methyl (5Z)-5-ethylidene-4-[2-oxo-2-[[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]oxan-2-yl]methoxy]ethyl]-6-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate

Details

• Internal ID: bbec1fd5-8e86-48b7-9573-b49997d64d66
• Taxonomy: Lipids and lipid-like molecules > Saccharolipids
• IUPAC Name: methyl (5Z)-5-ethylidene-4-[2-oxo-2-[[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]oxan-2-yl]methoxy]ethyl]-6-[(2S,3R,4S,5R,6R)-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)OCC3C(C(C(C(O3)OCCC4=CC=C(C=C4)O)O)O)O
• SMILES (Isomeric): C/C=C\1/C(C(=COC1O[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)CO)O)O)O)C(=O)OC)CC(=O)OC[C@@H]3[C@H]([C@@H]([C@H]([C@@H](O3)OCCC4=CC=C(C=C4)O)O)O)O
• InChI: InChI=1S/C31H42O17/c1-3-16-17(18(28(41)42-2)12-45-29(16)48-31-27(40)24(37)22(35)19(11-32)46-31)10-21(34)44-13-20-23(36)25(38)26(39)30(47-20)43-9-8-14-4-6-15(33)7-5-14/h3-7,12,17,19-20,22-27,29-33,35-40H,8-11,13H2,1-2H3/b16-3-/t17?,19-,20-,22+,23-,24+,25+,26-,27-,29?,30-,31+/m1/s1
• InChI Key: STKUCSFEBXPTAY-OSFBGUPWSA-N
• Popularity: 20 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₄₂O₁₇
• Molecular Weight: 686.70 g/mol
• Exact Mass: 686.24219987 g/mol
• Topological Polar Surface Area (TPSA): 261.00 Ų
• XlogP: -2.20
• Atomic LogP (AlogP): -2.52
• H-Bond Acceptor: 17
• H-Bond Donor: 8
• Rotatable Bonds: 12

Synonyms

• 202586-63-8

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7620	76.20%
Caco-2	-	0.8863	88.63%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8005	80.05%
OATP2B1 inhibitior	-	0.8626	86.26%
OATP1B1 inhibitior	+	0.7180	71.80%
OATP1B3 inhibitior	+	0.9354	93.54%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.6602	66.02%
P-glycoprotein inhibitior	+	0.6340	63.40%
P-glycoprotein substrate	+	0.5842	58.42%
CYP3A4 substrate	+	0.6864	68.64%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8777	87.77%
CYP3A4 inhibition	-	0.8330	83.30%
CYP2C9 inhibition	-	0.8130	81.30%
CYP2C19 inhibition	-	0.7570	75.70%
CYP2D6 inhibition	-	0.8920	89.20%
CYP1A2 inhibition	-	0.8437	84.37%
CYP2C8 inhibition	+	0.8168	81.68%
CYP inhibitory promiscuity	-	0.8237	82.37%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6363	63.63%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9214	92.14%
Skin irritation	-	0.8111	81.11%
Skin corrosion	-	0.9541	95.41%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4687	46.87%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.8499	84.99%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.5893	58.93%
Acute Oral Toxicity (c)	III	0.6690	66.90%
Estrogen receptor binding	+	0.8117	81.17%
Androgen receptor binding	+	0.5956	59.56%
Thyroid receptor binding	-	0.5479	54.79%
Glucocorticoid receptor binding	+	0.7103	71.03%
Aromatase binding	+	0.5333	53.33%
PPAR gamma	+	0.6778	67.78%
Honey bee toxicity	-	0.7063	70.63%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.8327	83.27%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5880	P60568	Interleukin-2	2.59 nM	Kd	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.66%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.51%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.47%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	93.35%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.93%	86.33%
CHEMBL2581	P07339	Cathepsin D	92.91%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	92.58%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.97%	94.45%
CHEMBL3437	Q16853	Amine oxidase, copper containing	88.64%	94.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	87.00%	95.64%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.21%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.69%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.07%	94.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.47%	94.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.13%	96.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.68%	95.83%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.42%	89.00%

Plants that contains it

• Ligustrum lucidum
• Tetradium ruticarpum

Cross-Links

• PubChem: 101934343
• NPASS: NPC50103