(2R)-2,3-Dihydro-2beta-[4-(beta-D-glucopyranosyloxy)-3-methoxyphenyl]-3alpha-(hydroxymethyl)-7-methoxy-5-(3-hydroxy-1-propenyl)benzofuran

Details

• Internal ID: ac1c1d9c-5c7a-4f7d-a392-f4d0ab713caa
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-[(2R,3S)-3-(hydroxymethyl)-5-[(E)-3-hydroxyprop-1-enyl]-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy]oxane-3,4,5-triol
• SMILES (Canonical): COC1=CC(=CC2=C1OC(C2CO)C3=CC(=C(C=C3)OC4C(C(C(C(O4)CO)O)O)O)OC)C=CCO
• SMILES (Isomeric): COC1=CC(=CC2=C1O[C@H]([C@@H]2CO)C3=CC(=C(C=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OC)/C=C/CO
• InChI: InChI=1S/C26H32O11/c1-33-18-10-14(5-6-17(18)35-26-23(32)22(31)21(30)20(12-29)36-26)24-16(11-28)15-8-13(4-3-7-27)9-19(34-2)25(15)37-24/h3-6,8-10,16,20-24,26-32H,7,11-12H2,1-2H3/b4-3+/t16-,20-,21-,22+,23-,24+,26-/m1/s1
• InChI Key: SPWHQAUMLDQOFU-AQRJENMISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₂O₁₁
• Molecular Weight: 520.50 g/mol
• Exact Mass: 520.19446183 g/mol
• Topological Polar Surface Area (TPSA): 168.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): 0.10
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 9

Synonyms

• (2R)-2,3-Dihydro-2beta-[4-(beta-D-glucopyranosyloxy)-3-methoxyphenyl]-3alpha-(hydroxymethyl)-7-methoxy-5-(3-hydroxy-1-propenyl)benzofuran
• 107870-87-1
• 4-[(2R,3S)-2,3-Dihydro-3-(hydroxymethyl)-5-[(1E)-3-hydroxy-1-propen-1-yl]-7-methoxy-2-benzofuranyl]-2-methoxyphenyl beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5971	59.71%
Caco-2	-	0.8320	83.20%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6141	61.41%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8275	82.75%
OATP1B3 inhibitior	+	0.9744	97.44%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8440	84.40%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.7463	74.63%
CYP3A4 substrate	+	0.6236	62.36%
CYP2C9 substrate	-	0.6243	62.43%
CYP2D6 substrate	-	0.7977	79.77%
CYP3A4 inhibition	-	0.8418	84.18%
CYP2C9 inhibition	-	0.8087	80.87%
CYP2C19 inhibition	-	0.7157	71.57%
CYP2D6 inhibition	-	0.8635	86.35%
CYP1A2 inhibition	-	0.8855	88.55%
CYP2C8 inhibition	+	0.6984	69.84%
CYP inhibitory promiscuity	+	0.6891	68.91%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5372	53.72%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9480	94.80%
Skin irritation	-	0.8307	83.07%
Skin corrosion	-	0.9485	94.85%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6899	68.99%
Micronuclear	+	0.6759	67.59%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.8531	85.31%
Respiratory toxicity	-	0.6444	64.44%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.5977	59.77%
Acute Oral Toxicity (c)	III	0.6909	69.09%
Estrogen receptor binding	+	0.8295	82.95%
Androgen receptor binding	+	0.5697	56.97%
Thyroid receptor binding	+	0.5787	57.87%
Glucocorticoid receptor binding	+	0.5446	54.46%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.5971	59.71%
Honey bee toxicity	-	0.7750	77.50%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.8550	85.50%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.13%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.79%	85.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.95%	96.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.46%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.60%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.82%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	90.78%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.10%	86.92%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.38%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.75%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.07%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.35%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.73%	97.14%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.42%	89.62%
CHEMBL2581	P07339	Cathepsin D	80.28%	98.95%

Plants that contains it

• Arum italicum
• Pedicularis torta
• Sarcandra glabra

Cross-Links

• PubChem: 66552022
• NPASS: NPC267026
• LOTUS: LTS0172561
• wikiData: Q105257632