NCBI Taxonomy: 4439

Plumbago (ncbi_taxid: 4439)

found 117 associated metabolites at genus taxonomy rank level.

Ancestor: Plumbaginaceae

Child Taxonomies: Plumbago auriculata, Plumbago indica, Plumbago caerulea, Plumbago europaea, Plumbago scandens, Plumbago zeylanica, Plumbago stenophylla, unclassified Plumbago (in: eudicots)

Lupenone

(1S,3aR,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-1-Isopropyl-3a,5a,5b,8,8,11a-hexamethyl-1,2,3,3a,4,5,5a,5b,6,7,7a,8,11a,11b,12,13,13a,13b-octadecahydro-9H-cyclopenta[a]chrysen-9-one

C30H48O (424.3705)


Lupenone is a triterpenoid. It has a role as a metabolite. It derives from a hydride of a lupane. Lupenone is a natural product found in Liatris acidota, Euphorbia larica, and other organisms with data available. A natural product found in Cupania cinerea. Lupenone, isolated from Musa basjoo, belongs to lupane type triterpenoids. Lupenone shows various pharmacological activities including anti-inflammatory, anti-virus, anti-diabetes, anti-cancer, improving Chagas disease without major toxicity[1][2]. Lupenone is an orally active lupine-type triterpenoid that can be isolated from Musa basjoo. Lupenone Lupenone plays a role through the PI3K/Akt/mTOR and NF-κB signaling pathways. Lupenone has anti-inflammatory, antiviral, antidiabetic and anticancer activities[1][2][3]. Lupenone, isolated from Musa basjoo, belongs to lupane type triterpenoids. Lupenone shows various pharmacological activities including anti-inflammatory, anti-virus, anti-diabetes, anti-cancer, improving Chagas disease without major toxicity[1][2].

   

4-Hydroxybenzaldehyde

4-hydroxybenzaldehyde

C7H6O2 (122.0368)


4-Hydroxybenzaldehyde, also known as 4-formylphenol or 4-hydroxybenzenecarbonal, belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group. A hydroxybenzaldehyde that is benzaldehyde substituted with a hydroxy group at position C-4. 4-Hydroxybenzaldehyde exists in all living organisms, ranging from bacteria to humans. 4-Hydroxybenzaldehyde is a sweet, almond, and balsam tasting compound. 4-Hydroxybenzaldehyde is found, on average, in the highest concentration within vinegars and oats. 4-Hydroxybenzaldehyde has also been detected, but not quantified, in several different foods, such as cardoons, colorado pinyons, oyster mushrooms, common chokecherries, and potato. This could make 4-hydroxybenzaldehyde a potential biomarker for the consumption of these foods. 4-hydroxybenzaldehyde is a hydroxybenzaldehyde that is benzaldehyde substituted with a hydroxy group at position C-4. It has a role as a plant metabolite, a mouse metabolite and an EC 1.14.17.1 (dopamine beta-monooxygenase) inhibitor. 4-Hydroxybenzaldehyde is a natural product found in Ficus septica, Visnea mocanera, and other organisms with data available. Occurs naturally combined in many glycosides. Constituent of vanillin. Isol. in free state from opium poppy (Papaver somniferum) A hydroxybenzaldehyde that is benzaldehyde substituted with a hydroxy group at position C-4. 4-Hydroxybenzaldehyde. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=123-08-0 (retrieved 2024-07-02) (CAS RN: 123-08-0). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations. p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations. p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations.

   

Campesterol

(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

C28H48O (400.3705)


Campesterol is a phytosterol, meaning it is a steroid derived from plants. As a food additive, phytosterols have cholesterol-lowering properties (reducing cholesterol absorption in intestines), and may act in cancer prevention. Phytosterols naturally occur in small amount in vegetable oils, especially soybean oil. One such phytosterol complex, isolated from vegetable oil, is cholestatin, composed of campesterol, stigmasterol, and brassicasterol, and is marketed as a dietary supplement. Sterols can reduce cholesterol in human subjects by up to 15\\\\\%. The mechanism behind phytosterols and the lowering of cholesterol occurs as follows : the incorporation of cholesterol into micelles in the gastrointestinal tract is inhibited, decreasing the overall amount of cholesterol absorbed. This may in turn help to control body total cholesterol levels, as well as modify HDL, LDL and TAG levels. Many margarines, butters, breakfast cereals and spreads are now enriched with phytosterols and marketed towards people with high cholesterol and a wish to lower it. -- Wikipedia. Campesterol is a member of phytosterols, a 3beta-sterol, a 3beta-hydroxy-Delta(5)-steroid and a C28-steroid. It has a role as a mouse metabolite. It derives from a hydride of a campestane. Campesterol is a natural product found in Haplophyllum bucharicum, Bugula neritina, and other organisms with data available. Campesterol is a steroid derivative that is the simplest sterol, characterized by the hydroxyl group in position C-3 of the steroid skeleton, and saturated bonds throughout the sterol structure, with the exception of the 5-6 double bond in the B ring. Campesterol. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=474-62-4 (retrieved 2024-07-01) (CAS RN: 474-62-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Campesterol is a plant sterol with cholesterol lowering and anticarcinogenic effects. Campesterol is a plant sterol with cholesterol lowering and anticarcinogenic effects.

   

Stigmasterol

(3S,8S,9S,10R,13R,14S,17R)-17-((2R,5S,E)-5-ethyl-6-methylhept-3-en-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

C29H48O (412.3705)


Stigmasterol is a phytosterol, meaning it is steroid derived from plants. As a food additive, phytosterols have cholesterol-lowering properties (reducing cholesterol absorption in intestines), and may act in cancer prevention. Phytosterols naturally occur in small amount in vegetable oils, especially soybean oil. One such phytosterol complex, isolated from vegetable oil, is cholestatin, composed of campesterol, stigmasterol, and brassicasterol, and is marketed as a dietary supplement. Sterols can reduce cholesterol in human subjects by up to 15\\%. The mechanism behind phytosterols and the lowering of cholesterol occurs as follows : the incorporation of cholesterol into micelles in the gastrointestinal tract is inhibited, decreasing the overall amount of cholesterol absorbed. This may in turn help to control body total cholesterol levels, as well as modify HDL, LDL and TAG levels. Many margarines, butters, breakfast cereals and spreads are now enriched with phytosterols and marketed towards people with high cholesterol and a wish to lower it. Stigmasterol is found to be associated with phytosterolemia, which is an inborn error of metabolism. Stigmasterol is a 3beta-sterol that consists of 3beta-hydroxystigmastane having double bonds at the 5,6- and 22,23-positions. It has a role as a plant metabolite. It is a 3beta-sterol, a stigmastane sterol, a 3beta-hydroxy-Delta(5)-steroid and a member of phytosterols. It derives from a hydride of a stigmastane. Stigmasterol is a natural product found in Ficus auriculata, Xylopia aromatica, and other organisms with data available. Stigmasterol is a steroid derivative characterized by the hydroxyl group in position C-3 of the steroid skeleton, and unsaturated bonds in position 5-6 of the B ring, and position 22-23 in the alkyl substituent. Stigmasterol is found in the fats and oils of soybean, calabar bean and rape seed, as well as several other vegetables, legumes, nuts, seeds, and unpasteurized milk. See also: Comfrey Root (part of); Saw Palmetto (part of); Plantago ovata seed (part of). Stigmasterol is an unsaturated plant sterol occurring in the plant fats or oils of soybean, calabar bean, and rape seed, and in a number of medicinal herbs, including the Chinese herbs Ophiopogon japonicus (Mai men dong) and American Ginseng. Stigmasterol is also found in various vegetables, legumes, nuts, seeds, and unpasteurized milk. A 3beta-sterol that consists of 3beta-hydroxystigmastane having double bonds at the 5,6- and 22,23-positions. C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol

