Classification Term: 691

Oxepanes (ontology term: CHEMONTID:0001729)

Compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms." []

found 41 associated metabolites at class metabolite taxonomy ontology rank level.

Ancestor: Organoheterocyclic compounds

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

1,2-Epoxy-p-menth-8-ene

1-Methyl-4-(1-methylethenyl)-7-oxabicyclo[4.1.0]heptane, 9ci

C10H16O (152.12010859999998)


1,2-epoxy-p-menth-8-ene, also known as limonene-1,2-epoxide or 1,2-epoxylimonene, is a member of the class of compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms. 1,2-epoxy-p-menth-8-ene is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 1,2-epoxy-p-menth-8-ene is a green tasting compound found in lemon and wild celery, which makes 1,2-epoxy-p-menth-8-ene a potential biomarker for the consumption of these food products. 1,2-Epoxy-p-menth-8-ene is found in citrus. 1,2-Epoxy-p-menth-8-ene is isolated from oil of Cymbopogon species, orange (Citrus sinensis), Japanese pepper tree (Zanthoxylum piperitum) and other

   

(1xi,4xi,6xi)-Carvone oxide

7-Oxabicyclo[4.1.0]heptan-2-one, 1-methyl-4-(1-methylethenyl)-, (1R,4R,6R)-

C10H14O2 (166.09937440000002)


(1xi,4xi,6xi)-Carvone oxide is found in herbs and spices. (1xi,4xi,6xi)-Carvone oxide is isolated from spearmint oil. Isolated from spearmint oil. (1xi,4xi,6xi)-Carvone oxide is found in herbs and spices.

   

(+)-Rotundifolone

(1S,6S)-6-methyl-3-(propan-2-ylidene)-7-oxabicyclo[4.1.0]heptan-2-one

C10H14O2 (166.09937440000002)


(+)-rotundifolone, also known as lippione, is a member of the class of compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms (+)-rotundifolone is slightly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (+)-rotundifolone can be found in spearmint, which makes (+)-rotundifolone a potential biomarker for the consumption of this food product.

   

4-Vinylcyclohexene dioxide

3-(1,2-Epoxyethyl)-7-oxabicyclo(4.1.0)heptane

C8H12O2 (140.0837252)


D009676 - Noxae > D002273 - Carcinogens

   

Levoglucosan

6,8-Dioxabicyclo[3.2.1]octane b-delta-glucopyranose deriv.

C6H10O5 (162.052821)


Levoglucosan is an anhydrohexose that is the 1,6-anhydro-derivative of beta-D-glucopyranose. It is formed from the pyrolysis of carbohydrates, such as starch and cellulose. As a result, levoglucosan is often used as a chemical tracer for biomass burning in atmospheric chemistry studies, particularly with respect to airborne particulate matter. Levoglucosan in urine has been shown to be highly correlated with regional fires and as a biomarker for wood smoke exposure (PMID: 19165390). This is because the gas emitted by the pyrolysis of wood (biomass) contains significant amounts of levoglucosan. The hydrolysis of levoglucosan generates the fermentable sugar glucose, and therefore lignocellulosic material exhibits great potential as a renewable feedstock for the production of bioethanol. Levoglucosan can also be utilized in the synthesis of chiral polymers such as unhydrolysable glucose polymers. Levoglucosan is also produced via caramelization of sugar. Consumption of caramel or caramel-containing sweets can lead to a short-term 5X increase in urinary levels of levoglucosan (from 20 uM/mM creatinine to 100 uM/mM creatinine) (PMID: 19707249). Urinary levoglucosan levels increase within 2 h of caramel consumption and return to pre-exposure levels within 24 h. These data suggest that diet is a major factor in determining urinary levoglucosan levels and that recent dietary history needs to be taken into account to use levoglucosan as a marker for wood smoke exposure. Excretory levels of levoglucosan vary widely from zero up to 5.3 mmol/L (PMID: 3757263, 16448658, 16317539). Levoglucosan (1,6-Anhydro-β-D-glucopyranose) is an anhydrosugar produced through glucan pyrolysis and is widely found in nature[1].

   

Rotundifolone

6-Methyl-3-(1-methylethylidene)-7-oxabicyclo[4.1.0]heptan-2-one, 9ci

C10H14O2 (166.09937440000002)


Rotundifolone is found in cornmint. Rotundifolone is a constituent of Mentha rotundifolia and other Mentha species Rotundifolone is a flavouring ingredient. Constituent of Mentha rotundifolia and other Mentha subspecies Flavouring ingredient. Rotundifolone is found in cornmint, spearmint, and herbs and spices.

