2-[(2S,3S,4S)-3-[(1R)-1-acetyloxyethyl]-2-[(2S,3R,4S,5S,6R)-6-(acetyloxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-5-methoxycarbonyl-3,4-dihydro-2H-pyran-4-yl]acetic acid

Details

• Internal ID: fbfd73d7-e1f0-4481-9108-a9e6b8230778
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: 2-[(2S,3S,4S)-3-[(1R)-1-acetyloxyethyl]-2-[(2S,3R,4S,5S,6R)-6-(acetyloxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-5-methoxycarbonyl-3,4-dihydro-2H-pyran-4-yl]acetic acid
• InChI: InChI=1S/C21H30O14/c1-8(33-10(3)23)15-11(5-14(24)25)12(19(29)30-4)6-32-20(15)35-21-18(28)17(27)16(26)13(34-21)7-31-9(2)22/h6,8,11,13,15-18,20-21,26-28H,5,7H2,1-4H3,(H,24,25)/t8-,11-,13-,15-,16-,17+,18-,20+,21+/m1/s1
• InChI Key: FWVFWBXGZOLBJL-IVKCGISMSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₀O₁₄
• Molecular Weight: 506.50 g/mol
• Exact Mass: 506.16355563 g/mol
• Topological Polar Surface Area (TPSA): 205.00 Ų
• XlogP: -1.90
• Atomic LogP (AlogP): -1.55
• H-Bond Acceptor: 13
• H-Bond Donor: 4
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5949	59.49%
Caco-2	-	0.8221	82.21%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6775	67.75%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7912	79.12%
OATP1B3 inhibitior	+	0.9249	92.49%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.4760	47.60%
P-glycoprotein inhibitior	-	0.5202	52.02%
P-glycoprotein substrate	-	0.6695	66.95%
CYP3A4 substrate	+	0.6220	62.20%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8930	89.30%
CYP3A4 inhibition	-	0.9278	92.78%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9218	92.18%
CYP2D6 inhibition	-	0.8994	89.94%
CYP1A2 inhibition	-	0.9346	93.46%
CYP2C8 inhibition	-	0.5991	59.91%
CYP inhibitory promiscuity	-	0.9390	93.90%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7070	70.70%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9139	91.39%
Skin irritation	-	0.7565	75.65%
Skin corrosion	-	0.9547	95.47%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6068	60.68%
Micronuclear	-	0.5767	57.67%
Hepatotoxicity	-	0.6646	66.46%
skin sensitisation	-	0.8780	87.80%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.6376	63.76%
Acute Oral Toxicity (c)	III	0.6488	64.88%
Estrogen receptor binding	+	0.7517	75.17%
Androgen receptor binding	-	0.5683	56.83%
Thyroid receptor binding	-	0.5624	56.24%
Glucocorticoid receptor binding	+	0.6598	65.98%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.5173	51.73%
Honey bee toxicity	-	0.8302	83.02%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.7141	71.41%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.97%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.54%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.72%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	93.88%	94.73%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.45%	91.11%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	91.18%	97.21%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.82%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.61%	96.00%
CHEMBL5028	O14672	ADAM10	85.20%	97.50%
CHEMBL221	P23219	Cyclooxygenase-1	82.65%	90.17%
CHEMBL5255	O00206	Toll-like receptor 4	81.45%	92.50%

Plants that contains it

• Calycophyllum spruceanum

Cross-Links

• PubChem: 162914618
• LOTUS: LTS0180932
• wikiData: Q105003604