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

Details

• Internal ID: 9b64c699-9807-4f24-b07e-6e28ec289618
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[(1R,2S)-1,3-dihydroxy-1-[(2S,3R)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]propan-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): COC1=CC(=CC2=C1OC(C2CO)C3=CC(=C(C=C3)O)OC)C(C(CO)OC4C(C(C(C(O4)CO)O)O)O)O
• SMILES (Isomeric): COC1=CC(=CC2=C1O[C@@H]([C@H]2CO)C3=CC(=C(C=C3)O)OC)[C@H]([C@H](CO)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
• InChI: InChI=1S/C26H34O13/c1-35-16-6-11(3-4-15(16)30)24-14(8-27)13-5-12(7-17(36-2)25(13)39-24)20(31)18(9-28)37-26-23(34)22(33)21(32)19(10-29)38-26/h3-7,14,18-24,26-34H,8-10H2,1-2H3/t14-,18-,19+,20+,21+,22-,23+,24+,26+/m0/s1
• InChI Key: PHVWPURLKVTAAF-JKYJSMOVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₄O₁₃
• Molecular Weight: 554.50 g/mol
• Exact Mass: 554.19994113 g/mol
• Topological Polar Surface Area (TPSA): 208.00 Ų
• XlogP: -1.60
• Atomic LogP (AlogP): -1.17
• H-Bond Acceptor: 13
• H-Bond Donor: 8
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5214	52.14%
Caco-2	-	0.8900	89.00%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6406	64.06%
OATP2B1 inhibitior	-	0.8600	86.00%
OATP1B1 inhibitior	+	0.8476	84.76%
OATP1B3 inhibitior	+	0.9707	97.07%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.5335	53.35%
P-glycoprotein inhibitior	-	0.6457	64.57%
P-glycoprotein substrate	-	0.6528	65.28%
CYP3A4 substrate	+	0.6225	62.25%
CYP2C9 substrate	-	0.8050	80.50%
CYP2D6 substrate	-	0.7781	77.81%
CYP3A4 inhibition	-	0.8680	86.80%
CYP2C9 inhibition	-	0.8041	80.41%
CYP2C19 inhibition	-	0.7368	73.68%
CYP2D6 inhibition	-	0.8960	89.60%
CYP1A2 inhibition	-	0.8780	87.80%
CYP2C8 inhibition	+	0.6207	62.07%
CYP inhibitory promiscuity	+	0.5781	57.81%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5671	56.71%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9334	93.34%
Skin irritation	-	0.8418	84.18%
Skin corrosion	-	0.9542	95.42%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7295	72.95%
Micronuclear	+	0.6759	67.59%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.8949	89.49%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.8233	82.33%
Acute Oral Toxicity (c)	III	0.7458	74.58%
Estrogen receptor binding	+	0.8284	82.84%
Androgen receptor binding	+	0.6036	60.36%
Thyroid receptor binding	+	0.6481	64.81%
Glucocorticoid receptor binding	+	0.5952	59.52%
Aromatase binding	+	0.5820	58.20%
PPAR gamma	+	0.6159	61.59%
Honey bee toxicity	-	0.7736	77.36%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.7088	70.88%

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	98.96%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.70%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.48%	85.14%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	90.35%	89.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.57%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.30%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	87.20%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.83%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.59%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.47%	97.09%
CHEMBL2581	P07339	Cathepsin D	85.98%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.23%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.15%	86.33%
CHEMBL2535	P11166	Glucose transporter	84.92%	98.75%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	83.05%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.90%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.02%	89.00%

Plants that contains it

• Itoa orientalis

Cross-Links

• PubChem: 162948102
• LOTUS: LTS0219487
• wikiData: Q105209258