2(5H)-Furanone

Details

• Internal ID: 1ba01f27-c049-45df-a878-3657810f6b3e
• Taxonomy: Organoheterocyclic compounds > Dihydrofurans > Furanones > Butenolides
• IUPAC Name: 2H-furan-5-one
• SMILES (Canonical): C1C=CC(=O)O1
• SMILES (Isomeric): C1C=CC(=O)O1
• InChI: InChI=1S/C4H4O2/c5-4-2-1-3-6-4/h1-2H,3H2
• InChI Key: VIHAEDVKXSOUAT-UHFFFAOYSA-N
• Popularity: 1,830 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄H₄O₂
• Molecular Weight: 84.07 g/mol
• Exact Mass: 84.021129366 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): 0.10
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• 497-23-4
• Furan-2(5H)-one
• BUTENOLIDE
• Isocrotonolactone
• 2-Buten-4-olide
• 2-Butenolide
• gamma-Crotonolactone
• 2-Oxo-2,5-dihydrofuran
• 2H-furan-5-one
• Crotonolactone
• 4-Hydroxy-2-butenoic acid lactone
• gamma-Crotolactone
• alpha,beta-Crotonolactone
• 2-(5H)-furanone
• delta,alpha,beta-Butenolide
• gamma-Hydroxycrotonic acid lactone
• 5H-furan-2-one
• but-2-en-4-olide
• 2-Butenoic acid gamma-lactone
• 2-Butenoic acid-gamma-lactone
• .gamma.-Crotonolactone
• C4H4O2
• 2-Buten-1,4-olide
• 2,5-dihydrofuran-2-one
• 4-Hydroxycrotonic acid gamma-lactone
• NSC 197009
• CCRIS 5722
• 2,5-Dihydrofuranone
• 2-Butenoic acid, 4-hydroxy-, gamma-lactone
• EINECS 207-839-3
• MFCD00005376
• BRN 0383585
• 4-Hydroxy-2-butenoic acid gamma-lactone
• UNII-8KXK25H388
• CHEMBL166223
• CHEBI:38118
• HSDB 8151
• 2-Butenoic acid-.gamma.-lactone
• 8KXK25H388
• .delta.,.alpha.,.beta.-Butenolide
• .gamma.-Hydroxycrotonic acid lactone
• NSC-197009
• 4-Hydroxy-2-butenoic acid .gamma.-lactone
• Crotonic acid, 4-hydroxy-, .gamma.-lactone
• 2-Butenoic acid, 4-hydroxy-, .gamma.-lactone
• 5-17-09-00112 (Beilstein Handbook Reference)
• Crotonic acid, 4-hydroxy-, gamma-lactone (6CI,7CI)
• .DELTA..alpha.,.beta.-Butolide
• 2-Butenoic acid, .gamma.-lactone
• .DELTA..alpha.,.beta.-Butenolide
• g-Crotonolactone
• ?-Crotonolactone
• 5H-furanone
• 2-B4O
• 2_5H_furanone
• CRATONE
• .gamma.-Crotolactone
• 5 H-Furan-2-one
• (5H)-furan-2-one
• alpha,alpha,beta-Butolide
• 2(5H)FURANONE
• .BETA.-CROTONOLACTONE
• 2(5H)-Furanone, 98%
• laquo gammaRaquo -crotolactone
• 4-Hydroxycrotonic acid lactone
• .alpha.,.beta.-Crotonolactone
• laquo gammaRaquo -crotonolactone
• DTXSID7075422
• FEMA NO. 4138
• VIHAEDVKXSOUAT-UHFFFAOYSA-
• BCP15247
• NSC51296
• BBL103594
• BDBM50360798
• NSC-51296
• NSC197009
• STL557404
• AKOS000268618
• CS-W008270
• HY-W008270
• laquo deltaRaquo ,alpha,beta-butenolide
• SB60895
• Crotonic acid, 4-hydroxy-, gamma-lactone
• LS-70308
• SY017893
• 2-Butenoic acid-laquo gammaRaquo -lactone
• 2-Oxo-2,5-dihydrofuran(2-[5H]-furanone)
• 5-OXO-2,5-DIHYDROFURAN-3-YL ESTER
• A7404
• AM20100212
• FT-0608698
• EN300-80159
• laquo gammaRaquo -hydroxycrotonic acid lactone
• C17601
• 2(5H)-Furanone (laquo gammaRaquo -crotonolactone)
• 4-Hydroxy-2-butenoic acid laquo gammaRaquo -lactone
• J-506134
• Q4596886
• Crotonic acid, 4-hydroxy-, laquo gammaRaquo -lactone
• 2-Butenoic acid, 4-hydroxy-, laquo gammaRaquo -lactone
• Z1219048777
• 4-HYDROXY-2-BUTENOIC ACID .GAMMA.-LACTONE [FHFI]
• InChI=1/C4H4O2/c5-4-2-1-3-6-4/h1-2H,3H2

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.7666	76.66%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	+	0.7714	77.14%
Subcellular localzation	Mitochondria	0.5256	52.56%
OATP2B1 inhibitior	-	0.8698	86.98%
OATP1B1 inhibitior	+	0.9582	95.82%
OATP1B3 inhibitior	+	0.9600	96.00%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9141	91.41%
P-glycoprotein inhibitior	-	0.9896	98.96%
P-glycoprotein substrate	-	0.9860	98.60%
CYP3A4 substrate	-	0.7651	76.51%
CYP2C9 substrate	-	0.8195	81.95%
CYP2D6 substrate	-	0.8925	89.25%
CYP3A4 inhibition	-	0.9877	98.77%
CYP2C9 inhibition	-	0.9347	93.47%
CYP2C19 inhibition	-	0.8677	86.77%
CYP2D6 inhibition	-	0.9482	94.82%
CYP1A2 inhibition	-	0.7446	74.46%
CYP2C8 inhibition	-	0.9963	99.63%
CYP inhibitory promiscuity	-	0.9013	90.13%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8044	80.44%
Carcinogenicity (trinary)	Non-required	0.5643	56.43%
Eye corrosion	+	0.9824	98.24%
Eye irritation	+	0.9964	99.64%
Skin irritation	+	0.8623	86.23%
Skin corrosion	+	0.6473	64.73%
Ames mutagenesis	-	0.9400	94.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8370	83.70%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	+	0.8875	88.75%
skin sensitisation	-	0.6331	63.31%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	-	0.8000	80.00%
Mitochondrial toxicity	-	0.8500	85.00%
Nephrotoxicity	+	0.7397	73.97%
Acute Oral Toxicity (c)	II	0.8122	81.22%
Estrogen receptor binding	-	0.9632	96.32%
Androgen receptor binding	-	0.8778	87.78%
Thyroid receptor binding	-	0.9383	93.83%
Glucocorticoid receptor binding	-	0.8702	87.02%
Aromatase binding	-	0.8917	89.17%
PPAR gamma	-	0.8876	88.76%
Honey bee toxicity	-	0.9400	94.00%
Biodegradation	+	0.9500	95.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	-	0.4078	40.78%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL261	P00915	Carbonic anhydrase I	13600 nM	Ki	PMID: 22137345
CHEMBL3594	Q16790	Carbonic anhydrase IX	4420 nM	Ki	PMID: 22137345

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.24%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.22%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.00%	96.77%

Plants that contains it

• Crocus sativus

Cross-Links

• PubChem: 10341
• NPASS: NPC147824
• ChEMBL: CHEMBL166223
• LOTUS: LTS0243199
• wikiData: Q4596886