Classification Term: 684

Naphthofurans (ontology term: CHEMONTID:0001634)

Compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings." []

found 32 associated metabolites at class metabolite taxonomy ontology rank level.

Ancestor: Organoheterocyclic compounds

Child Taxonomies: Dinaphthofurans, Furanonaphthodioxoles

Cafestol

5A,8-METHANO-5AH-CYCLOHEPTA(5,6)NAPHTHO(2,1-B)FURAN-7-METHANOL, 3B,4,5,6,7,8,9,10,10A,10B,11,12-DODECAHYDRO-7-HYDROXY-10B-METHYL-, (3BS-(3B.ALPHA.,5A.BETA.,7.BETA.,8.BETA.,10A.ALPHA.,10B.BETA.))-

C20H28O3 (316.2038338)


Cafestol is an organic heteropentacyclic compound and furan diterpenoid with formula C20H28O3 obtained from the unsaponifiable fraction of coffee oil (a lipid fraction obtained from coffee beans by organic solvent extraction). It has a role as a plant metabolite, an apoptosis inducer, a hypoglycemic agent, an angiogenesis inhibitor, an antineoplastic agent, an antioxidant and an anti-inflammatory agent. It is an organic heteropentacyclic compound, a tertiary alcohol, a diterpenoid, a member of furans and a primary alcohol. Cafestol is a natural product found in Coffea arabica, Diplospora dubia, and other organisms with data available. Cafestol is found in arabica coffee. Cafestol is a constituent of coffee bean oil. Cafestol is present in boiled-type coffee beverages. Possesses hypercholesterolaemic activity. Diterpenoid constits. of coffee products are associated with cardiotoxic properties Cafestol is a diterpene molecule present in coffee Cafestol is a diterpene molecule and is a constituent of coffee bean oil. It is found in boiled-type coffee beverages. Possesses hypercholesterolaemic activity. Diterpenoid constitsuents of coffee products are associated with cardiotoxic props. Cafestol, one of the major components of coffee, is a coffee-specific diterpene from. Cafestol is a ERK inhibitor for AP-1-targeted activity against PGE2 production and the mRNA expression of cyclooxygenase (COX)-2 in LPS-activated RAW264.7 cells. Cafestol has strong inhibitory activity on PGE2 production by suppressing the NF-kB activation pathway. Cafestol contributes to its beneficial effects through various biological activities such as chemopreventive, antitumorigenic, hepatoprotective, antioxidative and antiinflammatory effects[1]. Cafestol, one of the major components of coffee, is a coffee-specific diterpene from. Cafestol is a ERK inhibitor for AP-1-targeted activity against PGE2 production and the mRNA expression of cyclooxygenase (COX)-2 in LPS-activated RAW264.7 cells. Cafestol has strong inhibitory activity on PGE2 production by suppressing the NF-kB activation pathway. Cafestol contributes to its beneficial effects through various biological activities such as chemopreventive, antitumorigenic, hepatoprotective, antioxidative and antiinflammatory effects[1]. Cafestol, one of the major components of coffee, is a coffee-specific diterpene from. Cafestol is a ERK inhibitor for AP-1-targeted activity against PGE2 production and the mRNA expression of cyclooxygenase (COX)-2 in LPS-activated RAW264.7 cells. Cafestol has strong inhibitory activity on PGE2 production by suppressing the NF-kB activation pathway. Cafestol contributes to its beneficial effects through various biological activities such as chemopreventive, antitumorigenic, hepatoprotective, antioxidative and antiinflammatory effects[1].

   

Rifampin

(7S,9Z,11S,12R,13S,14R,15R,16R,17S,18S,21Z)-2,15,17,23,27,29-hexahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-{[(4-methylpiperazin-1-yl)imino]methyl}-6-oxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^{4,7}.0^{5,28}]triaconta-1(28),2,4,9,19,21,23,25(29),26-nonaen-13-yl acetate

C43H58N4O12 (822.4051028)


