Classification Term: 169832

Naphthalenes and naphthoquinones (ontology term: bdf68dd728a190ee8299fdc81a285c9a)

found 31 associated metabolites at sub_class metabolite taxonomy ontology rank level.

Ancestor: Aromatic polyketides

Child Taxonomies: There is no child term of current ontology term.

Juglone

InChI=1/C10H6O3/c11-7-4-5-9(13)10-6(7)2-1-3-8(10)12/h1-5,12

C10H6O3 (174.03169259999999)


Juglone is a hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogen at position 5 has been replaced by a hydroxy group. A plant-derived 1,4-naphthoquinone with confirmed antibacterial and antitumor activities. It has a role as a herbicide, a reactive oxygen species generator and a geroprotector. Juglone is a natural product found in Talaromyces diversus, Carya alba, and other organisms with data available. Occurs in Juglans subspecies and pecan nuts (Carya illinoensis). Juglone is found in many foods, some of which are common walnut, liquor, black walnut, and nuts. Juglone is found in black walnut. Juglone occurs in Juglans species and pecan nuts (Carya illinoensis D000074385 - Food Ingredients > D005503 - Food Additives > D005520 - Food Preservatives D009676 - Noxae > D003603 - Cytotoxins D000970 - Antineoplastic Agents D004791 - Enzyme Inhibitors

   

Torachrysone

1-(6-Methoxy-3-methyl-1,8-bis(oxidanyl)naphthalen-2-yl)ethanone

C14H14O4 (246.0892044)


Torachrysone is a member of naphthols. Torachrysone is a natural product found in Rheum palmatum, Rumex japonicus, and other organisms with data available. Isolated from seeds of Cassia tora (charota). Torachrysone is found in coffee and coffee products, herbs and spices, and pulses. Torachrysone is found in coffee and coffee products. Torachrysone is isolated from seeds of Cassia tora (charota).

   

Menadione

Vitamin K3: 1,4-dihydro-1,4-dioxo-2-methylnaphthalene

C11H8O2 (172.0524268)


Menadione is a synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation in vivo. -- Pubchem; Despite the fact that it can serve as a precursor to various types of vitamin K, menadione is generally not used as a nutritional supplement. Large doses of menadione have been reported to cause adverse outcomes including hemolytic anemia due to G6PD deficiency, neonatal brain or liver damage, or neonatal death in some cases. Moreover, menadione supplements have been banned by the FDA because of their high toxicity. It is sometimes called vitamin K3, although derivatives of naphthoquinone without the sidechain in the 3-position cannot exert all the functions of the K vitamins. Menadione is a vitamin precursor of K2 which utilizes alkylation in the liver to yield menaquinones (MK-n, n=1-13; K2 vitamers), and hence, is better classified as a provitamin. -- Wikipedia. B - Blood and blood forming organs > B02 - Antihemorrhagics > B02B - Vitamin k and other hemostatics > B02BA - Vitamin k D006401 - Hematologic Agents > D003029 - Coagulants > D006490 - Hemostatics D050299 - Fibrin Modulating Agents > D000933 - Antifibrinolytic Agents D018977 - Micronutrients > D014815 - Vitamins Prothrombogenic vitamin (synthetic) Menadione is a naphthoquinone that is converted into active vitamin K2 in the body. Menadione is a naphthoquinone that is converted into active vitamin K2 in the body.

   

Lapachol

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

C15H14O3 (242.0942894)


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].

   

Plumbagin

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

C11H8O3 (188.0473418)


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].

   

CERCOSPORIN

Cercosporin from Cercospora hayii

C29H26O10 (534.1525896)


An organic heterohexacyclic compound that is perylo[1,12-def][1,3]dioxepine-6,11-dione substituted by hydroxy groups at positions 5 and 12, by methoxy groups at positions 7 and 10, and by 2-hydroxypropyl groups at positions 8 and 9 (the R,R-stereoisomer). It is a phytotoxin which was first isolated from the pathogenic soybean fungus, Cercospora kikuchii and later found in multiple members of the genus Cercospora. CONFIDENCE isolated standard

   

Scytalone

3,4-Dihydro-3,6,8-trihydoroxy-1(2H)-napthalenone

C10H10O4 (194.057906)


   
   

Atovaquone

2-hydroxy-3-[(1r,4r)-4-(4-chlorophenyl)cyclohexyl]-1,4-dihydronaphthalene-1,4-dione

C22H19ClO3 (366.1022654000001)


Atovaquone is only found in individuals that have used or taken this drug. It is a hydroxynaphthoquinone that has antimicrobial activity and is being used in antimalarial protocols. [PubChem]Atovaquone is a hydroxy- 1, 4- naphthoquinone, an analog of ubiquinone, with antipneumocystis activity. The mechanism of action against Pneumocystis carinii has not been fully elucidated. In Plasmodium species, the site of action appears to be the cytochrome bc1 complex (Complex III). Several metabolic enzymes are linked to the mitochondrial electron transport chain via ubiquinone. Inhibition of electron transport by atovaquone will result in indirect inhibition of these enzymes. The ultimate metabolic effects of such blockade may include inhibition of nucleic acid and ATP synthesis. Atovaquone also has been shown to have good in vitro activity against Toxoplasma gondii. P - Antiparasitic products, insecticides and repellents > P01 - Antiprotozoals > P01A - Agents against amoebiasis and other protozoal diseases D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000981 - Antiprotozoal Agents C254 - Anti-Infective Agent > C276 - Antiparasitic Agent > C277 - Antiprotozoal Agent D004791 - Enzyme Inhibitors

   

Aurasperone D

5,6-dihydroxy-10-{5-hydroxy-6,8-dimethoxy-2-methyl-4-oxo-4H-benzo[g]chromen-7-yl}-8-methoxy-2-methyl-4H-benzo[g]chromen-4-one

C31H24O10 (556.1369404)


Aurasperone D is found in mango. Aurasperone D is a mycotoxin from Aspergillus niger infected mango fruits. Mycotoxin from Aspergillus niger infected mango fruits. Aurasperone D is found in mango.