   

alpha-Kessyl alcohol

1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0^{2,6}]dodecan-3-ol

C15H26O2 (238.1932696)


Constituent of Valeriana officinalis (valerian) and other subspecies alpha-Kessyl alcohol is found in tea, fats and oils, and herbs and spices. alpha-Kessyl alcohol is found in fats and oils. alpha-Kessyl alcohol is a constituent of Valeriana officinalis (valerian) and other species.

   

Kessyl glycol

1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecane-3,12-diol

C15H26O3 (254.1881846)


Constituent of the rhizomes of Valeriana officinalis (valerian). Kessyl glycol is found in tea, fats and oils, and herbs and spices. Kessyl glycol is found in fats and oils. Kessyl glycol is a constituent of the rhizomes of Valeriana officinalis (valerian).

   

3,4-Epoxy-p-menth-1(7)-ene

4-methylidene-1-(propan-2-yl)-7-oxabicyclo[4.1.0]heptane

C10H16O (152.12010859999998)


3,4-Epoxy-p-menth-1(7)-ene is found in herbs and spices. 3,4-Epoxy-p-menth-1(7)-ene is isolated from Zanthoxylum piperitum (Japanese pepper tree). Isolated from Zanthoxylum piperitum (Japanese pepper tree). 3,4-Epoxy-p-menth-1(7)-ene is found in herbs and spices.

   

Annuionone A

1,5-dimethyl-8-(3-oxobutyl)-6-oxabicyclo[3.2.1]octan-3-one

C13H20O3 (224.14123700000002)


Annuionone A is found in fats and oils. Annuionone A is a constituent of Helianthus annuus (sunflower) Constituent of Helianthus annuus (sunflower). Annuionone A is found in sunflower and fats and oils.

   

(5R,6S)-5,6-Epoxy-7-megastigmen-9-one

(3E)-4-{2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}but-3-en-2-one

C13H20O2 (208.14632200000003)


(5R,6S)-5,6-Epoxy-7-megastigmen-9-one is found in garden tomato. (5R,6S)-5,6-Epoxy-7-megastigmen-9-one is a constituent of tomatoes and carrots

   

6,8-Epoxy-p-menthane

4,7,7-Trimethyl-6-oxabicyclo[3.2.1]octane

C10H18O (154.1357578)


Minor constituent of caraway oil. 6,8-Epoxy-p-menthane is found in caraway, fats and oils, and herbs and spices. 6,8-Epoxy-p-menthane is found in caraway. 6,8-Epoxy-p-menthane is a minor constituent of caraway oil.

   

3(4->5)-Abeo-4,11:4,12-diepoxy-3-eudesmanol

5,9,12-trimethyl-11,14-dioxatetracyclo[6.4.1.1⁹,¹².0¹,⁵]tetradecan-2-ol

C15H24O3 (252.1725354)


3(4->5)-Abeo-4,11:4,12-diepoxy-3-eudesmanol is found in root vegetables. 3(4->5)-Abeo-4,11:4,12-diepoxy-3-eudesmanol is a constituent of Cyperus rotundus (nutgrass)

   

Isokessane

1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0^{2,6}]dodecane

C15H26O (222.1983546)


Constituent of Valeriana officinalis (valerian). Kessane is found in tea, fats and oils, and herbs and spices. Kessane is found in fats and oils. Kessane is a constituent of Valeriana officinalis (valerian).

   

5,9:6,9-Diepoxy-4-megastigmene

2,2,9-Trimethyl-8,12-dioxatricyclo[7.2.1.01,6]dodec-5-ene

C13H20O2 (208.14632200000003)


5,9:6,9-Diepoxy-4-megastigmene is found in alcoholic beverages. 5,9:6,9-Diepoxy-4-megastigmene is a constituent of quince fruit (Cydonia oblonga) brandy. Constituent of quince fruit (Cydonia oblonga) brandy. 5,9:6,9-Diepoxy-4-megastigmene is found in alcoholic beverages.

   

cis-Quinceoxepane

4-methyl-2-[(1Z)-3-methylbuta-1,3-dien-1-yl]oxepane

C12H20O (180.151407)


trans-Quinceoxepane is found in fruits. trans-Quinceoxepane is a constituent of quince fruit. Constituent of quince fruit. cis-Quinceoxepane is found in fruits.

   

Valeracetate

{1,5,9-trimethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-9-yl}methyl acetic acid

C17H28O3 (280.2038338)


Constituent of Valeriana officinalis (valerian). Valeracetate is found in tea, fats and oils, and herbs and spices. Valeracetate is found in fats and oils. Valeracetate is a constituent of Valeriana officinalis (valerian).

