A lactone having a five-membered lactone ring.
| Member | Definition | Role |
|---|
| (3S,3Ar,4S,9aS,9bR)-4-hydroxy-3,6,9-trimethyl-3,3a,4,5-tetrahydroazuleno[4,5-b]furan-2,7(9aH,9bH)-dione hydrate | | (3S,3Ar,4S,9aS,9bR)-4-hydroxy-3,6,9-trimethyl-3,3a,4,5-tetrahydroazuleno[4,5-b]furan-2,7(9aH,9bH)-dione hydrate |
| 2-acetylbutyrolactone | | 3-Acetyldihydro-2(3H)-furanone |
| 2-ethyl-2-methyl-4-butyrolactone | | alpha-EMGBL |
| 3-furancarboxylic acid, tetrahydro-4-methylene-5-oxo-2-propyl-, (2r,3s)-rel- | | 3-furancarboxylic acid, tetrahydro-4-methylene-5-oxo-2-propyl-, (2r,3s)-rel- |
| 4-methylene-2-octyl-5-oxo-3-oxolanecarboxylic acid | | 4-methylene-2-octyl-5-oxo-3-oxolanecarboxylic acid; 4-methylidene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid |
| 4-methylene-2-octyl-5-oxofuran-3-carboxylic acid | | (2R,3S)-C75; 3-Furancarboxylic acid, tetrahydro-4-methylene-2-octyl-5-oxo-, (2R,3S)-rel- |
| 4,5,6,7-tetrachlorophthalide | A member of the class of 2-benzofurans that is 2-benzofuran-1(3H)-one in which all or the hydrogens attached to the benzene ring are replaced by chlorines. A fungicide used for the control of rice blast, it is not approved for use within the European Union. | 4,5,6,7-tetrachloro-2-benzofuran-1(3H)-one |
| 4'-demethyldesoxypodophyllotoxin | A member of the class of furonaphthodioxoles that is (5R,5aR,8aR)-5,8,8a,9-tetrahydro-2H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one substituted at position 5 by a 4-hydroxy-3,5-dimethoxyphenyl group. | 4'-demethyldeoxypodophyllotoxin |
| 4'-epichaetoviridin A | An azaphilone that is the 4'-epimer of chaetoviridin A. It has been isolated from Chaetomium globosum. | 4'-epichaetoviridin A |
| albiflorin | A monoterpene glycoside with formula C23H28O11, originally isolated from the roots of Paeonia lactiflora. | albiflorin |
| alpha-peltatin | An organic heterotetracyclic compound that is 4'-demethylpodophyllotoxin which is substituted by a hydroxy group at position 10 but which is lacking the hydroxy group at position 9. It is found as a glucoside in the rhizomes of Podophyllum peltatum. | alpha-peltatin |
| andrographolide | A labdane diterpenoid isolated from the leaves and roots of Andrographis paniculata that exhibits anti-HIV, anti-inflammatory and antineoplastic properties. | andrographolide |
| anthricin | A member of the class of furonaphthodioxoles that is (5R,5aR,8aR)-5,8,8a,9-tetrahydro-2H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one substituted at position 5 by a 3,4,5-trimethoxyphenyl group. | deoxypodophyllotoxin |
| 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 |
| aromaticin | A sesquiterpene lactone that is 3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione substituted by methyl groups at positions 4a and 8 and a methylidene group at position 3. Isolated from the aerial parts of Inula hupehensis, it exhibits anti-inflammatory activity. | aromaticin |
| asperuloside | A iridoid monoterpenoid glycoside isolated from Galium verum. | asperuloside |
| beta-peltatin | An organic heterotetracyclic compound that is alpha-peltatin in which the phenolic hydroxy group of the 4-hydroxy-3,5-dimethoxyphenyl substitutent had been converted into the corresponding methyl ether. | beta-peltatin |
| bielschowskysin | A diterpenoid that is isolated from Pseudopterogorgia kallos and exhibits antimalarial and anticancer activity. | bielschowskysin |
| bigelovin | A sesquiterpene lactone that is 3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione substituted by methyl groups at positions 4a and 8, a methylidene group at position 3 and an acetoxy group at position 4. Isolated from Inula hupehensis, it exhibits antineoplastic activity. | bigelovin |
| butylidenephthalide | A gamma-lactone that is phthalide substituted by a butylidene group at position 3. Isolated from Ligusticum porteri, it exhibits hypoglycemic activity. | (Z)-3-butylidenephthalide |
| calcein am | An organic heteropentacyclic compound that is calcein in which all four carboxy group hydrogens have been substituted by (acetyloxy)methoxy groups and the hyrodgens of the two hydroxy groups have been substituted by acetyl groups. It is a a non-fluorescent probe cleaved to a fluorescent probe by non-specific intracellular esterases. | calcein am |
| carlactone | A gamma-lactone that is furan-2(5H)-one which is substituted by a methyl group at position 3 and by a [(1Z,3E)-2-methyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)buta-1,3-dien-1-yl]oxy group at position 5. | carlactone |