   

beta-Sitosterol

(3S,8S,9S,10R,13R,14S,17R)-17-((2R,5R)-5-ethyl-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

C29H50O (414.3861)


beta-Sitosterol, a main dietary phytosterol found in plants, may have the potential for prevention and therapy for human cancer. Phytosterols are plant sterols found in foods such as oils, nuts, and vegetables. Phytosterols, in the same way as cholesterol, contain a double bond and are susceptible to oxidation, and are characterized by anti-carcinogenic and anti-atherogenic properties (PMID:13129445, 11432711). beta-Sitosterol is a phytopharmacological extract containing a mixture of phytosterols, with smaller amounts of other sterols, bonded with glucosides. These phytosterols are commonly derived from the South African star grass, Hypoxis rooperi, or from species of Pinus and Picea. The purported active constituent is termed beta-sitosterol. Additionally, the quantity of beta-sitosterol-beta-D-glucoside is often reported. Although the exact mechanism of action of beta-sitosterols is unknown, it may be related to cholesterol metabolism or anti-inflammatory effects (via interference with prostaglandin metabolism). Compared with placebo, beta-sitosterol improved urinary symptom scores and flow measures (PMID:10368239). A plant food-based diet modifies the serum beta-sitosterol concentration in hyperandrogenic postmenopausal women. This finding indicates that beta-sitosterol can be used as a biomarker of exposure in observational studies or as a compliance indicator in dietary intervention studies of cancer prevention (PMID:14652381). beta-Sitosterol induces apoptosis and activates key caspases in MDA-MB-231 human breast cancer cells (PMID:12579296). Sitosterol is a member of the class of phytosterols that is stigmast-5-ene substituted by a beta-hydroxy group at position 3. It has a role as a sterol methyltransferase inhibitor, an anticholesteremic drug, an antioxidant, a plant metabolite and a mouse metabolite. It is a 3beta-sterol, a stigmastane sterol, a 3beta-hydroxy-Delta(5)-steroid, a C29-steroid and a member of phytosterols. It derives from a hydride of a stigmastane. Active fraction of Solanum trilobatum; reduces side-effects of radiation-induced toxicity. Beta-Sitosterol is a natural product found in Elodea canadensis, Ophiopogon intermedius, and other organisms with data available. beta-Sitosterol is one of several phytosterols (plant sterols) with chemical structures similar to that of cholesterol. Sitosterols are white, waxy powders with a characteristic odor. They are hydrophobic and soluble in alcohols. beta-Sitosterol is found in many foods, some of which are ginseng, globe artichoke, sesbania flower, and common oregano. C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents D009676 - Noxae > D000963 - Antimetabolites Beta-Sitosterol (purity>98\\%) is a plant sterol. Beta-Sitosterol (purity>98\\%) interfere with multiple cell signaling pathways, including cell cycle, apoptosis, proliferation, survival, invasion, angiogenesis, metastasis and inflammation[1]. Beta-Sitosterol (purity>98\%) is a plant sterol. Beta-Sitosterol (purity>98\%) interfere with multiple cell signaling pathways, including cell cycle, apoptosis, proliferation, survival, invasion, angiogenesis, metastasis and inflammation[1].

   

beta-Sitosterol 3-O-beta-D-galactopyranoside

(2R,3R,4S,5S,6R)-2-(((3S,8S,9S,10R,13R,14S,17R)-17-((2R,5R)-5-Ethyl-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

C35H60O6 (576.439)


Daucosterol is a steroid saponin that is sitosterol attached to a beta-D-glucopyranosyl residue at position 3 via a glycosidic linkage. It has bee isolated from Panax japonicus var. major and Breynia fruticosa. It has a role as a plant metabolite. It is a steroid saponin, a beta-D-glucoside and a monosaccharide derivative. It is functionally related to a sitosterol. It derives from a hydride of a stigmastane. Sitogluside is a natural product found in Ophiopogon intermedius, Ophiopogon jaburan, and other organisms with data available. beta-Sitosterol 3-O-beta-D-galactopyranoside is found in herbs and spices. beta-Sitosterol 3-O-beta-D-galactopyranoside is a constituent of Hibiscus sabdariffa (roselle) leaves. C308 - Immunotherapeutic Agent Daucosterol is a natural sterol compound. Daucosterol is a natural sterol compound.

   

Lupeyl acetate

[(1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-1-isopropenyl-3a,5a,5b,8,8,11a-hexamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-yl] acetate

C32H52O2 (468.3967)


Lupeol acetate is an organic molecular entity. It has a role as a metabolite. Lupeol acetate is a natural product found in Euphorbia dracunculoides, Euphorbia larica, and other organisms with data available. Lupeol acetate, a derivative of Lupeol, suppresses the progression of rheumatoid arthritis (RA) by inhibiting the activation of macrophages and osteoclastogenesis through downregulations of TNF-α, IL-1β, MCP-1, COX-2, VEGF and granzyme B[1]. Lupeol acetate, a derivative of Lupeol, suppresses the progression of rheumatoid arthritis (RA) by inhibiting the activation of macrophages and osteoclastogenesis through downregulations of TNF-α, IL-1β, MCP-1, COX-2, VEGF and granzyme B[1].

   

Isoshinanolone

(3R,4R)-4,8-dihydroxy-3-methyl-1,2,3,4-tetrahydronaphthalen-1-one

C11H12O3 (192.0786)


Isoshinanolone is a member of tetralins. Isoshinanolone is a natural product found in Ancistrocladus heyneanus, Dioncophyllum thollonii, and other organisms with data available.

   
   

Lapachol

4-hydroxy-3-(3-methylbut-2-en-1-yl)-1,2-dihydronaphthalene-1,2-dione

C15H14O3 (242.0943)


Lapachol is a hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone substituted by hydroxy and 3-methylbut-2-en-1-yl groups at positions 2 and 3, respectively. It is a natural compound that exhibits antibacterial and anticancer properties, first isolated in 1882 from the bark of Tabebuia avellanedae. It has a role as a plant metabolite, an antineoplastic agent, an antibacterial agent and an anti-inflammatory agent. It is a hydroxy-1,4-naphthoquinone and an olefinic compound. NA is a natural product found in Plenckia populnea, Stereospermum colais, and other organisms with data available. A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone substituted by hydroxy and 3-methylbut-2-en-1-yl groups at positions 2 and 3, respectively. It is a natural compound that exhibits antibacterial and anticancer properties, first isolated in 1882 from the bark of Tabebuia avellanedae. D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000981 - Antiprotozoal Agents D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000871 - Anthelmintics D000890 - Anti-Infective Agents > D000935 - Antifungal Agents D000890 - Anti-Infective Agents > D000998 - Antiviral Agents D000970 - Antineoplastic Agents [Raw Data] CB290_Lapachol_pos_40eV_CB000086.txt [Raw Data] CB290_Lapachol_pos_50eV_CB000086.txt [Raw Data] CB290_Lapachol_pos_10eV_CB000086.txt [Raw Data] CB290_Lapachol_pos_30eV_CB000086.txt [Raw Data] CB290_Lapachol_pos_20eV_CB000086.txt [Raw Data] CB290_Lapachol_neg_10eV_000049.txt [Raw Data] CB290_Lapachol_neg_20eV_000049.txt [Raw Data] CB290_Lapachol_neg_40eV_000049.txt [Raw Data] CB290_Lapachol_neg_50eV_000049.txt [Raw Data] CB290_Lapachol_neg_30eV_000049.txt Lapachol is a naphthoquinone that was first isolated from Tabebuia avellanedae (Bignoniaceae)[1]. Lapachol shows anti-abscess, anti-ulcer, antileishmanial, anticarcinomic, antiedemic, anti-inflammatory, antimalarial, antiseptic, antitumor, antiviral, antibacterial, antifungal and pesticidal activities[2]. Lapachol is a naphthoquinone that was first isolated from Tabebuia avellanedae (Bignoniaceae)[1]. Lapachol shows anti-abscess, anti-ulcer, antileishmanial, anticarcinomic, antiedemic, anti-inflammatory, antimalarial, antiseptic, antitumor, antiviral, antibacterial, antifungal and pesticidal activities[2].

