methyl (2S,3R,4S)-4-[[(2R,4aR,6S,7R,8R,8aS)-6-[[(3S,4R,4aS)-4-ethenyl-8-oxo-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl]oxy]-7,8-dihydroxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-2-yl]methyl]-3-ethenyl-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: 31875ea3-e98c-4b53-8b82-a5962d276768
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: methyl (2S,3R,4S)-4-[[(2R,4aR,6S,7R,8R,8aS)-6-[[(3S,4R,4aS)-4-ethenyl-8-oxo-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl]oxy]-7,8-dihydroxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-2-yl]methyl]-3-ethenyl-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(C1CC2OCC3C(O2)C(C(C(O3)OC4C(C5CCOC(=O)C5=CO4)C=C)O)O)C=C)OC6C(C(C(C(O6)CO)O)O)O
• SMILES (Isomeric): COC(=O)C1=CO[C@H]([C@@H]([C@@H]1C[C@@H]2OC[C@@H]3[C@@H](O2)[C@@H]([C@H]([C@@H](O3)O[C@H]4[C@@H]([C@@H]5CCOC(=O)C5=CO4)C=C)O)O)C=C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
• InChI: InChI=1S/C33H44O18/c1-4-13-15-6-7-43-29(41)17(15)10-45-30(13)50-33-26(39)24(37)27-20(48-33)12-44-21(49-27)8-16-14(5-2)31(46-11-18(16)28(40)42-3)51-32-25(38)23(36)22(35)19(9-34)47-32/h4-5,10-11,13-16,19-27,30-39H,1-2,6-9,12H2,3H3/t13-,14-,15+,16+,19-,20-,21-,22-,23+,24-,25-,26-,27-,30+,31+,32+,33+/m1/s1
• InChI Key: HADYJKOVEHJYKM-VLTHOYLRSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₄O₁₈
• Molecular Weight: 728.70 g/mol
• Exact Mass: 728.25276455 g/mol
• Topological Polar Surface Area (TPSA): 248.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -2.17
• H-Bond Acceptor: 18
• H-Bond Donor: 6
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6263	62.63%
Caco-2	-	0.8743	87.43%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8064	80.64%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7853	78.53%
OATP1B3 inhibitior	+	0.9463	94.63%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.6123	61.23%
P-glycoprotein inhibitior	+	0.6784	67.84%
P-glycoprotein substrate	+	0.5933	59.33%
CYP3A4 substrate	+	0.7112	71.12%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8638	86.38%
CYP3A4 inhibition	-	0.9280	92.80%
CYP2C9 inhibition	-	0.8876	88.76%
CYP2C19 inhibition	-	0.8361	83.61%
CYP2D6 inhibition	-	0.9061	90.61%
CYP1A2 inhibition	-	0.8440	84.40%
CYP2C8 inhibition	+	0.6993	69.93%
CYP inhibitory promiscuity	-	0.9121	91.21%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6098	60.98%
Eye corrosion	-	0.9802	98.02%
Eye irritation	-	0.9090	90.90%
Skin irritation	-	0.7618	76.18%
Skin corrosion	-	0.9398	93.98%
Ames mutagenesis	-	0.5070	50.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7145	71.45%
Micronuclear	-	0.7641	76.41%
Hepatotoxicity	-	0.6466	64.66%
skin sensitisation	-	0.8618	86.18%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.5723	57.23%
Acute Oral Toxicity (c)	III	0.5555	55.55%
Estrogen receptor binding	+	0.8006	80.06%
Androgen receptor binding	+	0.6791	67.91%
Thyroid receptor binding	-	0.5429	54.29%
Glucocorticoid receptor binding	+	0.6338	63.38%
Aromatase binding	+	0.5836	58.36%
PPAR gamma	+	0.6899	68.99%
Honey bee toxicity	-	0.7015	70.15%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.7360	73.60%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL220	P22303	Acetylcholinesterase	97.15%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.11%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.73%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.88%	97.09%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	91.01%	91.24%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.22%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.22%	86.92%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.15%	96.00%
CHEMBL2581	P07339	Cathepsin D	88.09%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.03%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	84.99%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.80%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.07%	89.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.70%	95.83%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.33%	99.17%
CHEMBL5028	O14672	ADAM10	82.14%	97.50%
CHEMBL5255	O00206	Toll-like receptor 4	81.78%	92.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.13%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.11%	85.14%

Plants that contains it

• Lonicera caerulea

Cross-Links

• PubChem: 101922273
• LOTUS: LTS0099889
• wikiData: Q105024815