NCBI Taxonomy: 8399
Rana (ncbi_taxid: 8399)
found 19 associated metabolites at genus taxonomy rank level.
Ancestor: Ranidae
Child Taxonomies: Rana, Aquarana, Pantherana, Trypheropsis, unclassified Rana, Rana incertae sedis
linolenate(18:3)
alpha-Linolenic acid (ALA) is a polyunsaturated fatty acid (PUFA). It is a member of the group of essential fatty acids called omega-3 fatty acids. alpha-Linolenic acid, in particular, is not synthesized by mammals and therefore is an essential dietary requirement for all mammals. Certain nuts (English walnuts) and vegetable oils (canola, soybean, flaxseed/linseed, olive) are particularly rich in alpha-linolenic acid. Omega-3 fatty acids get their name based on the location of one of their first double bond. In all omega-3 fatty acids, the first double bond is located between the third and fourth carbon atom counting from the methyl end of the fatty acid (n-3). Although humans and other mammals can synthesize saturated and some monounsaturated fatty acids from carbon groups in carbohydrates and proteins, they lack the enzymes necessary to insert a cis double bond at the n-6 or the n-3 position of a fatty acid. Omega-3 fatty acids like alpha-linolenic acid are important structural components of cell membranes. When incorporated into phospholipids, they affect cell membrane properties such as fluidity, flexibility, permeability, and the activity of membrane-bound enzymes. Omega-3 fatty acids can modulate the expression of a number of genes, including those involved with fatty acid metabolism and inflammation. alpha-Linolenic acid and other omega-3 fatty acids may regulate gene expression by interacting with specific transcription factors, including peroxisome proliferator-activated receptors (PPARs) and liver X receptors (LXRs). alpha-Linolenic acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism. α-Linolenic acid can be obtained by humans only through their diets. Humans lack the desaturase enzymes required for processing stearic acid into A-linoleic acid or other unsaturated fatty acids. Dietary α-linolenic acid is metabolized to stearidonic acid, a precursor to a collection of polyunsaturated 20-, 22-, 24-, etc fatty acids (eicosatetraenoic acid, eicosapentaenoic acid, docosapentaenoic acid, tetracosapentaenoic acid, 6,9,12,15,18,21-tetracosahexaenoic acid, docosahexaenoic acid).[12] Because the efficacy of n−3 long-chain polyunsaturated fatty acid (LC-PUFA) synthesis decreases down the cascade of α-linolenic acid conversion, DHA synthesis from α-linolenic acid is even more restricted than that of EPA.[13] Conversion of ALA to DHA is higher in women than in men.[14] α-Linolenic acid, also known as alpha-linolenic acid (ALA) (from Greek alpha meaning "first" and linon meaning flax), is an n−3, or omega-3, essential fatty acid. ALA is found in many seeds and oils, including flaxseed, walnuts, chia, hemp, and many common vegetable oils. In terms of its structure, it is named all-cis-9,12,15-octadecatrienoic acid.[2] In physiological literature, it is listed by its lipid number, 18:3 (n−3). It is a carboxylic acid with an 18-carbon chain and three cis double bonds. The first double bond is located at the third carbon from the methyl end of the fatty acid chain, known as the n end. Thus, α-linolenic acid is a polyunsaturated n−3 (omega-3) fatty acid. It is a regioisomer of gamma-linolenic acid (GLA), an 18:3 (n−6) fatty acid (i.e., a polyunsaturated omega-6 fatty acid with three double bonds). Alpha-linolenic acid is a linolenic acid with cis-double bonds at positions 9, 12 and 15. Shown to have an antithrombotic effect. It has a role as a micronutrient, a nutraceutical and a mouse metabolite. It is an omega-3 fatty acid and a linolenic acid. It is a conjugate acid of an alpha-linolenate and a (9Z,12Z,15Z)-octadeca-9,12,15-trienoate. Alpha-linolenic acid (ALA) is a polyunsaturated omega-3 fatty acid. It is a component of many common vegetable oils and is important to human