   

Myricitrin

5,7-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one

C21H20O12 (464.0955)


Myricitrin is a chemical compound. It can be isolated from the root bark of Myrica cerifera (Bayberry, a small tree native to North America). Myricetin 3-rhamnoside is found in many foods, some of which are common grape, black walnut, highbush blueberry, and lentils. Myricitrin is found in black walnut. Myricitrin is a chemical compound. It can be isolated from the root bark of Myrica cerifera (Bayberry, a small tree native to North America) Acquisition and generation of the data is financially supported in part by CREST/JST. [Raw Data] CB067_Myricitrin_pos_30eV_CB000029.txt [Raw Data] CB067_Myricitrin_pos_40eV_CB000029.txt [Raw Data] CB067_Myricitrin_pos_10eV_CB000029.txt [Raw Data] CB067_Myricitrin_pos_50eV_CB000029.txt [Raw Data] CB067_Myricitrin_pos_20eV_CB000029.txt [Raw Data] CB067_Myricitrin_neg_40eV_000020.txt [Raw Data] CB067_Myricitrin_neg_30eV_000020.txt [Raw Data] CB067_Myricitrin_neg_50eV_000020.txt [Raw Data] CB067_Myricitrin_neg_10eV_000020.txt [Raw Data] CB067_Myricitrin_neg_20eV_000020.txt Myricitrin is a major antioxidant flavonoid[1]. Myricitrin is a major antioxidant flavonoid[1].

   

Plumbagin

5-hydroxy-2-methyl-1,4-dihydronaphthalene-1,4-dione

C11H8O3 (188.0473)


Plumbagin, also known as 5-hydroxy-2-methyl-1,4-naphthoquinone or 2-methyljuglone, is a member of the class of compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). Plumbagin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Plumbagin can be found in black walnut, common walnut, japanese persimmon, and persimmon, which makes plumbagin a potential biomarker for the consumption of these food products. Plumbagin is named after the plant genus Plumbago, from which it was originally isolated. It is also commonly found in the carnivorous plant genera Drosera and Nepenthes. It is also a component of the black walnut drupe . D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000871 - Anthelmintics D012102 - Reproductive Control Agents > D003270 - Contraceptive Agents C274 - Antineoplastic Agent > C2189 - Signal Transduction Inhibitor D020011 - Protective Agents > D002316 - Cardiotonic Agents D006401 - Hematologic Agents > D000925 - Anticoagulants D000970 - Antineoplastic Agents D002317 - Cardiovascular Agents D007155 - Immunologic Factors Plumbagin (2-Methyljuglone) is a naphthoquinone isolated from Plumbago zeylanica, exhibits anticancer and antiproliferative activities[1]. Plumbagin (2-Methyljuglone) is a naphthoquinone isolated from Plumbago zeylanica, exhibits anticancer and antiproliferative activities[1].

   

Xanthyletin

8,8-dimethyl-2H,8H-pyrano[3,2-g]chromen-2-one

C14H12O3 (228.0786)


Xanthyletin is a member of the class of compounds known as linear pyranocoumarins. Linear pyranocoumarins are organic compounds containing a pyran (or a hydrogenated derivative) linearly fused to a coumarin moiety. Xanthyletin is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Xanthyletin can be found in lemon, lime, mandarin orange (clementine, tangerine), and sweet orange, which makes xanthyletin a potential biomarker for the consumption of these food products.

   

Droserone

Droserone

C11H8O4 (204.0423)


   

TG(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))

1,3-bis[(9Z,12Z)-octadeca-9,12-dienoyloxy]propan-2-yl (9Z,12Z)-octadeca-9,12-dienoate

C57H98O6 (878.7363)


TG(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) is a trilinoleic acid triglyceride. Triglycerides (TGs) are also known as triacylglycerols or triacylglycerides, meaning that they are glycerides in which the glycerol is esterified with three fatty acid groups (i.e. fatty acid tri-esters of glycerol). TGs may be divided into three general types with respect to their acyl substituents. They are simple or monoacid if they contain only one type of fatty acid, diacid if they contain two types of fatty acids and triacid if three different acyl groups. Chain lengths of the fatty acids in naturally occurring triglycerides can be of varying lengths and saturations but 16, 18 and 20 carbons are the most common. TG(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)), in particular, consists of one chain of linoleic acid at the C-1 position, one chain of linoleic acid at the C-2 position and one chain of linoleic acid at the C-3 position. TGs are the main constituent of vegetable oil and animal fats. TGs are major components of very low density lipoprotein (VLDL) and chylomicrons, play an important role in metabolism as energy sources and transporters of dietary fat. They contain more than twice the energy (9 kcal/g) of carbohydrates and proteins. In the intestine, triglycerides are split into glycerol and fatty acids (this process is called lipolysis) with the help of lipases and bile secretions, which can then move into blood vessels. The triglycerides are rebuilt in the blood from their fragments and become constituents of lipoproteins, which deliver the fatty acids to and from fat cells among other functions. Various tissues can release the free fatty acids and take them up as a source of energy. Fat cells can synthesize and store triglycerides. When the body requires fatty acids as an energy source, the hormone glucagon signals the breakdown of the triglycerides by hormone-sensitive lipase to release free fatty acids. As the brain cannot utilize fatty acids as an energy source, the glycerol component of triglycerides can be converted into glucose for brain fuel when it is broken down. (www.cyberlipid.org, www.wikipedia.org)TAGs can serve as fatty acid stores in all cells, but primarily in adipocytes of adipose tissue. The major building block for the synthesis of triacylglycerides, in non-adipose tissue, is glycerol. Adipocytes lack glycerol kinase and so must use another route to TAG synthesis. Specifically, dihydroxyacetone phosphate (DHAP), which is produced during glycolysis, is the precursor for TAG synthesis in adipose tissue. DHAP can also serve as a TAG precursor in non-adipose tissues, but does so to a much lesser extent than glycerol. The use of DHAP for the TAG backbone depends on whether the synthesis of the TAGs occurs in the mitochondria and ER or the ER and the peroxisomes. The ER/mitochondria pathway requires the action of glycerol-3-phosphate dehydrogenase to convert DHAP to glycerol-3-phosphate. Glycerol-3-phosphate acyltransferase then esterifies a fatty acid to glycerol-3-phosphate thereby generating lysophosphatidic acid. The ER/peroxisome reaction pathway uses the peroxisomal enzyme DHAP acyltransferase to acylate DHAP to acyl-DHAP which is then reduced by acyl-DHAP reductase. The fatty acids that are incorporated into TAGs are activated to acyl-CoAs through the action of acyl-CoA synthetases. Two molecules of acyl-CoA are esterified to glycerol-3-phosphate to yield 1,2-diacylglycerol phosphate (also known as phosphatidic acid). The phosphate is then removed by phosphatidic acid phosphatase (PAP1), to generate 1,2-diacylglycerol. This diacylglycerol serves as the substrate for addition of the third fatty acid to make TAG. Intestinal monoacylglycerols, derived from dietary fats, can also serve as substrates for the synthesis of 1,2-diacylglycerols. 1,2,3-trilinoleoylglycerol is a triglyceride formed by acylation of the three hydroxy groups of glycerol with linoleic acid. It has a role as a mouse metabolite. It is a triglyceride, a TG(18:2/18:2/18:2) and a linoleoyl containing 1,2,3-triacyl-sn-glycerol. It is functionally related to a linoleic acid. Trilinolein is a natural product found in Lysiphlebia japonica, Phoradendron reichenbachianum, and other organisms with data available. See also: Coix lacryma-jobi seed (part of). D006401 - Hematologic Agents > D010975 - Platelet Aggregation Inhibitors Trilinolein is an endogenous metabolite. Trilinolein is an endogenous metabolite.

