methyl (2S,3R,4R)-3-acetyl-4-(2-hydroxyethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate

Details

• Internal ID: 55a89956-4cad-4761-8538-beedd518f167
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: methyl (2S,3R,4R)-3-acetyl-4-(2-hydroxyethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate
• SMILES (Canonical): CC(=O)C1C(C(=COC1OC2C(C(C(C(O2)CO)O)O)O)C(=O)OC)CCO
• SMILES (Isomeric): CC(=O)[C@@H]1[C@H](C(=CO[C@H]1O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)C(=O)OC)CCO
• InChI: InChI=1S/C17H26O11/c1-7(20)11-8(3-4-18)9(15(24)25-2)6-26-16(11)28-17-14(23)13(22)12(21)10(5-19)27-17/h6,8,10-14,16-19,21-23H,3-5H2,1-2H3/t8-,10+,11+,12+,13-,14+,16-,17-/m0/s1
• InChI Key: ZHZLKLUSFUQKQE-GAENFNLHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₆O₁₁
• Molecular Weight: 406.40 g/mol
• Exact Mass: 406.14751164 g/mol
• Topological Polar Surface Area (TPSA): 172.00 Ų
• XlogP: -2.60
• Atomic LogP (AlogP): -2.58
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8681	86.81%
Caco-2	-	0.8499	84.99%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7789	77.89%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7515	75.15%
OATP1B3 inhibitior	+	0.9410	94.10%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.7935	79.35%
P-glycoprotein inhibitior	-	0.8485	84.85%
P-glycoprotein substrate	-	0.7782	77.82%
CYP3A4 substrate	+	0.6120	61.20%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8875	88.75%
CYP3A4 inhibition	-	0.9252	92.52%
CYP2C9 inhibition	-	0.8884	88.84%
CYP2C19 inhibition	-	0.9000	90.00%
CYP2D6 inhibition	-	0.9127	91.27%
CYP1A2 inhibition	-	0.9233	92.33%
CYP2C8 inhibition	-	0.6296	62.96%
CYP inhibitory promiscuity	-	0.9531	95.31%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7048	70.48%
Eye corrosion	-	0.9877	98.77%
Eye irritation	-	0.9586	95.86%
Skin irritation	-	0.7876	78.76%
Skin corrosion	-	0.9476	94.76%
Ames mutagenesis	+	0.5122	51.22%
Human Ether-a-go-go-Related Gene inhibition	-	0.5864	58.64%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.7449	74.49%
skin sensitisation	-	0.8840	88.40%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.6098	60.98%
Acute Oral Toxicity (c)	III	0.6878	68.78%
Estrogen receptor binding	+	0.6890	68.90%
Androgen receptor binding	-	0.5261	52.61%
Thyroid receptor binding	-	0.5865	58.65%
Glucocorticoid receptor binding	-	0.5183	51.83%
Aromatase binding	-	0.6089	60.89%
PPAR gamma	-	0.5424	54.24%
Honey bee toxicity	-	0.8201	82.01%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.8200	82.00%
Fish aquatic toxicity	-	0.7380	73.80%

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	96.44%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.15%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	91.52%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.98%	99.17%
CHEMBL2581	P07339	Cathepsin D	85.95%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.82%	96.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.16%	96.95%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.46%	91.24%

Plants that contains it

• Lamium album

Cross-Links

• PubChem: 163022426
• LOTUS: LTS0270681
• wikiData: Q105376162