ChemFOnt: Showing chemical card for Stearidonic acid (CFc000002802)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:46 UTC

Chemfont ID

CFc000002802

Molecule Identification

Common Name

Stearidonic acid

Definition

Stearidonic acid is found in dietary plant oils which are metabolized to longer-chain, more unsaturated (n-3) 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 EPA content of human lipids and that combinations of gamma-linolenic acid and stearidonic acid eicosapentaenoic 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 in order to influence cellular responses and functions in desirable ways. (PMID: 15120716 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Stearidonate	Generator

Chemical Formula

C₁₈H₂₈O₂

Average Molecular Weight

276.4137

Monoisotopic Molecular Weight

276.20893014

IUPAC Name

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

Traditional Name

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

CAS Registry Number

20290-75-9

SMILES

[H]\C(CC)=C(\[H])C\C([H])=C(\[H])C\C([H])=C(/[H])C\C([H])=C(/[H])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-DFARDDQGSA-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

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

Not Available

Functional Ontology

Physiological effect

Not Available

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 20671299)

Placenta (HMDB: HMDB0006547)

Biofluid or Excreta

Feces (PMID: 26476344)

Cellular substructure

Extracellular (HMDB: HMDB0006547)
Membrane (HMDB: HMDB0006547)

Exogenous (HMDB: HMDB0006547)

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Anchovy (FooDB: FOOD00566)
Blue whiting (FooDB: FOOD00567)
Carp bream (FooDB: FOOD00568)
Clupeinae (Herring, Sardine, Sprat) (FooDB: FOOD00520)
Burbot (FooDB: FOOD00313)
Sturgeon (FooDB: FOOD00570)
Charr (FooDB: FOOD00571)
Gadus (Common cod) (FooDB: FOOD00515)
Common dab (FooDB: FOOD00574)
Spiny dogfish (FooDB: FOOD00575)
Anguilliformes (FooDB: FOOD00577)
Flatfish (FooDB: FOOD00535)
Garfish (FooDB: FOOD00579)
Haddock (FooDB: FOOD00374)
Gadiformes (FooDB: FOOD00580)
Atlantic halibut (FooDB: FOOD00516)
Greenland halibut/turbot (FooDB: FOOD00370)
Lake trout (FooDB: FOOD00582)
Lemon sole (FooDB: FOOD00583)
Common ling (FooDB: FOOD00397)
Lumpsucker (FooDB: FOOD00585)
Scombridae (Bonito, Mackerel, Tuna) (FooDB: FOOD00586)
Norway haddock (FooDB: FOOD00588)
Norway pout (FooDB: FOOD00590)
Perciformes (FooDB: FOOD00527)
Northern pike (FooDB: FOOD00431)
Pikeperch (FooDB: FOOD00595)
Pleuronectidae (Dab, Halibut, Plaice) (FooDB: FOOD00596)
Pollock (FooDB: FOOD00513)
Rainbow trout (FooDB: FOOD00444)
Pacific ocean perch (FooDB: FOOD00598)
Salmonidae (Salmon, Trout) (FooDB: FOOD00493)
True sole (FooDB: FOOD00604)
Catfish (FooDB: FOOD00605)
Thunnus (FooDB: FOOD00607)
Turbot (FooDB: FOOD00364)
Whitefish (FooDB: FOOD00503)
Whiting (FooDB: FOOD00504)
Atlantic wolffish (FooDB: FOOD00296)
Fishes (FooDB: FOOD00865)

Other fish product (FooDB: FOOD00665)

True frog (FooDB: FOOD00578)

True seal (FooDB: FOOD00600)

Red algae (FooDB: FOOD00601)
Kombu (FooDB: FOOD00602)
Agar (FooDB: FOOD00284)

Cetacea (Dolphin, Porpoise, Whale) (FooDB: FOOD00609)

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)

Other fruit product (FooDB: FOOD00765)
Fruit preserve (FooDB: FOOD00660)

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)

Distilled beverage

Spirit (FooDB: FOOD00276)
Gin (FooDB: FOOD00625)
Liquor (FooDB: FOOD00616)
Rum (FooDB: FOOD00629)
Vodka (FooDB: FOOD00622)
Whisky (FooDB: FOOD00623)

