ChemFOnt: Showing chemical card for Steridonic acid (CFc000333471)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:13:35 UTC

Chemfont ID

CFc000333471

Molecule Identification

Common Name

Steridonic acid

Definition

Stearidonic acid, also known as SDA or stearidonate, belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Stearidonic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It is biosynthesized from linolenic acid by the enzyme delta-6-desaturase. Natural sources of this fatty acid are in the blackcurrant and echium, and the cyanobacterium spirulina (a rich source of vitamins and minerals). Stearidonic acid is found in dietary plant oils which are metabolized to longer-chain, more unsaturated (n-3) polyunsaturated fatty acids (PUFA). These oils appear to possess hypotriglyceridemic properties typically associated with fish oils (PMID: 15173404 ). Stearidonic acid may be used as a precursor to increase the eicosapentaenoic acid (EPA) content of human lipids and that combinations of gamma-linolenic acid and stearidonic acid can be used to manipulate the fatty acid compositions of lipid pools in subtle ways. Such effects may offer new strategies for manipulation of cell composition to influence cellular responses and functions in desirable ways (PMID: 15120716 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(6Z,9Z,12Z,15Z)-Octadecatetraenoic acid	ChEBI
6,9,12,15-Octadecatetraenoic acid	ChEBI
SDA	ChEBI
6Z,9Z,12Z,15Z-Octadecatetraenoic acid	Kegg
(6Z,9Z,12Z,15Z)-Octadeca-6,9,12,15-tetraenoic acid	Kegg
(6Z,9Z,12Z,15Z)-Octadecatetraenoate	Generator
6,9,12,15-Octadecatetraenoate	Generator
6Z,9Z,12Z,15Z-Octadecatetraenoate	Generator
(6Z,9Z,12Z,15Z)-Octadeca-6,9,12,15-tetraenoate	Generator
Stearidonate	Generator
Stearidonic acid C18:4	HMDB
FA(18:4(6Z,9Z,12Z,15Z))	HMDB
FA(18:4n3)	HMDB
Moroctic acid	HMDB

Chemical Formula

C₁₈H₂₈O₂

Average Molecular Weight

276.4137

Monoisotopic Molecular Weight

276.20893014

IUPAC Name

(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoic acid

Traditional Name

stearidonic acid

CAS Registry Number

20290-75-9

SMILES

CC\C=C/C\C=C/C\C=C/C\C=C/CCCCC(O)=O

InChI Identifier

InChI=1S/C18H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10,12-13H,2,5,8,11,14-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9-,13-12-

InChI Key

JIWBIWFOSCKQMA-LTKCOYKYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic acids and derivatives

Alternative Parents

Substituents

Octadecanoid
Long-chain fatty acid
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

long-chain fatty acid (CHEBI:32389 )
omega-3 fatty acid (CHEBI:32389 )
octadecatetraenoic acid (CHEBI:32389 )
Polyunsaturated fatty acids (C16300 )
Unsaturated fatty acids (LMFA01030357 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0006547)

Excreta

Biofluid or Excreta

Feces (HMDB: HMDB0006547)
Urine (HMDB: HMDB0006547)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0006547)

Source

Endogenous

Endogenous (HMDB: HMDB0006547)

Plant

Animal

Animal (HMDB: HMDB0006547)

Exogenous

Food

Food (HMDB: HMDB0006547)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Herb and spice

Oilseed crop

Borage (FooDB: FOOD00026)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0006547)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0006547)

Lipid metabolism pathway (HMDB: HMDB0006547)

Cellular process

Cell signaling (HMDB: HMDB0006547)

Biochemical process

Lipid transport (HMDB: HMDB0006547)

Role

Biological role

Energy source (HMDB: HMDB0006547)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0006547)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0005 g/L	ALOGPS
logP	6.19	ALOGPS
logP	5.7	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	4.92	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	12	ChemAxon
Refractivity	90.75 m³·mol⁻¹	ChemAxon
Polarizability	33.11 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