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3-hydroxymethyl-4-methyl-furan-2(5H)-one
A butenolide that is furan-2(5H)-one substituted by a hydroxymethyl group at position 3 and a methyl group at position 4. Isolated from an edible mushroom Mycoleptodonoides aitchisonii, it exhibits protective activity against endoplasmic reticulum (ER) stress dependent cell death.


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03. Biological Effects of Specific Chemicals: biochemical uses [CHEBI:52206] > metabolite [CHEBI:25212] > secondary metabolite [CHEBI:26619]
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05. Industrial Uses: pharmaceutical [CHEBI:52217]
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more general categories    information about this item
03. Biological Effects of Specific Chemicals 
03. Biological Effects of Specific Chemicals
 biochemical uses [CHEBI:52206] (3306) 
 metabolite [CHEBI:25212] (2692) 
 secondary metabolite [CHEBI:26619] (2225) 
 3-hydroxymethyl-4-methyl-furan-2(5H)-one [CHEBI:66047] (1)
05. Industrial Uses 
05. Industrial Uses
 pharmaceutical [CHEBI:52217] (1978) 
 drug [CHEBI:23888] (1930) 
 protective agent [CHEBI:50267] (74) 
 neuroprotective agent [CHEBI:63726] (30) 
 3-hydroxymethyl-4-methyl-furan-2(5H)-one [CHEBI:66047] (1)
08. Chemical Category 
08. Chemical Category
 main group molecular entity [CHEBI:33579] (25650) 
 s-block molecular entity [CHEBI:33674] (7287) 
 hydrogen molecular entity [CHEBI:33608] (6932) 
 hydroxides [CHEBI:24651] (5641) 
 organic hydroxy compound [CHEBI:33822] (3050) 
 alcohol [CHEBI:30879] (1371) 
 primary alcohol [CHEBI:15734] (167) 
 3-hydroxymethyl-4-methyl-furan-2(5H)-one [CHEBI:66047] (1)
 p-block molecular entity [CHEBI:33675] (25343) 
 chalcogen molecular entity [CHEBI:33304] (15225) 
 oxygen molecular entity [CHEBI:25806] (14414) 
 hydroxides [CHEBI:24651] (5641) 
 organic hydroxy compound [CHEBI:33822] (3050) 
 alcohol [CHEBI:30879] (1371) 
 primary alcohol [CHEBI:15734] (167) 
 3-hydroxymethyl-4-methyl-furan-2(5H)-one [CHEBI:66047] (1)
 organooxygen compound [CHEBI:36963] (11352) 
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic ester [CHEBI:33308] (1495) 
 lactone [CHEBI:25000] (516) 
 gamma-lactone [CHEBI:37581] (157) 
 butenolide [CHEBI:50523] (45) 
 3-hydroxymethyl-4-methyl-furan-2(5H)-one [CHEBI:66047] (1)
 oxacycle [CHEBI:38104] (2002) 
 furans [CHEBI:24129] (114) 
 butenolide [CHEBI:50523] (45) 
 3-hydroxymethyl-4-methyl-furan-2(5H)-one [CHEBI:66047] (1)
 lactone [CHEBI:25000] (516) 
 gamma-lactone [CHEBI:37581] (157) 
 butenolide [CHEBI:50523] (45) 
 3-hydroxymethyl-4-methyl-furan-2(5H)-one [CHEBI:66047] (1)
 organochalcogen compound [CHEBI:36962] (11874) 
 organooxygen compound [CHEBI:36963] (11352) 
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic ester [CHEBI:33308] (1495) 
 lactone [CHEBI:25000] (516) 
 gamma-lactone [CHEBI:37581] (157) 
 butenolide [CHEBI:50523] (45) 
 3-hydroxymethyl-4-methyl-furan-2(5H)-one [CHEBI:66047] (1)
 oxacycle [CHEBI:38104] (2002) 
 furans [CHEBI:24129] (114) 
 butenolide [CHEBI:50523] (45) 
 3-hydroxymethyl-4-methyl-furan-2(5H)-one [CHEBI:66047] (1)
 lactone [CHEBI:25000] (516) 
 gamma-lactone [CHEBI:37581] (157) 
