Furaneol

Details

• Internal ID: bd0d69cb-f982-414f-bfd4-593318f01e6d
• Taxonomy: Organoheterocyclic compounds > Dihydrofurans > Furanones
• IUPAC Name: 4-hydroxy-2,5-dimethylfuran-3-one
• SMILES (Canonical): CC1C(=O)C(=C(O1)C)O
• SMILES (Isomeric): CC1C(=O)C(=C(O1)C)O
• InChI: InChI=1S/C6H8O3/c1-3-5(7)6(8)4(2)9-3/h3,8H,1-2H3
• InChI Key: INAXVXBDKKUCGI-UHFFFAOYSA-N
• Popularity: 437 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₈O₃
• Molecular Weight: 128.13 g/mol
• Exact Mass: 128.047344113 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 0.76
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 3658-77-3
• 4-hydroxy-2,5-dimethylfuran-3(2H)-one
• 4-Hydroxy-2,5-dimethyl-3(2H)-furanone
• 4-Hydroxy-2,5-dimethyl-3(2H)furanone
• 2,5-Dimethyl-4-hydroxy-3(2H)-furanone
• Pineapple ketone
• Dimethylhydroxy furanone
• Alletone
• 3(2H)-Furanone, 4-hydroxy-2,5-dimethyl-
• 4-hydroxy-2,5-dimethylfuran-3-one
• Strawberry furanone
• 4-hydroxy-2,5-dimethyl-3-furanone
• Coe 536
• FEMA No. 3174
• FEMA 3174
• 2,5-Dimethyl-4-hydroxy-2,3-dihydrofuran-3-one
• 2,5-Dimethyl-3-hydroxy-4-oxo-4,5-dihydrofuran
• 4-Hydroxy-2,5-dimethylfuran-2(3H)-one
• EINECS 222-908-8
• 4-hydroxy-2,5-dimethyl-2,3-dihydrofuran-3-one
• UNII-20PI8YZP7A
• 3(2H)-FURANONE, 2,5-DIMETHYL-4-HYDROXY-
• BRN 1281357
• 20PI8YZP7A
• CCRIS 8102
• DTXSID0041517
• CHEBI:76247
• 4-Hydroxy-2,5-dimethyl-3(2H)-furanone (natural)
• MFCD00010706
• 192466-95-8
• 2,5-Dimethyl-4-hydroxy-3(2H)-furanone-13C2
• Furaneol Natural
• Nat. Furaneol
• Furaneol,Synthetic
• ALNOSE
• HDMF
• dimethylhydroxyfuranone
• (+/-)-Furaneol
• SCHEMBL57008
• CHEMBL3186302
• DIMETHYL DIHYDROFURANOLONE
• DTXCID8021517
• HSDB 8322
• HY-N7093
• Tox21_300823
• 2,5-DIMETHYLDIHYDROFURANOLONE
• AC8010
• s5178
• AKOS015900499
• CS-W013470
• DIMETHYLHYDROXY FURANONE [INCI]
• LS-2407
• SB60884
• NCGC00248185-01
• NCGC00254727-01
• 2,5-dimethyl-4-hydroxy-3[2H] furanone
• 4-hydroxy-2,5-dimethyl-3-oxo-2H-furan
• AC-14027
• AS-15673
• SY035594
• CAS-3658-77-3
• 2,5-dimethyl-4-hydroxy-3-(2H)-furanone
• 2.5-dimethyl-4-hydroxy-3-(2H)-furanone
• 3(2h)-furanona, 4-hidroxi-2,5-dimetil-
• 4-hydroxy-2,5-dimethyl-furan-3(2H)-one
• 2,5-dimethyl-4-hydroxy-(2h)-furan-3-one
• 2,5-dimethyl-4-hydroxy-3-oxo-(2H)-furan
• D1569
• D1884
• FT-0610446
• C20717
• EN300-175904
• 2,3-Dihydro-4-hydroxy-2,5-dimethyl-3-furanone
• 4-oxo-3-hydroxy-2,5-dimethyl-4,5-dihydrofuran
• 4- hydroxy- 2, 5- dimethylfuran- 2(3H)- one
• A823300
• Q250455
• Q-100434
• 4 - hydroxy - 2,5 - dimethylfuran - 2(3H) - one
• 4-HYDROXY-2,5-DIMETHYL-3(2H)-FURANONE [FCC]
• 4-HYDROXY-2,5-DIMETHYL-3(2H)-FURANONE [FHFI]
• Z1255395050
• 4-Hydroxy-2,5-dimethyl-3(2H)-furanone, >=99.0% (GC)
• 4-Hydroxy-2,5-dimethyl-3(2H)-furanone, >=98%, FCC, FG
• 4-Hydroxy-2,5-dimethyl-3(2H)-furanone, analytical standard
• 4-Hydroxy-2,5-dimethyl-3(2H)-furanone, natural, >=98%, FG
• InChI=1/C6H8O3/c1-3-5(7)6(8)4(2)9-3/h3,8H,1-2H
• 4-Hydroxy-2,5-dimethyl-3(2H)-furanone, 15 wt. % (in propylene glycol), FG

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9915	99.15%
Caco-2	-	0.7262	72.62%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7381	73.81%
OATP2B1 inhibitior	-	0.8615	86.15%
OATP1B1 inhibitior	+	0.9235	92.35%
OATP1B3 inhibitior	+	0.9721	97.21%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9471	94.71%
P-glycoprotein inhibitior	-	0.9756	97.56%
P-glycoprotein substrate	-	0.9806	98.06%
CYP3A4 substrate	-	0.6584	65.84%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8810	88.10%
CYP3A4 inhibition	-	0.9486	94.86%
CYP2C9 inhibition	-	0.9699	96.99%
CYP2C19 inhibition	-	0.8480	84.80%
CYP2D6 inhibition	-	0.9593	95.93%
CYP1A2 inhibition	-	0.6142	61.42%
CYP2C8 inhibition	-	0.9904	99.04%
CYP inhibitory promiscuity	-	0.6809	68.09%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8928	89.28%
Carcinogenicity (trinary)	Non-required	0.4339	43.39%
Eye corrosion	+	0.5867	58.67%
Eye irritation	+	0.8328	83.28%
Skin irritation	+	0.6515	65.15%
Skin corrosion	-	0.7111	71.11%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8249	82.49%
Micronuclear	+	0.6200	62.00%
Hepatotoxicity	+	0.7283	72.83%
skin sensitisation	-	0.5372	53.72%
Respiratory toxicity	-	0.8000	80.00%
Reproductive toxicity	-	0.5778	57.78%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	+	0.6724	67.24%
Acute Oral Toxicity (c)	III	0.5093	50.93%
Estrogen receptor binding	-	0.8993	89.93%
Androgen receptor binding	-	0.8488	84.88%
Thyroid receptor binding	-	0.7227	72.27%
Glucocorticoid receptor binding	-	0.8964	89.64%
Aromatase binding	-	0.7752	77.52%
PPAR gamma	-	0.8143	81.43%
Honey bee toxicity	-	0.9457	94.57%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.6861	68.61%
Fish aquatic toxicity	-	0.4760	47.60%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.60%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.41%	95.56%

Plants that contains it

• Capsicum annuum
• Fragaria × ananassa

Cross-Links

• PubChem: 19309
• NPASS: NPC107703
• LOTUS: LTS0178287
• wikiData: Q250455