NCGC00384878-01_C17H26O10_2H-Pyran-5-carboxylic acid, 3-ethenyl-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-4-(2-hydroxyethyl)-, methyl ester, (2S,3R,4S)-

Details

• Internal ID: a63e732a-e6f5-44cc-b3af-b6ffbf829d9d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: methyl (2S,3R,4S)-3-ethenyl-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): COC(=O)C1=COC(C(C1CCO)C=C)OC2C(C(C(C(O2)CO)O)O)O
• SMILES (Isomeric): COC(=O)C1=CO[C@H]([C@@H]([C@@H]1CCO)C=C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
• InChI: InChI=1S/C17H26O10/c1-3-8-9(4-5-18)10(15(23)24-2)7-25-16(8)27-17-14(22)13(21)12(20)11(6-19)26-17/h3,7-9,11-14,16-22H,1,4-6H2,2H3/t8-,9+,11-,12-,13+,14-,16+,17+/m1/s1
• InChI Key: GHRNLKSWTKHISE-NRZPKYKESA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₆O₁₀
• Molecular Weight: 390.40 g/mol
• Exact Mass: 390.15259702 g/mol
• Topological Polar Surface Area (TPSA): 155.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -1.98
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

• NCGC00384878-01_C17H26O10_2H-Pyran-5-carboxylic acid, 3-ethenyl-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-4-(2-hydroxyethyl)-, methyl ester, (2S,3R,4S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8297	82.97%
Caco-2	-	0.8576	85.76%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7795	77.95%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7638	76.38%
OATP1B3 inhibitior	+	0.9498	94.98%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8468	84.68%
P-glycoprotein inhibitior	-	0.8611	86.11%
P-glycoprotein substrate	-	0.7968	79.68%
CYP3A4 substrate	+	0.6135	61.35%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8634	86.34%
CYP3A4 inhibition	-	0.9438	94.38%
CYP2C9 inhibition	-	0.9030	90.30%
CYP2C19 inhibition	-	0.8633	86.33%
CYP2D6 inhibition	-	0.9105	91.05%
CYP1A2 inhibition	-	0.9241	92.41%
CYP2C8 inhibition	+	0.4460	44.60%
CYP inhibitory promiscuity	-	0.9235	92.35%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7320	73.20%
Eye corrosion	-	0.9838	98.38%
Eye irritation	-	0.9653	96.53%
Skin irritation	-	0.7969	79.69%
Skin corrosion	-	0.9406	94.06%
Ames mutagenesis	-	0.5378	53.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.5431	54.31%
Micronuclear	-	0.8341	83.41%
Hepatotoxicity	-	0.7091	70.91%
skin sensitisation	-	0.8570	85.70%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	+	0.6738	67.38%
Acute Oral Toxicity (c)	III	0.6009	60.09%
Estrogen receptor binding	+	0.6243	62.43%
Androgen receptor binding	-	0.5442	54.42%
Thyroid receptor binding	+	0.5384	53.84%
Glucocorticoid receptor binding	-	0.5190	51.90%
Aromatase binding	+	0.5253	52.53%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.7991	79.91%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.8400	84.00%
Fish aquatic toxicity	-	0.7270	72.70%

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	94.92%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.72%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	90.16%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.56%	86.92%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.83%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.77%	99.17%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	84.63%	91.24%
CHEMBL2581	P07339	Cathepsin D	84.49%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.40%	86.33%

Plants that contains it

• Curtia tenuifolia
• Eucnide bartonioides
• Fontanesia fortunei
• Gentiana verna

Cross-Links

• PubChem: 14488076
• LOTUS: LTS0153902
• wikiData: Q104403311