ChemFOnt: Showing chemical card for gamma-Linolenic acid (CFc000001769)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:29 UTC

Chemfont ID

CFc000001769

Molecule Identification

Common Name

gamma-Linolenic acid

Definition

gamma-Linolenic acid, also known as 18:3n6 or GLA, belongs to the class of organic compounds known as linoleic acids and derivatives. These are derivatives of linoleic acid. Linoleic acid is a polyunsaturated omega-6 18-carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. gamma-Linolenic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. gamma-Linolenic acid is an omega-6 fatty acid produced in the body as the delta 6-desaturase metabolite of linoleic acid. It is converted into dihomo-gamma-linolenic acid, a biosynthetic precursor of monoenoic prostaglandins such as PGE1 (PubChem).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Gamolenate	Generator

Chemical Formula

C₁₈H₃₀O₂

Average Molecular Weight

278.4296

Monoisotopic Molecular Weight

278.224580204

IUPAC Name

(6Z,9E,12Z)-octadeca-6,9,12-trienoic acid

Traditional Name

(6Z,9E,12Z)-octadeca-6,9,12-trienoic acid

CAS Registry Number

506-26-3

SMILES

[H]\C(CCCCC)=C(/[H])CC([H])=C([H])C\C([H])=C(\[H])CCCCC(O)=O

InChI Identifier

InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10,12-13H,2-5,8,11,14-17H2,1H3,(H,19,20)/b7-6-,10-9+,13-12-

InChI Key

VZCCETWTMQHEPK-XQYVMNDBSA-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

Not Available

Functional Ontology

Not Available

Adipose tissue (HMDB: HMDB0003073)

Epithelium

Epidermis (HMDB: HMDB0003073)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 18953024)

Cell

Hematocyte

Platelet (HMDB: HMDB0003073)

Organ

Placenta (HMDB: HMDB0003073)

Excreta

Biofluid or Excreta

Feces (PMID: 27543620)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0003073)

Avocado (FooDB: FOOD00130)
Pepper (FooDB: FOOD00040)

Cabbage

Broccoli (FooDB: FOOD00034)
Cauliflower (FooDB: FOOD00031)

Root vegetable

Carrot (FooDB: FOOD00245)
Wild carrot (FooDB: FOOD00072)

Mushroom

Common mushroom (FooDB: FOOD00547)
Morchella (Morel) (FooDB: FOOD00731)

Onion-family vegetable

Allium (FooDB: FOOD00005)

Tuber

Potato (FooDB: FOOD00175)

Animal origin

Swine

Domestic pig (FooDB: FOOD00536)

Bovine

Cattle (Beef, Veal) (FooDB: FOOD00495)

Venison

Deer (FooDB: FOOD00524)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Tortilla (FooDB: FOOD00709)
Piki bread (FooDB: FOOD00806)

Pulse

Bean

Common bean (FooDB: FOOD00134)
Bean (FooDB: FOOD00621)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

Dish

Ground meat

Sausage (FooDB: FOOD00652)
Cold cut (FooDB: FOOD00770)

Other dish

Pasta dish

Potato dish

Potato puffs (FooDB: FOOD00846)

Tex-mex cuisine

Chili (FooDB: FOOD00707)
Burrito (FooDB: FOOD00704)
Taco (FooDB: FOOD00708)

American cuisine

Hushpuppy (FooDB: FOOD00762)

Sandwich

Mexican cuisine

Quesadilla (FooDB: FOOD00748)

Asian cuisine

Egg roll (FooDB: FOOD00717)

Latin american cuisine

Tamale (FooDB: FOOD00795)
Empanada (FooDB: FOOD00830)
Pupusa (FooDB: FOOD00829)
Arepa (FooDB: FOOD00831)

Fat and oil

Vegetable fat

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

Milk and milk product

Fermented milk product

Cheese (FooDB: FOOD00617)
Processed cheese (FooDB: FOOD00711)

Other milk product

Cream (FooDB: FOOD00650)

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Date (FooDB: FOOD00135)

Citrus

Lemon (FooDB: FOOD00054)

Drupe

European plum (FooDB: FOOD00147)

Cocoa and cocoa product

Cocoa product

Chocolate (FooDB: FOOD00687)

Coffee and coffee product

Pastry (FooDB: FOOD00641)
Cake (FooDB: FOOD00636)
Pudding (FooDB: FOOD00734)

Other confectionery

Honey (FooDB: FOOD00626)

Candy

Other candy (FooDB: FOOD00679)
Candy bar (FooDB: FOOD00841)

Frozen dessert

Milkshake (FooDB: FOOD00826)

Spread

Dulce de leche (FooDB: FOOD00714)

Egg

Eggs (FooDB: FOOD00619)

Aquatic origin

Fish product

Other fish product (FooDB: FOOD00665)

Fish

Flatfish (FooDB: FOOD00535)
Haddock (FooDB: FOOD00374)
Rainbow trout (FooDB: FOOD00444)
Catfish (FooDB: FOOD00605)
Channel catfish (FooDB: FOOD00324)
Pacific cod (FooDB: FOOD00337)
Hippoglossus (Common halibut) (FooDB: FOOD00375)
Painted comber (FooDB: FOOD00294)
Alaska pollock (FooDB: FOOD00497)
Pacific rockfish (FooDB: FOOD00426)
Atlantic salmon (FooDB: FOOD00455)
Pink salmon (FooDB: FOOD00450)
Sockeye salmon (FooDB: FOOD00453)
Swordfish (FooDB: FOOD00487)
Yellowfin tuna (FooDB: FOOD00511)

