Classification Term: 1868

Angular furanocoumarins (ontology term: CHEMONTID:0002568)

Furanocoumarins, with a structure characterized by a furan ring angularly fused to a coumarin." []

found 30 associated metabolites at category metabolite taxonomy ontology rank level.

Ancestor: Furanocoumarins

Child Taxonomies: Aflatoxins

Angelicin

2-Propenoic acid, 3-(4-hydroxy-5-benzofuranyl)-, .delta.-lactone

C11H6O3 (186.0317)


Angelicin is a furanocoumarin. Angelicin is a natural product found in Cullen cinereum, Psoralea glabra, and other organisms with data available. Angelicin is found in coriander. Angelicin is a constituent of roots and leaves of angelica (Angelica archangelica). Angelicin is found in roots and on surface of parsnips and diseased celery.Angelicin is a furanocoumarin. It can be found in Bituminaria bituminosa. It is present in the list of IARC Group 3 carcinogens (Angelicin plus ultraviolet A radiation). (Wikipedia). See also: Angelica archangelica root (part of); Cullen corylifolium fruit (part of). Angelicin is found in coriander. Angelicin is a constituent of roots and leaves of angelica (Angelica archangelica). Angelicin is found in roots and on surface of parsnips and diseased celery.Angelicin is a furanocoumarin. It can be found in Bituminaria bituminosa. It is present in the list of IARC Group 3 carcinogens (Angelicin plus ultraviolet A radiation). (Wikipedia). Constituent of roots and leaves of angelica (Angelica archangelica). Found in roots and on surface of parsnips and diseased celery D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D014149 - Tranquilizing Agents D011838 - Radiation-Sensitizing Agents > D017319 - Photosensitizing Agents > D011564 - Furocoumarins D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents > D007364 - Intercalating Agents D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants D002491 - Central Nervous System Agents > D000927 - Anticonvulsants Angelicin is a natural tricyclic aromatic hydrocarbon compound that is structurally related to psoralen and has anti-cancer, anti-inflammatory, anti-viral and other activities. Cytotoxic, IC50: 49.56 μM; inhibits MHV-68, IC50: 5.39 μg/ml (28.95 μM). Angelicin is a natural tricyclic aromatic hydrocarbon compound that is structurally related to psoralen and has anti-cancer, anti-inflammatory, anti-viral and other activities. Cytotoxic, IC50: 49.56 μM; inhibits MHV-68, IC50: 5.39 μg/ml (28.95 μM).

   

Isobergapten

5-BENZOFURANACRYLIC ACID, 4-HYDROXY-6-METHOXY-, .DELTA.-LACTONE

C12H8O4 (216.0423)


Isobergapten is a furanocoumarin. Isobergapten is a natural product found in Dorstenia psilurus, Saposhnikovia divaricata, and other organisms with data available. Isobergapten is a furocoumarin. Furocoumarins, are phototoxic and photocarcinogenic. They intercalate DNA and photochemically induce mutations. Furocoumarins are botanical phytoalexins found to varying extents in a variety of vegetables and fruits, notably citrus fruits. The levels of furocoumarins present in our diets, while normally well below that causing evident acute phototoxicity, do cause pharmacologically relevant drug interactions. Some are particularly active against cytochrome P450s. For example, in humans, bergamottin and dihydroxybergamottin are responsible for the grapefruit juice effect, in which these furanocoumarins affect the metabolism of certain drugs. Isobergapten is a member of the class of compounds known as angular furanocoumarins. Angular furanocoumarins are furanocoumarins, with a structure characterized by a furan ring angularly fused to a coumarin. Isobergapten is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Isobergapten can be found in parsnip, which makes isobergapten a potential biomarker for the consumption of this food product. Isobergapten is a non-carcinogenic (not listed by IARC) potentially toxic compound. Furocoumarin toxins can cause stomach ache and may also cause a painful skin reaction when contact with the parsnip plant is combined with UV rays from sunlight (L579) (T3DB). Isobergapten is an allelopathic inhibitor isolated from seeds of Hevacleum laciniatum[1]. Isobergapten is an allelopathic inhibitor isolated from seeds of Hevacleum laciniatum[1].

