Protoanemonin

Details

• Internal ID: dfaf5cdc-1271-416f-8793-db446a3f4be4
• Taxonomy: Organoheterocyclic compounds > Dihydrofurans > Furanones > Butenolides
• IUPAC Name: 5-methylidenefuran-2-one
• SMILES (Canonical): C=C1C=CC(=O)O1
• SMILES (Isomeric): C=C1C=CC(=O)O1
• InChI: InChI=1S/C5H4O2/c1-4-2-3-5(6)7-4/h2-3H,1H2
• InChI Key: RNYZJZKPGHQTJR-UHFFFAOYSA-N
• Popularity: 296 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅H₄O₂
• Molecular Weight: 96.08 g/mol
• Exact Mass: 96.021129366 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 0.61
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• 5-Methylenefuran-2(5H)-one
• 108-28-1
• 5-methylene-2(5H)-furanone
• 5-methylidenefuran-2-one
• 2(5H)-Furanone, 5-methylene-
• 4-Methylenebut-2-en-4-olide
• Protoanemonene
• cis-4-Methylenebut-2-en-4-olide
• UNII-66FQZ1A5SO
• 66FQZ1A5SO
• EINECS 203-567-4
• ISOMYCIN
• PROTOANEMONIN [MI]
• 5-methylenfuran-2(5H)-on
• 2,4-PENTADIEN-4-OLIDE
• CHEBI:28906
• DTXSID10148346
• RNYZJZKPGHQTJR-UHFFFAOYSA-N
• 5-methylidene-2,5-dihydrofuran-2-one
• 5-METHYLENE-2,5-DIHYDROFURAN-2-ONE
• FT-0619081
• 4-hydroxy-2,4-pentadienoic acid gamma-lactone
• C07090
• A937279
• Q421294

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9970	99.70%
Caco-2	+	0.6780	67.80%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.8286	82.86%
Subcellular localzation	Mitochondria	0.5106	51.06%
OATP2B1 inhibitior	-	0.8728	87.28%
OATP1B1 inhibitior	+	0.9465	94.65%
OATP1B3 inhibitior	+	0.9532	95.32%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9515	95.15%
P-glycoprotein inhibitior	-	0.9886	98.86%
P-glycoprotein substrate	-	0.9947	99.47%
CYP3A4 substrate	-	0.7318	73.18%
CYP2C9 substrate	-	0.6133	61.33%
CYP2D6 substrate	-	0.8756	87.56%
CYP3A4 inhibition	-	0.9502	95.02%
CYP2C9 inhibition	-	0.9413	94.13%
CYP2C19 inhibition	-	0.7218	72.18%
CYP2D6 inhibition	-	0.9579	95.79%
CYP1A2 inhibition	-	0.8035	80.35%
CYP2C8 inhibition	-	0.9904	99.04%
CYP inhibitory promiscuity	-	0.7709	77.09%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7644	76.44%
Carcinogenicity (trinary)	Non-required	0.4902	49.02%
Eye corrosion	+	0.9600	96.00%
Eye irritation	+	0.9920	99.20%
Skin irritation	+	0.7687	76.87%
Skin corrosion	-	0.6510	65.10%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8646	86.46%
Micronuclear	+	0.6100	61.00%
Hepatotoxicity	+	0.8500	85.00%
skin sensitisation	+	0.7470	74.70%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	-	0.7000	70.00%
Mitochondrial toxicity	-	0.7250	72.50%
Nephrotoxicity	+	0.7499	74.99%
Acute Oral Toxicity (c)	II	0.4863	48.63%
Estrogen receptor binding	-	0.9624	96.24%
Androgen receptor binding	-	0.8339	83.39%
Thyroid receptor binding	-	0.8257	82.57%
Glucocorticoid receptor binding	-	0.8804	88.04%
Aromatase binding	-	0.8818	88.18%
PPAR gamma	-	0.8482	84.82%
Honey bee toxicity	-	0.8893	88.93%
Biodegradation	+	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.7364	73.64%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.67%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.83%	91.11%
CHEMBL2581	P07339	Cathepsin D	83.73%	98.95%

Plants that contains it

• Caltha palustris
• Clematis aristata
• Clematis chinensis
• Clematis hexapetala
• Clematis montana
• Clematis vitalba
• Pulsatilla chinensis
• Ranunculus acris
• Ranunculus bulbosus
• Ranunculus ficaria
• Ranunculus sceleratus

Cross-Links

• PubChem: 66948
• NPASS: NPC75426
• LOTUS: LTS0133358
• wikiData: Q421294