1.0 2010-04-08 22:05:35 UTC 2019-11-26 02:58:12 UTC FDB002943 Gamolenic acid A minor component of many animal lipids Although GLA is an n?6 fatty acid, a type of acid which is generally pro-inflammatory, it has anti-inflammatory properties. (See discussion at Essential fatty acid interactions: The paradox of dietary GLA.); An omega-6 fatty acid produced in the body as the delta 6-desaturase metabolite of linoleic acid. It is converted to dihomo-gamma-linolenic acid, a biosynthetic precursor of monoenoic prostaglandins such as PGE1. (From Merck Index, 11th ed) -- Pubchem; From GLA, the body forms dihomo-?-linolenic acid (DGLA). This is one of the body's three sources of eicosanoids (along with AA and EPA.) DGLA is the precursor of the prostaglandin PGH1, which in turn forms PGE1 and the thromboxane TXA1. PGE1 has a role in regulation of immune system function and is used as the medicine alprostadil. TXA1 modulates the pro-inflammatory properties of the thromboxane TXA2.; GLA is categorized as an n?6 (also called ??6 or omega-6) fatty acid, meaning that the first double bond on the methyl end (designated with n or ?) is the sixth bond. In physiological literature, GLA is designated as 18:3 (n?6). Chemically, GLA is a carboxylic acid with an 18-carbon chain and three cis double bonds. It is an isomer of ?-linolenic acid, which is the n?3 fatty acid found in flax seed.; The human body produces GLA from linoleic acid (LA). This reaction is catalyzed by ?6-desaturase (D6D), an enzyme which allows the creation of a double bond on the sixth carbon counting from the carboxyl terminus. LA is consumed sufficiently in most diets, from such abundant sources as cooking oils and meats. However, a lack of GLA can occur when there is a reduction of the efficiency of the D6D conversion (for instance, as people grow older or when there are specific dietary deficiencies) or in disease states where there is excessive consumption of GLA metabolites.; ?-Linolenic acid (gamma-linolenic acid or GLA, sometimes called gamoleic acid) is a fatty acid found primarily in vegetable oils. It is sold as a dietary supplement for treating problems with inflammation and auto-immune diseases. The efficacy of such use is disputed. (6,9,12)-linolenate (6,9,12)-linolenic acid (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid (6Z,9Z,12Z)-Octadecatrienoate (6Z,9Z,12Z)-Octadecatrienoic acid (Z,Z,Z)-6,9,12-Octadecatrienoate (Z,Z,Z)-6,9,12-Octadecatrienoic acid &laquo;gamma&raquo;-linolenic acid 18:3 (N-6) 6-cis,9-cis,12-cis-Octadecatrienoate 6-cis,9-cis,12-cis-Octadecatrienoic acid 6,9,12-all-cis-Octadecatrienoate 6,9,12-all-cis-Octadecatrienoic acid 6,9,12-Octadecatrienoate 6,9,12-Octadecatrienoic acid 6,9,12-Octadecatrienoic acid, (6Z,9Z,12Z)- 6,9,12-Octadecatrienoic acid, (Z,Z,Z)- 6(Z),9(Z),12(Z)-Octadecatrienoate 