3-ethenyl-4-(2-methoxy-2-oxoethyl)-2-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylic acid

Details

• Internal ID: f97f5d97-ad91-490c-b022-2e0b1a0090ff
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: 3-ethenyl-4-(2-methoxy-2-oxoethyl)-2-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylic acid
• SMILES (Canonical): COC(=O)CC1C(C(OC=C1C(=O)O)OC2C(C(C(C(O2)CO)O)O)O)C=C
• SMILES (Isomeric): COC(=O)CC1C(C(OC=C1C(=O)O)OC2C(C(C(C(O2)CO)O)O)O)C=C
• InChI: InChI=1S/C17H24O11/c1-3-7-8(4-11(19)25-2)9(15(23)24)6-26-16(7)28-17-14(22)13(21)12(20)10(5-18)27-17/h3,6-8,10,12-14,16-18,20-22H,1,4-5H2,2H3,(H,23,24)
• InChI Key: UVIHEQDHSJMULB-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₄O₁₁
• Molecular Weight: 404.40 g/mol
• Exact Mass: 404.13186158 g/mol
• Topological Polar Surface Area (TPSA): 172.00 Ų
• XlogP: -1.60
• Atomic LogP (AlogP): -1.89
• H-Bond Acceptor: 10
• 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	-	0.7180	71.80%
Caco-2	-	0.8834	88.34%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7284	72.84%
OATP2B1 inhibitior	-	0.8579	85.79%
OATP1B1 inhibitior	+	0.7190	71.90%
OATP1B3 inhibitior	+	0.9540	95.40%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.7955	79.55%
P-glycoprotein inhibitior	-	0.8263	82.63%
P-glycoprotein substrate	-	0.8421	84.21%
CYP3A4 substrate	+	0.5579	55.79%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8811	88.11%
CYP3A4 inhibition	-	0.9123	91.23%
CYP2C9 inhibition	-	0.8834	88.34%
CYP2C19 inhibition	-	0.8817	88.17%
CYP2D6 inhibition	-	0.9207	92.07%
CYP1A2 inhibition	-	0.9157	91.57%
CYP2C8 inhibition	-	0.6532	65.32%
CYP inhibitory promiscuity	-	0.8946	89.46%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7762	77.62%
Eye corrosion	-	0.9854	98.54%
Eye irritation	-	0.9248	92.48%
Skin irritation	-	0.7911	79.11%
Skin corrosion	-	0.9460	94.60%
Ames mutagenesis	-	0.5293	52.93%
Human Ether-a-go-go-Related Gene inhibition	-	0.7020	70.20%
Micronuclear	-	0.6541	65.41%
Hepatotoxicity	-	0.7305	73.05%
skin sensitisation	-	0.8742	87.42%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	+	0.5856	58.56%
Acute Oral Toxicity (c)	III	0.5450	54.50%
Estrogen receptor binding	+	0.5781	57.81%
Androgen receptor binding	-	0.5204	52.04%
Thyroid receptor binding	-	0.5172	51.72%
Glucocorticoid receptor binding	+	0.6010	60.10%
Aromatase binding	+	0.5890	58.90%
PPAR gamma	+	0.5402	54.02%
Honey bee toxicity	-	0.8059	80.59%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.7900	79.00%
Fish aquatic toxicity	+	0.7606	76.06%

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	95.36%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.57%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.18%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.58%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.13%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	84.70%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.74%	86.33%
CHEMBL5028	O14672	ADAM10	82.88%	97.50%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.12%	86.92%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.62%	93.00%

Plants that contains it

• Lonicera japonica
• Strychnos spinosa
• Syringa reticulata

Cross-Links

• PubChem: 73076227
• LOTUS: LTS0110457
• wikiData: Q105279883