1(3H)-Isobenzofuranone, 5-hydroxy-3-[(4-hydroxyphenyl)methylene]-

Details

• Internal ID: ac660b56-5611-4b46-9093-a9a5b9dacf99
• Taxonomy: Organoheterocyclic compounds > Isocoumarans > Isobenzofuranones
• IUPAC Name: (3Z)-5-hydroxy-3-[(4-hydroxyphenyl)methylidene]-2-benzofuran-1-one
• SMILES (Canonical): C1=CC(=CC=C1C=C2C3=C(C=CC(=C3)O)C(=O)O2)O
• SMILES (Isomeric): C1=CC(=CC=C1/C=C\2/C3=C(C=CC(=C3)O)C(=O)O2)O
• InChI: InChI=1S/C15H10O4/c16-10-3-1-9(2-4-10)7-14-13-8-11(17)5-6-12(13)15(18)19-14/h1-8,16-17H/b14-7-
• InChI Key: NUBHVIPBAZTUQY-AUWJEWJLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₀O₄
• Molecular Weight: 254.24 g/mol
• Exact Mass: 254.05790880 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.77
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• NUBHVIPBAZTUQY-AUWJEWJLSA-N
• 5-Hydroxy-3-[(4-hydroxyphenyl)methylene]isobenzofuran-1(3H)-one
• (3Z)-5-Hydroxy-3-(4-hydroxybenzylidene)-2-benzofuran-1(3H)-one #
• 56783-95-0

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9962	99.62%
Caco-2	-	0.6333	63.33%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6402	64.02%
OATP2B1 inhibitior	-	0.7158	71.58%
OATP1B1 inhibitior	+	0.8332	83.32%
OATP1B3 inhibitior	+	0.8091	80.91%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.5145	51.45%
P-glycoprotein inhibitior	-	0.9025	90.25%
P-glycoprotein substrate	-	0.9497	94.97%
CYP3A4 substrate	-	0.5859	58.59%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8009	80.09%
CYP3A4 inhibition	-	0.5470	54.70%
CYP2C9 inhibition	+	0.7146	71.46%
CYP2C19 inhibition	+	0.5774	57.74%
CYP2D6 inhibition	-	0.8678	86.78%
CYP1A2 inhibition	+	0.8244	82.44%
CYP2C8 inhibition	-	0.5897	58.97%
CYP inhibitory promiscuity	+	0.7823	78.23%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9118	91.18%
Carcinogenicity (trinary)	Warning	0.3585	35.85%
Eye corrosion	-	0.9796	97.96%
Eye irritation	+	0.9775	97.75%
Skin irritation	+	0.5518	55.18%
Skin corrosion	-	0.9840	98.40%
Ames mutagenesis	-	0.5370	53.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.8838	88.38%
Micronuclear	+	0.9200	92.00%
Hepatotoxicity	+	0.6479	64.79%
skin sensitisation	-	0.6120	61.20%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	+	0.5253	52.53%
Acute Oral Toxicity (c)	III	0.4598	45.98%
Estrogen receptor binding	+	0.8415	84.15%
Androgen receptor binding	+	0.8892	88.92%
Thyroid receptor binding	+	0.5689	56.89%
Glucocorticoid receptor binding	+	0.8710	87.10%
Aromatase binding	+	0.9034	90.34%
PPAR gamma	+	0.7706	77.06%
Honey bee toxicity	-	0.8850	88.50%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9930	99.30%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	98.62%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.03%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.42%	95.56%
CHEMBL2581	P07339	Cathepsin D	94.36%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.88%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.24%	89.00%
CHEMBL242	Q92731	Estrogen receptor beta	89.15%	98.35%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	85.11%	90.93%
CHEMBL3401	O75469	Pregnane X receptor	84.11%	94.73%
CHEMBL3194	P02766	Transthyretin	83.55%	90.71%
CHEMBL4208	P20618	Proteasome component C5	81.09%	90.00%
CHEMBL2535	P11166	Glucose transporter	80.85%	98.75%
CHEMBL2039	P27338	Monoamine oxidase B	80.21%	92.51%

Plants that contains it

• Eleutherococcus senticosus

Cross-Links

• PubChem: 5377379
• NPASS: NPC153745