   
   
   
   

Alteichin

Alterperylenol

C20H14O6 (350.0790344)


   

Deoxylapachol

2-Deoxylapachol;1,4-Naphthalenedione, 2-(3-methyl-2-butenyl)-

C15H14O2 (226.09937440000002)


2-demethylmenaquinone is a naphthoquinone and a member of p-quinones. It has a role as an Escherichia coli metabolite. Deoxylapachol is a natural product found in Tectona grandis, Handroanthus impetiginosus, and other organisms with data available. Deoxylapachol is a major cytotoxic component of New Zealand brown alga, Landsburgia quercifolia. Deoxylapachol has antifungal and anti-cancer activity[1]. Deoxylapachol is a major cytotoxic component of New Zealand brown alga, Landsburgia quercifolia. Deoxylapachol has antifungal and anti-cancer activity[1].

   
   
   
   

Burseran

PODOPHYLLOTOXIN, SECODEOXY CYCLIC ETHER

C22H26O6 (386.17292960000003)


A lignan that consists of tetrahydrofuran substituted by a 5-methyl-1,3-benzodioxole group at position 3 and a 3,4,5-trimethoxybenzyl group at position 4 (the 3S,4S stereoisomer).

   

Flaviolin

2,5,7-Trihydroxy-1,4-naphthalenedione

C10H6O5 (206.0215226)


A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone having three hydroxy substituents placed at the 2-, 5- and 7-positions.

   

lapachol

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

C15H14O3 (242.0942894)


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].

   

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 (188.0473418)


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].

   

Alkannin

5,8-dihydroxy-2-[(1S)-1-hydroxy-4-methylpent-3-en-1-yl]-1,4-dihydronaphthalene-1,4-dione

C16H16O5 (288.0997686)


Alkannin is a hydroxy-1,4-naphthoquinone. Alkannin is a natural product found in Arnebia hispidissima, Alkanna cappadocica, and other organisms with data available. D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics D000893 - Anti-Inflammatory Agents D018501 - Antirheumatic Agents (-)-Alkannin, found in Alkanna tinctoria, is used as a food coloring. (-)-Alkannin shows anticancer activity, arrests cell cycle, and induces apoptosis. (-)-Alkannin improves hepatic inflammation in a Rho-kinase pathway[1][2][3]. (-)-Alkannin, found in Alkanna tinctoria, is used as a food coloring. (-)-Alkannin shows anticancer activity, arrests cell cycle, and induces apoptosis. (-)-Alkannin improves hepatic inflammation in a Rho-kinase pathway[1][2][3]. (-)-Alkannin, found in Alkanna tinctoria, is used as a food coloring. (-)-Alkannin shows anticancer activity, arrests cell cycle, and induces apoptosis. (-)-Alkannin improves hepatic inflammation in a Rho-kinase pathway[1][2][3]. (-)-Alkannin, found in Alkanna tinctoria, is used as a food coloring. (-)-Alkannin shows anticancer activity, arrests cell cycle, and induces apoptosis. (-)-Alkannin improves hepatic inflammation in a Rho-kinase pathway[1][2][3].

   

menadione

2-Methyl-1,4-naphthoquinone

C11H8O2 (172.0524268)


A member of the class of 1,4-naphthoquinones that is 1,4-naphthoquinone which is substituted at position 2 by a methyl group. It is used as a nutritional supplement and for the treatment of hypoprothrombinemia. B - Blood and blood forming organs > B02 - Antihemorrhagics > B02B - Vitamin k and other hemostatics > B02BA - Vitamin k D006401 - Hematologic Agents > D003029 - Coagulants > D006490 - Hemostatics D050299 - Fibrin Modulating Agents > D000933 - Antifibrinolytic Agents D018977 - Micronutrients > D014815 - Vitamins Menadione is a naphthoquinone that is converted into active vitamin K2 in the body. Menadione is a naphthoquinone that is converted into active vitamin K2 in the body.

   

ATOVAQUONE

Atovaquone (Atavaquone)

C22H19ClO3 (366.1022654000001)


P - Antiparasitic products, insecticides and repellents > P01 - Antiprotozoals > P01A - Agents against amoebiasis and other protozoal diseases D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000981 - Antiprotozoal Agents C254 - Anti-Infective Agent > C276 - Antiparasitic Agent > C277 - Antiprotozoal Agent D004791 - Enzyme Inhibitors

   

Torachrysone

1-(1,8-dihydroxy-6-methoxy-3-methyl-naphthalen-2-yl)ethanone

C14H14O4 (246.0892044)