Any cyclic ether in which the oxygen atom forms part of a 3-membered ring.
| Member | Definition | Role |
|---|
| 1,2-epoxy-3-(p-nitrophenoxy)propane | An epoxide that is oxirane substituted by a (4-nitrophenoxy)methyl group. | 1,2-epoxy-3-(4-nitrophenoxy)propane |
| 1,2-epoxybutane | | 1,2-Epoxybutane |
| 1,2,7,8-diepoxyoctane | | 1,2:7,8-diepoxyoctane |
| 2-methyl-1,2-epoxypropane | | 2,2-Dimethyloxirane |
| 2-pinene oxide | An epoxide of alpha-pinene. | alpha-pinene oxide |
| 2,3-oxidosqualene | A squalene triterpenoid obtained by formal epoxidation across the 2,3 C=C bond of squalene. | 2,3-epoxysqualene |
| 4-vinyl-1-cyclohexene dioxide | The diepoxide of 4-vinylcyclohexene. | 4-vinylcyclohexene dioxide |
| 7-deacetylgedunin | A limonoid that is the 7-deacetyl derivative of gedunin. It has been isolated from Azadirachta indica. | 7-deacetylgedunin |
| 7,8-dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide | | benzo[a]pyrene diol epoxide I |
| aloxistatin | An L-leucine derivative that is the amide obtained by formal condensation of the carboxy group of (2S,3S)-3-(ethoxycarbonyl)oxirane-2-carboxylic acid with the amino group of N-(3-methylbutyl)-L-leucinamide. | aloxistatin |
| anticapsin | An alanine derivative that is L-alanine bearing a 5-oxo-7-oxabicyclo[4.1.0]hept-2-yl substituent at position 3. | anticapsin zwitterion; anticapsin |
| arglabin | An organic heterotetracyclic compound and guaianolide sesquiterpene lactone that is acrylic acid which is substituted at position 2 by a 4-hydroxy-3,8-dimethyl-1,3a,4,5,6,7-hexahydroazulen-5-yl group in which the double bond in the 7-membered ring has been epoxidised and in which the hydroxy group and the carboxy group have undergone formal condensation to give the corresponding gamma-lactone. It is found in Artemisia glabella. Arglabin-DMA HCl, the hydrochloride salt of the adduct resulting from the conjugate addition of dimethylamine to the ene-lactone moiety, has been successfully used in Khazakhstan for the treatment of breast, colon, ovarian and lung cancers. | arglabin |
| asukamycin | A polyketide that is a member of the manumycin family of antibiotics and exhibits strong antibacterial, antifungal, and antineoplastic activities. Isolated from from the actinomycete bacterium Streptomyces nodosus subsp. asukaensis. | asukamycin |
| azadirachtin | A member of the family of azadirachtins that is isolated from the neem tree (Azadirachta indica). | azadirachtin A |
| BDA-366 | A member of the class of anthraquinone that is 1,4-diamino-9,10-anthraquinone in which the two amino groups are carrying 3-(diethylamino)-2-hydroxypropyl and (oxiran-2-yl)methyl substituents. It exhibits anti-cancer properties. | BDA-366 |
| bisphenol f diglycidyl ether | An aromatic ether that is bisphenol F where the hydrogens of both hydroxy groups have been replaced by a oxiran-2-ylmethyl group. | bisphenol F diglycidyl ether |
| bromobenzene 3,4-oxide | | Bromobenzene-3,4-oxide |
| carbamazepine epoxide | An epoxide and metabolite of carbamazepine. | carbamazepine-10,11-epoxide |
| carfilzomib | A synthetic tetrapeptide consisting of morpholin-4-acetyl, L-2-amino-4-phenylbutanoyl, L-leucyl and L-phenylalanyl residues joined in sequence with the C-terminus connected to the amino group of (2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]-1-oxopentan-1-one via an amide linkage. Used for the treatment of patients with multiple myeloma | carfilzomib |
| caryophyllene oxide | | caryophyllene oxide |
| cathestatin b | A carboxamide obtained by the formal condensation of the carboxylic group of oxirane-2,3-dicarboxylic acid with the amino group of N-(4-aminobutyl)-L-tyrosinamide (the 2S,3S stereoisomer). An antibiotic isolated from the fermentation broth of Penicillium citrinum, it acts as a potent inhibitor of cysteine protease. | cathestatin B |