   

Xanthoxyletin

7-HYDROXY-5-METHOXY-2,2-DIMETHYL-2H-1-BENZOPYRAN-6-ACRYLIC ACID .DELTA.-LACTONE

C15H14O4 (258.0892)


Xanthoxyletin is a member of coumarins. It has a role as a metabolite. Xanthoxyletin is a natural product found in Zanthoxylum dipetalum, Murraya siamensis, and other organisms with data available. Isolated from Zanthoxylum americanum (prickly ash). Xanthoxyletin is found in lemon, sweet orange, and herbs and spices. Xanthoxyletin is found in herbs and spices. Xanthoxyletin is isolated from Zanthoxylum americanum (prickly ash). A natural product found in Clausena harmandiana.

   

Seselin

2H-1-Benzopyran-6-acrylic acid, 5-hydroxy-2,2-dimethyl-, .delta.-lactone

C14H12O3 (228.0786)


Seselin is a member of coumarins. It has a role as a metabolite. Seselin is a natural product found in Haplophyllum cappadocicum, Haplophyllum dshungaricum, and other organisms with data available. Constituent of Carum roxburghianum (Bishops weed). Seselin is found in many foods, some of which are sweet orange, herbs and spices, anise, and wild celery. Seselin is found in anise. Seselin is a constituent of Carum roxburghianum (Bishops weed) A natural product found in Citropsis articulata.

   

alpha-Hydrojuglone 4-O-b-D-glucoside

2-[(4,8-dihydroxynaphthalen-1-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

C16H18O8 (338.1002)


alpha-Hydrojuglone 4-O-b-D-glucoside is found in black walnut. alpha-Hydrojuglone 4-O-b-D-glucoside is isolated from Juglans specie Isolated from Juglans subspecies alpha-Hydrojuglone 4-O-b-D-glucoside is found in black walnut, common walnut, and nuts.

   

Sitoindoside I

(6-{[14-(5-ethyl-6-methylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl hexadecanoic acid

C51H90O7 (814.6686)


Sitoindoside I is found in fruits. Sitoindoside I is a constituent of fruits of banana (Musa paradisiaca) Constituent of fruits of banana (Musa paradisiaca). Sitoindoside I is found in spearmint and fruits.

   

5-Methoxyseselin

5-methoxy-8,8-dimethyl-2H,8H-pyrano[2,3-f]chromen-2-one

C15H14O4 (258.0892)


Consit. of Citrus grandis (pummelo). 5-Methoxyseselin is found in citrus. 5-Methoxyseselin is found in citrus. Consit. of Citrus grandis (pummelo

   

lapachol

4-hydroxy-3-(3-methylbut-2-en-1-yl)-1,2-dihydronaphthalene-1,2-dione

C15H14O3 (242.0943)


D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000981 - Antiprotozoal Agents D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000871 - Anthelmintics D000890 - Anti-Infective Agents > D000935 - Antifungal Agents D000890 - Anti-Infective Agents > D000998 - Antiviral Agents D000970 - Antineoplastic Agents Lapachol is a naphthoquinone that was first isolated from Tabebuia avellanedae (Bignoniaceae)[1]. Lapachol shows anti-abscess, anti-ulcer, antileishmanial, anticarcinomic, antiedemic, anti-inflammatory, antimalarial, antiseptic, antitumor, antiviral, antibacterial, antifungal and pesticidal activities[2]. Lapachol is a naphthoquinone that was first isolated from Tabebuia avellanedae (Bignoniaceae)[1]. Lapachol shows anti-abscess, anti-ulcer, antileishmanial, anticarcinomic, antiedemic, anti-inflammatory, antimalarial, antiseptic, antitumor, antiviral, antibacterial, antifungal and pesticidal activities[2].

   

Lupenone

1,2,5,14,18,18-hexamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-17-one

C30H48O (424.3705)


1,2,5,14,18,18-hexamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-17-one belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 1,2,5,14,18,18-hexamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-17-one is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Lupenone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Lupenone is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

   

Lupeol acetate

1,2,5,14,18,18-hexamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-17-yl acetate

C32H52O2 (468.3967)


   

trilinoelaidin

1,3-Bis(octadeca-9,12-dienoyloxy)propan-2-yl octadeca-9,12-dienoic acid

C57H98O6 (878.7363)


   

Suberosin

7-Methoxy-6-(3-methylbut-2-en-1-yl)-2H-chromen-2-one

C15H16O3 (244.1099)


Suberosin, also known as 7-methoxy-6-prenylcoumarin, belongs to coumarins and derivatives class of compounds. Those are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). Suberosin is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Suberosin can be found in lemon, mandarin orange (clementine, tangerine), and sweet orange, which makes suberosin a potential biomarker for the consumption of these food products. Suberosin, isolated from Plumbago zeylanica, exhibits anti-inflammatory and anticoagulant activity. Suberosin suppresses PHA-induced PBMC proliferation and arrested cell cycle progression from the G1 transition to the S phase through the modulation of the transcription factors NF-AT and NF-κB[1][2]. Suberosin, isolated from Plumbago zeylanica, exhibits anti-inflammatory and anticoagulant activity. Suberosin suppresses PHA-induced PBMC proliferation and arrested cell cycle progression from the G1 transition to the S phase through the modulation of the transcription factors NF-AT and NF-κB[1][2].

   

Plumbagin

InChI=1/C11H8O3/c1-6-5-9(13)10-7(11(6)14)3-2-4-8(10)12/h2-5,12H,1H

C11H8O3 (188.0473)


Plumbagin is a hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogens at positions 2 and 5 are substituted by methyl and hydroxy groups, respectively. It has a role as a metabolite, an immunological adjuvant, an anticoagulant and an antineoplastic agent. It is a member of phenols and a hydroxy-1,4-naphthoquinone. Plumbagin is a compound investigated for its anticancer activity. It has been found that it inactivates the Akt/NF-kB, MMP-9 and VEGF pathways. Plumbagin is a natural product found in Drosera slackii, Diospyros hebecarpa, and other organisms with data available. Synthetic Plumbagin PCUR-101 is a synthetic form of the plant-derived medicinal agent, plumbagin, with potential antineoplastic activity. Plumbagin may act by inhibiting the expression of protein kinase C epsilon (PKCe), signal transducers and activators of transcription 3 phosphorylation (Stat3), protein kinase B (AKT), and certain epithelial-to-mesenchymal transition (EMT) markers, including vimentin and slug. This results in possible inhibition of proliferation in susceptible tumor cells. PKCe, Stat3, AKT, and the EMT markers vimentin and slug have been linked to the induction and progression of prostate cancer. A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogens at positions 2 and 5 are substituted by methyl and hydroxy groups, respectively. D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000871 - Anthelmintics D012102 - Reproductive Control Agents > D003270 - Contraceptive Agents C274 - Antineoplastic Agent > C2189 - Signal Transduction Inhibitor D020011 - Protective Agents > D002316 - Cardiotonic Agents D006401 - Hematologic Agents > D000925 - Anticoagulants D000970 - Antineoplastic Agents D002317 - Cardiovascular Agents D007155 - Immunologic Factors relative retention time with respect to 9-anthracene Carboxylic Acid is 0.955 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.957 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.960 Plumbagin (2-Methyljuglone) is a naphthoquinone isolated from Plumbago zeylanica, exhibits anticancer and antiproliferative activities[1]. Plumbagin (2-Methyljuglone) is a naphthoquinone isolated from Plumbago zeylanica, exhibits anticancer and antiproliferative activities[1].

