(3Z)-3-butylidene-4-hydroxy-2-benzofuran-1(3H)-one

Details

• Internal ID: 7ad25766-41cd-45c4-84ce-c14bdbf9c132
• Taxonomy: Organoheterocyclic compounds > Isocoumarans > Isobenzofuranones
• IUPAC Name: (3Z)-3-butylidene-4-hydroxy-2-benzofuran-1-one
• SMILES (Canonical): CCCC=C1C2=C(C=CC=C2O)C(=O)O1
• SMILES (Isomeric): CCC/C=C\1/C2=C(C=CC=C2O)C(=O)O1
• InChI: InChI=1S/C12H12O3/c1-2-3-7-10-11-8(12(14)15-10)5-4-6-9(11)13/h4-7,13H,2-3H2,1H3/b10-7-
• InChI Key: FCZPMYNMCGYTCA-YFHOEESVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₂O₃
• Molecular Weight: 204.22 g/mol
• Exact Mass: 204.078644241 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.70
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• (3Z)-3-butylidene-4-hydroxy-2-benzofuran-1(3H)-one
• SCHEMBL17552282
• 3-[(Z)-Butylidene]-4-hydroxyisobenzofuran-1(3H)-one
• 1(3H)-isobenzofuranone, 3-butylidene-4-hydroxy-, (3Z)-
• InChI=1/C12H12O3/c1-2-3-7-10-11-8(12(14)15-10)5-4-6-9(11)13/h4-7,13H,2-3H2,1H3/b10-7

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.9282	92.82%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Plasma membrane	0.5556	55.56%
OATP2B1 inhibitior	-	0.8636	86.36%
OATP1B1 inhibitior	+	0.8823	88.23%
OATP1B3 inhibitior	+	0.9684	96.84%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8935	89.35%
P-glycoprotein inhibitior	-	0.9490	94.90%
P-glycoprotein substrate	-	0.9097	90.97%
CYP3A4 substrate	-	0.5510	55.10%
CYP2C9 substrate	-	0.6054	60.54%
CYP2D6 substrate	-	0.7867	78.67%
CYP3A4 inhibition	-	0.8300	83.00%
CYP2C9 inhibition	-	0.5932	59.32%
CYP2C19 inhibition	+	0.6496	64.96%
CYP2D6 inhibition	-	0.8981	89.81%
CYP1A2 inhibition	+	0.8257	82.57%
CYP2C8 inhibition	-	0.7671	76.71%
CYP inhibitory promiscuity	+	0.6107	61.07%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.4349	43.49%
Eye corrosion	-	0.8726	87.26%
Eye irritation	+	0.9652	96.52%
Skin irritation	-	0.5590	55.90%
Skin corrosion	-	0.9162	91.62%
Ames mutagenesis	+	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7001	70.01%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	+	0.5042	50.42%
skin sensitisation	+	0.6932	69.32%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	-	0.6000	60.00%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.6562	65.62%
Acute Oral Toxicity (c)	III	0.4917	49.17%
Estrogen receptor binding	+	0.5973	59.73%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.6002	60.02%
Aromatase binding	-	0.6814	68.14%
PPAR gamma	+	0.7159	71.59%
Honey bee toxicity	-	0.9689	96.89%
Biodegradation	+	0.5250	52.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9720	97.20%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.86%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.62%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	93.09%	94.73%
CHEMBL1951	P21397	Monoamine oxidase A	91.98%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.14%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.30%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.88%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.07%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.18%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.37%	99.17%

Plants that contains it

• Conioselinum anthriscoides
• Ligusticum officinale

Cross-Links

• PubChem: 642373
• NPASS: NPC143110