6(Z),9(Z),12(Z)-Octadecatrienoic acid 6Z,9Z,12Z-octadecatrienoate 6Z,9Z,12Z-octadecatrienoic acid Acido gamolenico Acidum gamolenicum all-cis-6,9,12-octadecatrienoate all-cis-6,9,12-octadecatrienoic acid C18:3 (N-6) C18:3, N-6,9,12 all-cis cis-6, cis-9, cis-12-octadecatrienoic acid cis-6,cis-9,cis-12-Octadecatrienoic acid cis-Delta(6,9,12)-octadecatrienoate cis-Delta(6,9,12)-octadecatrienoic acid cis-δ(6,9,12)-octadecatrienoate cis-δ(6,9,12)-octadecatrienoic acid cis,cis,cis-6,9,12-Octadecatrienoic acid Efamast Efemast Efomase Epogam g-Linolenate g-Linolenic acid g-Linolensaeure Gamma-linolenate Gamma-linolenic acid gamma-Linolensaeure Gamma-llnolenic acid Gammalinolenic acid Gammolin Gamoleate Gamoleic acid Gamolenate Gamolenic acid Gamolenic acid (inn) Gamolenic acid [inn:ban] Gamolenic acid, BAN, INN GLA Ligla Octadeca-6,9,12-triensaeure Unigam Viacutan γ-linolenate γ-linolenic acid γ-linolensaeure C18H30O2 278.4296 278.224580204 (6Z,9E,12Z)-octadeca-6,9,12-trienoic acid (6Z,9E,12Z)-octadeca-6,9,12-trienoic acid 506-26-3 CCCCC\C=C/C\C=C\C\C=C/CCCCC(O)=O 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- VZCCETWTMQHEPK-XQYVMNDBSA-N 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. Lineolic acids and derivatives Organic compounds Lipids and lipid-like molecules Fatty Acyls Lineolic acids and derivatives Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Long-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Straight chain fatty acids Unsaturated fatty acids Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Fatty acid Hydrocarbon derivative Long-chain fatty acid Monocarboxylic acid or derivatives Octadecanoid Organic oxide Organic oxygen compound Organooxygen compound Straight chain fatty acid Unsaturated fatty acid Solid logp 6.59 ALOGPS logs -6.04 ALOGPS solubility 2.54e-04 g/l ALOGPS logp 6.06 ChemAxon pka_strongest_acidic 4.92 ChemAxon iupac (6Z,9E,12Z)-octadeca-6,9,12-trienoic acid ChemAxon average_mass 278.4296 ChemAxon mono_mass 278.224580204 ChemAxon smiles CCCCC\C=C/C\C=C\C\C=C/CCCCC(O)=O ChemAxon formula C18H30O2 ChemAxon inchi 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- ChemAxon inchikey VZCCETWTMQHEPK-XQYVMNDBSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 89.64 ChemAxon polarizability 33.97 ChemAxon rotatable_bond_count 13 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Alpha Linolenic Acid and Linoleic Acid Metabolism SMP00018 map00592 HMDB03073 28661 #<Reference:0x000055ce3185ab60> #<Reference:0x000055ce3185a958> #<Reference:0x000055ce3185a7a0> #<Reference:0x000055ce3185a5e8> #<Reference:0x000055ce3185a430> #<Reference:0x000055ce3185a278> #<Reference:0x000055ce3185a0c0> #<Reference:0x000055ce31859f08> #<Reference:0x000055ce31859d50> #<Reference:0x000055ce31859b98> #<Reference:0x000055ce318599e0> Alaska pollock Type 1 specific Theragra chalcogramma 