3-[(2R,3S)-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]prop-2-enal

Details

• Internal ID: c018983b-d774-427e-b2b6-c1d71c26c051
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: 3-[(2R,3S)-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]prop-2-enal
• SMILES (Canonical): COC1=CC(=CC2=C1OC(C2CO)C3=CC(=C(C(=C3)OC)O)OC)C=CC=O
• SMILES (Isomeric): COC1=CC(=CC2=C1O[C@H]([C@@H]2CO)C3=CC(=C(C(=C3)OC)O)OC)C=CC=O
• InChI: InChI=1S/C21H22O7/c1-25-16-9-13(10-17(26-2)19(16)24)20-15(11-23)14-7-12(5-4-6-22)8-18(27-3)21(14)28-20/h4-10,15,20,23-24H,11H2,1-3H3/t15-,20+/m1/s1
• InChI Key: YJXKBHCATWSLFQ-QRWLVFNGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₇
• Molecular Weight: 386.40 g/mol
• Exact Mass: 386.13655304 g/mol
• Topological Polar Surface Area (TPSA): 94.40 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.84
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9919	99.19%
Caco-2	+	0.5276	52.76%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7511	75.11%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7864	78.64%
OATP1B3 inhibitior	-	0.2201	22.01%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8608	86.08%
P-glycoprotein inhibitior	+	0.7854	78.54%
P-glycoprotein substrate	-	0.7490	74.90%
CYP3A4 substrate	+	0.5582	55.82%
CYP2C9 substrate	+	0.6044	60.44%
CYP2D6 substrate	-	0.7908	79.08%
CYP3A4 inhibition	+	0.5431	54.31%
CYP2C9 inhibition	+	0.8172	81.72%
CYP2C19 inhibition	+	0.7643	76.43%
CYP2D6 inhibition	-	0.8604	86.04%
CYP1A2 inhibition	+	0.6480	64.80%
CYP2C8 inhibition	+	0.5997	59.97%
CYP inhibitory promiscuity	+	0.9393	93.93%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5202	52.02%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.8120	81.20%
Skin irritation	-	0.8093	80.93%
Skin corrosion	-	0.9673	96.73%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5882	58.82%
Micronuclear	+	0.7200	72.00%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.7946	79.46%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.5775	57.75%
Acute Oral Toxicity (c)	III	0.5221	52.21%
Estrogen receptor binding	+	0.8686	86.86%
Androgen receptor binding	+	0.5918	59.18%
Thyroid receptor binding	+	0.7183	71.83%
Glucocorticoid receptor binding	+	0.7445	74.45%
Aromatase binding	-	0.5203	52.03%
PPAR gamma	+	0.6035	60.35%
Honey bee toxicity	-	0.8551	85.51%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9629	96.29%

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	97.84%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.75%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.67%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.84%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.44%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.32%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	90.47%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.87%	86.92%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.26%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.53%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.93%	95.89%
CHEMBL2581	P07339	Cathepsin D	80.58%	98.95%

Plants that contains it

• Zanthoxylum integrifoliolum

Cross-Links

• PubChem: 162882897
• LOTUS: LTS0054312
• wikiData: Q105349532