| cerulenin | An epoxydodecadienamide isolated from several species, including Acremonium, Acrocylindrum and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function. | cerulenin |
| chaetoglobosin A | A cytochalasan alkaloid isolated from Chaetomium globosum and Calonectria morganii. | chaetoglobosin A |
| conduritol epoxide | An epoxide resulting from the epoxidation of the double bond of a conduritol. | conduritol epoxide |
| cyclopenin | | (-)-cyclopenine |
| daphnetoxin | A daphnane-type orthoester diterpene with potential cholesterol-lowering activity, found exclusively in plants of the family Thymelaeaceae. | daphnetoxin |
| dieldrin | An organochlorine compound resulting from the epoxidation of the double bond of aldrin. It is the active metabolite of the proinsecticde aldrin. | dieldrin |
| diepoxybutane | | diepoxybutane |
| disparlure | | 2-methyl-7S,8R-Epoxy-octadecane |
| epichlorohydrin | An epoxide that is 1,2-epoxypropene in which one of the methyl hydrogens is substituted by chlorine. | epichlorohydrin |
| epothilone a | An epithilone that is epothilone C in which the double bond in the macrocyclic lactone ring has been oxidised to the corresponding epoxide (the 13R,14S diastereoisomer). | epothilone A |
| epothilone b | An epithilone that is epithilone D in which the double bond in the macrocyclic ring has been oxidised to the corresponding epoxide (the S,S stereoisomer). | epothilone B |
| epoxiconazole | An epoxide that is oxirane substituted by a 2-chlorophenyl, 4-fluorophenyl and a 1H-1,2,4-triazol-1-ylmethyl groups. | 1-{[3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole |
| epoxyazadiradione | A limonoid that is azadiradione with an epoxy group across positions 14 and 15. Isolated from Azadirachta indica it exhibits insecticidal activitry against mosquitoes. | epoxyazadiradione |
| ethoglucid | | Triethylene glycol diglycidyl ether |
| fosfomycin | A phosphonic acid having an (R,S)-1,2-epoxypropyl group attached to phosphorus. | fosfomycin |
| gedunin | A pentacyclic triterpenoid natural product found particularly in Azadirachta indica and Cedrela odorata. | gedunin |
| glycidol | | glycidol |
| glycidyl methacrylate | An enoate ester obtained by formal condensation of the carboxy group of methacrylic acid with the hydroxy group of glycidol. | glycidyl methacrylate |
| glycinaldehyde | | Glycidaldehyde |
| hypothemycin | A macrolide that is isolated from the cultured broth of Hypomyces subiculosus and shows antifungal activity and inhibits the growth of some human cancer cells. | hypothemycin |
| ixabepilone | A macrocycle that is a lactam analogue of epothilone B. Binds directly to beta-tubulin subunits on microtubules, leading to suppression of microtubule dynamics. | ixabepilone |
| laulimalide | A macrolide with formula C30H42O7 that is isolated from the marine sponges, Cacospongia mycofijiensis and Hyattella sp. | laulimalide |
| limonin | | limonin |
| manumycin | A polyketide with formula C31H38N2O7 initially isolated from Streptomyces parvulus as a result of a random screening program for farnesyl transferase (FTase) inhibitors. It is a natural product that exhibits anticancer and antibiotic properties. | manumycin A |
| maytansine | An organic heterotetracyclic compound and 19-membered macrocyclic lactam antibiotic originally isolated from the Ethiopian shrub Maytenus serrata but also found in other Maytenus species. It exhibits cytotoxicity against many tumour cell lines. | maytansine |
| monorden | An antifungal macrolactone antibiotic, obtained from Diheterospora chlamydosporia and Chaetomium chiversii that inhibits protein tyrosine kinase and heat shock protein 90 (Hsp90). | radicicol |
| muconomycin a | A trichothecene antibiotic which incorporates a triester macrocyclic structure and an exocyclic methylene epoxide group. | verrucarin A |