A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160) J - Antiinfectives for systemic use > J04 - Antimycobacterials > J04A - Drugs for treatment of tuberculosis > J04AB - Antibiotics D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D000995 - Antitubercular Agents D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D007917 - Leprostatic Agents D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D012294 - Rifamycins C254 - Anti-Infective Agent > C52588 - Antibacterial Agent > C280 - Antitubercular Agent D065693 - Cytochrome P-450 Enzyme Inducers > D065697 - Cytochrome P-450 CYP2C19 Inducers D065693 - Cytochrome P-450 Enzyme Inducers > D065695 - Cytochrome P-450 CYP2B6 Inducers D065693 - Cytochrome P-450 Enzyme Inducers > D065698 - Cytochrome P-450 CYP2C9 Inducers D065693 - Cytochrome P-450 Enzyme Inducers > D065696 - Cytochrome P-450 CYP2C8 Inducers D065693 - Cytochrome P-450 Enzyme Inducers > D065701 - Cytochrome P-450 CYP3A Inducers D004791 - Enzyme Inhibitors > D019384 - Nucleic Acid Synthesis Inhibitors C471 - Enzyme Inhibitor > C25995 - RNA Polymerase Inhibitor

   

Rifapentine

(7S,9Z,11S,12R,13S,14R,15R,16R,17S,18S,21Z)-26-[(1E)-[(4-cyclopentylpiperazin-1-yl)imino]methyl]-2,15,17,23,27,29-hexahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6-oxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^{4,7}.0^{5,28}]triaconta-1(28),2,4,9,19,21,23,25(29),26-nonaen-13-yl acetate

C47H64N4O12 (876.4520504)


Rifapentine is only found in individuals that have used or taken this drug. It is an antibiotic drug used in the treatment of tuberculosis.Rifapentine has shown higher bacteriostatic and bactericidal activities especially against intracellular bacteria growing in human monocyte-derived macrophages. Rifapentine inhibits DNA-dependent RNA polymerase in susceptible strains of M. tuberculosis. Rifapentine acts via the inhibition of DNA-dependent RNA polymerase, leading to a suppression of RNA synthesis and cell death. J - Antiinfectives for systemic use > J04 - Antimycobacterials > J04A - Drugs for treatment of tuberculosis > J04AB - Antibiotics D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D000995 - Antitubercular Agents D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D007917 - Leprostatic Agents D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D012294 - Rifamycins C254 - Anti-Infective Agent > C52588 - Antibacterial Agent > C280 - Antitubercular Agent

   

Mascaroside

14,17,18-trihydroxy-12-methyl-17-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6-dien-10-one

C26H36O11 (524.2257506)


Mascaroside is found in coffee and coffee products. Mascaroside is a bitter principle from green beans of Malagasy coffee (Coffea vianneyi Bitter principle from green beans of Malagasy coffee (Coffea vianneyi). Mascaroside is found in coffee and coffee products.

   

Dunnione

2,3,3-trimethyl-2H,3H,4H,5H-naphtho[1,2-b]furan-4,5-dione

C15H14O3 (242.0942894)


   

Diosbulbin B

(3R,5S,6R,8R,11R,12S,13S)-3-(Furan-3-yl)-5-methyl-2,9,14-trioxapentacyclo[11.2.1.18,11.01,5.06,12]heptadecane-10,15-dione

C19H20O6 (344.125982)


Diosbulbin B is found in root vegetables. Diosbulbin B is a constituent of Dioscorea bulbifera (air potato). Constituent of Dioscorea bulbifera (air potato). Diosbulbin B is found in root vegetables. Diosbulbin B is a diterpene lactone isolated from D. bulbifera L., with anti-tumor activity. Diosbulbin B can induce liver injury[1][2]. Diosbulbin B is a diterpene lactone isolated from D. bulbifera L., with anti-tumor activity. Diosbulbin B can induce liver injury[1][2].

   

(3b,6b,8a,12a)-8,12-Epoxy-7(11)-eremophilene-6,8,12-trimethoxy-3-ol

2,4,9a-trimethoxy-3,4a,5-trimethyl-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-6-ol

C18H30O5 (326.209313)


(3b,6b,8a,12a)-8,12-Epoxy-7(11)-eremophilene-6,8,12-trimethoxy-3-ol is found in green vegetables. (3b,6b,8a,12a)-8,12-Epoxy-7(11)-eremophilene-6,8,12-trimethoxy-3-ol is a constituent of Petasites japonicus (sweet coltsfoot) Constituent of Petasites japonicus (sweet coltsfoot). (3b,6b,8a,12a)-8,12-Epoxy-7(11)-eremophilene-6,8,12-trimethoxy-3-ol is found in green vegetables.

   

Ambronide

3a,6,6,9a-tetramethyl-dodecahydronaphtho[2,1-b]furan

C16H28O (236.2140038)


Ambronide is a flavouring ingredient. Flavouring ingredient Ambroxide is a naturally occurring terpenoid. Ambroxide is one of the key constituents of ambergris.

