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

Details

• Internal ID: a33e3384-ebe0-45aa-a6aa-dbdb80d5ac27
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: methyl 4-[2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl]-5-ethylidene-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
• SMILES (Canonical): CC=C1C(C(=COC1OC2C(C(C(C(O2)CO)O)O)O)C(=O)OC)CC(=O)OCCC3=CC(=C(C=C3)O)O
• SMILES (Isomeric): CC=C1C(C(=COC1OC2C(C(C(C(O2)CO)O)O)O)C(=O)OC)CC(=O)OCCC3=CC(=C(C=C3)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/h3-5,8,11,14,18,20-22,24-28,30-32H,6-7,9-10H2,1-2H3
• InChI Key: RFWGABANNQMHMZ-UHFFFAOYSA-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: -0.40
• Atomic LogP (AlogP): -0.63
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 9

Synonyms

• C25-H32-O13
• methyl (4S,5E,6S)-4-[2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl]-5-ethylidene-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
• DTXSID00872007
• 2H-Pyran-4-acetic acid, 3-ethylidene-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-, 2-(3,4-dihydroxyphenyl)ethyl ester, (2S-(2alpha,3E,4beta))-
• BCP13595
• FT-0639038
• methyl 4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-3-ethylidene-2-(hexopyranosyloxy)-3,4-dihydro-2H-pyran-5-carboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6945	69.45%
Caco-2	-	0.8953	89.53%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.8147	81.47%
OATP2B1 inhibitior	-	0.8627	86.27%
OATP1B1 inhibitior	+	0.7472	74.72%
OATP1B3 inhibitior	+	0.9291	92.91%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.6581	65.81%
P-glycoprotein inhibitior	-	0.5319	53.19%
P-glycoprotein substrate	+	0.5091	50.91%
CYP3A4 substrate	+	0.6707	67.07%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8751	87.51%
CYP3A4 inhibition	-	0.8260	82.60%
CYP2C9 inhibition	-	0.8144	81.44%
CYP2C19 inhibition	-	0.7130	71.30%
CYP2D6 inhibition	-	0.8882	88.82%
CYP1A2 inhibition	-	0.7231	72.31%
CYP2C8 inhibition	+	0.7839	78.39%
CYP inhibitory promiscuity	-	0.8709	87.09%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7317	73.17%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9318	93.18%
Skin irritation	-	0.8241	82.41%
Skin corrosion	-	0.9590	95.90%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6876	68.76%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.9000	90.00%
skin sensitisation	-	0.8298	82.98%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.7341	73.41%
Acute Oral Toxicity (c)	III	0.6219	62.19%
Estrogen receptor binding	+	0.8336	83.36%
Androgen receptor binding	+	0.7042	70.42%
Thyroid receptor binding	-	0.5101	51.01%
Glucocorticoid receptor binding	+	0.7409	74.09%
Aromatase binding	-	0.5195	51.95%
PPAR gamma	+	0.6853	68.53%
Honey bee toxicity	-	0.7106	71.06%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9239	92.39%

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	98.90%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.19%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	94.54%	91.49%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	94.02%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.11%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	92.79%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.54%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.70%	94.45%
CHEMBL2581	P07339	Cathepsin D	90.85%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.05%	96.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	84.87%	96.90%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.21%	95.89%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	84.14%	95.64%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.12%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.83%	89.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.37%	95.83%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.07%	94.00%
CHEMBL3194	P02766	Transthyretin	80.20%	90.71%

Plants that contains it

• Fraxinus americana
• Fraxinus angustifolia
• Fraxinus chinensis
• Fraxinus chinensis subsp. chinensis
• Fraxinus chinensis subsp. rhynchophylla
• Fraxinus excelsior
• Fraxinus insularis
• Fraxinus ornus
• Fraxinus stylosa
• Inga velutina
• Jasminum grandiflorum
• Ligustrum japonicum
• Ligustrum lucidum
• Ligustrum vulgare
• Olea europaea
• Osmanthus heterophyllus
• Phillyrea latifolia
• Syringa reticulata
• Syringa reticulata subsp. amurensis
• Syringa vulgaris
• Tetradium ruticarpum

Cross-Links

• PubChem: 3789874
• NPASS: NPC76773
• LOTUS: LTS0045872
• wikiData: Q105235680