   

Pimpinellidine

2H-Furo(2,3-h)-1-benzopyran-2-one, 5,6-dimethoxy-

C13H10O5 (246.0528)


Pimpinellin is a furanocoumarin. Pimpinellin is a natural product found in Dorstenia psilurus, Clausena anisata, and other organisms with data available. Pimpinellin is a furocoumarin. Furocoumarins, are phototoxic and photocarcinogenic. They intercalate DNA and photochemically induce mutations. Furocoumarins are botanical phytoalexins found to varying extents in a variety of vegetables and fruits, notably citrus fruits. The levels of furocoumarins present in our diets, while normally well below that causing evident acute phototoxicity, do cause pharmacologically relevant drug interactions. Some are particularly active against cytochrome P450s. For example, in humans, bergamottin and dihydroxybergamottin are responsible for the grapefruit juice effect, in which these furanocoumarins affect the metabolism of certain drugs. Aglycone from hydrolysis of leaves and stems of Lycopersicon pimpinellifolium (currant tomato). Pimpinellidine is found in garden tomato. D011838 - Radiation-Sensitizing Agents > D017319 - Photosensitizing Agents > D011564 - Furocoumarins Pimpinellin is a constituent of Cyrtomium fortumei (J.). Pimpinellin inhibits the growth of tumor cells via the induction of tumor cell apoptosis[1]. Pimpinellin is a constituent of Cyrtomium fortumei (J.). Pimpinellin inhibits the growth of tumor cells via the induction of tumor cell apoptosis[1].

   

Sphondin

2H-Furo(2,3-h)-1-benzopyran-2-one, 6-methoxy-

C12H8O4 (216.0423)


Sphondin is a member of the class of compounds known as angular furanocoumarins. Angular furanocoumarins are furanocoumarins, with a structure characterized by a furan ring angularly fused to a coumarin. Sphondin is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Sphondin can be found in parsnip, which makes sphondin a potential biomarker for the consumption of this food product. Sphondin is a non-carcinogenic (not listed by IARC) potentially toxic compound. The furocoumarin 8-methoxypsoralen is carcinogenic to humans, and possibly 5-methoxypsoralen as well (L135). There is some evidence from mouse studies that other furocoumarins are carcinogenic when combined with exposure to UVA radiation (A15105). The SKLM regards the additional risk of skin cancer arising from the consumption of typical quantities of furocoumarin-containing foods, which remain significantly below the range of phototoxic doses, as insignificant. However, the consumption of phototoxic quantities cannot be ruled out for certain foods, particularly celery and parsnips, that may lead to significant increases in furocoumarin concentrations, depending on the storage, processing and production conditions (L2157) Furocoumarin photochemotherapy is known to induce a number of side-effects including erythema, edema, hyperpigmentation, and premature aging of skin. All photobiological effects of furocoumarins result from their photochemical reactions. Because many dietary or water soluble furocoumarins are strong inhibitors of cytochrome P450s, they will also cause adverse drug reactions when taken with other drugs. Cause of phototoxicity in patient with vitiligo (L579) (T3DB). Sphondin is a furanocoumarin. Sphondin is a natural product found in Heracleum lehmannianum, Heracleum asperum, and other organisms with data available. A furanocoumarin derivative isolated from Heracleum laciniatum (L579). Furocoumarins, are phototoxic and photocarcinogenic. They intercalate DNA and photochemically induce mutations. Furocoumarins are botanical phytoalexins found to varying extents in a variety of vegetables and fruits, notably citrus fruits. The levels of furocoumarins present in our diets, while normally well below that causing evident acute phototoxicity, do cause pharmacologically relevant drug interactions. Some are particularly active against cytochrome P450s. For example, in humans, bergamottin and dihydroxybergamottin are responsible for the grapefruit juice effect, in which these furanocoumarins affect the metabolism of certain drugs. Sphondin possesses an inhibitory effect on IL-1β-induced increase in the level of COX-2 protein and PGE2 release in A549 cells[1]. Sphondin possesses an inhibitory effect on IL-1β-induced increase in the level of COX-2 protein and PGE2 release in A549 cells[1].