| chaetoviridin a | An azaphilone that is 6H-furo[2,3-h]isochromene-6,8(6aH)-dione substituted by a chloro group at position 5, a 3-hydroxy-2-methylbutanoyl group at position 9, a methyl group at position 6a and a 3-methylpent-1-en-1yl group at position 3. Isolated from Chaetomium globosum, it exhibits natifungal activity against plant pathogenic fungi. | chaetoviridin A |
| chaetoviridin E | An azaphilone that is 6H-furo[2,3-h]isochromene-6,8(6aH)-dione substituted by a chloro group at position 5, a methyl group at position 6a, a 2-methylbut-2-enoyl group at position 9 and a 3-methylpent-1-en-1-yl group at position 3. It has been isolated from Chaetomium globosum. | chaetoviridin E |
| confertin | A pseudoguaianolide that is decahydroazuleno[6,5-b]furan-2(3H)-one substituted by an oxo group at position 5, methyl groups at positions 4a and 8 and a methylidene group at position 3. It has been isolated from the aerial parts of Inula hupehensis. | confertin |
| decan-4-olide | A gamma-lactone that is oxolan-2-one substituted by a hexyl group at position 5. | gamma-decalactone |
| dehydrocostus lactone | An organic heterotricyclic compound and guaianolide sesquiterpene lactone that is acrylic acid which is substituted at position 2 by a 4-hydroxy-3,8-bis(methylene)decahydoazulen-5-yl group and in which the hydroxy group and the carboxy group have undergone formal condensation to afford the corresponding gamma-lactone. | dehydrocostus lactone |
| eplerenone | | eplerenone |
| ergolide | A sesquiterpene lactone that is decahydroazuleno[6,5-b]furan-2,5-dione substituted by methyl groups at positions 4a and 8, a methylidene group at position 3 and an acetyloxy group at position 4. It has been isolated from the aerial parts of Inula hupehensis. | ergolide |
| eupatolide | A germacranolide with formula C15H20O3, isolated from several Inula species. It exhibits anti-cancer properties. | eupatolide |
| fluorescein | A xanthene dye that is highly fluorescent, detectable even when present in minute quantities. Used forensically to detect traces of blood, in analytical chemistry as an indicator in silver nitrate titrations and in microscopy. | fluorescein (lactone form) |
| fumimycin | A member of the class of 1-benzofurans that is 1-benzofuran-2(3H)-one substituted by a propenyl group at position 4, hydroxy groups at positions 5 and 6, methyl group at position 3 and a [(2E)-3-carboxyprop-2-enoyl]nitrilo group at position 3. Isolated from the fermentation broth of Aspergillus fumisynnematus F746, it exhibits antibacterial activity. | fumimycin |
| gallein | A xanthene dye that is fluoran carrying four hydroxy substituents at positions 3', 4', 5' and 6'. | gallein |
| gamma-dodecalactone | A gamma-lactone that is oxolan-2-one substituted by an octyl group at position 5. | gamma-dodecalactone |
| glucono-1,4-lactone | | Gulono-1,4-lactone |
| gulonolactone | | D-(-)-Gulono-gamma-lactone |
| helenalin | A sesquiterpene lactone that is 3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione substituted by a hydroxy group at position 4, methyl groups at positions 4a and 8 and a methylidene group at position 3 (the 3aS,4S,4aR,7aR,8R,9aR stereoisomer). | helenalin |
| heparin | | Neocnidilide |
| himbacine | A piperidine alkaloid that is decahydronaphtho[2,3-c]furan-1(3H)-one substituted by a methyl group at position 3 and a 2-[(2R,6S)-1,6-dimethylpiperidin-2-yl]ethenyl group at position 4. It has been isolated from the bark of Australian magnolias. | himbacine |
| hinokinin | A lignan that is dihydrofuran-2(3H)-one (gamma-butyrolactone) substituted by a 3,4-methylenedioxybenzyl group at positions 3 and 4 (the 3R,4R-diastereoisomer). | hinokinin |
| hydroxyachillin | | (3S,3aR,4S,9aS,9bR)-4-hydroxy-3,6,9-trimethyl-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione |
| inuviscolide | A sesquiterpene lactone that is decahydroazuleno[6,5-b]furan-2(3H)-one substituted by a hydroxy group at position 5, a methyl group at position 5 and methylidene groups at positions 3 and 8 (the 3aR,4aR,5R,7aS,9aS stereoisomer). Isolated from the aerial parts of Inula hupehensis, it exhibits anti-inflammatory activity. | inuviscolide |
| lactonamycin | An organic heterohexacyclic compound isolated from the culture broth of Streptomyces rishiriensis. It is an antibiotic with antibacterial activity. | lactonamycin |
| lancifodilactone g | A triterpenoid that is a nortriterpenoid isolated from Schisandra lancifolia and has been shown to exhibit anti-HIV activity. | lancifodilactone G |