nutrition. alpha-Linolenic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Linolenic Acid is a natural product found in Prunus mume, Dipteryx lacunifera, and other organisms with data available. Linolenic Acid is an essential fatty acid belonging to the omega-3 fatty acids group. It is highly concentrated in certain plant oils and has been reported to inhibit the synthesis of prostaglandin resulting in reduced inflammation and prevention of certain chronic diseases. Alpha-linolenic acid (ALA) is a polyunsaturated omega-3 fatty acid. It is a component of many common vegetable oils and is important to human nutrition. A fatty acid that is found in plants and involved in the formation of prostaglandins. Seed oils are the richest sources of α-linolenic acid, notably those of hempseed, chia, perilla, flaxseed (linseed oil), rapeseed (canola), and soybeans. α-Linolenic acid is also obtained from the thylakoid membranes in the leaves of Pisum sativum (pea leaves).[3] Plant chloroplasts consisting of more than 95 percent of photosynthetic thylakoid membranes are highly fluid due to the large abundance of ALA, evident as sharp resonances in high-resolution carbon-13 NMR spectra.[4] Some studies state that ALA remains stable during processing and cooking.[5] However, other studies state that ALA might not be suitable for baking as it will polymerize with itself, a feature exploited in paint with transition metal catalysts. Some ALA may also oxidize at baking temperatures. Gamma-linolenic acid (γ-Linolenic acid) is an omega-6 (n-6), 18 carbon (18C-) polyunsaturated fatty acid (PUFA) extracted from Perilla frutescens. Gamma-linolenic acid supplements could restore needed PUFAs and mitigate the disease[1]. Gamma-linolenic acid (γ-Linolenic acid) is an omega-6 (n-6), 18 carbon (18C-) polyunsaturated fatty acid (PUFA) extracted from Perilla frutescens. Gamma-linolenic acid supplements could restore needed PUFAs and mitigate the disease[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1].
Retinal
A carotenoid constituent of visual pigments. It is the oxidized form of retinol which functions as the active component of the visual cycle. It is bound to the protein opsin forming the complex rhodopsin. When stimulated by visible light, the retinal component of the rhodopsin complex undergoes isomerization at the 11-position of the double bond to the cis-form; this is reversed in "dark" reactions to return to the native trans-configuration. [HMDB]. Retinal is found in many foods, some of which are flaxseed, pepper (c. baccatum), climbing bean, and other soy product. Retinal is a carotenoid constituent of visual pigments. It is the oxidized form of retinol which functions as the active component of the visual cycle. It is bound to the protein opsin forming the complex rhodopsin. When stimulated by visible light, the retinal component of the rhodopsin complex undergoes isomerization at the 11-position of the double bond to the cis-form; this is reversed in "dark" reactions to return to the native trans-configuration. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids CONFIDENCE standard compound; INTERNAL_ID 142
7-Ketocholesterol
7-Ketocholesterol is a major oxidation product of cholesterol (oxysterol) found in human atherosclerotic plaque and is more atherogenic than cholesterol in some animal studies. Oxysterols (oxygenated forms of cholesterol) are present at low levels in the circulation and accumulate is plasma and tissues in some pathologies. In atherosclerotic lesions, 7-oxygenated oxysterols, predominantly 7-ketocholesterol, accumulate and have been implicated in the pathology of the disease. There is some in vivo and in vitro evidence that sterol 27-hydroxylase acts on 7-ketocholesterol to initiate its degradation to more polar, water-soluble products. Recent studies indicate an alternative mechanism, in which 7-ketocholesterol is reduced to 7 beta-hydroxycholesterol by 11 beta-hydroxysteroid dehydrogenase type 1. 