1042646 0.0 0.0 0.0 mg/100 g Allium Type 1 specific Allium 4678 0.0 0.0 0.0 mg/100 g Almond Type 1 specific Prunus dulcis 3755 0.0 0.0 0.0 mg/100 g Amaranth Type 1 specific Amaranthus 3564 0.0 0.0 0.0 mg/100 g American lobster Type 1 specific Homarus americanus 6706 0.0 0.0 0.0 mg/100 g Arabica coffee Type 1 specific Coffea arabica 13443 0.0 0.0 0.0 mg/100 g Arepa Type 2 specific 2.0 2.0 2.0 mg/100 g Atlantic salmon Type 1 specific Salmo salar 8030 20.0 20.0 20.0 mg/100 g Avocado Type 1 specific Persea americana 3435 15.0 15.0 15.0 mg/100 g Bagel Type 2 specific 0.0 0.0 0.0 mg/100 g Baked beans Type 2 specific 0.0 0.0 0.0 mg/100 g Bean Type 1 specific 0.0 0.0 0.0 mg/100 g Biscuit Type 2 specific 4.166667 20.0 0.0 mg/100 g Bivalvia (Clam, Mussel, Oyster) Type 1 specific Bivalvia 6544 0.0 0.0 0.0 mg/100 g Black walnut Type 1 specific Juglans nigra 16719 0.0 0.0 0.0 mg/100 g Blackcurrant Type 1 specific Ribes nigrum 78511 11136.25 17000.0 5272.5 mg/100 g Blue crab Type 1 specific Callinectes sapidus 6763 0.0 0.0 0.0 mg/100 g Borage Type 1 specific Borago officinalis 13363 21716.666667 24900.0 19000.0 mg/100 g Brazil nut Type 1 specific Bertholletia excelsa 3645 17.0 17.0 17.0 mg/100 g Breakfast cereal Type 2 specific 0.0 0.0 0.0 mg/100 g Breakfast sandwich Type 2 specific 0.0 0.0 0.0 mg/100 g Broccoli Type 1 specific Brassica oleracea var. italica 36774 0.0 0.0 0.0 mg/100 g Burrito Type 2 specific 0.666667 1.0 0.0 mg/100 g Cake Type 2 specific 22.5 37.0 0.0 mg/100 g Candy bar Type 2 specific 0.0 0.0 0.0 mg/100 g Canola Type 2 specific 138011 0.0 0.0 0.0 mg/100 g Carrot Type 1 specific Daucus carota ssp. sativus 79200 120.5 120.5 120.5 mg/100 g Catfish Type 1 specific Siluriformes 7995 13.0 13.0 13.0 mg/100 g Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 9.260274 33.0 0.0 mg/100 g Cauliflower Type 1 specific Brassica oleracea var. botrytis 3715 0.0 0.0 0.0 mg/100 g Channel catfish Type 1 specific Ictalurus punctatus 7998 18.0 18.0 18.0 mg/100 g Cheese Type 2 specific 3.222222 9.0 0.0 mg/100 g Cherimoya Type 1 specific Annona cherimola 49314 0.0 0.0 0.0 mg/100 g Chili Type 2 specific 0.5 1.0 0.0 mg/100 g Chinese cinnamon Type 1 specific Cinnamomum aromaticum 119260 0.0 0.0 0.0 mg/100 g Chocolate Type 2 specific 0.0 0.0 0.0 mg/100 g Coconut Type 1 specific Cocos nucifera 13894 0.0 0.0 0.0 mg/100 g Coffee Type 1 generic Coffea 13442 0.0 0.0 0.0 mg/100 g Cold cut Type 2 specific 0.0 0.0 0.0 mg/100 g Common bean Type 1 specific Phaseolus vulgaris 3885 6.0 53.0 0.0 mg/100 g Common grape Type 1 specific Vitis vinifera 29760 1.0 1.0 1.0 mg/100 g Common mushroom Type 1 specific Agaricus bisporus 5341 0.0 0.0 0.0 mg/100 g Common oregano Type 1 specific Origanum vulgare 39352 0.0 0.0 0.0 mg/100 g Cooking oil Type 2 specific 0.0 0.0 0.0 mg/100 g Corn Type 1 specific Zea mays 4577 0.076923 1.0 0.0 mg/100 