| mupirocin | An alpha,beta-unsaturated ester resulting from the formal condensation of the alcoholic hydroxy group of 9-hydroxynonanoic acid with the carboxy group of (2E)-4-[(2S)-tetrahydro-2H-pyran-2-yl]-3-methylbut-2-enoic acid in which the tetrahydropyranyl ring is substituted at positions 3 and 4 by hydroxy groups and at position 5 by a {(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl}methyl group. Originally isolated from the Gram-negative bacterium Pseudomonas fluorescens, it is used as a topical antibiotic for the treatment of Gram-positive bacterial infections. | mupirocin |
| myriaporone 3 | A member of the class of oxanes isolated from the Mediterranean bryozoan Myriapora truncata and has been shown to exhibit inhibitory activity against murine leukemia cells. | myriaporone 3 |
| natamycin | A macrolide antibiotic that has formula C33H47NO13, produced by several Streptomyces species including Streptomyces natalensis. It exhibits broad spectrum antifungal activity and used in eye drops, and as a food preservative, and also as a postharvest biofungicide for citrus and other fruit crops. | natamycin |
| nucleoside oq | A 7-deazaguanine ribonucleoside obtained by formal epoxidation of the cyclohexene moiety of queuosine. | epoxyqueuosine |
| oxypeucadanin, (s)-(-)-isomer | A furanocoumarin that is 7H-furo[3,2-g][1]benzopyran-7-one substituted by a [(2S)-3,3-dimethyloxiran-2-yl]methoxy group at position 4. | oxypeucedanin |
| panaxydol | | panaxydol |
| picrotin | An organic heteropentacyclic compound that is picrotoxinin in which the olefinic double bond has undergone addition of water to give the corresponding tertiary alcohol. It is the less toxic component of picrotoxin, lacking GABA activity. | picrotin |
| picrotoxinin | A picrotoxane sesquiterpenoid that is 3a,4,5,6,7,7a-hexahydro-1H-indene-3,7-dicarboxylic acid which is substituted at positions 3a, 6, and 7a by methyl, isopropenyl, and hydroxy groups, respectively; in which the double bond at position 2-3 has been epoxidised; and in which the carboxy groups at positions 3 and 7 have undergone gamma-lactone formation by O-alkylation to positions 4 and 5, respectively. A component of picrotoxin. | picrotoxinin |
| poloxalene | | Poloxamer |
| propylene oxide | An epoxide that is oxirane substituted by a methyl group at position 2. | 1,2-epoxypropane |
| psorospermin | An organic heterotetracyclic compound that is 1,2-dihydro-6H-furo[2,3-c]xanthene substituted by a hydroxy group at position 10, a methoxy group at position 5 nad a 2-methyloxiran-2-yl group at position 2. | psorospermin |
| quinine | An Aspidosperma alkaloid with molecular formula C21H24N2O3 found in the roots of Madagascar periwinkle (Catharanthus roseus, formerly known as Vinca rosea). | lochnericine |
| rediocide a | A diterpenoid of the class of daphnane-type terpenes. It is isolated from Trigonostemon reidioides and has been shown to exhibit insecticidal activity. | rediocide A |
| rhizoxin | An macrolide antibiotic isolated from the pathogenic plant fungus Rhizopus microsporus. It also exhibits antitumour and antimitotic activity. | rhizoxin |
| rosaramicin | A macrolide antibiotic with activity against Neisseria gonorrhoeae, Chlamydia trachomatis, Ureaplasma urealyticum and Mycoplasma hominis. | rosaramicin |
| stilbene oxide | | stilbene oxide |
| styrene oxide | An epoxide that is oxirane in which one of the hydrogens has been replaced by a phenyl group. | styrene oxide |
| trapoxin a | A homodetic cyclic tetrapeptide constructed from L-phenylalanyl (x2), D-pipecolinyl and L-2-amino-8-oxo-9,10-epoxydecanoyl residues. | trapoxin A |
| trichloroepoxyethane | | trichloroepoxyethane |
| triptolide | | Triptolide |
| troleandomycin | A semi-synthetic macrolide antibiotic obtained by acetylation of the three free hydroxy groups of oleandomycin. Troleandomycin is only found in individuals that have taken the drug. | troleandomycin |