3-[2-(4-Hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoic acid

Details

• Internal ID: 77ea7cf9-d7e2-4c55-a2a4-5e7881c85acd
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: 3-[2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoic acid
• SMILES (Canonical): COC1=CC(=CC2=C1OC(C2CO)C3=CC(=C(C(=C3)OC)O)OC)C=CC(=O)O
• SMILES (Isomeric): COC1=CC(=CC2=C1OC(C2CO)C3=CC(=C(C(=C3)OC)O)OC)C=CC(=O)O
• InChI: InChI=1S/C21H22O8/c1-26-15-8-12(9-16(27-2)19(15)25)20-14(10-22)13-6-11(4-5-18(23)24)7-17(28-3)21(13)29-20/h4-9,14,20,22,25H,10H2,1-3H3,(H,23,24)
• InChI Key: MXADFNHTWMJYES-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₈
• Molecular Weight: 402.40 g/mol
• Exact Mass: 402.13146766 g/mol
• Topological Polar Surface Area (TPSA): 115.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.73
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9868	98.68%
Caco-2	-	0.5423	54.23%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7278	72.78%
OATP2B1 inhibitior	-	0.8610	86.10%
OATP1B1 inhibitior	+	0.7979	79.79%
OATP1B3 inhibitior	-	0.2742	27.42%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8340	83.40%
P-glycoprotein inhibitior	+	0.7641	76.41%
P-glycoprotein substrate	-	0.7074	70.74%
CYP3A4 substrate	+	0.5406	54.06%
CYP2C9 substrate	-	0.5983	59.83%
CYP2D6 substrate	-	0.8436	84.36%
CYP3A4 inhibition	-	0.5318	53.18%
CYP2C9 inhibition	+	0.7990	79.90%
CYP2C19 inhibition	+	0.6579	65.79%
CYP2D6 inhibition	-	0.8707	87.07%
CYP1A2 inhibition	-	0.6061	60.61%
CYP2C8 inhibition	+	0.7343	73.43%
CYP inhibitory promiscuity	+	0.9035	90.35%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.4776	47.76%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.8357	83.57%
Skin irritation	-	0.8156	81.56%
Skin corrosion	-	0.9699	96.99%
Ames mutagenesis	-	0.6954	69.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6254	62.54%
Micronuclear	+	0.7574	75.74%
Hepatotoxicity	-	0.8375	83.75%
skin sensitisation	-	0.8220	82.20%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.5941	59.41%
Acute Oral Toxicity (c)	III	0.4860	48.60%
Estrogen receptor binding	+	0.8803	88.03%
Androgen receptor binding	+	0.6356	63.56%
Thyroid receptor binding	+	0.7408	74.08%
Glucocorticoid receptor binding	+	0.7822	78.22%
Aromatase binding	-	0.5152	51.52%
PPAR gamma	+	0.5985	59.85%
Honey bee toxicity	-	0.8764	87.64%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9794	97.94%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.03%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.44%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.73%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.20%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.04%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.13%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.49%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.45%	86.92%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.14%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	82.42%	94.73%
CHEMBL3194	P02766	Transthyretin	81.82%	90.71%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.29%	95.89%

Plants that contains it

• Selaginella moellendorffii

Cross-Links

• PubChem: 162953889
• LOTUS: LTS0092231
• wikiData: Q105173938