Crustacean

Mollusk

Bivalvia (Clam, Mussel, Oyster) (FooDB: FOOD00531)
Eastern oyster (FooDB: FOOD00356)
Scallop (FooDB: FOOD00462)

Beverage

Other beverage

Fruit juice (FooDB: FOOD00763)
Horchata (FooDB: FOOD00823)

Nutritional beverage

Nutritional drink (FooDB: FOOD00754)

Salad dressing (FooDB: FOOD00645)

Sauce

Sauce (FooDB: FOOD00646)

Syrup (FooDB: FOOD00673)
Cooking oil (FooDB: FOOD00779)

Wrapper

Pie crust (FooDB: FOOD00780)
Edible shell (FooDB: FOOD00839)

Gourd

Cucurbita (FooDB: FOOD00066)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Alpha Linolenic Acid and Linoleic Acid Metabolism (PathBank: SMP0087171)
Triacylglycerol Degradation TG(16:0/16:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0012473)
Triacylglycerol Degradation TG(16:0/18:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0012485)
Triacylglycerol Degradation TG(16:0/18:1(9Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012497)
Triacylglycerol Degradation TG(16:0/18:1(11Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012509)
Triacylglycerol Degradation TG(16:0/18:2(9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012521)
Triacylglycerol Degradation TG(16:0/18:3(6Z,9Z,12Z)/16:0) (PathBank: SMP0012528)
Triacylglycerol Degradation TG(16:0/18:3(6Z,9Z,12Z)/18:0) (PathBank: SMP0012529)
Triacylglycerol Degradation TG(16:0/18:3(6Z,9Z,12Z)/18:1(9Z)) (PathBank: SMP0012530)
Triacylglycerol Degradation TG(16:0/18:3(6Z,9Z,12Z)/18:1(11Z)) (PathBank: SMP0012531)
Triacylglycerol Degradation TG(16:0/18:3(6Z,9Z,12Z)/18:2(9Z,12Z)) (PathBank: SMP0012532)
Triacylglycerol Degradation TG(16:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012533)
Triacylglycerol Degradation TG(16:0/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0012534)
Triacylglycerol Degradation TG(16:0/18:3(6Z,9Z,12Z)/20:0) (PathBank: SMP0012535)
Triacylglycerol Degradation TG(16:0/18:3(6Z,9Z,12Z)/20:1(11Z)) (PathBank: SMP0012536)
Triacylglycerol Degradation TG(16:0/18:3(6Z,9Z,12Z)/20:1(13Z)) (PathBank: SMP0012537)
Triacylglycerol Degradation TG(16:0/18:3(6Z,9Z,12Z)/22:0) (PathBank: SMP0012538)
Triacylglycerol Degradation TG(16:0/18:3(6Z,9Z,12Z)/22:1(13Z)) (PathBank: SMP0012539)
Triacylglycerol Degradation TG(16:0/18:3(9Z,12Z,15Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012545)
Triacylglycerol Degradation TG(16:0/20:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0012557)
Triacylglycerol Degradation TG(16:0/20:1(11Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012569)
Triacylglycerol Degradation TG(16:0/20:1(13Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012581)
Triacylglycerol Degradation TG(16:0/22:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0012593)
Triacylglycerol Degradation TG(16:0/22:1(13Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012605)
Triacylglycerol Degradation TG(18:0/16:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0012617)
Triacylglycerol Degradation TG(18:0/18:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0012629)
Triacylglycerol Degradation TG(18:0/18:1(9Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012641)
Triacylglycerol Degradation TG(18:0/18:1(11Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012653)
Triacylglycerol Degradation TG(18:0/18:2(9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012665)
Triacylglycerol Degradation TG(18:0/18:3(6Z,9Z,12Z)/16:0) (PathBank: SMP0012672)
Triacylglycerol Degradation TG(18:0/18:3(6Z,9Z,12Z)/18:0) (PathBank: SMP0012673)
Triacylglycerol Degradation TG(18:0/18:3(6Z,9Z,12Z)/18:1(9Z)) (PathBank: SMP0012674)
Triacylglycerol Degradation TG(18:0/18:3(6Z,9Z,12Z)/18:1(11Z)) (PathBank: SMP0012675)
Triacylglycerol Degradation TG(18:0/18:3(6Z,9Z,12Z)/18:2(9Z,12Z)) (PathBank: SMP0012676)
Triacylglycerol Degradation TG(18:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012677)
Triacylglycerol Degradation TG(18:0/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0012678)
Triacylglycerol Degradation TG(18:0/18:3(6Z,9Z,12Z)/20:0) (PathBank: SMP0012679)
Triacylglycerol Degradation TG(18:0/18:3(6Z,9Z,12Z)/20:1(11Z)) (PathBank: SMP0012680)
Triacylglycerol Degradation TG(18:0/18:3(6Z,9Z,12Z)/20:1(13Z)) (PathBank: SMP0012681)
Triacylglycerol Degradation TG(18:0/18:3(6Z,9Z,12Z)/22:0) (PathBank: SMP0012682)
Triacylglycerol Degradation TG(18:0/18:3(6Z,9Z,12Z)/22:1(13Z)) (PathBank: SMP0012683)
Triacylglycerol Degradation TG(18:0/18:3(9Z,12Z,15Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012689)
Triacylglycerol Degradation TG(18:0/20:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0012701)
Triacylglycerol Degradation TG(18:0/20:1(11Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012713)
Triacylglycerol Degradation TG(18:0/20:1(13Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012725)
Triacylglycerol Degradation TG(18:0/22:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0012737)
Triacylglycerol Degradation TG(18:0/22:1(13Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012749)
Triacylglycerol Degradation TG(18:1(9Z)/16:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0012761)
Triacylglycerol Degradation TG(18:1(9Z)/18:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0012773)
Triacylglycerol Degradation TG(18:1(9Z)/18:1(9Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012785)
Triacylglycerol Degradation TG(18:1(9Z)/18:1(11Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012797)
Triacylglycerol Degradation TG(18:1(9Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012809)
Triacylglycerol Degradation TG(18:1(9Z)/18:3(6Z,9Z,12Z)/16:0) (PathBank: SMP0012816)
Triacylglycerol Degradation TG(18:1(9Z)/18:3(6Z,9Z,12Z)/18:0) (PathBank: SMP0012817)
Triacylglycerol Degradation TG(18:1(9Z)/18:3(6Z,9Z,12Z)/18:1(9Z)) (PathBank: SMP0012818)
Triacylglycerol Degradation TG(18:1(9Z)/18:3(6Z,9Z,12Z)/18:1(11Z)) (PathBank: SMP0012819)
Triacylglycerol Degradation TG(18:1(9Z)/18:3(6Z,9Z,12Z)/18:2(9Z,12Z)) (PathBank: SMP0012820)
Triacylglycerol Degradation TG(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012821)
Triacylglycerol Degradation TG(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0012822)
Triacylglycerol Degradation TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:0) (PathBank: SMP0012823)
Triacylglycerol Degradation TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:1(11Z)) (PathBank: SMP0012824)