7-Ketocholesterol can inhibit cholesterol 7 alpha-hydroxylase, the rate-limiting step in bile acid biosynthesis, as well as strongly inhibiting HMG-CoA reductase, the rate-limiting enzyme in cholesterol biosynthesis. It has even been suggested that 7-ketocholesterol is formed enzymically as an endogenous regulator of cholesterol biosynthesis. However, when tested as a pharmacological cholesterol-lowering agent, inhibition of HMG-CoA reductase was rapidly overcome and the 7-ketocholesterol metabolised. In vitro, 7-ketocholesterol has wide-ranging and potent effects, most of which have the potential to contribute to atherosclerosis. For example, 7-ketocholesterol can be cytotoxic and can induce apoptosis in vascular cells. These effects, either individually or more likely, in combination, all implicate 7-ketocholesterol in the initiation and development of atherosclerosis, but further work is needed to establish whether or not its role is a direct causal one. 7-Ketocholesterol is the second most abundant oxysterol found in human atherosclerotic plaque, after the enzymically formed 27-hydroxycholesterol (cholest-5-ene-3beta,27-diol). 7-Ketocholesterol differs from cholesterol by a ketone functional group present at the 7-position. It is produced from cholesterol via the epimeric cholesterol 7-hydroperoxides (cholest-5-ene-3beta-ol-7-hydroperoxide) which decompose to the epimeric 7-hydroxycholesterols (cholest-5-ene-3beta,7-diol) and 7-ketocholesterol. 7-Ketocholesterol is a major dietary oxysterol. It has also been widely suggested that 7-ketocholesterol present in atherosclerotic tissue may be derived from the diet. Certainly, 7-ketocholesterol is a major oxysterol found in cholesterol-rich processed foodstuffs. Dietary 7-ketocholesterol is rapidly metabolised by the liver to 7beta-hydroxycholesterol (cholest-5-ene-3beta,7beta-diol), unusual bile acids and perhaps even cholesterol itself. Its conversion to 7beta-hydroxycholesterol is well documented. (PMID: 15798369, 10224662). 7-Ketocholesterol is a major oxidation product of cholesterol (oxysterol) found in human atherosclerotic plaque and is more atherogenic than cholesterol in some animal studies. Oxysterols (oxygenated forms of cholesterol) are present at low levels in the circulation and accumulate is plasma and tissues in some pathologies. In atherosclerotic lesions, 7-oxygenated oxysterols, predominantly 7-ketocholesterol, accumulate and have been implicated in the pathology of the disease. There is some in vivo and in vitro evidence that sterol 27-hydroxylase acts on 7-ketocholesterol to initiate its degradation to more polar, water-soluble products. Recent studies indicate an alternative mechanism, in which 7-ketocholesterol is reduced to 7 beta-hydroxycholesterol by 11 beta-hydroxysteroid dehydrogenase type 1. 7-Ketocholesterol, toxic oxysterol, inhibits the rate-limiting step in bile acid biosynthesis cholesterol 7 alpha-hydroxylase, as well as strongly inhibiting HMG-CoA reductase (the rate-limiting enzyme in cholesterol biosynthesis). 7-Ketocholesterol induces cell apoptosis[1].
7-KETOCHOLESTEROL
A cholestanoid that consists of cholesterol bearing an oxo substituent at position 7. D004791 - Enzyme Inhibitors 7-Ketocholesterol, toxic oxysterol, inhibits the rate-limiting step in bile acid biosynthesis cholesterol 7 alpha-hydroxylase, as well as strongly inhibiting HMG-CoA reductase (the rate-limiting enzyme in cholesterol biosynthesis). 7-Ketocholesterol induces cell apoptosis[1].
α-Linolenic acid
α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1].
linoleic
Linolelaidic acid (Linoelaidic acid), an omega-6 trans fatty acid, acts as a source of energy. Linolelaidic acid is an essential nutrient, adding in enteral, parenteral, and infant formulas. Linolelaidic acid can be used for heart diseases research[1]. Linolelaidic acid (Linoelaidic acid), an omega-6 trans fatty acid, acts as a source of energy. Linolelaidic acid is an essential nutrient, adding in enteral, parenteral, and infant formulas. Linolelaidic acid can be used for heart diseases research[1].