 butenolide [CHEBI:50523] (45) 
 3-hydroxymethyl-4-methyl-furan-2(5H)-one [CHEBI:66047] (1)
 carbon group molecular entity [CHEBI:33582] (23847) 
 organic molecular entity [CHEBI:50860] (23769) 
 heteroorganic entity [CHEBI:33285] (15197) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organic heteromonocyclic compound [CHEBI:25693] (2004) 
 furans [CHEBI:24129] (114) 
 butenolide [CHEBI:50523] (45) 
 3-hydroxymethyl-4-methyl-furan-2(5H)-one [CHEBI:66047] (1)
 oxacycle [CHEBI:38104] (2002) 
 furans [CHEBI:24129] (114) 
 butenolide [CHEBI:50523] (45) 
 3-hydroxymethyl-4-methyl-furan-2(5H)-one [CHEBI:66047] (1)
 lactone [CHEBI:25000] (516) 
 gamma-lactone [CHEBI:37581] (157) 
 butenolide [CHEBI:50523] (45) 
 3-hydroxymethyl-4-methyl-furan-2(5H)-one [CHEBI:66047] (1)
 organochalcogen compound [CHEBI:36962] (11874) 
 organooxygen compound [CHEBI:36963] (11352) 
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic ester [CHEBI:33308] (1495) 
 lactone [CHEBI:25000] (516) 
 gamma-lactone [CHEBI:37581] (157) 
 butenolide [CHEBI:50523] (45) 
 3-hydroxymethyl-4-methyl-furan-2(5H)-one [CHEBI:66047] (1)
 oxacycle [CHEBI:38104] (2002) 
 furans [CHEBI:24129] (114) 
 butenolide [CHEBI:50523] (45) 
 3-hydroxymethyl-4-methyl-furan-2(5H)-one [CHEBI:66047] (1)
 lactone [CHEBI:25000] (516) 
 gamma-lactone [CHEBI:37581] (157) 
 butenolide [CHEBI:50523] (45) 
 3-hydroxymethyl-4-methyl-furan-2(5H)-one [CHEBI:66047] (1)
 organic hydroxy compound [CHEBI:33822] (3050) 
 alcohol [CHEBI:30879] (1371) 
 primary alcohol [CHEBI:15734] (167) 
 3-hydroxymethyl-4-methyl-furan-2(5H)-one [CHEBI:66047] (1)
 ester [CHEBI:35701] (3370) 
 lactone [CHEBI:25000] (516) 
 gamma-lactone [CHEBI:37581] (157) 
 butenolide [CHEBI:50523] (45) 
 3-hydroxymethyl-4-methyl-furan-2(5H)-one [CHEBI:66047] (1)
 carboxylic ester [CHEBI:33308] (1495) 
 lactone [CHEBI:25000] (516) 
 gamma-lactone [CHEBI:37581] (157) 
 butenolide [CHEBI:50523] (45) 
 3-hydroxymethyl-4-methyl-furan-2(5H)-one [CHEBI:66047] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organic heteromonocyclic compound [CHEBI:25693] (2004) 
 furans [CHEBI:24129] (114) 
 butenolide [CHEBI:50523] (45) 
 3-hydroxymethyl-4-methyl-furan-2(5H)-one [CHEBI:66047] (1)
 oxacycle [CHEBI:38104] (2002) 
 furans [CHEBI:24129] (114) 
 butenolide [CHEBI:50523] (45) 
 3-hydroxymethyl-4-methyl-furan-2(5H)-one [CHEBI:66047] (1)
 lactone [CHEBI:25000] (516) 
 gamma-lactone [CHEBI:37581] (157) 
 butenolide [CHEBI:50523] (45) 
 3-hydroxymethyl-4-methyl-furan-2(5H)-one [CHEBI:66047] (1)
 organic oxo compound [CHEBI:36587] (5932) 
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic ester [CHEBI:33308] (1495) 
 lactone [CHEBI:25000] (516) 
 gamma-lactone [CHEBI:37581] (157) 
 butenolide [CHEBI:50523] (45) 
 3-hydroxymethyl-4-methyl-furan-2(5H)-one [CHEBI:66047] (1)
 polyatomic entity [CHEBI:36357] (18777) 
 molecule [CHEBI:25367] (11520) 
 cyclic compound [CHEBI:33595] (7817) 
 monocyclic compound [CHEBI:33661] (2007) 
 heteromonocyclic compound [CHEBI:33670] (2004) 
 organic heteromonocyclic compound [CHEBI:25693] (2004) 
 furans [CHEBI:24129] (114) 
 butenolide [CHEBI:50523] (45) 
 3-hydroxymethyl-4-methyl-furan-2(5H)-one [CHEBI:66047] (1)