   

Suberosin

2H-1-Benzopyran-2-one, 7-methoxy-6-(3-methyl-2-butenyl)- (9CI)

C15H16O3 (244.1099)


Suberosin is a member of the class of coumarins in which the coumarin ring is substituted at positions 6 and 7 by a 3-methylbut-2-en-1-yl group and a methoxy group, respectively. A natural product found in Citropsis articulata. It has a role as a plant metabolite and an anticoagulant. It is a member of coumarins and an aromatic ether. It is functionally related to a 7-demethylsuberosin. Suberosin is a natural product found in Zanthoxylum ovalifolium, Prangos bucharica, and other organisms with data available. A member of the class of coumarins in which the coumarin ring is substituted at positions 6 and 7 by a 3-methylbut-2-en-1-yl group and a methoxy group, respectively. A natural product found in Citropsis articulata. Suberosin, isolated from Plumbago zeylanica, exhibits anti-inflammatory and anticoagulant activity. Suberosin suppresses PHA-induced PBMC proliferation and arrested cell cycle progression from the G1 transition to the S phase through the modulation of the transcription factors NF-AT and NF-κB[1][2]. Suberosin, isolated from Plumbago zeylanica, exhibits anti-inflammatory and anticoagulant activity. Suberosin suppresses PHA-induced PBMC proliferation and arrested cell cycle progression from the G1 transition to the S phase through the modulation of the transcription factors NF-AT and NF-κB[1][2].

   

Myricitrin

5,7-dihydroxy-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one

C21H20O12 (464.0955)


Myricitrin is a glycosyloxyflavone that consists of myricetin attached to a alpha-L-rhamnopyranosyl residue at position 3 via a glycosidic linkage. Isolated from Myrica cerifera, it exhibits anti-allergic activity. It has a role as an anti-allergic agent, an EC 1.14.13.39 (nitric oxide synthase) inhibitor, an EC 2.7.11.13 (protein kinase C) inhibitor and a plant metabolite. It is a pentahydroxyflavone, a glycosyloxyflavone, an alpha-L-rhamnoside and a monosaccharide derivative. It is functionally related to a myricetin. It is a conjugate acid of a myricitrin(1-). Myricitrin is a natural product found in Syzygium levinei, Limonium aureum, and other organisms with data available. A glycosyloxyflavone that consists of myricetin attached to a alpha-L-rhamnopyranosyl residue at position 3 via a glycosidic linkage. Isolated from Myrica cerifera, it exhibits anti-allergic activity. Myricitrin is a major antioxidant flavonoid[1]. Myricitrin is a major antioxidant flavonoid[1].

   

3-chloro-5-hydroxy-2-methylnaphthalene-1,4-dione

3-chloro-5-hydroxy-2-methylnaphthalene-1,4-dione

C11H7ClO3 (222.0084)


   

Elliptinone

Elliptinone

C22H14O6 (374.079)


   

Maritinone

Maritinone

C22H14O6 (374.079)


   

Isozeylanone

Isozeylanone

C22H14O6 (374.079)


   

Lupeol acetate

Acetic acid (1R,3aR,4S,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-1-isopropenyl-3a,5a,5b,8,8,11a-hexamethyl-eicosahydro-cyclopenta[a]chrysen-9-yl ester

C32H52O2 (468.3967)


Lupeol acetate, a derivative of Lupeol, suppresses the progression of rheumatoid arthritis (RA) by inhibiting the activation of macrophages and osteoclastogenesis through downregulations of TNF-α, IL-1β, MCP-1, COX-2, VEGF and granzyme B[1]. Lupeol acetate, a derivative of Lupeol, suppresses the progression of rheumatoid arthritis (RA) by inhibiting the activation of macrophages and osteoclastogenesis through downregulations of TNF-α, IL-1β, MCP-1, COX-2, VEGF and granzyme B[1].

   

sitosterol

17-(5-ethyl-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

C29H50O (414.3861)


A member of the class of phytosterols that is stigmast-5-ene substituted by a beta-hydroxy group at position 3. C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents D009676 - Noxae > D000963 - Antimetabolites Beta-Sitosterol (purity>98\\%) is a plant sterol. Beta-Sitosterol (purity>98\\%) interfere with multiple cell signaling pathways, including cell cycle, apoptosis, proliferation, survival, invasion, angiogenesis, metastasis and inflammation[1]. Beta-Sitosterol (purity>98\%) is a plant sterol. Beta-Sitosterol (purity>98\%) interfere with multiple cell signaling pathways, including cell cycle, apoptosis, proliferation, survival, invasion, angiogenesis, metastasis and inflammation[1].

   

CHEMBL3753045

CHEMBL3753045

C16H16O3 (256.1099)


   

5-Hydroxy-3-methoxy-2-methyl-1,4-naphthochinon

5-Hydroxy-3-methoxy-2-methyl-1,4-naphthochinon

C12H10O4 (218.0579)


   

Lupenone

(1R,3aR,4S,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-1-Isopropenyl-3a,5a,5b,8,8,11a-hexamethyl-eicosahydro-cyclopenta[a]chrysen-9-one

C30H48O (424.3705)


Lupenone, isolated from Musa basjoo, belongs to lupane type triterpenoids. Lupenone shows various pharmacological activities including anti-inflammatory, anti-virus, anti-diabetes, anti-cancer, improving Chagas disease without major toxicity[1][2]. Lupenone is an orally active lupine-type triterpenoid that can be isolated from Musa basjoo. Lupenone Lupenone plays a role through the PI3K/Akt/mTOR and NF-κB signaling pathways. Lupenone has anti-inflammatory, antiviral, antidiabetic and anticancer activities[1][2][3]. Lupenone, isolated from Musa basjoo, belongs to lupane type triterpenoids. Lupenone shows various pharmacological activities including anti-inflammatory, anti-virus, anti-diabetes, anti-cancer, improving Chagas disease without major toxicity[1][2].

   

Daucosterol

(2R,3R,4S,5S,6R)-2-(((3S,8S,9S,10R,13R,14S,17R)-17-((2R,5R)-5-Ethyl-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

C35H60O6 (576.439)


Daucosterol is a steroid saponin that is sitosterol attached to a beta-D-glucopyranosyl residue at position 3 via a glycosidic linkage. It has bee isolated from Panax japonicus var. major and Breynia fruticosa. It has a role as a plant metabolite. It is a steroid saponin, a beta-D-glucoside and a monosaccharide derivative. It is functionally related to a sitosterol. It derives from a hydride of a stigmastane. Sitogluside is a natural product found in Ophiopogon intermedius, Ophiopogon jaburan, and other organisms with data available. A steroid saponin that is sitosterol attached to a beta-D-glucopyranosyl residue at position 3 via a glycosidic linkage. It has bee isolated from Panax japonicus var. major and Breynia fruticosa. C308 - Immunotherapeutic Agent Daucosterol is a natural sterol compound. Daucosterol is a natural sterol compound.

   

3,3-Methylenebis(2-methyl-5-hydroxy-1,4-naphthoquinone)

3,3-Methylenebis(2-methyl-5-hydroxy-1,4-naphthoquinone)

C23H16O6 (388.0947)


   

2,2-Oxybis(3-methyl-8-hydroxy-1,4-naphthoquinone)

2,2-Oxybis(3-methyl-8-hydroxy-1,4-naphthoquinone)

C22H14O7 (390.0739)


   

Campesterol

Campesterol

C28H48O (400.3705)


Disclaimer: While authors make an effort to ensure that the content of this record is accurate, the authors make no representations or warranties in relation to the accuracy or completeness of the record. This record do not reflect any viewpoints of the affiliation and organization to which the authors belong. Campesterol is a plant sterol with cholesterol lowering and anticarcinogenic effects. Campesterol is a plant sterol with cholesterol lowering and anticarcinogenic effects.

