(2S,3R,4S,5S,6R)-2-[[(2R,3R)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-7-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 1843a615-0269-4520-b4c0-afa18fa875bc
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[[(2R,3R)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-7-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): COC1=C(C=CC(=C1)C2C(C3=C(O2)C(=CC(=C3)CCCO)OC4C(C(C(C(O4)CO)O)O)O)CO)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)[C@H]2[C@H](C3=C(O2)C(=CC(=C3)CCCO)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)CO)O
• InChI: InChI=1S/C25H32O11/c1-33-17-9-13(4-5-16(17)29)23-15(10-27)14-7-12(3-2-6-26)8-18(24(14)36-23)34-25-22(32)21(31)20(30)19(11-28)35-25/h4-5,7-9,15,19-23,25-32H,2-3,6,10-11H2,1H3/t15-,19+,20+,21-,22+,23-,25+/m0/s1
• InChI Key: WGTYXIDAEFJHPD-JORXNSFBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₂O₁₁
• Molecular Weight: 508.50 g/mol
• Exact Mass: 508.19446183 g/mol
• Topological Polar Surface Area (TPSA): 179.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.29
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5698	56.98%
Caco-2	-	0.8544	85.44%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6730	67.30%
OATP2B1 inhibitior	-	0.8600	86.00%
OATP1B1 inhibitior	+	0.8199	81.99%
OATP1B3 inhibitior	+	0.9664	96.64%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.6541	65.41%
P-glycoprotein inhibitior	-	0.5426	54.26%
P-glycoprotein substrate	-	0.6354	63.54%
CYP3A4 substrate	+	0.6470	64.70%
CYP2C9 substrate	-	0.8002	80.02%
CYP2D6 substrate	-	0.7492	74.92%
CYP3A4 inhibition	-	0.9188	91.88%
CYP2C9 inhibition	-	0.8194	81.94%
CYP2C19 inhibition	-	0.8052	80.52%
CYP2D6 inhibition	-	0.8535	85.35%
CYP1A2 inhibition	-	0.7985	79.85%
CYP2C8 inhibition	+	0.7821	78.21%
CYP inhibitory promiscuity	-	0.6885	68.85%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5245	52.45%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9389	93.89%
Skin irritation	-	0.8084	80.84%
Skin corrosion	-	0.9476	94.76%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8023	80.23%
Micronuclear	-	0.5241	52.41%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.8933	89.33%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.7118	71.18%
Acute Oral Toxicity (c)	III	0.7379	73.79%
Estrogen receptor binding	+	0.7472	74.72%
Androgen receptor binding	+	0.5840	58.40%
Thyroid receptor binding	+	0.5344	53.44%
Glucocorticoid receptor binding	-	0.5242	52.42%
Aromatase binding	+	0.5333	53.33%
PPAR gamma	+	0.6248	62.48%
Honey bee toxicity	-	0.8271	82.71%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	-	0.5481	54.81%

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	99.15%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.77%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.77%	85.14%
CHEMBL2581	P07339	Cathepsin D	93.05%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.91%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.33%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.92%	86.92%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.07%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	88.91%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.51%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.63%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.50%	97.09%
CHEMBL1951	P21397	Monoamine oxidase A	83.19%	91.49%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.08%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.36%	95.83%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.06%	92.62%

Plants that contains it

• Anethum graveolens

Cross-Links

• PubChem: 11972294
• NPASS: NPC298505