Triacylglycerol Degradation TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:1(13Z)) (PathBank: SMP0012825)
Triacylglycerol Degradation TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:0) (PathBank: SMP0012826)
Triacylglycerol Degradation TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:1(13Z)) (PathBank: SMP0012827)
Triacylglycerol Degradation TG(18:1(9Z)/18:3(9Z,12Z,15Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012833)
Triacylglycerol Degradation TG(18:1(9Z)/20:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0012845)
Triacylglycerol Degradation TG(18:1(9Z)/20:1(11Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012857)
Triacylglycerol Degradation TG(18:1(9Z)/20:1(13Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012869)
Triacylglycerol Degradation TG(18:1(9Z)/22:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0012881)
Triacylglycerol Degradation TG(18:1(9Z)/22:1(13Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012893)
Triacylglycerol Degradation TG(18:1(11Z)/16:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0012905)
Triacylglycerol Degradation TG(18:1(11Z)/18:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0012917)
Triacylglycerol Degradation TG(18:1(11Z)/18:1(9Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012929)
Triacylglycerol Degradation TG(18:1(11Z)/18:1(11Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012941)
Triacylglycerol Degradation TG(18:1(11Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012953)
Triacylglycerol Degradation TG(18:1(11Z)/18:3(6Z,9Z,12Z)/16:0) (PathBank: SMP0012960)
Triacylglycerol Degradation TG(18:1(11Z)/18:3(6Z,9Z,12Z)/18:0) (PathBank: SMP0012961)
Triacylglycerol Degradation TG(18:1(11Z)/18:3(6Z,9Z,12Z)/18:1(9Z)) (PathBank: SMP0012962)
Triacylglycerol Degradation TG(18:1(11Z)/18:3(6Z,9Z,12Z)/18:1(11Z)) (PathBank: SMP0012963)
Triacylglycerol Degradation TG(18:1(11Z)/18:3(6Z,9Z,12Z)/18:2(9Z,12Z)) (PathBank: SMP0012964)
Triacylglycerol Degradation TG(18:1(11Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012965)
Triacylglycerol Degradation TG(18:1(11Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0012966)
Triacylglycerol Degradation TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:0) (PathBank: SMP0012967)
Triacylglycerol Degradation TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:1(11Z)) (PathBank: SMP0012968)
Triacylglycerol Degradation TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:1(13Z)) (PathBank: SMP0012969)
Triacylglycerol Degradation TG(18:1(11Z)/18:3(6Z,9Z,12Z)/22:0) (PathBank: SMP0012970)
Triacylglycerol Degradation TG(18:1(11Z)/18:3(6Z,9Z,12Z)/22:1(13Z)) (PathBank: SMP0012971)
Triacylglycerol Degradation TG(18:1(11Z)/18:3(9Z,12Z,15Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012977)
Triacylglycerol Degradation TG(18:1(11Z)/20:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0012989)
Triacylglycerol Degradation TG(18:1(11Z)/20:1(11Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013001)
Triacylglycerol Degradation TG(18:1(11Z)/20:1(13Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013013)
Triacylglycerol Degradation TG(18:1(11Z)/22:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0013025)
Triacylglycerol Degradation TG(18:1(11Z)/22:1(13Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013037)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/16:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0013049)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/18:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0013061)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/18:1(9Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013073)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/18:1(11Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013085)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013097)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/16:0) (PathBank: SMP0013104)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:0) (PathBank: SMP0013105)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:1(9Z)) (PathBank: SMP0013106)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:1(11Z)) (PathBank: SMP0013107)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:2(9Z,12Z)) (PathBank: SMP0013108)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013109)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0013110)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:0) (PathBank: SMP0013111)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:1(11Z)) (PathBank: SMP0013112)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:1(13Z)) (PathBank: SMP0013113)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:0) (PathBank: SMP0013114)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:1(13Z)) (PathBank: SMP0013115)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013121)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/20:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0013133)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/20:1(11Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013145)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/20:1(13Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013157)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/22:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0013169)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/22:1(13Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013181)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/16:0/16:0) (PathBank: SMP0013188)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/16:0/18:0) (PathBank: SMP0013189)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/16:0/18:1(9Z)) (PathBank: SMP0013190)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/16:0/18:1(11Z)) (PathBank: SMP0013191)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/16:0/18:2(9Z,12Z)) (PathBank: SMP0013192)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/16:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0013193)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/16:0/18:3(9Z,12Z,15Z)) (PathBank: SMP0013194)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/16:0/20:0) (PathBank: SMP0013195)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/16:0/20:1(11Z)) (PathBank: SMP0013196)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/16:0/20:1(13Z)) (PathBank: SMP0013197)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/16:0/22:0) (PathBank: SMP0013198)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/16:0/22:1(13Z)) (PathBank: SMP0013199)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:0/16:0) (PathBank: SMP0013200)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:0/18:0) (PathBank: SMP0013201)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:0/18:1(9Z)) (PathBank: SMP0013202)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:0/18:1(11Z)) (PathBank: SMP0013203)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:0/18:2(9Z,12Z)) (PathBank: SMP0013204)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0013205)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:0/18:3(9Z,12Z,15Z)) (PathBank: SMP0013206)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:0/20:0) (PathBank: SMP0013207)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:0/20:1(11Z)) (PathBank: SMP0013208)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:0/20:1(13Z)) (PathBank: SMP0013209)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:0/22:0) (PathBank: SMP0013210)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:0/22:1(13Z)) (PathBank: SMP0013211)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:1(9Z)/16:0) (PathBank: SMP0013212)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:1(9Z)/18:0) (PathBank: SMP0013213)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:1(9Z)/18:1(9Z)) (PathBank: SMP0013214)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:1(9Z)/18:1(11Z)) (PathBank: SMP0013215)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)) (PathBank: SMP0013216)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:1(9Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013217)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:1(9Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0013218)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:1(9Z)/20:0) (PathBank: SMP0013219)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:1(9Z)/20:1(11Z)) (PathBank: SMP0013220)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:1(9Z)/20:1(13Z)) (PathBank: SMP0013221)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:1(9Z)/22:0) (PathBank: SMP0013222)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:1(9Z)/22:1(13Z)) (PathBank: SMP0013223)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:1(11Z)/16:0) (PathBank: SMP0013224)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:1(11Z)/18:0) (PathBank: SMP0013225)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:1(11Z)/18:1(9Z)) (PathBank: SMP0013226)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:1(11Z)/18:1(11Z)) (PathBank: SMP0013227)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)) (PathBank: SMP0013228)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:1(11Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013229)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:1(11Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0013230)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:1(11Z)/20:0) (PathBank: SMP0013231)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:1(11Z)/20:1(11Z)) (PathBank: SMP0013232)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:1(11Z)/20:1(13Z)) (PathBank: SMP0013233)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:1(11Z)/22:0) (PathBank: SMP0013234)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:1(11Z)/22:1(13Z)) (PathBank: SMP0013235)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:2(9Z,12Z)/16:0) (PathBank: SMP0013236)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:2(9Z,12Z)/18:0) (PathBank: SMP0013237)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0013238)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)) (PathBank: SMP0013239)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) (PathBank: SMP0013240)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013241)
Triacylglycerol Degradation TG(20:0/18:3(6Z,9Z,12Z)/16:0) (PathBank: SMP0013533)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:2(9Z,12Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0013242)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:2(9Z,12Z)/20:0) (PathBank: SMP0013243)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:2(9Z,12Z)/20:1(11Z)) (PathBank: SMP0013244)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:2(9Z,12Z)/20:1(13Z)) (PathBank: SMP0013245)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:2(9Z,12Z)/22:0) (PathBank: SMP0013246)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:2(9Z,12Z)/22:1(13Z)) (PathBank: SMP0013247)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/16:0) (PathBank: SMP0013248)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/18:0) (PathBank: SMP0013249)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/18:1(9Z)) (PathBank: SMP0013250)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/18:1(11Z)) (PathBank: SMP0013251)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/18:2(9Z,12Z)) (PathBank: SMP0013252)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013253)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0013254)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:0) (PathBank: SMP0013255)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:1(11Z)) (PathBank: SMP0013256)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:1(13Z)) (PathBank: SMP0013257)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:0) (PathBank: SMP0013258)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:1(13Z)) (PathBank: SMP0013259)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/16:0) (PathBank: SMP0013260)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/18:0) (PathBank: SMP0013261)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/18:1(9Z)) (PathBank: SMP0013262)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/18:1(11Z)) (PathBank: SMP0013263)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/18:2(9Z,12Z)) (PathBank: SMP0013264)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013265)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0013266)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:0) (PathBank: SMP0013267)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:1(11Z)) (PathBank: SMP0013268)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:1(13Z)) (PathBank: SMP0013269)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:0) (PathBank: SMP0013270)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:1(13Z)) (PathBank: SMP0013271)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:0/16:0) (PathBank: SMP0013272)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:0/18:0) (PathBank: SMP0013273)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:0/18:1(9Z)) (PathBank: SMP0013274)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:0/18:1(11Z)) (PathBank: SMP0013275)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:0/18:2(9Z,12Z)) (PathBank: SMP0013276)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0013277)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:0/18:3(9Z,12Z,15Z)) (PathBank: SMP0013278)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:0/20:0) (PathBank: SMP0013279)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:0/20:1(11Z)) (PathBank: SMP0013280)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:0/20:1(13Z)) (PathBank: SMP0013281)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:0/22:0) (PathBank: SMP0013282)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:0/22:1(13Z)) (PathBank: SMP0013283)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:1(11Z)/16:0) (PathBank: SMP0013284)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:1(11Z)/18:0) (PathBank: SMP0013285)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:1(11Z)/18:1(9Z)) (PathBank: SMP0013286)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:1(11Z)/18:1(11Z)) (PathBank: SMP0013287)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:1(11Z)/18:2(9Z,12Z)) (PathBank: SMP0013288)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:1(11Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013289)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:1(11Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0013290)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:1(11Z)/20:0) (PathBank: SMP0013291)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:1(11Z)/20:1(11Z)) (PathBank: SMP0013292)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:1(11Z)/20:1(13Z)) (PathBank: SMP0013293)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:1(11Z)/22:0) (PathBank: SMP0013294)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:1(11Z)/22:1(13Z)) (PathBank: SMP0013295)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:1(13Z)/16:0) (PathBank: SMP0013296)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:1(13Z)/18:0) (PathBank: SMP0013297)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:1(13Z)/18:1(9Z)) (PathBank: SMP0013298)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:1(13Z)/18:1(11Z)) (PathBank: SMP0013299)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:1(13Z)/18:2(9Z,12Z)) (PathBank: SMP0013300)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:1(13Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013301)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:1(13Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0013302)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:1(13Z)/20:0) (PathBank: SMP0013303)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:1(13Z)/20:1(11Z)) (PathBank: SMP0013304)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:1(13Z)/20:1(13Z)) (PathBank: SMP0013305)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:1(13Z)/22:0) (PathBank: SMP0013306)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:1(13Z)/22:1(13Z)) (PathBank: SMP0013307)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/22:0/16:0) (PathBank: SMP0013308)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/22:0/18:0) (PathBank: SMP0013309)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/22:0/18:1(9Z)) (PathBank: SMP0013310)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/22:0/18:1(11Z)) (PathBank: SMP0013311)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/22:0/18:2(9Z,12Z)) (PathBank: SMP0013312)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/22:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0013313)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/22:0/18:3(9Z,12Z,15Z)) (PathBank: SMP0013314)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/22:0/20:0) (PathBank: SMP0013315)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/22:0/20:1(11Z)) (PathBank: SMP0013316)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/22:0/20:1(13Z)) (PathBank: SMP0013317)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/22:0/22:0) (PathBank: SMP0013318)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/22:0/22:1(13Z)) (PathBank: SMP0013319)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/22:1(13Z)/16:0) (PathBank: SMP0013320)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/22:1(13Z)/18:0) (PathBank: SMP0013321)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/22:1(13Z)/18:1(9Z)) (PathBank: SMP0013322)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/22:1(13Z)/18:1(11Z)) (PathBank: SMP0013323)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/22:1(13Z)/18:2(9Z,12Z)) (PathBank: SMP0013324)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/22:1(13Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013325)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/22:1(13Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0013326)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/22:1(13Z)/20:0) (PathBank: SMP0013327)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/22:1(13Z)/20:1(11Z)) (PathBank: SMP0013328)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/22:1(13Z)/20:1(13Z)) (PathBank: SMP0013329)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/22:1(13Z)/22:0) (PathBank: SMP0013330)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/22:1(13Z)/22:1(13Z)) (PathBank: SMP0013331)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/16:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0013337)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/18:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0013349)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/18:1(9Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013361)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/18:1(11Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013372)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013383)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/18:3(6Z,9Z,12Z)/16:0) (PathBank: