(4S,5Z,6S)-4-[2-[2-(3,4-dihydroxyphenyl)-2-ethoxy-ethoxy]-2-oxo-ethyl]-5-ethylidene-6-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-4H-pyran-3-carboxylic acid

Details

• Internal ID: 657e1793-70a0-4e45-b81a-698ecd3a1c87
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: (4S,5Z,6S)-4-[2-[2-(3,4-dihydroxyphenyl)-2-ethoxyethoxy]-2-oxoethyl]-5-ethylidene-6-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylic acid
• SMILES (Canonical): CCOC(COC(=O)CC1C(=COC(C1=CC)OC2C(C(C(C(O2)CO)O)O)O)C(=O)O)C3=CC(=C(C=C3)O)O
• SMILES (Isomeric): CCOC(COC(=O)C[C@@H]\1C(=CO[C@H](/C1=C\C)OC2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)C(=O)O)C3=CC(=C(C=C3)O)O
• InChI: InChI=1S/C26H34O14/c1-3-13-14(8-20(30)37-11-19(36-4-2)12-5-6-16(28)17(29)7-12)15(24(34)35)10-38-25(13)40-26-23(33)22(32)21(31)18(9-27)39-26/h3,5-7,10,14,18-19,21-23,25-29,31-33H,4,8-9,11H2,1-2H3,(H,34,35)/b13-3-/t14-,18+,19?,21+,22-,23+,25-,26?/m0/s1
• InChI Key: FLJQUNOIHGJLJL-RTYBPYBCSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₄O₁₄
• Molecular Weight: 570.50 g/mol
• Exact Mass: 570.19485575 g/mol
• Topological Polar Surface Area (TPSA): 222.00 Ų
• XlogP: -1.00
• Atomic LogP (AlogP): -0.19
• H-Bond Acceptor: 13
• H-Bond Donor: 7
• Rotatable Bonds: 11

Synonyms

• 2H-Pyran-4-acetic acid, 5-carboxy-3-ethylidene-2-(D-glucopyranosyloxy)-3,4-dihydro-, 2-(3,4-dihydroxyphenyl)-2-ethoxyethyl ester, (2S,3Z,4S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5526	55.26%
Caco-2	-	0.9008	90.08%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7788	77.88%
OATP2B1 inhibitior	-	0.8655	86.55%
OATP1B1 inhibitior	+	0.7665	76.65%
OATP1B3 inhibitior	+	0.9462	94.62%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.6023	60.23%
P-glycoprotein inhibitior	-	0.5448	54.48%
P-glycoprotein substrate	-	0.5234	52.34%
CYP3A4 substrate	+	0.6364	63.64%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8781	87.81%
CYP3A4 inhibition	-	0.7123	71.23%
CYP2C9 inhibition	-	0.7022	70.22%
CYP2C19 inhibition	-	0.6435	64.35%
CYP2D6 inhibition	-	0.9084	90.84%
CYP1A2 inhibition	-	0.7824	78.24%
CYP2C8 inhibition	+	0.6313	63.13%
CYP inhibitory promiscuity	-	0.6521	65.21%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6710	67.10%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9265	92.65%
Skin irritation	-	0.8210	82.10%
Skin corrosion	-	0.9484	94.84%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4012	40.12%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	-	0.7677	76.77%
skin sensitisation	-	0.7785	77.85%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.7892	78.92%
Acute Oral Toxicity (c)	III	0.6675	66.75%
Estrogen receptor binding	+	0.8320	83.20%
Androgen receptor binding	+	0.6635	66.35%
Thyroid receptor binding	-	0.5277	52.77%
Glucocorticoid receptor binding	+	0.7098	70.98%
Aromatase binding	-	0.4917	49.17%
PPAR gamma	+	0.6743	67.43%
Honey bee toxicity	-	0.7269	72.69%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9667	96.67%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.07%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.42%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	93.84%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.38%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	92.73%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.25%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.54%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.42%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.97%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.24%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.94%	89.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	84.15%	95.64%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	83.58%	82.50%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	82.64%	94.08%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.34%	90.71%
CHEMBL3194	P02766	Transthyretin	82.13%	90.71%
CHEMBL5255	O00206	Toll-like receptor 4	81.89%	92.50%

Plants that contains it

• Ligustrum lucidum

Cross-Links

• PubChem: 6476721
• NPASS: NPC152575