5-[(Z)-beta-Hydroxycinnamoyl]-4-methoxybenzofuran

Details

• Internal ID: 7848fd65-41c2-4960-a258-d9d16952c772
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Chalcones and dihydrochalcones > Furanochalcones
• IUPAC Name: (Z)-3-hydroxy-1-(4-methoxy-1-benzofuran-5-yl)-3-phenylprop-2-en-1-one
• SMILES (Canonical): COC1=C(C=CC2=C1C=CO2)C(=O)C=C(C3=CC=CC=C3)O
• SMILES (Isomeric): COC1=C(C=CC2=C1C=CO2)C(=O)/C=C(/C3=CC=CC=C3)\O
• InChI: InChI=1S/C18H14O4/c1-21-18-13(7-8-17-14(18)9-10-22-17)16(20)11-15(19)12-5-3-2-4-6-12/h2-11,19H,1H3/b15-11-
• InChI Key: IHWPQGIYXJKCOV-PTNGSMBKSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₄O₄
• Molecular Weight: 294.30 g/mol
• Exact Mass: 294.08920892 g/mol
• Topological Polar Surface Area (TPSA): 59.70 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 4.22
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• CHEMBL458131
• IHWPQGIYXJKCOV-PTNGSMBKSA-N
• BDBM50548259
• 5-[(Z)-beta-Hydroxycinnamoyl]-4-methoxybenzofuran

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8374	83.74%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7174	71.74%
OATP2B1 inhibitior	-	0.7277	72.77%
OATP1B1 inhibitior	+	0.9376	93.76%
OATP1B3 inhibitior	+	0.9925	99.25%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	+	0.5756	57.56%
P-glycoprotein substrate	-	0.9307	93.07%
CYP3A4 substrate	-	0.5453	54.53%
CYP2C9 substrate	-	0.8097	80.97%
CYP2D6 substrate	-	0.8487	84.87%
CYP3A4 inhibition	+	0.5217	52.17%
CYP2C9 inhibition	+	0.7371	73.71%
CYP2C19 inhibition	+	0.9289	92.89%
CYP2D6 inhibition	-	0.8721	87.21%
CYP1A2 inhibition	+	0.9802	98.02%
CYP2C8 inhibition	+	0.6160	61.60%
CYP inhibitory promiscuity	+	0.9459	94.59%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Danger	0.5629	56.29%
Eye corrosion	-	0.9777	97.77%
Eye irritation	-	0.4819	48.19%
Skin irritation	-	0.6315	63.15%
Skin corrosion	-	0.9795	97.95%
Ames mutagenesis	-	0.5770	57.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	+	0.8659	86.59%
Hepatotoxicity	+	0.5659	56.59%
skin sensitisation	-	0.7864	78.64%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.8028	80.28%
Acute Oral Toxicity (c)	II	0.3616	36.16%
Estrogen receptor binding	+	0.9278	92.78%
Androgen receptor binding	+	0.9198	91.98%
Thyroid receptor binding	+	0.6229	62.29%
Glucocorticoid receptor binding	+	0.8174	81.74%
Aromatase binding	+	0.8298	82.98%
PPAR gamma	+	0.8015	80.15%
Honey bee toxicity	-	0.8851	88.51%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6155	61.55%
Fish aquatic toxicity	+	0.9844	98.44%

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	94.13%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.63%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.83%	99.23%
CHEMBL2535	P11166	Glucose transporter	90.36%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.79%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.17%	99.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.30%	95.50%
CHEMBL2581	P07339	Cathepsin D	84.08%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.31%	96.00%

Plants that contains it

• Citrus trifoliata
• Millettia pulchra
• Millettia sanagana
• Pongamia pinnata
• Pongamia pinnata var. pinnata
• Tephrosia purpurea

Cross-Links

• PubChem: 5320675
• NPASS: NPC263676
• ChEMBL: CHEMBL458131
• LOTUS: LTS0004467
• wikiData: Q105113284