2'-Hydroxyfurano[2'',3'':4',3']chalcone

Details

• Internal ID: 0a52f3fa-8c58-48e6-aa28-b1c57c7e7d98
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Chalcones and dihydrochalcones > Furanochalcones
• IUPAC Name: (E)-1-(4-hydroxy-1-benzofuran-5-yl)-3-phenylprop-2-en-1-one
• SMILES (Canonical): C1=CC=C(C=C1)C=CC(=O)C2=C(C3=C(C=C2)OC=C3)O
• SMILES (Isomeric): C1=CC=C(C=C1)/C=C/C(=O)C2=C(C3=C(C=C2)OC=C3)O
• InChI: InChI=1S/C17H12O3/c18-15(8-6-12-4-2-1-3-5-12)13-7-9-16-14(17(13)19)10-11-20-16/h1-11,19H/b8-6+
• InChI Key: WXWGKIBMPDYPTH-SOFGYWHQSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₂O₃
• Molecular Weight: 264.27 g/mol
• Exact Mass: 264.078644241 g/mol
• Topological Polar Surface Area (TPSA): 50.40 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 4.03
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• CHEMBL2259856
• CHEBI:168932
• LMPK12120002
• (E)-1-(4-hydroxy-1-benzouran-5-yl)-3-phenylprop-2-en-1-one
• (E)-1-(4-hydroxybenzofuran-5-yl)-3-phenyl-prop-2-en-1-one
• (e)-1-(4-hydroxybenzofuran-5-yl)-3-phenylprop-2-en-1-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.5054	50.54%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5930	59.30%
OATP2B1 inhibitior	-	0.7213	72.13%
OATP1B1 inhibitior	+	0.9064	90.64%
OATP1B3 inhibitior	+	0.9747	97.47%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.5672	56.72%
P-glycoprotein inhibitior	-	0.7620	76.20%
P-glycoprotein substrate	-	0.9391	93.91%
CYP3A4 substrate	-	0.6005	60.05%
CYP2C9 substrate	-	0.6154	61.54%
CYP2D6 substrate	-	0.8621	86.21%
CYP3A4 inhibition	-	0.8283	82.83%
CYP2C9 inhibition	+	0.5000	50.00%
CYP2C19 inhibition	+	0.8074	80.74%
CYP2D6 inhibition	-	0.8965	89.65%
CYP1A2 inhibition	+	0.9541	95.41%
CYP2C8 inhibition	+	0.6862	68.62%
CYP inhibitory promiscuity	+	0.8016	80.16%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Warning	0.3825	38.25%
Eye corrosion	-	0.9727	97.27%
Eye irritation	+	0.8776	87.76%
Skin irritation	+	0.7368	73.68%
Skin corrosion	-	0.9872	98.72%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7513	75.13%
Micronuclear	+	0.8359	83.59%
Hepatotoxicity	-	0.5277	52.77%
skin sensitisation	+	0.5459	54.59%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.8610	86.10%
Acute Oral Toxicity (c)	II	0.3929	39.29%
Estrogen receptor binding	+	0.9665	96.65%
Androgen receptor binding	+	0.9006	90.06%
Thyroid receptor binding	+	0.6915	69.15%
Glucocorticoid receptor binding	+	0.8427	84.27%
Aromatase binding	+	0.9509	95.09%
PPAR gamma	+	0.9064	90.64%
Honey bee toxicity	-	0.8944	89.44%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.9847	98.47%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.63%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.95%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	90.54%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.19%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.21%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.12%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.75%	96.00%
CHEMBL2581	P07339	Cathepsin D	84.39%	98.95%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.24%	95.50%
CHEMBL3401	O75469	Pregnane X receptor	80.96%	94.73%

Plants that contains it

• Derris ovalifolia
• Millettia pulchra

Cross-Links

• PubChem: 13963932
• LOTUS: LTS0175523
• wikiData: Q76423476