methyl (2S,3S,4S)-4-[2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl]-3-ethenyl-2-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate

Details

• Internal ID: fca1725a-0685-430b-9aa1-8cd125c6a696
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: methyl (2S,3S,4S)-4-[2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl]-3-ethenyl-2-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate
• SMILES (Canonical): COC(=O)C1=COC(C(C1CC(=O)OCCC2=CC(=C(C=C2)O)O)C=C)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): COC(=O)C1=CO[C@H]([C@H]([C@@H]1CC(=O)OCCC2=CC(=C(C=C2)O)O)C=C)O[C@H]3[C@H]([C@@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C25H32O13/c1-3-13-14(9-19(29)35-7-6-12-4-5-16(27)17(28)8-12)15(23(33)34-2)11-36-24(13)38-25-22(32)21(31)20(30)18(10-26)37-25/h3-5,8,11,13-14,18,20-22,24-28,30-32H,1,6-7,9-10H2,2H3/t13-,14-,18+,20+,21+,22-,24-,25-/m0/s1
• InChI Key: WWKVQWHAWPZZDB-IUZZVVFPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₂O₁₃
• Molecular Weight: 540.50 g/mol
• Exact Mass: 540.18429107 g/mol
• Topological Polar Surface Area (TPSA): 202.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.78
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6846	68.46%
Caco-2	-	0.9061	90.61%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.8060	80.60%
OATP2B1 inhibitior	-	0.8592	85.92%
OATP1B1 inhibitior	+	0.7770	77.70%
OATP1B3 inhibitior	+	0.9463	94.63%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.4730	47.30%
P-glycoprotein inhibitior	-	0.5769	57.69%
P-glycoprotein substrate	-	0.5660	56.60%
CYP3A4 substrate	+	0.6764	67.64%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.8663	86.63%
CYP3A4 inhibition	-	0.8380	83.80%
CYP2C9 inhibition	-	0.7966	79.66%
CYP2C19 inhibition	-	0.6831	68.31%
CYP2D6 inhibition	-	0.8869	88.69%
CYP1A2 inhibition	-	0.7491	74.91%
CYP2C8 inhibition	+	0.7565	75.65%
CYP inhibitory promiscuity	-	0.8813	88.13%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7296	72.96%
Eye corrosion	-	0.9861	98.61%
Eye irritation	-	0.9274	92.74%
Skin irritation	-	0.8176	81.76%
Skin corrosion	-	0.9512	95.12%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6744	67.44%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.8010	80.10%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.5977	59.77%
Acute Oral Toxicity (c)	III	0.6328	63.28%
Estrogen receptor binding	+	0.8010	80.10%
Androgen receptor binding	+	0.6653	66.53%
Thyroid receptor binding	+	0.5483	54.83%
Glucocorticoid receptor binding	+	0.6537	65.37%
Aromatase binding	-	0.4866	48.66%
PPAR gamma	+	0.6741	67.41%
Honey bee toxicity	-	0.6968	69.68%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.9478	94.78%

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	99.07%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.16%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	96.78%	91.49%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.69%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	91.81%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.54%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.34%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.45%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.64%	90.71%
CHEMBL2581	P07339	Cathepsin D	86.68%	98.95%
CHEMBL4208	P20618	Proteasome component C5	86.50%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.48%	95.89%
CHEMBL3437	Q16853	Amine oxidase, copper containing	84.51%	94.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	84.23%	91.24%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.98%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.39%	96.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.93%	96.90%
CHEMBL340	P08684	Cytochrome P450 3A4	80.98%	91.19%

Plants that contains it

• Olea europaea

Cross-Links

• PubChem: 154497128
• LOTUS: LTS0223764
• wikiData: Q105314122