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

Details

• Internal ID: adb67258-904e-43a7-bca9-ef3a3616f0bc
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: 4-[(2S,3R)-3-(hydroxymethyl)-7-methoxy-5-prop-2-enyl-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenol
• SMILES (Canonical): COC1=CC(=CC2=C1OC(C2CO)C3=CC(=C(C=C3)O)OC)CC=C
• SMILES (Isomeric): COC1=CC(=CC2=C1O[C@@H]([C@H]2CO)C3=CC(=C(C=C3)O)OC)CC=C
• InChI: InChI=1S/C20H22O5/c1-4-5-12-8-14-15(11-21)19(25-20(14)18(9-12)24-3)13-6-7-16(22)17(10-13)23-2/h4,6-10,15,19,21-22H,1,5,11H2,2-3H3/t15-,19+/m0/s1
• InChI Key: SCJINMBKEKPVHB-HNAYVOBHSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₂O₅
• Molecular Weight: 342.40 g/mol
• Exact Mass: 342.14672380 g/mol
• Topological Polar Surface Area (TPSA): 68.20 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.35
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9859	98.59%
Caco-2	+	0.6420	64.20%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6799	67.99%
OATP2B1 inhibitior	-	0.8600	86.00%
OATP1B1 inhibitior	+	0.8092	80.92%
OATP1B3 inhibitior	+	0.9044	90.44%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6435	64.35%
P-glycoprotein inhibitior	-	0.4726	47.26%
P-glycoprotein substrate	-	0.7975	79.75%
CYP3A4 substrate	+	0.5548	55.48%
CYP2C9 substrate	-	0.8027	80.27%
CYP2D6 substrate	+	0.4783	47.83%
CYP3A4 inhibition	+	0.7214	72.14%
CYP2C9 inhibition	+	0.8249	82.49%
CYP2C19 inhibition	+	0.8397	83.97%
CYP2D6 inhibition	-	0.7401	74.01%
CYP1A2 inhibition	+	0.6648	66.48%
CYP2C8 inhibition	+	0.7870	78.70%
CYP inhibitory promiscuity	+	0.9590	95.90%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9308	93.08%
Carcinogenicity (trinary)	Non-required	0.5393	53.93%
Eye corrosion	-	0.9864	98.64%
Eye irritation	-	0.9111	91.11%
Skin irritation	-	0.7836	78.36%
Skin corrosion	-	0.9364	93.64%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4351	43.51%
Micronuclear	+	0.7500	75.00%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.6800	68.00%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	+	0.4542	45.42%
Acute Oral Toxicity (c)	III	0.5452	54.52%
Estrogen receptor binding	+	0.6921	69.21%
Androgen receptor binding	+	0.5480	54.80%
Thyroid receptor binding	+	0.6156	61.56%
Glucocorticoid receptor binding	+	0.6876	68.76%
Aromatase binding	-	0.5085	50.85%
PPAR gamma	-	0.4902	49.02%
Honey bee toxicity	-	0.8383	83.83%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9734	97.34%

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	98.02%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.72%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.47%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.36%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.96%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.94%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.09%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.96%	86.92%
CHEMBL1951	P21397	Monoamine oxidase A	85.01%	91.49%
CHEMBL2581	P07339	Cathepsin D	83.76%	98.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.31%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.03%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	82.66%	94.73%

Plants that contains it

• Kadsura angustifolia

Cross-Links

• PubChem: 14258445
• LOTUS: LTS0224289
• wikiData: Q105250179