g Corn chip Type 2 specific 0.0 0.0 0.0 mg/100 g Cracker Type 2 specific 12.5 39.0 0.0 mg/100 g Cream Type 2 specific 18.0 18.0 18.0 mg/100 g Cucurbita Type 1 specific Cucurbita 3660 0.0 0.0 0.0 mg/100 g Date Type 1 specific Phoenix dactylifera 42345 0.0 0.0 0.0 mg/100 g Deer Type 1 specific Cervidae 9850 0.833333 4.0 0.0 mg/100 g Domestic pig Type 1 specific Sus scrofa domestica 9825 1.044776 24.0 0.0 mg/100 g Dulce de leche Type 2 specific 2.0 2.0 2.0 mg/100 g Eastern oyster Type 1 specific Crassostrea virginica 6565 4.0 4.0 4.0 mg/100 g Edible shell Type 2 specific 0.0 0.0 0.0 mg/100 g Egg roll Type 2 specific 20.0 20.0 20.0 mg/100 g Eggs Unknown generic 15.0 22.0 11.0 mg/100 g Empanada Type 2 specific 3.0 3.0 3.0 mg/100 g European plum Type 1 specific Prunus domestica 3758 0.0 0.0 0.0 mg/100 g Evening primrose Type 1 specific Oenothera biennis 3942 2673.0 2673.0 2673.0 mg/100 g Feijoa Type 1 specific Feijoa sellowiana 260130 0.0 0.0 0.0 mg/100 g Flatfish Type 1 specific Pleuronectiformes 8252 1.0 1.0 1.0 mg/100 g Flaxseed Type 1 specific Linum usitatissimum 4006 0.0 0.0 0.0 mg/100 g French plantain Type 1 specific Musa X paradisiaca 89151 2.0 3.0 1.0 mg/100 g French toast Type 2 specific 0.0 0.0 0.0 mg/100 g Fruit juice Type 2 specific 0.0 0.0 0.0 mg/100 g Frybread Type 2 specific 2.0 4.0 0.0 mg/100 g Garlic Type 1 specific Allium sativum 4682 0.0 0.0 0.0 mg/100 g Ginger Type 1 specific Zingiber officinale 94328 0.0 0.0 0.0 mg/100 g Gooseberry Type 1 specific Ribes uva-crispa 135518 Green zucchini Type 1 specific Cucurbita pepo var. cylindrica 0.0 0.0 0.0 mg/100 g Haddock Type 1 specific Melanogrammus aeglefinus 8056 0.0 0.0 0.0 mg/100 g Hamburger Type 2 specific 0.0 0.0 0.0 mg/100 g Hippoglossus (Common halibut) Type 1 specific Hippoglossus 8266 0.0 0.0 0.0 mg/100 g Honey Type 2 specific 0.0 0.0 0.0 mg/100 g Horchata Type 2 specific 0.0 0.0 0.0 mg/100 g Hushpuppy Type 2 specific 1.0 1.0 1.0 mg/100 g Jackfruit Type 1 specific Artocarpus heterophyllus 3489 0.0 0.0 0.0 mg/100 g Japanese pumpkin Type 1 specific Cucurbita maxima 3661 0.0 0.0 0.0 mg/100 g Kiwi Type 1 specific Actinidia chinensis 3625 9.0 9.0 9.0 mg/100 g Lemon Type 1 specific Citrus limon 2708 0.0 0.0 0.0 mg/100 g Macaroni and cheese Type 2 specific 1.166667 2.0 1.0 mg/100 g Mamey sapote Type 1 specific Pouteria sapota 233744 0.0 0.0 0.0 mg/100 g Margarine Type 2 specific 229.571429 590.0 60.0 mg/100 g Margarine-like spread Type 2 specific 59.888889 171.0 14.0 mg/100 g Milk (Cow) Type 2 specific 2765.5065 2837.338 2693.675 uM Milkshake Type 2 specific 3.0 3.0 3.0 mg/100 g Millet Type 1 specific Panicum miliaceum 4540 0.0 0.0 0.0 mg/100 g Mixed nuts Type 2 specific 0.0 0.0 0.0 mg/100 g Morchella (Morel) Type 1 specific Morchellaceae 5192 0.0 0.0 0.0 mg/100 g Nutritional drink Type 2 specific 0.0 0.0 0.0 mg/100 g Opium poppy