(2S,3R,4S,5S,6R)-2-[4-[(E)-2-[(2S,3S)-3-[(2S,3S)-3-(3,5-dihydroxyphenyl)-4-hydroxy-2-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-2,3-dihydro-1-benzofuran-6-yl]-4-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-6-yl]ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: b78c74a3-aabe-47c4-9e9d-d03ea6c3b3e6
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[4-[(E)-2-[(2S,3S)-3-[(2S,3S)-3-(3,5-dihydroxyphenyl)-4-hydroxy-2-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-2,3-dihydro-1-benzofuran-6-yl]-4-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-6-yl]ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C1=CC(=CC=C1C=CC2=CC(=C3C(C(OC3=C2)C4=CC=C(C=C4)O)C5=CC(=C6C(C(OC6=C5)C7=CC=C(C=C7)OC8C(C(C(C(O8)CO)O)O)O)C9=CC(=CC(=C9)O)O)O)O)OC1C(C(C(C(O1)CO)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1/C=C/C2=CC(=C3[C@@H]([C@H](OC3=C2)C4=CC=C(C=C4)O)C5=CC(=C6[C@@H]([C@H](OC6=C5)C7=CC=C(C=C7)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)C9=CC(=CC(=C9)O)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
• InChI: InChI=1S/C54H52O19/c55-22-39-45(62)47(64)49(66)53(72-39)68-33-11-3-24(4-12-33)1-2-25-15-35(60)43-37(16-25)70-51(26-5-9-30(57)10-6-26)42(43)29-19-36(61)44-38(20-29)71-52(41(44)28-17-31(58)21-32(59)18-28)27-7-13-34(14-8-27)69-54-50(67)48(65)46(63)40(23-56)73-54/h1-21,39-42,45-67H,22-23H2/b2-1+/t39-,40-,41+,42+,45-,46-,47+,48+,49-,50-,51-,52-,53-,54-/m1/s1
• InChI Key: DFTCAVAURYWFND-YDTSXNSISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₅₂O₁₉
• Molecular Weight: 1005.00 g/mol
• Exact Mass: 1004.31027942 g/mol
• Topological Polar Surface Area (TPSA): 318.00 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 3.27
• H-Bond Acceptor: 19
• H-Bond Donor: 13
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5892	58.92%
Caco-2	-	0.8657	86.57%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6106	61.06%
OATP2B1 inhibitior	-	0.5703	57.03%
OATP1B1 inhibitior	+	0.8725	87.25%
OATP1B3 inhibitior	+	0.9649	96.49%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8160	81.60%
P-glycoprotein inhibitior	+	0.7298	72.98%
P-glycoprotein substrate	-	0.8116	81.16%
CYP3A4 substrate	+	0.6343	63.43%
CYP2C9 substrate	-	0.8137	81.37%
CYP2D6 substrate	-	0.8014	80.14%
CYP3A4 inhibition	-	0.8884	88.84%
CYP2C9 inhibition	-	0.8675	86.75%
CYP2C19 inhibition	-	0.7045	70.45%
CYP2D6 inhibition	-	0.8053	80.53%
CYP1A2 inhibition	-	0.8621	86.21%
CYP2C8 inhibition	+	0.7659	76.59%
CYP inhibitory promiscuity	+	0.6287	62.87%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5320	53.20%
Eye corrosion	-	0.9923	99.23%
Eye irritation	-	0.8981	89.81%
Skin irritation	-	0.8137	81.37%
Skin corrosion	-	0.9545	95.45%
Ames mutagenesis	-	0.5237	52.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.8258	82.58%
Micronuclear	+	0.6459	64.59%
Hepatotoxicity	-	0.8425	84.25%
skin sensitisation	-	0.8530	85.30%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.5834	58.34%
Acute Oral Toxicity (c)	III	0.5369	53.69%
Estrogen receptor binding	+	0.7231	72.31%
Androgen receptor binding	+	0.6641	66.41%
Thyroid receptor binding	+	0.5697	56.97%
Glucocorticoid receptor binding	+	0.6342	63.42%
Aromatase binding	+	0.5687	56.87%
PPAR gamma	+	0.7337	73.37%
Honey bee toxicity	-	0.7161	71.61%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9041	90.41%

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	99.64%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.74%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	94.67%	95.93%
CHEMBL1951	P21397	Monoamine oxidase A	94.45%	91.49%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.06%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	92.28%	94.73%
CHEMBL3194	P02766	Transthyretin	91.88%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.68%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.42%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.09%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.48%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.40%	86.92%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.83%	99.15%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	87.48%	91.71%
CHEMBL4208	P20618	Proteasome component C5	85.41%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.20%	86.33%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	83.29%	89.67%
CHEMBL2581	P07339	Cathepsin D	83.19%	98.95%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	81.68%	97.33%

Plants that contains it

• Gnetum gnemon

Cross-Links

• PubChem: 101197165
• LOTUS: LTS0014241
• wikiData: Q104667145