(E)-3-[4-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoic acid

Details

• Internal ID: 80639891-c7e2-4bec-a40f-94844fbcf6f2
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: (E)-3-[4-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoic acid
• SMILES (Canonical): C1C(C(C(O1)OC2C(C(C(OC2OC3=CC=C(C=C3)C=CC(=O)O)CO)O)O)O)(CO)O
• SMILES (Isomeric): C1[C@@]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=CC=C(C=C3)/C=C/C(=O)O)CO)O)O)O)(CO)O
• InChI: InChI=1S/C20H26O12/c21-7-12-14(25)15(26)16(32-19-17(27)20(28,8-22)9-29-19)18(31-12)30-11-4-1-10(2-5-11)3-6-13(23)24/h1-6,12,14-19,21-22,25-28H,7-9H2,(H,23,24)/b6-3+/t12-,14-,15+,16-,17+,18-,19+,20-/m1/s1
• InChI Key: DAVWDWCHQLSZAZ-TXPDJQHQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₁₂
• Molecular Weight: 458.40 g/mol
• Exact Mass: 458.14242626 g/mol
• Topological Polar Surface Area (TPSA): 196.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -2.57
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6452	64.52%
Caco-2	-	0.8994	89.94%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.7055	70.55%
OATP2B1 inhibitior	-	0.8519	85.19%
OATP1B1 inhibitior	+	0.9305	93.05%
OATP1B3 inhibitior	+	0.9555	95.55%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.6001	60.01%
P-glycoprotein inhibitior	-	0.7347	73.47%
P-glycoprotein substrate	-	0.8451	84.51%
CYP3A4 substrate	+	0.5986	59.86%
CYP2C9 substrate	-	0.6067	60.67%
CYP2D6 substrate	-	0.8749	87.49%
CYP3A4 inhibition	-	0.8736	87.36%
CYP2C9 inhibition	-	0.9181	91.81%
CYP2C19 inhibition	-	0.8804	88.04%
CYP2D6 inhibition	-	0.8862	88.62%
CYP1A2 inhibition	-	0.9262	92.62%
CYP2C8 inhibition	-	0.5857	58.57%
CYP inhibitory promiscuity	-	0.7381	73.81%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5499	54.99%
Eye corrosion	-	0.9925	99.25%
Eye irritation	-	0.9365	93.65%
Skin irritation	-	0.8088	80.88%
Skin corrosion	-	0.9482	94.82%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3850	38.50%
Micronuclear	-	0.6067	60.67%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.7984	79.84%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.6375	63.75%
Nephrotoxicity	-	0.7562	75.62%
Acute Oral Toxicity (c)	III	0.6689	66.89%
Estrogen receptor binding	+	0.6481	64.81%
Androgen receptor binding	+	0.5372	53.72%
Thyroid receptor binding	+	0.5742	57.42%
Glucocorticoid receptor binding	-	0.4933	49.33%
Aromatase binding	+	0.7353	73.53%
PPAR gamma	+	0.7857	78.57%
Honey bee toxicity	-	0.7641	76.41%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.6672	66.72%

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	98.39%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.07%	96.00%
CHEMBL226	P30542	Adenosine A1 receptor	95.86%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.30%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	94.12%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.04%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.74%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.69%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.55%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.83%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.79%	95.89%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.38%	86.92%
CHEMBL4208	P20618	Proteasome component C5	82.77%	90.00%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	82.73%	89.67%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.46%	94.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.49%	99.17%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.48%	97.36%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.47%	91.07%

Plants that contains it

• Salvia officinalis

Cross-Links

• PubChem: 102461464
• LOTUS: LTS0274171
• wikiData: Q104974028