(2S,3R,4S,5S,6R)-2-[3-[(1S,2S,3S,4S)-2,3-bis(4-hydroxyphenyl)-4-[3-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]cyclobutyl]-5-hydroxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: e696e611-3a4a-4730-9a94-cc4eb5f33afb
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes > Stilbene glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[3-[(1S,2S,3S,4S)-2,3-bis(4-hydroxyphenyl)-4-[3-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]cyclobutyl]-5-hydroxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C1=CC(=CC=C1C2C(C(C2C3=CC(=CC(=C3)OC4C(C(C(C(O4)CO)O)O)O)O)C5=CC(=CC(=C5)OC6C(C(C(C(O6)CO)O)O)O)O)C7=CC=C(C=C7)O)O
• SMILES (Isomeric): C1=CC(=CC=C1[C@H]2[C@@H]([C@@H]([C@H]2C3=CC(=CC(=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)C5=CC(=CC(=C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O)C7=CC=C(C=C7)O)O
• InChI: InChI=1S/C40H44O16/c41-15-27-33(47)35(49)37(51)39(55-27)53-25-11-19(9-23(45)13-25)31-29(17-1-5-21(43)6-2-17)30(18-3-7-22(44)8-4-18)32(31)20-10-24(46)14-26(12-20)54-40-38(52)36(50)34(48)28(16-42)56-40/h1-14,27-52H,15-16H2/t27-,28-,29+,30+,31+,32+,33-,34-,35+,36+,37-,38-,39-,40-/m1/s1
• InChI Key: AQUVKJKVASGNFO-XSLSTOLESA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₄₄O₁₆
• Molecular Weight: 780.80 g/mol
• Exact Mass: 780.26293531 g/mol
• Topological Polar Surface Area (TPSA): 280.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 0.32
• H-Bond Acceptor: 16
• H-Bond Donor: 12
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8669	86.69%
Caco-2	-	0.9086	90.86%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.6892	68.92%
OATP2B1 inhibitior	-	0.5714	57.14%
OATP1B1 inhibitior	+	0.8995	89.95%
OATP1B3 inhibitior	+	0.9506	95.06%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7130	71.30%
P-glycoprotein inhibitior	+	0.6011	60.11%
P-glycoprotein substrate	-	0.9325	93.25%
CYP3A4 substrate	+	0.5095	50.95%
CYP2C9 substrate	-	0.7913	79.13%
CYP2D6 substrate	-	0.8145	81.45%
CYP3A4 inhibition	-	0.9106	91.06%
CYP2C9 inhibition	-	0.8945	89.45%
CYP2C19 inhibition	-	0.8829	88.29%
CYP2D6 inhibition	-	0.9319	93.19%
CYP1A2 inhibition	-	0.9375	93.75%
CYP2C8 inhibition	+	0.6227	62.27%
CYP inhibitory promiscuity	-	0.6950	69.50%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5297	52.97%
Eye corrosion	-	0.9931	99.31%
Eye irritation	-	0.8895	88.95%
Skin irritation	-	0.8426	84.26%
Skin corrosion	-	0.9633	96.33%
Ames mutagenesis	-	0.6291	62.91%
Human Ether-a-go-go-Related Gene inhibition	+	0.8695	86.95%
Micronuclear	-	0.5041	50.41%
Hepatotoxicity	-	0.8625	86.25%
skin sensitisation	-	0.9016	90.16%
Respiratory toxicity	-	0.7000	70.00%
Reproductive toxicity	-	0.5778	57.78%
Mitochondrial toxicity	-	0.6750	67.50%
Nephrotoxicity	+	0.5066	50.66%
Acute Oral Toxicity (c)	III	0.5589	55.89%
Estrogen receptor binding	+	0.7982	79.82%
Androgen receptor binding	+	0.6589	65.89%
Thyroid receptor binding	+	0.5795	57.95%
Glucocorticoid receptor binding	-	0.7073	70.73%
Aromatase binding	+	0.5626	56.26%
PPAR gamma	+	0.7844	78.44%
Honey bee toxicity	-	0.7882	78.82%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.6481	64.81%

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	98.87%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.16%	97.09%
CHEMBL1951	P21397	Monoamine oxidase A	92.70%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	92.31%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.28%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.34%	86.92%
CHEMBL226	P30542	Adenosine A1 receptor	88.08%	95.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.02%	95.89%
CHEMBL2581	P07339	Cathepsin D	84.06%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.27%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.47%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.28%	86.33%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	81.69%	89.67%
CHEMBL3194	P02766	Transthyretin	80.36%	90.71%

Plants that contains it

• Aconitum seravschanicum
• Adansonia grandidieri
• Alkekengi officinarum
• Aphyllocladus denticulatus
• Bassia muricata
• Dendriopoterium menendezii
• Dianthera secunda
• Dodonaea viscosa
• Dysoxylum cumingianum
• Enceliopsis argophylla
• Flacourtia jangomas
• Galatella sedifolia subsp. sedifolia
• Lavandula angustifolia subsp. pyrenaica
• Miliusa velutina
• Neobalanocarpus heimii
• Onobrychis arenaria
• Psychotria stachyoides
• Reynoutria japonica
• Senecio subdentatus
• Teucrium yemense
• Trichotosia mollis

Cross-Links

• PubChem: 10327899
• NPASS: NPC53168
• LOTUS: LTS0048212
• wikiData: Q104665453