Type 1 specific Papaver somniferum 3469 0.0 0.0 0.0 mg/100 g Oriental wheat Type 1 specific Triticum turanicum 376534 0.0 0.0 0.0 mg/100 g Other bread Type 2 specific 16.8 55.0 0.0 mg/100 g Other candy Type 2 specific 0.0 0.0 0.0 mg/100 g Other dish Type 2 specific 1.684211 6.0 0.0 mg/100 g Other fish product Type 2 specific 0.0 0.0 0.0 mg/100 g Other pasta dish Type 2 specific 0.0 0.0 0.0 mg/100 g Other sandwich Type 2 specific 2.0 2.0 2.0 mg/100 g Other snack food Type 2 specific 0.0 0.0 0.0 mg/100 g Other soy product Type 2 specific 0.0 0.0 0.0 mg/100 g Pacific cod Type 1 specific Gadus macrocephalus 80720 0.0 0.0 0.0 mg/100 g Pacific rockfish Type 1 specific Sebastes 34820 1.0 1.0 1.0 mg/100 g Painted comber Type 1 specific Serranus scriba 349661 1.0 1.0 1.0 mg/100 g Pan dulce Type 2 specific 1.0 1.0 1.0 mg/100 g Pancake Type 2 specific 3.5 7.0 0.0 mg/100 g Papaya Type 1 specific Carica papaya 3649 0.0 0.0 0.0 mg/100 g Parsley Type 1 specific Petroselinum crispum 4043 16.0 16.0 16.0 mg/100 g Pasta Type 2 specific 0.307692 4.0 0.0 mg/100 g Pastry Type 2 specific 0.0 0.0 0.0 mg/100 g Peanut Type 1 specific Arachis hypogaea 3818 14.333333 38.0 0.0 mg/100 g Pepper Type 1 specific Capsicum annuum 4072 4.666667 14.0 0.0 mg/100 g Pepper (Spice) Type 1 specific Piper nigrum 13216 0.0 0.0 0.0 mg/100 g Pie crust Type 2 specific 0.0 0.0 0.0 mg/100 g Piki bread Type 2 specific 0.0 0.0 0.0 mg/100 g Pine nut Type 1 specific Pinus 3337 52.0 52.0 52.0 mg/100 g Pink salmon Type 1 specific Oncorhynchus gorbuscha 8017 3.0 4.0 2.0 mg/100 g Pizza Type 2 specific 2.490196 6.0 0.0 mg/100 g Popcorn Type 2 specific 0.0 0.0 0.0 mg/100 g Potato Type 1 specific Solanum tuberosum 4113 0.52381 9.0 0.0 mg/100 g Potato chip Type 2 specific 0.0 0.0 0.0 mg/100 g Potato puffs Type 2 specific 0.0 0.0 0.0 mg/100 g Processed cheese Type 2 specific 8.0 43.0 1.0 mg/100 g Pudding Type 2 specific 0.0 0.0 0.0 mg/100 g Pupusa Type 2 specific 2.666667 4.0 1.0 mg/100 g Quesadilla Type 2 specific 4.0 4.0 4.0 mg/100 g Rainbow trout Type 1 specific Oncorhynchus mykiss 8022 2.666667 8.0 0.0 mg/100 g Ravioli Type 2 specific 0.5 1.0 0.0 mg/100 g Robusta coffee Type 1 specific Coffea canephora 49390 0.0 0.0 0.0 mg/100 g Salad Type 2 specific 18.0 27.0 1.0 mg/100 g Salad dressing Type 2 specific 0.0 0.0 0.0 mg/100 g Sauce Type 2 specific 0.0 0.0 0.0 mg/100 g Sausage Type 2 specific 9.47619 50.0 0.0 mg/100 g Scallop Type 1 specific Pectinidae 6566 0.0 0.0 0.0 mg/100 g Shrimp Type 1 specific Caridea 6694 0.75 4.0 0.0 mg/100 g Snack bar Type 2 specific 1.0 4.0 0.0 mg/100 g Sockeye salmon Type 1 specific Oncorhynchus nerka 8023 4.5 5.0 4.0 mg/100 g Sorghum Type 1 specific Sorghum bicolor 4558 0.0 0.0 0.0 mg/100 g Soup Type 2 specific 0.0 0.0 0.0 mg/100 g Soy bean Type 1 specific Glycine max 3847 0.0 0.0 0.0 mg/100 g Spelt Type 1 specific Triticum