SMP0013389)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/18:3(6Z,9Z,12Z)/18:0) (PathBank: SMP0013390)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/18:3(6Z,9Z,12Z)/18:1(9Z)) (PathBank: SMP0013391)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/18:3(6Z,9Z,12Z)/18:1(11Z)) (PathBank: SMP0013392)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/18:3(6Z,9Z,12Z)/18:2(9Z,12Z)) (PathBank: SMP0013393)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013394)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0013395)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/18:3(6Z,9Z,12Z)/20:0) (PathBank: SMP0013396)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/18:3(6Z,9Z,12Z)/20:1(11Z)) (PathBank: SMP0013397)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/18:3(6Z,9Z,12Z)/20:1(13Z)) (PathBank: SMP0013398)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/18:3(6Z,9Z,12Z)/22:0) (PathBank: SMP0013399)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/18:3(6Z,9Z,12Z)/22:1(13Z)) (PathBank: SMP0013400)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013406)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/20:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0013418)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/20:1(11Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013430)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/20:1(13Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013442)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/22:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0013454)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/22:1(13Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013466)
Triacylglycerol Degradation TG(20:0/16:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0013478)
Triacylglycerol Degradation TG(20:0/18:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0013490)
Triacylglycerol Degradation TG(20:0/18:1(9Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013502)
Triacylglycerol Degradation TG(20:0/18:1(11Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013514)
Triacylglycerol Degradation TG(20:0/18:2(9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013526)
Triacylglycerol Degradation TG(20:0/18:3(6Z,9Z,12Z)/18:0) (PathBank: SMP0013534)
Triacylglycerol Degradation TG(20:0/18:3(6Z,9Z,12Z)/18:1(9Z)) (PathBank: SMP0013535)
Triacylglycerol Degradation TG(20:0/18:3(6Z,9Z,12Z)/18:1(11Z)) (PathBank: SMP0013536)
Triacylglycerol Degradation TG(20:0/18:3(6Z,9Z,12Z)/18:2(9Z,12Z)) (PathBank: SMP0013537)
Triacylglycerol Degradation TG(20:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013538)
Triacylglycerol Degradation TG(20:0/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0013539)
Triacylglycerol Degradation TG(20:0/18:3(6Z,9Z,12Z)/20:0) (PathBank: SMP0013540)
Triacylglycerol Degradation TG(20:0/18:3(6Z,9Z,12Z)/20:1(11Z)) (PathBank: SMP0013541)
Triacylglycerol Degradation TG(20:0/18:3(6Z,9Z,12Z)/20:1(13Z)) (PathBank: SMP0013542)
Triacylglycerol Degradation TG(20:0/18:3(6Z,9Z,12Z)/22:0) (PathBank: SMP0013543)
Triacylglycerol Degradation TG(20:0/18:3(6Z,9Z,12Z)/22:1(13Z)) (PathBank: SMP0013544)
Triacylglycerol Degradation TG(20:0/18:3(9Z,12Z,15Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013550)
Triacylglycerol Degradation TG(20:0/20:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0013562)
Triacylglycerol Degradation TG(20:0/20:1(11Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013574)
Triacylglycerol Degradation TG(20:0/20:1(13Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013586)
Triacylglycerol Degradation TG(20:0/22:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0013598)
Triacylglycerol Degradation TG(20:0/22:1(13Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013610)
Triacylglycerol Degradation TG(20:1(11Z)/16:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0013622)
Triacylglycerol Degradation TG(20:1(11Z)/18:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0013634)
Triacylglycerol Degradation TG(20:1(11Z)/18:1(9Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013646)
Triacylglycerol Degradation TG(20:1(11Z)/18:1(11Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013658)
Triacylglycerol Degradation TG(20:1(11Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013670)
Triacylglycerol Degradation TG(20:1(11Z)/18:3(6Z,9Z,12Z)/16:0) (PathBank: SMP0013677)
Triacylglycerol Degradation TG(20:1(11Z)/18:3(6Z,9Z,12Z)/18:0) (PathBank: SMP0013678)
Triacylglycerol Degradation TG(20:1(11Z)/18:3(6Z,9Z,12Z)/18:1(9Z)) (PathBank: SMP0013679)
Triacylglycerol Degradation TG(20:1(11Z)/18:3(6Z,9Z,12Z)/18:1(11Z)) (PathBank: SMP0013680)
Triacylglycerol Degradation TG(20:1(11Z)/18:3(6Z,9Z,12Z)/18:2(9Z,12Z)) (PathBank: SMP0013681)
Triacylglycerol Degradation TG(20:1(11Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013682)
Triacylglycerol Degradation TG(20:1(11Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0013683)
Triacylglycerol Degradation TG(20:1(11Z)/18:3(6Z,9Z,12Z)/20:0) (PathBank: SMP0013684)
Triacylglycerol Degradation TG(20:1(11Z)/18:3(6Z,9Z,12Z)/20:1(11Z)) (PathBank: SMP0013685)
Triacylglycerol Degradation TG(20:1(11Z)/18:3(6Z,9Z,12Z)/20:1(13Z)) (PathBank: SMP0013686)
Triacylglycerol Degradation TG(20:1(11Z)/18:3(6Z,9Z,12Z)/22:0) (PathBank: SMP0013687)
Triacylglycerol Degradation TG(20:1(11Z)/18:3(6Z,9Z,12Z)/22:1(13Z)) (PathBank: SMP0013688)
Triacylglycerol Degradation TG(20:1(11Z)/18:3(9Z,12Z,15Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013694)
Triacylglycerol Degradation TG(20:1(11Z)/20:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0013706)
Triacylglycerol Degradation TG(20:1(11Z)/20:1(11Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013718)
Triacylglycerol Degradation TG(20:1(11Z)/20:1(13Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013730)
Triacylglycerol Degradation TG(20:1(11Z)/22:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0013742)
Triacylglycerol Degradation TG(20:1(11Z)/22:1(13Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013754)
Triacylglycerol Degradation TG(20:1(13Z)/16:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0013767)
Triacylglycerol Degradation TG(20:1(13Z)/18:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0013779)
Triacylglycerol Degradation TG(20:1(13Z)/18:1(9Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013791)