   

Norambreinolide

3a,6,6,9a-tetramethyldecahydronaphtho[2,1-b]Furan-2(1H)-one

C16H26O2 (250.1932696)


Norambreinolide is found in herbs and spices. Norambreinolide is used to enhance the flavour of beverages and foodstuffs. Norambreinolide is a flavouring ingredient. Norambreinolide is a constituent of labdanum oil and clary sage (Salvia sclarea). It is used to enhance the flavour of beverages and foodstuffs. Flavouring ingredient. Constituent of labdanum oil and clary sage (Salvia sclarea). Norambreinolide is found in herbs and spices. Sclareolide is isolated from the flower of Perilla frutescens with antibacterial and cytotoxic activities[1]. Sclareolide is isolated from the flower of Perilla frutescens with antibacterial and cytotoxic activities[1].

   

Mozambioside

17-hydroxy-17-(hydroxymethyl)-12-methyl-14-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6-dien-10-one

C26H36O10 (508.2308356)


Mozambioside is found in coffee and coffee products. Mozambioside is isolated from beans of arabica coffee (Coffea arabica) and wild coffee sp. (Coffea pseudozanguebariae). Isolated from beans of arabica coffee (Coffea arabica) and wild coffee species (Coffea pseudozanguebariae). Mozambioside is found in coffee and coffee products.

   

O-Formyloreadone

6,6-Dimethyl-9-oxo-1H,3H,5H,5ah,6H,7H,8H,9H,9ah,9BH-naphtho[1,2-c]furan-1-yl formic acid

C15H20O4 (264.13615200000004)


O-Formyloreadone is found in mushrooms. O-Formyloreadone is a metabolite of Marasmius oreades (fairy ring mushroom Metabolite of Marasmius oreades (fairy ring mushroom). O-Formyloreadone is found in mushrooms.

   

2,3-Secoporrigenin

2-{5,7,9,13-tetramethyl-16-oxo-5,17-dioxaspiro[oxane-2,6-pentacyclo[10.7.0.0²,⁹.0⁴,⁸.0¹⁴,¹⁸]nonadecane]-13-yl}acetic acid

C27H40O6 (460.28247400000004)


(6beta,25S)-2,3-Secospirostan-3,6-olid-2-oic acid is found in onion-family vegetables. (6beta,25S)-2,3-Secospirostan-3,6-olid-2-oic acid is a constituent of Allium porrum (leek)

   

Marasmal

(3S,8R,10S,10aR,10bS)-3,8,10-trihydroxy-7,7-dimethyl-1-oxo-1H,3H,6H,6aH,7H,8H,9H,10H,10bH-naphtho[1,8a-c]furan-4-carbaldehyde

C15H20O6 (296.125982)


Marasmal is found in mushrooms. Marasmal is a metabolite of Marasmius oreades (fairy ring mushroom). Metabolite of Marasmius oreades (fairy ring mushroom). Marasmal is found in mushrooms.

   

Dehydrooreadone

1-hydroxy-6,6-dimethyl-1H,3H,5H,5aH,6H,9H,9aH,9bH-naphtho[1,2-c]furan-9-one

C14H18O3 (234.1255878)


Dehydrooreadone is found in mushrooms. Dehydrooreadone is a metabolite of Marasmius oreades (fairy ring mushroom Metabolite of Marasmius oreades (fairy ring mushroom). Dehydrooreadone is found in mushrooms.

   

3beta-Hydroxycinnamolide

7-hydroxy-6,6,9a-trimethyl-1H,3H,5H,5aH,6H,7H,8H,9H,9aH,9bH-naphtho[1,2-c]furan-3-one

C15H22O3 (250.1568862)


3beta-Hydroxycinnamolide is found in mushrooms. 3beta-Hydroxycinnamolide is a constituent of Marasmius oreades (fairy ring mushroom). Constituent of Marasmius oreades (fairy ring mushroom). 3beta-Hydroxycinnamolide is found in mushrooms.

   

Diosbulbin A

Methyl 3-(furan-3-yl)-8-hydroxy-5-methyl-14-oxo-2,13-dioxatetracyclo[10.2.1.0¹,⁵.0⁶,¹¹]pentadecane-10-carboxylic acid

C20H24O7 (376.1521954)


Diosbulbin A is found in root vegetables. Diosbulbin A is a constituent of Dioscorea bulbifera (air potato) Constituent of Dioscorea bulbifera (air potato). Diosbulbin A is found in root vegetables.