   

p-Hydroxybenzaldehyde

p-Hydroxybenzaldehyde

C7H6O2 (122.0368)


p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations. p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations. p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations.

   

4-Hydroxybenzaldehyde

4-hydroxybenzaldehyde

C7H6O2 (122.0368)


p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations. p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations. p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations.

   

Xanthyletin

2,2-dimethylpyrano[3,2-g]chromen-8-one

C14H12O3 (228.0786)


   

Sitoindoside I

(6-{[14-(5-ethyl-6-methylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl hexadecanoate

C51H90O7 (814.6686)


A steroid saponin that is sitosterol attached to a 6-O-hexadecanoyl-beta-D-glucopyranosyl residue at position 3 via a glycosidic linkage. It has been isolated from Breynia fruticosa.

   

Xanthoxyloin

5-Methoxy-8,8-dimethyl-2H,8H-benzo[1,2-b:5,4-b']dipyran-2-one,9CI

C15H14O4 (258.0892)


   

alpha-Hydrojuglone-4-glucoside

2-[(4,8-dihydroxynaphthalen-1-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

C16H18O8 (338.1002)


   

5-Methoxyseselin

5-methoxy-8,8-dimethyl-2H,8H-pyrano[2,3-f]chromen-2-one

C15H14O4 (258.0892)


   

Harzol

(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methyl-heptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

C29H50O (414.3861)


C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents D009676 - Noxae > D000963 - Antimetabolites Beta-Sitosterol (purity>98\\%) is a plant sterol. Beta-Sitosterol (purity>98\\%) interfere with multiple cell signaling pathways, including cell cycle, apoptosis, proliferation, survival, invasion, angiogenesis, metastasis and inflammation[1]. Beta-Sitosterol (purity>98\%) is a plant sterol. Beta-Sitosterol (purity>98\%) interfere with multiple cell signaling pathways, including cell cycle, apoptosis, proliferation, survival, invasion, angiogenesis, metastasis and inflammation[1].

   

Stigmasterin

(3S,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methyl-hept-3-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

C29H48O (412.3705)


C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol

   

FR-0985

4-08-00-00251 (Beilstein Handbook Reference)

C7H6O2 (122.0368)


p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations. p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations. p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations.

   

84-99-1

2-Propenoic acid, 3-(7-hydroxy-5-methoxy-2,2-dimethyl-2H-1-benzopyran-6-yl)-, .delta.-lactone

C15H14O4 (258.0892)


   

Tecomin

InChI=1\C15H14O3\c1-9(2)7-8-12-13(16)10-5-3-4-6-11(10)14(17)15(12)18\h3-7,18H,8H2,1-2H

C15H14O3 (242.0943)


D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000981 - Antiprotozoal Agents D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000871 - Anthelmintics D000890 - Anti-Infective Agents > D000935 - Antifungal Agents D000890 - Anti-Infective Agents > D000998 - Antiviral Agents D000970 - Antineoplastic Agents Lapachol is a naphthoquinone that was first isolated from Tabebuia avellanedae (Bignoniaceae)[1]. Lapachol shows anti-abscess, anti-ulcer, antileishmanial, anticarcinomic, antiedemic, anti-inflammatory, antimalarial, antiseptic, antitumor, antiviral, antibacterial, antifungal and pesticidal activities[2]. Lapachol is a naphthoquinone that was first isolated from Tabebuia avellanedae (Bignoniaceae)[1]. Lapachol shows anti-abscess, anti-ulcer, antileishmanial, anticarcinomic, antiedemic, anti-inflammatory, antimalarial, antiseptic, antitumor, antiviral, antibacterial, antifungal and pesticidal activities[2].

   

Lupeol acetate

1,2,5,14,18,18-hexamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-17-yl acetate

C32H52O2 (468.3967)


Lupeyl acetate, also known as lupeyl acetic acid, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Lupeyl acetate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Lupeyl acetate can be found in burdock, date, and fig, which makes lupeyl acetate a potential biomarker for the consumption of these food products. Lupeol acetate, a derivative of Lupeol, suppresses the progression of rheumatoid arthritis (RA) by inhibiting the activation of macrophages and osteoclastogenesis through downregulations of TNF-α, IL-1β, MCP-1, COX-2, VEGF and granzyme B[1]. Lupeol acetate, a derivative of Lupeol, suppresses the progression of rheumatoid arthritis (RA) by inhibiting the activation of macrophages and osteoclastogenesis through downregulations of TNF-α, IL-1β, MCP-1, COX-2, VEGF and granzyme B[1].

   

Trilinolein

glycerol trilinoleate

C57H98O6 (878.7363)


Constituent of seed oils rich in linoleic acid, e.g., sunflower oil. Glycerol trilinoleate is found in fats and oils. Trilinolein is an endogenous metabolite. Trilinolein is an endogenous metabolite.

   

16-hydroxy-5-(prop-1-en-2-yl)-4,14-dioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1(9),3(7),5,10,12,15-hexaene-2,8-dione

16-hydroxy-5-(prop-1-en-2-yl)-4,14-dioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1(9),3(7),5,10,12,15-hexaene-2,8-dione

C17H10O5 (294.0528)


   

4-(2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-methyl-4-oxobutanoic acid

4-(2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-methyl-4-oxobutanoic acid

C17H22O10 (386.1213)


   

2-methyl-4-oxochromene-8-carboxylic acid

2-methyl-4-oxochromene-8-carboxylic acid

C11H8O4 (204.0423)


   

(2r)-2-[(4r)-2-iminoimidazolidin-4-yl]-3-[(2r)-4-methyl-5-oxo-2h-furan-2-yl]propanoic acid

(2r)-2-[(4r)-2-iminoimidazolidin-4-yl]-3-[(2r)-4-methyl-5-oxo-2h-furan-2-yl]propanoic acid

C11H15N3O4 (253.1063)


   

5-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3,7-dimethoxychromen-4-one

5-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3,7-dimethoxychromen-4-one

C19H18O8 (374.1002)


   

3a,5a,5b,8,8,11a-hexamethyl-1-(prop-1-en-2-yl)-tetradecahydro-1h-cyclopenta[a]chrysen-9-one

3a,5a,5b,8,8,11a-hexamethyl-1-(prop-1-en-2-yl)-tetradecahydro-1h-cyclopenta[a]chrysen-9-one

C30H48O (424.3705)


   

(2r,5e)-2-[(4r)-1-(2,4-dihydroxybutyl)-2-iminoimidazolidin-4-yl]-7-hydroxy-6-methylhept-5-enoic acid

(2r,5e)-2-[(4r)-1-(2,4-dihydroxybutyl)-2-iminoimidazolidin-4-yl]-7-hydroxy-6-methylhept-5-enoic acid

C15H27N3O5 (329.1951)


   

(1r,3as,3bs,7s,9bs)-1-[(2r,5r)-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

(1r,3as,3bs,7s,9bs)-1-[(2r,5r)-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

C28H48O (400.3705)


   

(5s,7r,7ar)-2-(2-hydroxy-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}butyl)-3-imino-5-(2-methylprop-1-en-1-yl)-tetrahydro-1h-pyrrolo[1,2-c]imidazole-7-carboxylic acid

(5s,7r,7ar)-2-(2-hydroxy-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}butyl)-3-imino-5-(2-methylprop-1-en-1-yl)-tetrahydro-1h-pyrrolo[1,2-c]imidazole-7-carboxylic acid