Triacylglycerol Degradation TG(20:1(13Z)/18:1(11Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013803)
Triacylglycerol Degradation TG(20:1(13Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013815)
Triacylglycerol Degradation TG(20:1(13Z)/18:3(6Z,9Z,12Z)/16:0) (PathBank: SMP0013822)
Triacylglycerol Degradation TG(20:1(13Z)/18:3(6Z,9Z,12Z)/18:0) (PathBank: SMP0013823)
Triacylglycerol Degradation TG(20:1(13Z)/18:3(6Z,9Z,12Z)/18:1(9Z)) (PathBank: SMP0013824)
Triacylglycerol Degradation TG(20:1(13Z)/18:3(6Z,9Z,12Z)/18:1(11Z)) (PathBank: SMP0013825)
Triacylglycerol Degradation TG(20:1(13Z)/18:3(6Z,9Z,12Z)/18:2(9Z,12Z)) (PathBank: SMP0013826)
Triacylglycerol Degradation TG(20:1(13Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013827)
Triacylglycerol Degradation TG(20:1(13Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0013828)
Triacylglycerol Degradation TG(20:1(13Z)/18:3(6Z,9Z,12Z)/20:0) (PathBank: SMP0013829)
Triacylglycerol Degradation TG(20:1(13Z)/18:3(6Z,9Z,12Z)/20:1(11Z)) (PathBank: SMP0013830)
Triacylglycerol Degradation TG(20:1(13Z)/18:3(6Z,9Z,12Z)/20:1(13Z)) (PathBank: SMP0013831)
Triacylglycerol Degradation TG(20:1(13Z)/18:3(6Z,9Z,12Z)/22:0) (PathBank: SMP0013832)
Triacylglycerol Degradation TG(20:1(13Z)/18:3(6Z,9Z,12Z)/22:1(13Z)) (PathBank: SMP0013833)
Triacylglycerol Degradation TG(20:1(13Z)/18:3(9Z,12Z,15Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013839)
Triacylglycerol Degradation TG(20:1(13Z)/20:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0013851)
Triacylglycerol Degradation TG(20:1(13Z)/20:1(11Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013863)
Triacylglycerol Degradation TG(20:1(13Z)/20:1(13Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013875)
Triacylglycerol Degradation TG(20:1(13Z)/22:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0013887)
Triacylglycerol Degradation TG(20:1(13Z)/22:1(13Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013900)
Triacylglycerol Degradation TG(22:0/16:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0013912)
Triacylglycerol Degradation TG(22:0/18:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0013924)
Triacylglycerol Degradation TG(22:0/18:1(9Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013936)
Triacylglycerol Degradation TG(22:0/18:1(11Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013948)
Triacylglycerol Degradation TG(22:0/18:2(9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013960)
Triacylglycerol Degradation TG(22:0/18:3(6Z,9Z,12Z)/16:0) (PathBank: SMP0013967)
Triacylglycerol Degradation TG(22:0/18:3(6Z,9Z,12Z)/18:0) (PathBank: SMP0013968)
Triacylglycerol Degradation TG(22:0/18:3(6Z,9Z,12Z)/18:1(9Z)) (PathBank: SMP0013969)
Triacylglycerol Degradation TG(22:0/18:3(6Z,9Z,12Z)/18:1(11Z)) (PathBank: SMP0013970)
Triacylglycerol Degradation TG(22:0/18:3(6Z,9Z,12Z)/18:2(9Z,12Z)) (PathBank: SMP0013971)
Triacylglycerol Degradation TG(22:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013972)
Triacylglycerol Degradation TG(22:0/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0013973)
Triacylglycerol Degradation TG(22:0/18:3(6Z,9Z,12Z)/20:0) (PathBank: SMP0013974)
Triacylglycerol Degradation TG(22:0/18:3(6Z,9Z,12Z)/20:1(11Z)) (PathBank: SMP0013975)
Triacylglycerol Degradation TG(22:0/18:3(6Z,9Z,12Z)/20:1(13Z)) (PathBank: SMP0013976)
Triacylglycerol Degradation TG(22:0/18:3(6Z,9Z,12Z)/22:0) (PathBank: SMP0013977)
Triacylglycerol Degradation TG(22:0/18:3(6Z,9Z,12Z)/22:1(13Z)) (PathBank: SMP0013978)
Triacylglycerol Degradation TG(22:0/18:3(9Z,12Z,15Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013984)
Triacylglycerol Degradation TG(22:0/20:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0013996)
Triacylglycerol Degradation TG(22:0/20:1(11Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0014008)
Triacylglycerol Degradation TG(22:0/20:1(13Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0014022)
Triacylglycerol Degradation TG(22:0/22:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0014034)
Triacylglycerol Degradation TG(22:0/22:1(13Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0014046)
Triacylglycerol Degradation TG(22:1(13Z)/16:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0014058)
Triacylglycerol Degradation TG(22:1(13Z)/18:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0014070)
Triacylglycerol Degradation TG(22:1(13Z)/18:1(9Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0014082)
Triacylglycerol Degradation TG(22:1(13Z)/18:1(11Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0014094)
Triacylglycerol Degradation TG(22:1(13Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0014106)
Triacylglycerol Degradation TG(22:1(13Z)/18:3(6Z,9Z,12Z)/16:0) (PathBank: SMP0014113)
Triacylglycerol Degradation TG(22:1(13Z)/18:3(6Z,9Z,12Z)/18:0) (PathBank: SMP0014114)
Triacylglycerol Degradation TG(22:1(13Z)/18:3(6Z,9Z,12Z)/18:1(9Z)) (PathBank: SMP0014115)
Triacylglycerol Degradation TG(22:1(13Z)/18:3(6Z,9Z,12Z)/18:1(11Z)) (PathBank: SMP0014116)
Triacylglycerol Degradation TG(22:1(13Z)/18:3(6Z,9Z,12Z)/18:2(9Z,12Z)) (PathBank: SMP0014117)
Triacylglycerol Degradation TG(22:1(13Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0014118)
Triacylglycerol Degradation TG(22:1(13Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0014119)
Triacylglycerol Degradation TG(22:1(13Z)/18:3(6Z,9Z,12Z)/20:0) (PathBank: SMP0014120)
Triacylglycerol Degradation TG(22:1(13Z)/18:3(6Z,9Z,12Z)/20:1(11Z)) (PathBank: SMP0014121)
Triacylglycerol Degradation TG(22:1(13Z)/18:3(6Z,9Z,12Z)/20:1(13Z)) (PathBank: SMP0014122)
Triacylglycerol Degradation TG(22:1(13Z)/18:3(6Z,9Z,12Z)/22:0) (PathBank: SMP0014123)
Triacylglycerol Degradation TG(22:1(13Z)/18:3(6Z,9Z,12Z)/22:1(13Z)) (PathBank: SMP0014124)
Triacylglycerol Degradation TG(22:1(13Z)/18:3(9Z,12Z,15Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0014130)
Triacylglycerol Degradation TG(22:1(13Z)/20:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0014142)
Triacylglycerol Degradation TG(22:1(13Z)/20:1(11Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0014154)
Triacylglycerol Degradation TG(22:1(13Z)/20:1(13Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0014167)
Triacylglycerol Degradation TG(22:1(13Z)/22:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0014179)
Triacylglycerol Degradation TG(22:1(13Z)/22:1(13Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0014191)