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organic heteromonocyclic compound [CHEBI:25693] (2004) 
 furans [CHEBI:24129] (114) 
 butenolide [CHEBI:50523] (45) 
 3-hydroxymethyl-4-methyl-furan-2(5H)-one [CHEBI:66047] (1)
 oxacycle [CHEBI:38104] (2002) 
 furans [CHEBI:24129] (114) 
 butenolide [CHEBI:50523] (45) 
 3-hydroxymethyl-4-methyl-furan-2(5H)-one [CHEBI:66047] (1)
 lactone [CHEBI:25000] (516) 
 gamma-lactone [CHEBI:37581] (157) 
 butenolide [CHEBI:50523] (45) 
 3-hydroxymethyl-4-methyl-furan-2(5H)-one [CHEBI:66047] (1)
 heterocyclic compound [CHEBI:5686] (5275) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organic heteromonocyclic compound [CHEBI:25693] (2004) 
 furans [CHEBI:24129] (114) 
 butenolide [CHEBI:50523] (45) 
 3-hydroxymethyl-4-methyl-furan-2(5H)-one [CHEBI:66047] (1)
 oxacycle [CHEBI:38104] (2002) 
 furans [CHEBI:24129] (114) 
 butenolide [CHEBI:50523] (45) 
 3-hydroxymethyl-4-methyl-furan-2(5H)-one [CHEBI:66047] (1)
 lactone [CHEBI:25000] (516) 
 gamma-lactone [CHEBI:37581] (157) 
 butenolide [CHEBI:50523] (45) 
 3-hydroxymethyl-4-methyl-furan-2(5H)-one [CHEBI:66047] (1)
 heteromonocyclic compound [CHEBI:33670] (2004) 
 organic heteromonocyclic compound [CHEBI:25693] (2004) 
 furans [CHEBI:24129] (114) 
 butenolide [CHEBI:50523] (45) 
 3-hydroxymethyl-4-methyl-furan-2(5H)-one [CHEBI:66047] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organic heteromonocyclic compound [CHEBI:25693] (2004) 
 furans [CHEBI:24129] (114) 
 butenolide [CHEBI:50523] (45) 
 3-hydroxymethyl-4-methyl-furan-2(5H)-one [CHEBI:66047] (1)
 oxacycle [CHEBI:38104] (2002) 
 furans [CHEBI:24129] (114) 
 butenolide [CHEBI:50523] (45) 
 3-hydroxymethyl-4-methyl-furan-2(5H)-one [CHEBI:66047] (1)
 lactone [CHEBI:25000] (516) 
 gamma-lactone [CHEBI:37581] (157) 
 butenolide [CHEBI:50523] (45) 
 3-hydroxymethyl-4-methyl-furan-2(5H)-one [CHEBI:66047] (1)
 organic oxo compound [CHEBI:36587] (5932) 
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic ester [CHEBI:33308] (1495) 
 lactone [CHEBI:25000] (516) 
 gamma-lactone [CHEBI:37581] (157) 
 butenolide [CHEBI:50523] (45) 
 3-hydroxymethyl-4-methyl-furan-2(5H)-one [CHEBI:66047] (1)
 heteroatomic molecular entity [CHEBI:37577] (13672) 
 hydroxides [CHEBI:24651] (5641) 
 organic hydroxy compound [CHEBI:33822] (3050) 
 alcohol [CHEBI:30879] (1371) 
 primary alcohol [CHEBI:15734] (167) 
 3-hydroxymethyl-4-methyl-furan-2(5H)-one [CHEBI:66047] (1)
ChEBI Compound Accession Identifier  [CHEBI:66047]
ChEBI Compound Description  A butenolide that is furan-2(5H)-one substituted by a hydroxymethyl group at position 3 and a methyl group at position 4. Isolated from an edible mushroom Mycoleptodonoides aitchisonii, it exhibits protective activity against endoplasmic reticulum (ER) stress dependent cell death.
ChEBI Compound Identification Number  66047
ChEBI InChI Value  InChI=1S/C6H8O3/c1-4-3-9-6(8)5(4)2-7/h7H,2-3H2,1H3
ChEBI InChIKey Value  HVNDECDCMWQSGR-UHFFFAOYSA-N
ChEBI Compound Name  3-hydroxymethyl-4-methyl-furan-2(5H)-one
ChEBI SMILES Value  CC1=C(CO)C(=O)OC1
ChEBI Substance ID  160709842
ChEBI URL  ChEBI:66047
ChemSpider ID  NS
Ontomatica Chemical Accession Key (OnChAKey)  HVNDECDCMWQSGR_UHFFFAOYSA_N_000_000000
PubChem Compound ID  25178260