C20H33N3O8 (443.2268)


   

1',4-dihydroxy-1,6'-dimethyl-6,7-dihydro-[2,2'-binaphthalene]-5,5',8,8'-tetrone

1',4-dihydroxy-1,6'-dimethyl-6,7-dihydro-[2,2'-binaphthalene]-5,5',8,8'-tetrone

C22H16O6 (376.0947)


   

5-hydroxy-3-[(5-hydroxy-1,4-dioxonaphthalen-2-yl)methyl]-2-methylnaphthalene-1,4-dione

5-hydroxy-3-[(5-hydroxy-1,4-dioxonaphthalen-2-yl)methyl]-2-methylnaphthalene-1,4-dione

C22H14O6 (374.079)


   

(2s,4s)-4,8-dihydroxy-2-methyl-3,4-dihydro-2h-naphthalen-1-one

(2s,4s)-4,8-dihydroxy-2-methyl-3,4-dihydro-2h-naphthalen-1-one

C11H12O3 (192.0786)


   

(2s,3s)-3,5-dihydroxy-7-methoxy-2-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1-benzopyran-4-one

(2s,3s)-3,5-dihydroxy-7-methoxy-2-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1-benzopyran-4-one

C19H20O8 (376.1158)


   

5,6-dihydroxy-2-methylnaphthalene-1,4-dione

5,6-dihydroxy-2-methylnaphthalene-1,4-dione

C11H8O4 (204.0423)


   

(5s,7r,7ar)-2-(2,4-dihydroxybutyl)-3-imino-5-(2-methylprop-1-en-1-yl)-tetrahydro-1h-pyrrolo[1,2-c]imidazole-7-carboxylic acid

(5s,7r,7ar)-2-(2,4-dihydroxybutyl)-3-imino-5-(2-methylprop-1-en-1-yl)-tetrahydro-1h-pyrrolo[1,2-c]imidazole-7-carboxylic acid

C15H25N3O4 (311.1845)


   

(2r,5e)-7-hydroxy-2-[(4r)-2-iminoimidazolidin-4-yl]-6-methylhept-5-enoic acid

(2r,5e)-7-hydroxy-2-[(4r)-2-iminoimidazolidin-4-yl]-6-methylhept-5-enoic acid

C11H19N3O3 (241.1426)


   

(11r,12r)-2,12-dihydroxy-11-(3-hydroxy-5-methoxyphenyl)-8-methoxy-4,6,10-trioxatricyclo[7.4.0.0³,⁷]trideca-1,3(7),8-trien-13-one

(11r,12r)-2,12-dihydroxy-11-(3-hydroxy-5-methoxyphenyl)-8-methoxy-4,6,10-trioxatricyclo[7.4.0.0³,⁷]trideca-1,3(7),8-trien-13-one

C18H16O9 (376.0794)


   

2-methyl-5-[(3-methylbut-2-en-1-yl)oxy]naphthalene-1,4-dione

2-methyl-5-[(3-methylbut-2-en-1-yl)oxy]naphthalene-1,4-dione

C16H16O3 (256.1099)


   

(2r)-2-[(4r)-1-(2-hydroxy-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}butyl)-2-iminoimidazolidin-4-yl]-3-[(2r)-4-methyl-5-oxo-2h-furan-2-yl]propanoic acid

(2r)-2-[(4r)-1-(2-hydroxy-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}butyl)-2-iminoimidazolidin-4-yl]-3-[(2r)-4-methyl-5-oxo-2h-furan-2-yl]propanoic acid

C20H31N3O10 (473.2009)


   

methyl (3s)-4-(2-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-methyl-4-oxobutanoate

methyl (3s)-4-(2-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-methyl-4-oxobutanoate

C18H24O10 (400.1369)


   

4-(2,3-dihydroxyphenyl)-2-methyl-4-oxobutanoic acid

4-(2,3-dihydroxyphenyl)-2-methyl-4-oxobutanoic acid

C11H12O5 (224.0685)


   

(2r)-2-[(4r)-1-(2-hydroxy-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}butyl)-2-iminoimidazolidin-4-yl]-6-methylhept-5-enoic acid

(2r)-2-[(4r)-1-(2-hydroxy-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}butyl)-2-iminoimidazolidin-4-yl]-6-methylhept-5-enoic acid

C20H35N3O8 (445.2424)


   

(2s)-4-(2,3-dihydroxyphenyl)-2-methyl-4-oxobutanoic acid

(2s)-4-(2,3-dihydroxyphenyl)-2-methyl-4-oxobutanoic acid

C11H12O5 (224.0685)


   

methyl 4-(2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-methyl-4-oxobutanoate

methyl 4-(2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-methyl-4-oxobutanoate

C18H24O10 (400.1369)


   

(2'r,3'r,4'r)-4,4',8'-trihydroxy-2',7-dimethyl-3'-propyl-3',4'-dihydro-[1,2'-binaphthalene]-1',5,8-trione

(2'r,3'r,4'r)-4,4',8'-trihydroxy-2',7-dimethyl-3'-propyl-3',4'-dihydro-[1,2'-binaphthalene]-1',5,8-trione

C25H24O6 (420.1573)


   

(6-{[1-(5-ethyl-6-methylheptan-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl hexadecanoate

(6-{[1-(5-ethyl-6-methylheptan-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl hexadecanoate

C51H90O7 (814.6686)


   

(3r)-4-(2,3-dihydroxyphenyl)-3-methyl-4-oxobutanoic acid

(3r)-4-(2,3-dihydroxyphenyl)-3-methyl-4-oxobutanoic acid

C11H12O5 (224.0685)


   

5,7-dihydroxy-3-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)chromen-4-one

5,7-dihydroxy-3-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)chromen-4-one

C21H20O12 (464.0955)


   

4,4'-dihydroxy-7,7'-dimethyl-6,7-dihydro-[1,1'-binaphthalene]-5,5',8,8'-tetrone

4,4'-dihydroxy-7,7'-dimethyl-6,7-dihydro-[1,1'-binaphthalene]-5,5',8,8'-tetrone

C22H16O6 (376.0947)


   

4,8-dihydroxy-2-methyl-3,4-dihydro-2h-naphthalen-1-one

4,8-dihydroxy-2-methyl-3,4-dihydro-2h-naphthalen-1-one

C11H12O3 (192.0786)


   

2-{[1-(5-ethyl-6-methylheptan-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

2-{[1-(5-ethyl-6-methylheptan-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C35H60O6 (576.439)


   

16-methoxy-5-(prop-1-en-2-yl)-4,14-dioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1(9),3(7),5,10,12,15-hexaene-2,8-dione

16-methoxy-5-(prop-1-en-2-yl)-4,14-dioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1(9),3(7),5,10,12,15-hexaene-2,8-dione

C18H12O5 (308.0685)


   

(2r)-2-[(4r)-2-iminoimidazolidin-4-yl]-6-methylhept-5-enoic acid

(2r)-2-[(4r)-2-iminoimidazolidin-4-yl]-6-methylhept-5-enoic acid

C11H19N3O2 (225.1477)


   

(3s)-4-(2-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-methyl-4-oxobutanoic acid

(3s)-4-(2-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-methyl-4-oxobutanoic acid

C17H22O10 (386.1213)


   

4,8-dihydroxy-3-methyl-3,4-dihydro-2h-naphthalen-1-one

4,8-dihydroxy-3-methyl-3,4-dihydro-2h-naphthalen-1-one

C11H12O3 (192.0786)


   

(5s,7r,7ar)-3-imino-5-(2-methylprop-1-en-1-yl)-hexahydropyrrolo[1,2-c]imidazole-7-carboxylic acid