Role

Biological role

Modulator

Immunomodulator (HMDB: HMDB0003073)

Inhibitor

Enzyme inhibitor

Alpha-reductase inhibitor (HMDB: HMDB0003073)

Anti acne (HMDB: HMDB0003073)
Anti aggregant (HMDB: HMDB0003073)
Anti alcoholic (HMDB: HMDB0003073)
Anti arthritic (HMDB: HMDB0003073)
Anti asphyctic (HMDB: HMDB0003073)
Anti atherosclerotic (HMDB: HMDB0003073)
Anti eczemic (HMDB: HMDB0003073)
Anti hypercholesterolemic (HMDB: HMDB0003073)
Anti menorrhagic (HMDB: HMDB0003073)
Anti monosodium-glutamate (HMDB: HMDB0003073)
Anti obesity (HMDB: HMDB0003073)
Anti premenstrual syndrome (HMDB: HMDB0003073)
Anti prostatitic (HMDB: HMDB0003073)
Anti Raynaud's (HMDB: HMDB0003073)
Hypocholesterolemic (HMDB: HMDB0003073)
Hypotensive (HMDB: HMDB0003073)

Industrial application

Pharmaceutical industry

Antineoplastic agent

Antitumor (HMDB: HMDB0003073)

Biomarker

Isovaleric acidemia (MarkerDB: MDB00000409)

Vasodilator agent (HMDB: HMDB0003073)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.00025 g/L	ALOGPS
logP	6.59	ALOGPS
logP	6.06	ChemAxon
logS	-6	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	13	ChemAxon
Refractivity	89.64 m³·mol⁻¹	ChemAxon
Polarizability	33.97 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

FDB002943

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Gamma-Linolenic acid

METLIN ID

Not Available

PubChem Compound

92449664

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Gema H; Kavadia A; Dimou D; Tsagou V; Komaitis M; Aggelis G Production of gamma-linolenic acid by Cunninghamella echinulata cultivated on glucose and orange peel. Applied microbiology and biotechnology (2002), 58(3), 303-7.

Showing chemical card for gamma-Linolenic acid (CFc000001769)

MOL for CFc000001769 (gamma-Linolenic acid)

3D MOL for CFc000001769 (gamma-Linolenic acid)

3D SDF for CFc000001769 (gamma-Linolenic acid)

3D-SDF for CFc000001769 (gamma-Linolenic acid)

PDB for CFc000001769 (gamma-Linolenic acid)

3D PDB for CFc000001769 (gamma-Linolenic acid)

SMILES for CFc000001769 (gamma-Linolenic acid)

INCHI for CFc000001769 (gamma-Linolenic acid)

Structure for CFc000001769 (gamma-Linolenic acid)

3D Structure for CFc000001769 (gamma-Linolenic acid)