| marrubiin | | Marrubiin |
| matairesinol | A lignan that is gamma-butyrolactone in which the 3 and 4 positions are substituted by 4-hydroxy-3-methoxybenzyl groups (the 3R,4R-diastereomer). | (-)-matairesinol |
| monascin | An organic heterotricyclic compound that is 3a,4,8,9a-tetrahydro-2H-furo[3,2-g][2]benzopyran-2,9(3H)-dione that is substituted at positions 3, 6, and 9a by hexanoyl, (1E)-prop-1-en-1-yl and methyl groups, respectively (the 3S,3aR,9aR diastereoisomer). One of the azaphilonoid pigments in extracts of Monascus pilosus-fermented rice (red-mould rice), it is a potent inhibitor of carcinogenesis measured against chemical- or UV-initiated, phorbol-promoted mouse skin tumours. | monascin |
| monascorubrin | | monascorubrin |
| mycophenolate mofetil | A carboxylic ester resulting from the formal condensation between the carboxylic acid group of mycophenolic acid and the hydroxy group of 2-(morpholin-4-yl)ethanol. In the liver, it is metabolised to mycophenolic acid, an immunosuppressant for which it is a prodrug. It is widely used to prevent tissue rejection following organ transplants as well as for the treatment of certain autoimmune diseases. | mycophenolate mofetil |
| mycophenolic acid | A member of the class of 2-benzofurans that is 2-benzofuran-1(3H)-one which is substituted at positions 4, 5, 6, and 7 by methyl, methoxy, (2E)-5-carboxy-3-methylpent-2-en-1-yl, and hydroxy groups, respectively. It is an antibiotic produced by Penicillium brevi-compactum, P. stoloniferum, P. echinulatum and related species. An immunosuppressant, it is widely used (partiularly as its sodium salt and as the 2-(morpholin-4-yl)ethyl ester prodrug, mycophenolate mofetil) to prevent tissue rejection following organ transplants and for the treatment of certain autoimmune diseases. | mycophenolic acid |
| nephrosteranic acid | | Nephrosteranic acid |
| patulin | A furopyran and lactone that is (2H-pyran-3(6H)-ylidene)acetic acid which is substituted by hydroxy groups at positions 2 and 4 and in which the hydroxy group at position 4 has condensed with the carboxy group to give the corresponding bicyclic lactone. A mycotoxin produced by several species of Aspergillus and Penicillium, it has antibiotic properties but has been shown to be carcinogenic and mutagenic. | patulin |
| phthalide | A gamma-lactone that is 1,3-dihydro-2-benzofuran in which the hydrogens at position 1 are replaced by an oxo group. | 2-benzofuran-1(3H)-one |
| 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 |
| pyrethrosin | | Pyrethrosin |
| salvileucalin b | A diterpenoid with a rearranged neo-clerodane skeleton isolated from Salvia leucantha and has been shown exhibit antineoplastic activity. | salvileucalin B |
| savinin | A lignan that is dihydrofuran-2(3H)-one (gamma-butyrolactone) substituted by a 1,3-benzodioxol-5-ylmethylidene group at position 3 and a 1,3-benzodioxol-5-ylmethyl group at position 4 (the 3E,4R-isomer). It exhibits antiviral activity against SARS-CoV-2. | savinin |
| sphaeropsidin a | | Sphaeropsidin A |
| spirodiclofen | | spirodiclofen |
| sporothriolide | A furofuran that is (3aR,6aR)-hexahydrofuro[3,4-b]furan substituted by an oxo group at positions 2 and 4, methylene group at position 3 and by an hexyl group at position 6. It is a metabolite isolated from several species of fungi. | sporothriolide |
| teniposide | A furonaphthodioxole that is a synthetic derivative of podophyllotoxin with anti-tumour activity; causes single- and double-stranded breaks in DNA and DNA-protein cross-links and prevents repair by topoisomerase II binding. | teniposide |
| thunberginol f | An isobenzofuranone that is 2-benzofuran-1(3H)-one substituted by a hydroxy group at position 7 and a 3,4-dihydroxybenzylidene group at position 3. It has been isolated from the roots of Scorzonera judaica. | thunberginol F |
| top 53 | A furonaphthodioxole that is 4'-demethyldeoxypodophyllotoxin which is substituted at position 4 of the C-ring by a 2-{[2-(dimethylamino)ethyl](methyl)amino}ethyl group. While structurally related to etoposide, TOP-53 is significantly more toxic to non-small cell lung cancer cells, more active at generating chromosomal breaks, and displays improved cellular uptake and pharmacokinetics in animal lung tissues. | TOP-53 |
| tutin | | Tutin |
| zaluzanin C | A sesquiterpene lactone that is decahydroazuleno[4,5-b]furan-2(3H)-one substituted by methylidene groups at positions 3, 6 and 9 and a hydroxy group at position 8. | zaluzanin C |