(2R,3R)-7-methoxy-3-methyl-5-[(E)-prop-1-enyl]-2-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1-benzofuran

Details

• Internal ID: e7c7a397-5dc8-454e-8ccf-90f476ba7092
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: (2R,3R)-7-methoxy-3-methyl-5-[(E)-prop-1-enyl]-2-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1-benzofuran
• SMILES (Canonical): CC=CC1=CC2=C(C(=C1)OC)OC(C2C)C3=CC(=C(C(=C3)OC)OC)OC
• SMILES (Isomeric): C/C=C/C1=CC2=C(C(=C1)OC)O[C@H]([C@@H]2C)C3=CC(=C(C(=C3)OC)OC)OC
• InChI: InChI=1S/C22H26O5/c1-7-8-14-9-16-13(2)20(27-21(16)17(10-14)23-3)15-11-18(24-4)22(26-6)19(12-15)25-5/h7-13,20H,1-6H3/b8-7+/t13-,20-/m1/s1
• InChI Key: GPTWTKZDAAYJRN-RTJDVGLLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₆O₅
• Molecular Weight: 370.40 g/mol
• Exact Mass: 370.17802393 g/mol
• Topological Polar Surface Area (TPSA): 46.20 Ų
• XlogP: 4.70
• Atomic LogP (AlogP): 4.99
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

• 60297-83-8

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9968	99.68%
Caco-2	+	0.9266	92.66%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5942	59.42%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8891	88.91%
OATP1B3 inhibitior	+	0.9785	97.85%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8840	88.40%
P-glycoprotein inhibitior	+	0.8593	85.93%
P-glycoprotein substrate	-	0.8322	83.22%
CYP3A4 substrate	+	0.5331	53.31%
CYP2C9 substrate	+	0.6124	61.24%
CYP2D6 substrate	-	0.6772	67.72%
CYP3A4 inhibition	+	0.7385	73.85%
CYP2C9 inhibition	-	0.5460	54.60%
CYP2C19 inhibition	+	0.8340	83.40%
CYP2D6 inhibition	-	0.8550	85.50%
CYP1A2 inhibition	+	0.9033	90.33%
CYP2C8 inhibition	+	0.6977	69.77%
CYP inhibitory promiscuity	+	0.9717	97.17%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9308	93.08%
Carcinogenicity (trinary)	Danger	0.4852	48.52%
Eye corrosion	-	0.9850	98.50%
Eye irritation	-	0.7978	79.78%
Skin irritation	-	0.8078	80.78%
Skin corrosion	-	0.9773	97.73%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7785	77.85%
Micronuclear	+	0.6959	69.59%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.7996	79.96%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.7353	73.53%
Acute Oral Toxicity (c)	II	0.4899	48.99%
Estrogen receptor binding	+	0.8728	87.28%
Androgen receptor binding	-	0.6053	60.53%
Thyroid receptor binding	+	0.8028	80.28%
Glucocorticoid receptor binding	+	0.7211	72.11%
Aromatase binding	+	0.5200	52.00%
PPAR gamma	+	0.5531	55.31%
Honey bee toxicity	-	0.6949	69.49%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9828	98.28%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4302	P08183	P-glycoprotein 1	96.01%	92.98%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.72%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.27%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.15%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.32%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.21%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.79%	85.14%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.67%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.61%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	83.01%	94.73%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.09%	97.21%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	81.90%	94.03%

Plants that contains it

• Rhodostemonodaphne miranda

Cross-Links

• PubChem: 101288378
• LOTUS: LTS0029032
• wikiData: Q105015184