   

Archangelicin

2-(9-{[(2Z)-2-methylbut-2-enoyl]oxy}-2-oxo-2H,8H,9H-furo[2,3-H]chromen-8-yl)propan-2-yl (2Z)-2-methylbut-2-enoic acid

C24H26O7 (426.1678)


Constituent of the roots of Angelica archangelica (anglica). Archangelicin is found in many foods, some of which are fats and oils, green vegetables, herbs and spices, and angelica. Archangelicin is found in angelica. Archangelicin is a constituent of the roots of Angelica archangelica (anglica)

   

6'-O-Malonyldaidzin

3-oxo-3-[(3,4,5-trihydroxy-6-{[3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl)methoxy]propanoic acid

C24H22O12 (502.1111)


Present in soy foods; potential nutriceutical. 6-Malonyldaidzin is found in many foods, some of which are soy milk, soy sauce, soy bean, and soy yogurt. 6-O-Malonyldaidzin is found in miso. 6-O-Malonyldaidzin is present in soy foods; potential nutriceutical.

   

3'-(1'-(3-Methylbutanoyl))-angeloyl vaginidiol

8-{2-[(3-methylbutanoyl)oxy]propan-2-yl}-2-oxo-2H,8H,9H-furo[2,3-H]chromen-9-yl (2Z)-2-methylbut-2-enoic acid

C24H28O7 (428.1835)


3-(1-(3-Methylbutanoyl))-angeloyl vaginidiol is found in fats and oils. 3-(1-(3-Methylbutanoyl))-angeloyl vaginidiol is a constituent of the roots of Angelica archangelica (angelica). Constituent of the roots of Angelica archangelica (angelica). 3-(1-(3-Methylbutanoyl))-angeloyl vaginidiol is found in fats and oils, herbs and spices, and green vegetables.

   

Edultin

8-[2-(Acetyloxy)propan-2-yl]-2-oxo-2H,8H,9H-furo[2,3-H]chromen-9-yl (2Z)-2-methylbut-2-enoic acid

C21H22O7 (386.1365)


Edultin is found in green vegetables. Edultin is a constituent of Angelica edulis

   

MAB 4

8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(2-methyl-1-oxobutyl)-4-propyl-2H-furo[2,3-H]-1-benzopyran-2-one, 9ci

C22H28O6 (388.1886)


MAB 4 is found in fruits. MAB 4 is isolated from seeds of Mammea americana (mamey

   

Furomammea G

5-hydroxy-8-(2-hydroxypropan-2-yl)-6-(3-methylbutanoyl)-4-propyl-2H,8H,9H-furo[2,3-h]chromen-2-one

C22H28O6 (388.1886)


Furomammea G is found in fruits. Furomammea G is obtained from seeds of Mammea americana (mamey

   

Cyclomammein

2,3-Dihydro-4-hydroxy-2-(1-hydroxy-1-methylethyl)-5-(3-methyl-1-oxobutyl)-9-propyl-7H-furo[2,3-F][1]benzopyran-7-one, 9ci

C22H28O6 (388.1886)


Cyclomammein is found in fruits. Cyclomammein is found in seeds of Mammea americana (mamey) Beta-D-Glucose 6 phosphate (b-G6P) is the beta-anomer of glucose-6-phosphate. There are two anomers of glucose 6 phosphate, the alpha anomer and the beta anomer. Specifically, beta-D-Glucose 6-phosphate is glucose sugar phosphorylated on carbon 6. It is a very common metabolite in cells as the vast majority of glucose entering a cell will become phosphorylated in this way. The primary reason for the immediate phosphorylation of glucose is to prevent diffusion out of the cell. The phosphorylation adds a charged phosphate group so the glucose 6-phosphate cannot easily cross the cell membrane. b-G6P is involved in the glycolysis, gluconeogenesis, pentose phosphate, and glycogen and sucrose metabolic pathways [Kegg ID: C01172]. Beta-D-Glucose 6 phosphate can be generated through beta-D-fructose phosphate or alpha-D-glucose 6 phosphate (via glucose-6-phosphate isomerase) or beta-D glucose (via hexokinase). It can then be sent off to the pentose phosphate pathway which generates the useful cofactor NADPH as well as ribulose 5-phosphate, a carbon source for the synthesis of other molecules. Alternately if the cell needs energy or carbon skeletons for synthesis then glucose 6-phosphate is targeted for glycolysis. A third route is to have glucose 6 phosphate stored or converted to glycogen, especially if blood glucose levels are high