(1r)-4-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-18-[(4r)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-2-en-1-ol
(2s)-2-{[(2s)-2-({[(2r)-1-[(2s)-2-{[(2s)-2-{[2-({[(2s)-1-[(2s)-1-[(2s)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-1-hydroxyethylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-3-hydroxypropanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-1-hydroxy-3-phenylpropylidene]amino}-5-carbamimidamidopentanoic acid
C50H73N15O11 (1059.5613707999998)
(3s)-3-{[(2s)-2-{[(2s)-6-amino-2-{[(2s)-2-amino-1-hydroxy-3-(4-hydroxyphenyl)propylidene]amino}-1-hydroxyhexylidene]amino}-1,3-dihydroxypropylidene]amino}-3-{[(1s)-2-hydroxy-1-{[(1s)-1-{[(1s)-1-[({[(1s)-1-{[(1s)-1-(c-hydroxycarbonimidoyl)-3-(methylsulfanyl)propyl]-c-hydroxycarbonimidoyl}-3-methylbutyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-2-(4-hydroxyphenyl)ethyl]-c-hydroxycarbonimidoyl}-2-phenylethyl]-c-hydroxycarbonimidoyl}ethyl]-c-hydroxycarbonimidoyl}propanoic acid
(2s,3s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-({[(2s)-1-[(2s)-2-{[(2s)-2-amino-1-hydroxy-3-(3h-imidazol-4-yl)propylidene]amino}-3-(c-hydroxycarbonimidoyl)propanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-1-hydroxypropylidene]amino}-1,3-dihydroxypropylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-n-({[(1s)-1-{[(1s)-1-(c-hydroxycarbonimidoyl)-3-(methylsulfanyl)propyl]-c-hydroxycarbonimidoyl}-3-methylbutyl]-c-hydroxycarbonimidoyl}methyl)-3-methylpentanimidic acid
9a,11a-dimethyl-1-(6-methylheptan-2-yl)-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-4,7-diol
(3s)-3-{[(1s)-4-carbamimidamido-1-{[(1s)-1-{[(1s)-1-[({[(1s)-1-{[(1s)-1-(c-hydroxycarbonimidoyl)-3-(methylsulfanyl)propyl]-c-hydroxycarbonimidoyl}-3-methylbutyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-2-(4-hydroxyphenyl)ethyl]-c-hydroxycarbonimidoyl}-2-phenylethyl]-c-hydroxycarbonimidoyl}butyl]-c-hydroxycarbonimidoyl}-3-({[(2s)-1-[(2s)-2-({[(2s)-1-[(2s)-2,6-diaminohexanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-3-hydroxypropanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)propanoic acid
7-hydroxy-9a,11a-dimethyl-1-(6-methylheptan-2-yl)-1h,2h,3h,3ah,3bh,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-4-one
(2s)-2-{[(2s)-2-({[(2s)-1-[(2s)-2-{[(2s)-2-{[2-({[(2s)-1-[(2s)-1-[(2s)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-1-hydroxyethylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-3-hydroxypropanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-1-hydroxy-3-phenylpropylidene]amino}-5-carbamimidamidopentanoic acid
C50H73N15O11 (1059.5613707999998)
2-{[2-({[1-(2-{[2-({2-[({1-[1-(2-amino-5-carbamimidamidopentanoyl)pyrrolidine-2-carbonyl]pyrrolidin-2-yl}(hydroxy)methylidene)amino]-1-hydroxyethylidene}amino)-1-hydroxy-3-phenylpropylidene]amino}-3-hydroxypropanoyl)pyrrolidin-2-yl](hydroxy)methylidene}amino)-1-hydroxy-3-phenylpropylidene]amino}-5-carbamimidamidopentanoic acid
C50H73N15O11 (1059.5613707999998)
(2s)-2-{[(2s)-2-{[(2s)-6-amino-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-{[(2s,3r)-2-{[(2s,3s)-2-{[(2s)-2-({[(2s)-1-[(2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-3-phenylpropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-phenylpropanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-methylpentylidene]amino}-1,3-dihydroxybutylidene]amino}-1,3-dihydroxypropylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1,3-dihydroxypropylidene]amino}-1-hydroxyhexylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-4-methylpentanoic acid
(4r,7s,10s,13s,16s,19s,22r)-22-{[(2s,3s)-2-{[(2s)-2-{[(2s)-2-({[(2s)-1-[(2s)-2-{[(2s,3s)-2-{[(2s)-6-amino-2-{[(2s,3s)-2-{[(2s)-2-({2-[(2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-3-phenylpropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxyethylidene)amino]-1-hydroxyethylidene}amino)-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-methylpentylidene]amino}-1-hydroxyhexylidene]amino}-1-hydroxy-3-methylpentylidene]amino}-3-methylbutanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-1-hydroxypropylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-1-hydroxy-3-methylpentylidene]amino}-7,10-bis(4-aminobutyl)-6,9,12,15,18,21-hexahydroxy-13-[(1r)-1-hydroxyethyl]-16-isopropyl-19-methyl-1,2-dithia-5,8,11,14,17,20-hexaazacyclotricosa-5,8,11,14,17,20-hexaene-4-carboxylic acid
C97H167N23O22S3 (2102.1817562)