(2S,3R,4R,5R,6S)-2-[4-[(2R,3R)-3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]phenoxy]-6-methyloxane-3,4,5-triol

Details

• Internal ID: 3541cdec-7218-442f-af66-01cc6a9b64b5
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: (2S,3R,4R,5R,6S)-2-[4-[(2R,3R)-3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]phenoxy]-6-methyloxane-3,4,5-triol
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=CC=C(C=C2)C3C(C4=C(O3)C(=CC(=C4)CCCO)OC)CO)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=CC=C(C=C2)[C@H]3[C@H](C4=C(O3)C(=CC(=C4)CCCO)OC)CO)O)O)O
• InChI: InChI=1S/C25H32O9/c1-13-20(28)21(29)22(30)25(32-13)33-16-7-5-15(6-8-16)23-18(12-27)17-10-14(4-3-9-26)11-19(31-2)24(17)34-23/h5-8,10-11,13,18,20-23,25-30H,3-4,9,12H2,1-2H3/t13-,18-,20-,21+,22+,23-,25-/m0/s1
• InChI Key: UZKFZGJIIPOGLV-WOXHNLKXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₂O₉
• Molecular Weight: 476.50 g/mol
• Exact Mass: 476.20463259 g/mol
• Topological Polar Surface Area (TPSA): 138.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 1.04
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7328	73.28%
Caco-2	-	0.8116	81.16%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6798	67.98%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8371	83.71%
OATP1B3 inhibitior	+	0.9472	94.72%
MATE1 inhibitior	-	0.9212	92.12%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8112	81.12%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	+	0.5066	50.66%
CYP3A4 substrate	+	0.6581	65.81%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7646	76.46%
CYP3A4 inhibition	-	0.8846	88.46%
CYP2C9 inhibition	-	0.8608	86.08%
CYP2C19 inhibition	-	0.8420	84.20%
CYP2D6 inhibition	-	0.8689	86.89%
CYP1A2 inhibition	-	0.7937	79.37%
CYP2C8 inhibition	+	0.7534	75.34%
CYP inhibitory promiscuity	-	0.7024	70.24%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6001	60.01%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9587	95.87%
Skin irritation	-	0.8227	82.27%
Skin corrosion	-	0.9479	94.79%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8497	84.97%
Micronuclear	-	0.5041	50.41%
Hepatotoxicity	-	0.7250	72.50%
skin sensitisation	-	0.8769	87.69%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.6630	66.30%
Acute Oral Toxicity (c)	III	0.7586	75.86%
Estrogen receptor binding	+	0.7512	75.12%
Androgen receptor binding	+	0.5782	57.82%
Thyroid receptor binding	+	0.5613	56.13%
Glucocorticoid receptor binding	-	0.5425	54.25%
Aromatase binding	-	0.5171	51.71%
PPAR gamma	+	0.5281	52.81%
Honey bee toxicity	-	0.8228	82.28%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6604	66.04%
Fish aquatic toxicity	-	0.5180	51.80%

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	98.94%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.87%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.94%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.13%	99.17%
CHEMBL2581	P07339	Cathepsin D	92.56%	98.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.59%	86.92%
CHEMBL226	P30542	Adenosine A1 receptor	91.28%	95.93%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.12%	97.36%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	90.49%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.51%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.15%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.59%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	87.54%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.06%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.37%	85.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.19%	96.00%
CHEMBL4208	P20618	Proteasome component C5	83.84%	90.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.17%	92.62%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.60%	95.83%
CHEMBL2243	O00519	Anandamide amidohydrolase	80.08%	97.53%

Plants that contains it

• Betula pendula

Cross-Links

• PubChem: 163081211
• LOTUS: LTS0216851
• wikiData: Q105282242