spelta 58933 0.0 0.0 0.0 mg/100 g Stew Type 2 specific 4.8 8.0 0.0 mg/100 g Sunburst squash (pattypan squash) Type 1 specific Cucurbita pepo var. clypeata 0.0 0.0 0.0 mg/100 g Sunflower Type 1 specific Helianthus annuus 4232 3.0 6.0 0.0 mg/100 g Sweet basil Type 1 specific Ocimum basilicum 39350 4.0 4.0 4.0 mg/100 g Swordfish Type 1 specific Xiphias gladius 8245 1.0 1.0 1.0 mg/100 g Syrup Type 2 specific 0.0 0.0 0.0 mg/100 g Taco Type 2 specific 2.666667 4.0 2.0 mg/100 g Taco shell Type 2 0.0 0.0 0.0 mg/100 g Tamale Type 2 specific 1.25 3.0 0.0 mg/100 g Teff Type 1 specific Eragrostis tef 110835 0.0 0.0 0.0 mg/100 g Tortilla Type 2 specific 0.0 0.0 0.0 mg/100 g Tortilla chip Type 2 specific 0.0 0.0 0.0 mg/100 g Tostada shell Type 2 0.0 0.0 0.0 mg/100 g Vegetarian food Type 2 specific 0.0 0.0 0.0 mg/100 g Waffle Type 2 specific 1.333333 5.0 0.0 mg/100 g Wheat bread Type 2 specific 0.0 0.0 0.0 mg/100 g White bread Type 1 16.8 55.0 0.0 mg/100 g White mustard Type 1 specific Sinapis alba 3728 0.0 0.0 0.0 mg/100 g Wild carrot Type 1 specific Daucus carota 4039 120.5 120.5 120.5 mg/100 g Yellow pond-lily Type 1 specific Nuphar lutea 77113 0.0 0.0 0.0 mg/100 g Yellow zucchini Type 1 specific Cucurbita pepo var. cylindrica 0.0 0.0 0.0 mg/100 g Yellowfin tuna Type 1 specific Thunnus albacares 8236 0.0 0.0 0.0 mg/100 g Acyl-coenzyme A thioesterase 1 Q86TX2 ACOT1 Acyl-coenzyme A thioesterase 2, mitochondrial P49753 ACOT2 Acyl-coenzyme A thioesterase 4 Q8N9L9 ACOT4 Acyl-coenzyme A thioesterase 8 O14734 ACOT8 Bile acid-CoA:amino acid N-acyltransferase Q14032 BAAT Cytosolic acyl coenzyme A thioester hydrolase O00154 ACOT7 Alpha-reductase inhibitor 46 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. Anti asphyctic 132 Anti eczemic 247 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti hypercholesterolemic 342 Anti monosodium-glutamate 448 Anti premenstrual syndrome 534 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti Raynaud's 573 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti-acne 78 A drug used to treat or prevent skin disorders or for the routine care of skin. Anti-aggregant 94 Anti-alcoholic 98 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti-arthritic 131 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti-atherosclerotic 138 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres. Anti-menorrhagic 430 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti-obesity 486 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti-prostatitic 553 Antitumor 672 A substance that inhibits or prevents the proliferation of neoplasms. Hypocholesterolemic 1016 Hypotensive 1021 Immunomodulator 1031 Biologically active substance whose activity affects or plays a role in the functioning of the immune system. Vasodilator 1413 A drug used to cause dilation of the blood vessels.