   

Eremopetasitenin A1

5-Hydroxy-3,4,13-trimethyl-12-oxo-11,14-dioxatetracyclo[8.3.1.0¹,¹⁰.0³,⁸]tetradecan-2-yl (2E)-2-methylbut-2-enoic acid

C20H28O6 (364.1885788)


Eremopetasitenin B1 is found in green vegetables. Eremopetasitenin B1 is a constituent of Petasites japonicus (sweet coltsfoot)

   

Eremopetasitenin A2

2-Methoxy-3,4,13-trimethyl-12-oxo-11,14-dioxatetracyclo[8.3.1.0¹,¹⁰.0³,⁸]tetradecan-5-yl (2E)-3-(methylsulphanyl)prop-2-enoic acid

C20H28O6S (396.16065080000004)


Eremopetasitenin A2 is found in green vegetables. Eremopetasitenin A2 is a constituent of Petasites japonicus (sweet coltsfoot) Constituent of Petasites japonicus (sweet coltsfoot). Eremopetasitenin A2 is found in green vegetables.

   

(3b,6b,8b,12a)-8,12-Epoxy-7(11)-eremophilene-6-angeloyloxy-8,12-dimethoxy-3-ol

6-Hydroxy-2,9a-dimethoxy-3,4a,5-trimethyl-2H,4H,4ah,5H,6H,7H,8H,8ah,9H,9ah-naphtho[2,3-b]furan-4-yl (2E)-2-methylbut-2-enoic acid

C22H34O6 (394.2355264)


(3b,6b,8b,12a)-8,12-Epoxy-7(11)-eremophilene-6-angeloyloxy-8,12-dimethoxy-3-ol is found in green vegetables. (3b,6b,8b,12a)-8,12-Epoxy-7(11)-eremophilene-6-angeloyloxy-8,12-dimethoxy-3-ol is a constituent of Petasites japonicus (sweet coltsfoot) Constituent of Petasites japonicus (sweet coltsfoot). (3b,6b,8b,12a)-8,12-Epoxy-7(11)-eremophilene-6-angeloyloxy-8,12-dimethoxy-3-ol is found in green vegetables.

   

Diosbulbin C

3-(furan-3-yl)-8-hydroxy-5-methyl-14-oxo-2,13-dioxatetracyclo[10.2.1.0¹,⁵.0⁶,¹¹]pentadecane-10-carboxylic acid

C19H22O7 (362.1365462)


Diosbulbin C is found in root vegetables. Diosbulbin C is a constituent of Dioscorea bulbifera (air potato). Constituent of Dioscorea bulbifera (air potato). Diosbulbin C is found in root vegetables.

   

3alpha-Hydroxyoreadone

1,7-dihydroxy-6,6-dimethyl-1H,3H,5H,5aH,6H,7H,8H,9H,9aH,9bH-naphtho[1,2-c]furan-9-one

C14H20O4 (252.136152)


3alpha-Hydroxyoreadone is found in mushrooms. 3alpha-Hydroxyoreadone is a metabolite of Marasmius oreades (fairy ring mushroom Metabolite of Marasmius oreades (fairy ring mushroom). 3alpha-Hydroxyoreadone is found in mushrooms.

   

Cafamarine

17-hydroxy-12-(hydroxymethyl)-17-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6-dien-10-one

C26H36O10 (508.2308356)


Cafamarine is found in coffee and coffee products. Cafamarine occurs in coffee. Occurs in coffee. Cafamarine is found in coffee and coffee products.

   

Isolimonic acid

(2S,5aR,6R,7S,9bR)-9b-(2-carboxy-1-hydroxyethyl)-7-[(S)-uran-3-yl(hydroxy)methyl]-3,3,5a,7-tetramethyl-5-oxospiro[1,3a,4,8,9,9a-hexahydrobenzo[e][2]benzouran-6,3-oxirane]-2-carboxylic acid

C26H34O10 (506.2151864)


Isolimonic acid is found in citrus. Isolimonic acid is a constituent of Citrus species. Constituent of Citrus subspecies Isolimonic acid is found in citrus.