   

Apterin

9-hydroxy-8-[2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropan-2-yl]-8,9-dihydrofuro[2,3-h]chromen-2-one

C20H24O10 (424.1369)


Apterin is a furanocoumarin glucoside reported to dilate coronary arteries as well as block calcium channels. It can be found plants of the Apiaceae family. It has been isolated from the root of plants in the genus Angelica, including Garden Angelica and in Zizia aptera. Apterin is found in lovage and parsnip. Apterin is found in lovage. Apterin is a furanocoumarin glucoside reported to dilate coronary arteries as well as block calcium channels. It can be found plants of the Apiaceae family. It has been isolated from the root of plants in the genus Angelica, including Garden Angelica and in Zizia aptera. (Wikipedia

   

Edulisin II

2-{9-[(3-methylbut-2-enoyl)oxy]-2-oxo-2H,8H,9H-furo[2,3-H]chromen-8-yl}propan-2-yl 3-methylbut-2-enoic acid

C24H26O7 (426.1678)


Edulisin II is found in green vegetables. Edulisin II is a constituent of Angelica edulis

   

Furomammea D

2-(2-hydroperoxypropan-2-yl)-4-hydroxy-5-(3-methylbutanoyl)-9-propyl-2H,3H,7H-furo[2,3-f]chromen-7-one

C22H28O7 (404.1835)


Furomammea D is found in fruits. Furomammea D is isolated from Mammea americana (mamey). Isolated from Mammea americana (mamey). Furomammea D is found in fruits.

   

Cycloneomammein

2,3-Dihydro-4-hydroxy-2-(1-hydroxy-1-methylethyl)-5-(2-methyl-1-oxobutyl)-9-propyl-7H-furo[2,3-F][1]benzopyran-7-one, 9ci

C22H28O6 (388.1886)


Cycloneomammein is found in fruits. Cycloneomammein is a constituent of seeds of Mammea americana (mamey) Beta-D-Glucose 6 phosphate (b-G6P) is the beta-anomer of glucose-6-phosphate. There are two anomers of glucose 6 phosphate, the alpha anomer and the beta anomer. Specifically, beta-D-Glucose 6-phosphate is glucose sugar phosphorylated on carbon 6. It is a very common metabolite in cells as the vast majority of glucose entering a cell will become phosphorylated in this way. The primary reason for the immediate phosphorylation of glucose is to prevent diffusion out of the cell. The phosphorylation adds a charged phosphate group so the glucose 6-phosphate cannot easily cross the cell membrane. b-G6P is involved in the glycolysis, gluconeogenesis, pentose phosphate, and glycogen and sucrose metabolic pathways [Kegg ID: C01172]. Beta-D-Glucose 6 phosphate can be generated through beta-D-fructose phosphate or alpha-D-glucose 6 phosphate (via glucose-6-phosphate isomerase) or beta-D glucose (via hexokinase). It can then be sent off to the pentose phosphate pathway which generates the useful cofactor NADPH as well as ribulose 5-phosphate, a carbon source for the synthesis of other molecules. Alternately if the cell needs energy or carbon skeletons for synthesis then glucose 6-phosphate is targeted for glycolysis. A third route is to have glucose 6 phosphate stored or converted to glycogen, especially if blood glucose levels are high

   

Oroselone

8-(1-Methylethenyl)-2H-furo[2,3-H]-1-benzopyran-2-one, 9ci

C14H10O3 (226.063)


Constituent of Angelica archangelica (angelica). Oroselone is found in fats and oils, herbs and spices, and green vegetables. Oroselone is found in fats and oils. Oroselone is a constituent of Angelica archangelica (angelica).