   

1,2:3,4-Diepoxy-p-menth-8-ene

4-methyl-7-(prop-1-en-2-yl)-3,8-dioxatricyclo[5.1.0.0²,⁴]octane

C10H14O2 (166.09937440000002)


1,2:3,4-Diepoxy-p-menth-8-ene is found in herbs and spices. 1,2:3,4-Diepoxy-p-menth-8-ene is a constituent of parsley leaves (Petroselinum crispum). Constituent of parsley leaves (Petroselinum crispum). 1,2:3,4-Diepoxy-p-menth-8-ene is found in herbs and spices and parsley.

   

Annuionone C

6-[(1E)-3-hydroxybut-1-en-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-one

C13H20O3 (224.14123700000002)


Annuionone C is found in fats and oils. Annuionone C is a constituent of Helianthus annuus (sunflower) Constituent of Helianthus annuus (sunflower). Annuionone C is found in fats and oils.

   

Annuionone B

1,5-dimethyl-8-[(1E)-3-oxobut-1-en-1-yl]-6-oxabicyclo[3.2.1]octan-3-one

C13H18O3 (222.1255878)


Annuionone B is found in fats and oils. Annuionone B is a constituent of Helianthus annuus (sunflower) Constituent of Helianthus annuus (sunflower). Annuionone B is found in sunflower and fats and oils.

   

Epoxyoxophorone

1,3,3-Trimethyl-7-oxabicyclo-[4.1.0]-heptane-2,5-dione

C9H12O3 (168.0786402)


Epoxyoxophorone is used as a food additive [EAFUS] ("EAFUS: Everything Added to Food in the United States. [http://www.eafus.com/]")

   

Deoxyartemsinin

(1R,4R,5S,8R,9S,12S)-12-hydroxy-4,8,12-trimethyl-2,13-dioxatricyclo[7.4.1.0⁵,¹⁴]tetradec-6-en-3-one

C15H22O4 (266.1518012)


Deoxyartemsinin is a metabolite of artemisinin. Artemisinin, also known as Qinghaosu, and its derivatives are a group of drugs that possess the most rapid action of all current drugs against Plasmodium falciparum malaria. Treatments containing an artemisinin derivative (artemisinin-combination therapies, ACTs) are now standard treatment worldwide for P. falciparum malaria. The starting compound artemisinin is isolated from the plant Artemisia annua, sweet wormwood, an herb employed in Chinese traditional medicine. (Wikipedia)

   

cis-Cyclohexene Oxide

7-oxabicyclo 4.1.0 heptane

C6H10O (98.07316100000001)


   

5alpha-Hydroxytriptolide

8,13-dihydroxy-1-methyl-7-(propan-2-yl)-3,6,10,16-tetraoxaheptacyclo[11.7.0.0^{2,4}.0^{2,9}.0^{5,7}.0^{9,11}.0^{14,18}]icos-14(18)-en-17-one

C20H24O7 (376.1521954)


   

Conduritol epoxide

7-oxabicyclo[4.1.0]heptane-2,3,4,5-tetrol

C6H10O5 (162.052821)


D004791 - Enzyme Inhibitors

   

2-Propenoic acid, 2-methyl-, 7-oxabicyclo[4.1.0]hept-3-ylmethyl ester

2-Propenoic acid, 2-methyl-, 7-oxabicyclo[4.1.0]hept-3-ylmethyl ester

C11H16O3 (196.1099386)


   

Deepoxy-deoxynivalenol

3,10-dihydroxy-2-(hydroxymethyl)-1,5-dimethyl-12-methylidene-8-oxatricyclo[7.2.1.0^{2,7}]dodec-5-en-4-one

C15H20O5 (280.13106700000003)


D009676 - Noxae > D011042 - Poisons > D014255 - Trichothecenes D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins

   

Glucose ketone

1,4,5,6-tetrahydroxy-3-(hydroxymethyl)-2-oxabicyclo[4.1.0]heptan-7-one

C7H10O7 (206.042651)


   

Paeonimetabolin I

8-hydroxy-3,10-dimethyl-2,9-dioxatricyclo[4.3.1.0³,⁸]decan-5-one

C10H14O4 (198.0892044)


   

r-limonene

1-methyl-4-(prop-1-en-2-yl)-7,8,9-trioxabicyclo[4.2.1]nonane

C10H16O3 (184.1099386)


   

Tenacigenin B

1-{8,9,14-trihydroxy-7,11-dimethyl-2-oxapentacyclo[8.8.0.0¹,³.0³,⁷.0¹¹,¹⁶]octadecan-6-yl}ethan-1-one

C21H32O5 (364.2249622)


   

Tetrahydroaldosterone

1-{11,18-dihydroxy-14-methyl-17-oxapentacyclo[14.2.1.0^{1,5}.0^{6,15}.0^{9,14}]nonadecan-2-yl}-2-hydroxyethan-1-one

C21H32O5 (364.2249622)


   