   

25-O-Desacetyl rifabutin

(7S,9Z,11S,12R,13S,14R,15R,16R,17S,18S,19Z,21Z)-2,13,15,17,23,27,29-heptahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-{[(4-methylpiperazin-1-yl)imino]methyl}-8,30-dioxa-24-azatetracyclo[23.3.1.1⁴,⁷.0⁵,²⁸]triaconta-1(28),2,4,9,19,21,23,25(29),26-nonaen-6-one

C41H56N4O11 (780.3945386)


25-O-Desacetyl rifabutin is a metabolite of rifabutin. Rifabutin (Rfb) is a bactericidal antibiotic drug primarily used in the treatment of tuberculosis. The drug is a semi-synthetic derivative of rifamycin S. Its effect is based on blocking the DNA-dependent RNA-polymerase of the bacteria. It is effective against Gram-positive and some Gram-negative bacteria, but also against the highly resistant Mycobacteria, e.g. Mycobacterium tuberculosis, M. leprae and M. avium intracellulare. (Wikipedia)

   

31-Hydroxy rifabutin

(7S,9Z,11S,12R,13S,14R,15R,16R,17S,18R,19Z,21Z)-2,15,17,23-tetrahydroxy-18-(hydroxymethyl)-11-methoxy-3,7,12,14,16,22-hexamethyl-1-(2-methylpropyl)-6,32-dioxo-8,33-dioxa-24,27,29-triazaspiro[pentacyclo[23.6.1.1⁴,⁷.0⁵,³¹.0²⁶,³⁰]tritriacontane-28,4-piperidine]-1(31),2,4,9,19,21,23,25,29-nonaen-13-yl acetate

C46H62N4O12 (862.4364012)


31-Hydroxy rifabutin is a metabolite of rifabutin. Rifabutin (Rfb) is a bactericidal antibiotic drug primarily used in the treatment of tuberculosis. The drug is a semi-synthetic derivative of rifamycin S. Its effect is based on blocking the DNA-dependent RNA-polymerase of the bacteria. It is effective against Gram-positive and some Gram-negative bacteria, but also against the highly resistant Mycobacteria, e.g. Mycobacterium tuberculosis, M. leprae and M. avium intracellulare. (Wikipedia)

   

Atractylenolide I

3,8a-dimethyl-5-methylidene-2H,4H,4aH,5H,6H,7H,8H,8aH-naphtho[2,3-b]furan-2-one

C15H18O2 (230.1306728)


   

beta-Apopolygamatin

4-(1,3-benzodioxol-5-yl)-5,6-dimethoxy-4,9-dihydro-1H-benzo[f][2]benzofuran-3-one

C21H18O6 (366.1103328)


   

N,15-Didehydro-11,15-dideoxo-1-deoxy-1,15-epoxy-11-hydroxy-4-O-methyl-3-(4-((2,4,6-trimethylphenyl)methyl)-1-piperazinyl)rifamycin 8-(2,2-dimethylpropanoate)

21-(acetyloxy)-17,19,28-trihydroxy-6,23-dimethoxy-2,12,16,18,20,22,27-heptamethyl-7-{4-[(2,4,6-trimethylphenyl)methyl]piperazin-1-yl}-10,26,30-trioxa-31-azapentacyclo[25.2.1.1^{8,11}.0^{4,9}.0^{5,29}]hentriaconta-1(29),2,4,6,8,11(31),12,14,24-nonaen-3-yl 2,2-dimethylpropanoate

C57H77N3O12 (995.5506962000001)


   

Himbacine

4-[2-(1,6-dimethylpiperidin-2-yl)ethenyl]-3-methyl-decahydro-3H-naphtho[2,3-c]furan-1-one

C22H35NO2 (345.266765)


   

Vorapaxar

N-(9-{2-[5-(3-fluorophenyl)pyridin-2-yl]ethenyl}-1-methyl-3-oxo-dodecahydronaphtho[2,3-c]furan-6-yl)ethoxycarboximidate

C29H33FN2O4 (492.24242300000003)


   

16-O-Methylcafestol

[(1S,4S,12S,13R,16R,17R)-17-methoxy-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6-dien-17-yl]methanol

C21H30O3 (330.21948299999997)


16-o-methylcafestol, also known as 16-omc compound, is a member of the class of compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. 16-o-methylcafestol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 16-o-methylcafestol can be found in arabica coffee, which makes 16-o-methylcafestol a potential biomarker for the consumption of this food product.

   

dehydrokahweol

[(1R,4R,12S,13S,16S)-12-methyl-8-oxapentacyclo[14.2.1.0^{1,13}.0^{4,12}.0^{5,9}]nonadeca-5(9),6,10,17-tetraen-17-yl]methanol

C20H24O2 (296.17762039999997)