2-(3,4-Dihydroxyphenyl)ethyl 6-deoxyhexopyranosyl-(1->3)-[hexopyranosyl-(1->6)]-4-O-[3-(3,4-dihydroxyphenyl)prop-2-enoyl]hexopyranoside

Details

• Internal ID: e2243d71-7cfb-4191-9f3e-d1ea59c6274c
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Oligosaccharides
• IUPAC Name: [6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-3-yl] 3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(OC(C2OC(=O)C=CC3=CC(=C(C=C3)O)O)COC4C(C(C(C(O4)CO)O)O)O)OCCC5=CC(=C(C=C5)O)O)O)O)O)O
• SMILES (Isomeric): CC1C(C(C(C(O1)OC2C(C(OC(C2OC(=O)C=CC3=CC(=C(C=C3)O)O)COC4C(C(C(C(O4)CO)O)O)O)OCCC5=CC(=C(C=C5)O)O)O)O)O)O
• InChI: InChI=1S/C35H46O20/c1-14-24(42)26(44)29(47)35(51-14)55-32-30(48)34(49-9-8-16-3-6-18(38)20(40)11-16)53-22(13-50-33-28(46)27(45)25(43)21(12-36)52-33)31(32)54-23(41)7-4-15-2-5-17(37)19(39)10-15/h2-7,10-11,14,21-22,24-40,42-48H,8-9,12-13H2,1H3
• InChI Key: FSBUXLDOLNLABB-UHFFFAOYSA-N
• Popularity: 77 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₄₆O₂₀
• Molecular Weight: 786.70 g/mol
• Exact Mass: 786.25824385 g/mol
• Topological Polar Surface Area (TPSA): 324.00 Ų
• XlogP: -2.10
• Atomic LogP (AlogP): -3.19
• H-Bond Acceptor: 20
• H-Bond Donor: 12
• Rotatable Bonds: 13

Synonyms

• BCP18131
• 2-(3,4-Dihydroxyphenyl)ethyl 6-deoxyhexopyranosyl-(1->3)-[hexopyranosyl-(1->6)]-4-O-[3-(3,4-dihydroxyphenyl)prop-2-enoyl]hexopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7512	75.12%
Caco-2	-	0.9023	90.23%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.9143	91.43%
Subcellular localzation	Mitochondria	0.7836	78.36%
OATP2B1 inhibitior	-	0.8587	85.87%
OATP1B1 inhibitior	+	0.8606	86.06%
OATP1B3 inhibitior	+	0.9632	96.32%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8241	82.41%
P-glycoprotein inhibitior	-	0.4647	46.47%
P-glycoprotein substrate	-	0.5706	57.06%
CYP3A4 substrate	+	0.6614	66.14%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8696	86.96%
CYP3A4 inhibition	-	0.9295	92.95%
CYP2C9 inhibition	-	0.7548	75.48%
CYP2C19 inhibition	-	0.8660	86.60%
CYP2D6 inhibition	-	0.9109	91.09%
CYP1A2 inhibition	-	0.8666	86.66%
CYP2C8 inhibition	+	0.7078	70.78%
CYP inhibitory promiscuity	-	0.7002	70.02%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6737	67.37%
Eye corrosion	-	0.9920	99.20%
Eye irritation	-	0.9174	91.74%
Skin irritation	-	0.8386	83.86%
Skin corrosion	-	0.9560	95.60%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7265	72.65%
Micronuclear	-	0.6567	65.67%
Hepatotoxicity	-	0.9250	92.50%
skin sensitisation	-	0.8442	84.42%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	-	0.7375	73.75%
Nephrotoxicity	-	0.9491	94.91%
Acute Oral Toxicity (c)	III	0.7702	77.02%
Estrogen receptor binding	+	0.7963	79.63%
Androgen receptor binding	-	0.8512	85.12%
Thyroid receptor binding	+	0.5256	52.56%
Glucocorticoid receptor binding	+	0.5456	54.56%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7078	70.78%
Honey bee toxicity	-	0.6695	66.95%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.7970	79.70%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	501.2 nM	Potency	via Super-PRED
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	100 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.75%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.65%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	97.56%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.87%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.77%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.48%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.50%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	93.21%	94.73%
CHEMBL2581	P07339	Cathepsin D	92.89%	98.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.70%	86.92%
CHEMBL3194	P02766	Transthyretin	92.66%	90.71%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.11%	97.36%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	87.21%	80.78%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	83.83%	96.37%
CHEMBL226	P30542	Adenosine A1 receptor	83.74%	95.93%
CHEMBL4208	P20618	Proteasome component C5	83.43%	90.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.98%	96.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.87%	94.45%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.26%	94.80%

Plants that contains it

• Buddleja officinalis
• Cistanche deserticola
• Cistanche salsa
• Digitalis purpurea
• Echinacea angustifolia
• Jasminum mesnyi
• Ligustrum vulgare
• Marrubium velutinum
• Pedicularis condensata
• Penstemon crandallii
• Phlomis brunneogaleata
• Plantago maritima

Cross-Links

• PubChem: 4484390
• LOTUS: LTS0250978
• wikiData: Q105000560