Tripdiolide

8,19-dihydroxy-1-methyl-7-(propan-2-yl)-3,6,10,16-tetraoxaheptacyclo[11.7.0.0²,⁴.0²,⁹.0⁵,⁷.0⁹,¹¹.0¹⁴,¹⁸]icos-14(18)-en-17-one

C20H24O7 (376.1521954)


   

triptolide

6-Hydroxy-8b-methyl-6a-(propan-2-yl)-3b,4,4a,6,6a,7a,7b,8b,9,10-decahydrotrisoxireno[6,7:8a,9:4b,5]phenanthro[1,2-c]furan-1(3H)-one

C20H24O6 (360.1572804)


   

Triptonide

1-methyl-7-(propan-2-yl)-3,6,10,16-tetraoxaheptacyclo[11.7.0.0^{2,4}.0^{2,9}.0^{5,7}.0^{9,11}.0^{14,18}]icos-14(18)-ene-8,17-dione

C20H22O6 (358.1416312)


   

4-Oxahexacyclo[11.6.2.02,8.03,5.010,20.017,21]henicosane-6,7-diol

4-oxahexacyclo[11.6.2.0^{2,8}.0^{3,5}.0^{10,20}.0^{17,21}]henicosane-6,7-diol

C20H30O3 (318.21948299999997)


   

cis-Limonene-1,2-oxide

(1R,4R,6S)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptane

C10H16O (152.12010859999998)


(4r)-limonene 1alpha,2alpha-epoxide, also known as 1beta,2beta-epoxy-4betah-P-menth-8-ene, is a member of the class of compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms (4r)-limonene 1alpha,2alpha-epoxide is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (4r)-limonene 1alpha,2alpha-epoxide is a citrus and fresh tasting compound found in lemon and wild celery, which makes (4r)-limonene 1alpha,2alpha-epoxide a potential biomarker for the consumption of these food products. (4r)-limonene 1α,2α-epoxide, also known as 1beta,2beta-epoxy-4betah-P-menth-8-ene, is a member of the class of compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms (4r)-limonene 1α,2α-epoxide is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (4r)-limonene 1α,2α-epoxide is a citrus and fresh tasting compound found in lemon and wild celery, which makes (4r)-limonene 1α,2α-epoxide a potential biomarker for the consumption of these food products.

   

Piperitone oxide

6-methyl-3-(propan-2-yl)-7-oxabicyclo[4.1.0]heptan-2-one

C10H16O2 (168.1150236)


Piperitone oxide is a member of the class of compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms. Piperitone oxide is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). Piperitone oxide can be found in cornmint, orange mint, peppermint, and spearmint, which makes piperitone oxide a potential biomarker for the consumption of these food products.

   

(+)-1,2-Epoxyneomenthyl acetate

(2R,3S,6S)-6-Methyl-3-(propan-2-yl)-7-oxabicyclo[4.1.0]heptan-2-yl acetic acid

C12H20O3 (212.14123700000002)


(+)-1,2-epoxyneomenthyl acetate is a member of the class of compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms (+)-1,2-epoxyneomenthyl acetate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (+)-1,2-epoxyneomenthyl acetate can be found in cornmint, which makes (+)-1,2-epoxyneomenthyl acetate a potential biomarker for the consumption of this food product.

   

(±)-Limonene diepoxide

1-methyl-4-(2-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]heptane

C10H16O2 (168.1150236)


(±)-limonene diepoxide is a member of the class of compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms (±)-limonene diepoxide is slightly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (±)-limonene diepoxide can be found in wild celery, which makes (±)-limonene diepoxide a potential biomarker for the consumption of this food product.

   

1,6-anhydro-N-acetyl-beta-muramate

N-[(1R,2S,3R,4R,5R)-3-[(1R)-1-carboxyethoxy]-2-hydroxy-6,8-dioxabicyclo[3.2.1]octan-4-yl]ethanecarboximidate

C11H16NO7 (274.0926726)


1,6-anhydro-n-acetyl-beta-muramate is a member of the class of compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms. 1,6-anhydro-n-acetyl-beta-muramate is soluble (in water) and a weakly acidic compound (based on its pKa). 1,6-anhydro-n-acetyl-beta-muramate can be found in a number of food items such as lovage, french plantain, ceylon cinnamon, and garden cress, which makes 1,6-anhydro-n-acetyl-beta-muramate a potential biomarker for the consumption of these food products. 1,6-anhydro-n-acetyl-β-muramate is a member of the class of compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms. 1,6-anhydro-n-acetyl-β-muramate is soluble (in water) and a weakly acidic compound (based on its pKa). 1,6-anhydro-n-acetyl-β-muramate can be found in a number of food items such as lovage, french plantain, ceylon cinnamon, and garden cress, which makes 1,6-anhydro-n-acetyl-β-muramate a potential biomarker for the consumption of these food products.