   

8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one

6-butanoyl-5-hydroxy-8-(2-hydroxypropan-2-yl)-4-propyl-2H,8H,9H-furo[2,3-h]chromen-2-one

C21H26O6 (374.1729)


8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one is found in fruits. 8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one is a constituent of Mammea americana (mamey)

   

Cyclonormammein

5-butanoyl-4-hydroxy-2-(2-hydroxypropan-2-yl)-9-propyl-2H,3H,7H-furo[2,3-f]chromen-7-one

C21H26O6 (374.1729)


Cyclonormammein is found in fruits. Cyclonormammein is a constituent of Mammea americana (mamey)

   

Edulisin I

8-(2-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}propan-2-yl)-2-oxo-2H,8H,9H-furo[2,3-H]chromen-9-yl 3-methylbut-2-enoic acid

C28H26O8 (490.1628)


Edulisin I is found in green vegetables. Edulisin I is a constituent of Angelica edulis

   

Edulisin III

8-[2-(Acetyloxy)propan-2-yl]-2-oxo-2H,8H,9H-furo[2,3-H]chromen-9-yl 2-methylbutanoic acid

C21H24O7 (388.1522)


Edulisin III is found in green vegetables. Edulisin III is a constituent of Angelica edulis. Constituent of Angelica edulis. Edulisin III is found in green vegetables.

   

Edulisin IV

8-[2-(Acetyloxy)propan-2-yl]-2-oxo-2H,8H,9H-furo[2,3-H]chromen-9-yl propanoic acid

C19H20O7 (360.1209)


Edulisin IV is found in green vegetables. Edulisin IV is a constituent of Angelica edulis. Constituent of Angelica edulis. Edulisin IV is found in green vegetables.

   

Edulisin V

2-{9-[(2-methylbutanoyl)oxy]-2-oxo-2H,8H,9H-furo[2,3-H]chromen-8-yl}propan-2-yl (2Z)-2-methylbut-2-enoic acid

C24H28O7 (428.1835)


Edulisin V is found in green vegetables. Edulisin V is a constituent of Angelica edulis. Constituent of Angelica edulis. Edulisin V is found in green vegetables.

   

Archangin

8-(2-methoxypropan-2-yl)-2H-furo[2,3-h]chromen-2-one

C15H14O4 (258.0892)


Archangin is found in fats and oils. Archangin is from Angelica archangelica (angelica

   

4-Hydroxy-8-methoxy-2H-furo[2,3-h]-1-benzopyran-2-one

4-Hydroxy-8-methoxy-2H-furo[2,3-H]-1-benzopyran-2-one, 9ci

C12H8O5 (232.0372)


4-Hydroxy-8-methoxy-2H-furo[2,3-h]-1-benzopyran-2-one is found in tea. 4-Hydroxy-8-methoxy-2H-furo[2,3-h]-1-benzopyran-2-one is a constituent of the leaves of Camellia sinensis (Japanese tea)

   

Edulisin VI

8-(2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-2H-furo[2,3-h]chromen-2-one

C20H22O9 (406.1264)


Edulisin VI is found in green vegetables. Edulisin VI is a constituent of the fruit of Angelica edulis. Constituent of the fruit of Angelica edulis. Edulisin VI is found in green vegetables.

   

8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]1-benzopyran-2-one

8-(2-hydroxypropan-2-yl)-2H,8H,9H-furo[2,3-h]chromen-2-one

C14H14O4 (246.0892)


   

(3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one

16-hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0²,⁹.0³,⁷.0¹³,¹⁷]nonadeca-1,4,9,11,13(17)-pentaen-18-one

C17H14O6 (314.079)


   

Columbianadin

2-[(8S)-2-oxo-8,9-Dihydrofuro[2,3-H]chromen-8-yl]propan-2-yl (Z)-2-methylbut-2-enoic acid

C19H20O5 (328.1311)


   

Columbianetin acetate

2-{2-oxo-2H,8H,9H-furo[2,3-H]chromen-8-yl}propan-2-yl acetic acid

C16H16O5 (288.0998)


   

Zosimin

2-[(8S)-2-oxo-2H,8H,9H-furo[2,3-h]chromen-8-yl]propan-2-yl (2Z)-2-methylbut-2-enoate

C19H20O5 (328.1311)


Zosimin is a member of the class of compounds known as angular furanocoumarins. Angular furanocoumarins are furanocoumarins, with a structure characterized by a furan ring angularly fused to a coumarin. Zosimin is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Zosimin can be found in carrot and wild carrot, which makes zosimin a potential biomarker for the consumption of these food products. Columbianadin, a natural coumarin from Heracleum hemsleyanum, is known to have various biological activities including anti-inflammatory and anti-cancer effects. Columbianadin, a natural coumarin from Heracleum hemsleyanum, is known to have various biological activities including anti-inflammatory and anti-cancer effects.