(2R,3S,4S,5R,6R)-5-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-6-[(E)-3-[(2R,3S)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoxy]-2-(hydroxymethyl)oxane-3,4-diol

Details

• Internal ID: 0c1ea9ee-5dc2-40d0-b879-f4fac28cf574
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: (2R,3S,4S,5R,6R)-5-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-6-[(E)-3-[(2R,3S)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoxy]-2-(hydroxymethyl)oxane-3,4-diol
• SMILES (Canonical): COC1=CC(=CC2=C1OC(C2CO)C3=CC(=C(C=C3)O)OC)C=CCOC4C(C(C(C(O4)CO)O)O)OC5C(C(CO5)(CO)O)O
• SMILES (Isomeric): COC1=CC(=CC2=C1O[C@H]([C@@H]2CO)C3=CC(=C(C=C3)O)OC)/C=C/CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O[C@H]5[C@@H]([C@](CO5)(CO)O)O
• InChI: InChI=1S/C31H40O15/c1-40-20-10-16(5-6-19(20)35)25-18(11-32)17-8-15(9-21(41-2)26(17)45-25)4-3-7-42-29-27(24(37)23(36)22(12-33)44-29)46-30-28(38)31(39,13-34)14-43-30/h3-6,8-10,18,22-25,27-30,32-39H,7,11-14H2,1-2H3/b4-3+/t18-,22-,23-,24+,25+,27-,28+,29-,30+,31-/m1/s1
• InChI Key: CBEKDIBQFMJOKT-KVZWILQRSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₄₀O₁₅
• Molecular Weight: 652.60 g/mol
• Exact Mass: 652.23672056 g/mol
• Topological Polar Surface Area (TPSA): 226.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -1.09
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6667	66.67%
Caco-2	-	0.8897	88.97%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.5740	57.40%
OATP2B1 inhibitior	-	0.7251	72.51%
OATP1B1 inhibitior	+	0.8346	83.46%
OATP1B3 inhibitior	+	0.9676	96.76%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8563	85.63%
P-glycoprotein inhibitior	+	0.5936	59.36%
P-glycoprotein substrate	-	0.5133	51.33%
CYP3A4 substrate	+	0.6959	69.59%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8143	81.43%
CYP3A4 inhibition	-	0.8604	86.04%
CYP2C9 inhibition	-	0.8754	87.54%
CYP2C19 inhibition	-	0.8027	80.27%
CYP2D6 inhibition	-	0.8718	87.18%
CYP1A2 inhibition	-	0.8788	87.88%
CYP2C8 inhibition	+	0.7372	73.72%
CYP inhibitory promiscuity	-	0.6148	61.48%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5089	50.89%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9306	93.06%
Skin irritation	-	0.8105	81.05%
Skin corrosion	-	0.9406	94.06%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7672	76.72%
Micronuclear	+	0.6559	65.59%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.8447	84.47%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.6147	61.47%
Acute Oral Toxicity (c)	III	0.6060	60.60%
Estrogen receptor binding	+	0.8068	80.68%
Androgen receptor binding	+	0.6482	64.82%
Thyroid receptor binding	+	0.5824	58.24%
Glucocorticoid receptor binding	+	0.5556	55.56%
Aromatase binding	+	0.5810	58.10%
PPAR gamma	+	0.6916	69.16%
Honey bee toxicity	-	0.7341	73.41%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.8004	80.04%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.70%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.15%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.07%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.20%	96.00%
CHEMBL226	P30542	Adenosine A1 receptor	94.16%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.64%	97.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	93.16%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.95%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.92%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.43%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.23%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.16%	85.14%
CHEMBL4208	P20618	Proteasome component C5	85.15%	90.00%
CHEMBL3401	O75469	Pregnane X receptor	85.05%	94.73%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.67%	92.94%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.15%	99.17%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.81%	97.14%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.80%	95.83%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.10%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.08%	92.62%

Plants that contains it

• Barleria buxifolia

Cross-Links

• PubChem: 163188020
• LOTUS: LTS0173706
• wikiData: Q104952276