Fermented beverage

Beer (FooDB: FOOD00268)
Grape wine (FooDB: FOOD00612)

Fortified wines

Water (FooDB: FOOD00664)

Alcoholic beverage

Other alcoholic beverage (FooDB: FOOD00278)

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)

Other vegetable

Okra (FooDB: FOOD00420)

Stalk vegetable

Garden rhubarb (FooDB: FOOD00154)

Baby food (FooDB: FOOD00668)

Domestic pig (FooDB: FOOD00536)

Cattle (Beef, Veal) (FooDB: FOOD00495)

Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Turkey (FooDB: FOOD00494)
Chicken (FooDB: FOOD00329)

Mountain hare (FooDB: FOOD00581)
Rabbit (FooDB: FOOD00528)

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Cereal and cereal product

Other bread (FooDB: FOOD00269)

Wheat bread (FooDB: FOOD00808)
Rye bread (FooDB: FOOD00809)

Barley (FooDB: FOOD00088)
Common buckwheat (FooDB: FOOD00079)
Corn (FooDB: FOOD00205)
Millet (FooDB: FOOD00126)
Oat (FooDB: FOOD00022)
Rice (FooDB: FOOD00125)
Rye (FooDB: FOOD00169)
Wheat (FooDB: FOOD00561)
Hard wheat (FooDB: FOOD00242)
White bread (FooDB: FOOD00987)

Other bread product (FooDB: FOOD00805)

Crisp bread (FooDB: FOOD00640)

Sugar (FooDB: FOOD00651)

Salad dressing (FooDB: FOOD00645)

Sugar substitute (FooDB: FOOD00656)

Salt (FooDB: FOOD00647)
Vinegar (FooDB: FOOD00628)

Sauce (FooDB: FOOD00646)

Lentils (FooDB: FOOD00098)

Chickpea (FooDB: FOOD00047)
Common pea (FooDB: FOOD00141)

Soy bean (FooDB: FOOD00085)

Miso (FooDB: FOOD00695)
Soy milk (FooDB: FOOD00736)
Soy sauce (FooDB: FOOD00694)
Tofu (FooDB: FOOD00696)

Unclassified food or beverage

Unclassified food or beverage (FooDB: FOOD00672)

Sausage (FooDB: FOOD00652)
Meatball (FooDB: FOOD00653)
Pate (FooDB: FOOD00655)
Cold cut (FooDB: FOOD00770)

Dumpling (FooDB: FOOD00669)
Other dish (FooDB: FOOD00836)
Pizza (FooDB: FOOD00637)
Soup (FooDB: FOOD00670)

Margarine-like spread (FooDB: FOOD00844)
Margarine (FooDB: FOOD00843)

Fish oil (FooDB: FOOD00990)

Milk and milk product

Other milk product

Butter (FooDB: FOOD00648)
Casein (FooDB: FOOD00659)
Whey (FooDB: FOOD00658)
Cream (FooDB: FOOD00650)
Dried milk (FooDB: FOOD00689)

Fermented milk product

Cheese (FooDB: FOOD00617)
Yogurt (FooDB: FOOD00620)
Ymer (FooDB: FOOD00638)

Unfermented milk

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)

Pastry (FooDB: FOOD00641)
Gelatin dessert (FooDB: FOOD00725)

Other confectionery

Honey (FooDB: FOOD00626)
Marzipan (FooDB: FOOD00644)
Toffee (FooDB: FOOD00635)
Meringue (FooDB: FOOD00680)

Ice cream (FooDB: FOOD00624)
Other frozen dessert (FooDB: FOOD00729)

Chocolate spread (FooDB: FOOD00676)

Cocoa and cocoa product

Coffee and coffee product

Cracker (FooDB: FOOD00787)
Other snack food (FooDB: FOOD00639)

Eggs (FooDB: FOOD00619)

Endogenous (HMDB: HMDB0006547)

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Alpha Linolenic Acid and Linoleic Acid Metabolism (PathBank: SMP0087171)

Not Available

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	34.1 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Stearidonic acid

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available