosenoic acid)

INCHI for CFc000335853 (13-Eicosenoic acid)

Structure for CFc000335853 (13-Eicosenoic acid)

3D Structure for CFc000335853 (13-Eicosenoic acid)