(5s,7r,7ar)-3-imino-5-(2-methylprop-1-en-1-yl)-hexahydropyrrolo[1,2-c]imidazole-7-carboxylic acid

C11H17N3O2 (223.1321)


   

8,19-dihydroxy-2-methylpentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(13),4,6,8,15,17,19-heptaene-3,10,14,21-tetrone

8,19-dihydroxy-2-methylpentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(13),4,6,8,15,17,19-heptaene-3,10,14,21-tetrone

C22H14O6 (374.079)


   

methyl (3r)-4-(2-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-methyl-4-oxobutanoate

methyl (3r)-4-(2-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-methyl-4-oxobutanoate

C18H24O10 (400.1369)


   

2,12-dihydroxy-11-(3-hydroxy-5-methoxyphenyl)-8-methoxy-4,6,10-trioxatricyclo[7.4.0.0³,⁷]trideca-1,3(7),8-trien-13-one

2,12-dihydroxy-11-(3-hydroxy-5-methoxyphenyl)-8-methoxy-4,6,10-trioxatricyclo[7.4.0.0³,⁷]trideca-1,3(7),8-trien-13-one

C18H16O9 (376.0794)


   

1',8-dihydroxy-3,6'-dimethyl-[2,2'-binaphthalene]-1,4,5',8'-tetrone

1',8-dihydroxy-3,6'-dimethyl-[2,2'-binaphthalene]-1,4,5',8'-tetrone

C22H14O6 (374.079)


   

3,5-dihydroxy-7-methoxy-2-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1-benzopyran-4-one

3,5-dihydroxy-7-methoxy-2-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1-benzopyran-4-one

C19H20O8 (376.1158)


   

stigmast-5-en-3-ol, (3β)-

stigmast-5-en-3-ol, (3β)-

C29H50O (414.3861)


   

5,7-dihydroxy-8-methoxy-2-methylnaphthalene-1,4-dione

5,7-dihydroxy-8-methoxy-2-methylnaphthalene-1,4-dione

C12H10O5 (234.0528)


   

(3s,4r)-4,8-dihydroxy-3-methyl-3,4-dihydro-2h-naphthalen-1-one

(3s,4r)-4,8-dihydroxy-3-methyl-3,4-dihydro-2h-naphthalen-1-one

C11H12O3 (192.0786)


   

(2r,3r,4s,5s,6r)-2-[(4,8-dihydroxynaphthalen-1-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

(2r,3r,4s,5s,6r)-2-[(4,8-dihydroxynaphthalen-1-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

C16H18O8 (338.1002)


   

(3s,4s)-4,8-dihydroxy-3-methyl-3,4-dihydro-2h-naphthalen-1-one

(3s,4s)-4,8-dihydroxy-3-methyl-3,4-dihydro-2h-naphthalen-1-one

C11H12O3 (192.0786)


   

4-(2,3-dihydroxyphenyl)-3-methyl-4-oxobutanoic acid

4-(2,3-dihydroxyphenyl)-3-methyl-4-oxobutanoic acid

C11H12O5 (224.0685)


   

(3r)-4-(2-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-methyl-4-oxobutanoic acid

(3r)-4-(2-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-methyl-4-oxobutanoic acid

C17H22O10 (386.1213)


   

5-hydroxy-3-[(8-hydroxy-3-methyl-1,4-dioxonaphthalen-2-yl)methyl]-2-methylnaphthalene-1,4-dione

5-hydroxy-3-[(8-hydroxy-3-methyl-1,4-dioxonaphthalen-2-yl)methyl]-2-methylnaphthalene-1,4-dione

C23H16O6 (388.0947)


   

3a,5a,5b,8,8,11a-hexamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-yl acetate

3a,5a,5b,8,8,11a-hexamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-yl acetate

C32H52O2 (468.3967)


   

5,8-dihydroxy-2-methylnaphthalene-1,4-dione

5,8-dihydroxy-2-methylnaphthalene-1,4-dione

C11H8O4 (204.0423)


   

(2r)-6-hydroxy-2-[(4r)-2-iminoimidazolidin-4-yl]-6-methylheptanoic acid

(2r)-6-hydroxy-2-[(4r)-2-iminoimidazolidin-4-yl]-6-methylheptanoic acid

C11H21N3O3 (243.1583)


   

(2r)-2-[(4r)-1-(2,4-dihydroxybutyl)-2-iminoimidazolidin-4-yl]-3-[(2r)-4-methyl-5-oxo-2h-furan-2-yl]propanoic acid

(2r)-2-[(4r)-1-(2,4-dihydroxybutyl)-2-iminoimidazolidin-4-yl]-3-[(2r)-4-methyl-5-oxo-2h-furan-2-yl]propanoic acid

C15H23N3O6 (341.1587)


   

5-(2-hydroxypropan-2-yl)-16-methoxy-4,14-dioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1(9),3(7),5,10,12,15-hexaene-2,8-dione

5-(2-hydroxypropan-2-yl)-16-methoxy-4,14-dioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1(9),3(7),5,10,12,15-hexaene-2,8-dione

C18H14O6 (326.079)


   

5,6-dihydroxy-2-methyl-2,3-dihydronaphthalene-1,4-dione

5,6-dihydroxy-2-methyl-2,3-dihydronaphthalene-1,4-dione

C11H10O4 (206.0579)


   

(2r)-2-[(4r)-1-(2,4-dihydroxybutyl)-2-iminoimidazolidin-4-yl]-6-methylhept-5-enoic acid

(2r)-2-[(4r)-1-(2,4-dihydroxybutyl)-2-iminoimidazolidin-4-yl]-6-methylhept-5-enoic acid

C15H27N3O4 (313.2001)


   

(2s,11r)-8,19-dihydroxy-2-methylpentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(13),4,6,8,15,17,19-heptaene-3,10,14,21-tetrone

(2s,11r)-8,19-dihydroxy-2-methylpentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(13),4,6,8,15,17,19-heptaene-3,10,14,21-tetrone

C22H14O6 (374.079)


   

(1r,11r,13r)-5,16-dihydroxy-2-(8-hydroxy-3-methyl-1,4-dioxonaphthalen-2-yl)-1,13-dimethylpentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,15,17,19-hexaene-3,10,14,21-tetrone

(1r,11r,13r)-5,16-dihydroxy-2-(8-hydroxy-3-methyl-1,4-dioxonaphthalen-2-yl)-1,13-dimethylpentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,15,17,19-hexaene-3,10,14,21-tetrone

C34H24O9 (576.142)


   

(2r,5e)-7-hydroxy-2-[(4r)-1-(2-hydroxy-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}butyl)-2-iminoimidazolidin-4-yl]-6-methylhept-5-enoic acid

(2r,5e)-7-hydroxy-2-[(4r)-1-(2-hydroxy-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}butyl)-2-iminoimidazolidin-4-yl]-6-methylhept-5-enoic acid

C20H35N3O9 (461.2373)


   

5-hydroxy-3-methoxy-2-methylnaphthalene-1,4-dione

5-hydroxy-3-methoxy-2-methylnaphthalene-1,4-dione

C12H10O4 (218.0579)


   

5-hydroxy-3-[(8-hydroxy-3-methyl-1,4-dioxonaphthalen-2-yl)oxy]-2-methylnaphthalene-1,4-dione

5-hydroxy-3-[(8-hydroxy-3-methyl-1,4-dioxonaphthalen-2-yl)oxy]-2-methylnaphthalene-1,4-dione

C22H14O7 (390.0739)


   

(2r)-7-hydroxy-2-[(4r)-2-iminoimidazolidin-4-yl]-6-methylhept-5-enoic acid

(2r)-7-hydroxy-2-[(4r)-2-iminoimidazolidin-4-yl]-6-methylhept-5-enoic acid

C11H19N3O3 (241.1426)