methyl (4S,5E,6S)-4-[2-[(E,3S)-3,7-dimethyl-8-oxo-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoct-6-enoxy]-2-oxoethyl]-5-ethylidene-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate

Details

• Internal ID: bebe772c-2f71-4b0e-9e93-e9d975107591
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: methyl (4S,5E,6S)-4-[2-[(E,3S)-3,7-dimethyl-8-oxo-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoct-6-enoxy]-2-oxoethyl]-5-ethylidene-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
• SMILES (Canonical): CC=C1C(C(=COC1OC2C(C(C(C(O2)CO)O)O)O)C(=O)OC)CC(=O)OCCC(C)CCC=C(C)C(=O)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): C/C=C/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)CC(=O)OCC[C@@H](C)CC/C=C(\C)/C(=O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C33H50O18/c1-5-17-18(19(30(44)45-4)14-47-31(17)51-33-28(42)26(40)24(38)21(13-35)49-33)11-22(36)46-10-9-15(2)7-6-8-16(3)29(43)50-32-27(41)25(39)23(37)20(12-34)48-32/h5,8,14-15,18,20-21,23-28,31-35,37-42H,6-7,9-13H2,1-4H3/b16-8+,17-5+/t15-,18-,20+,21+,23+,24+,25-,26-,27+,28+,31-,32-,33-/m0/s1
• InChI Key: BNQQXLDDOHLSAR-AMXGYDOKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₅₀O₁₈
• Molecular Weight: 734.70 g/mol
• Exact Mass: 734.29971474 g/mol
• Topological Polar Surface Area (TPSA): 278.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): -2.19
• H-Bond Acceptor: 18
• H-Bond Donor: 8
• Rotatable Bonds: 15

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7270	72.70%
Caco-2	-	0.8654	86.54%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8561	85.61%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7576	75.76%
OATP1B3 inhibitior	+	0.8791	87.91%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	+	0.7674	76.74%
P-glycoprotein inhibitior	+	0.6999	69.99%
P-glycoprotein substrate	+	0.6156	61.56%
CYP3A4 substrate	+	0.6921	69.21%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8854	88.54%
CYP3A4 inhibition	-	0.8643	86.43%
CYP2C9 inhibition	-	0.9066	90.66%
CYP2C19 inhibition	-	0.8481	84.81%
CYP2D6 inhibition	-	0.9225	92.25%
CYP1A2 inhibition	-	0.8696	86.96%
CYP2C8 inhibition	+	0.6141	61.41%
CYP inhibitory promiscuity	-	0.9642	96.42%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7201	72.01%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9141	91.41%
Skin irritation	-	0.7584	75.84%
Skin corrosion	-	0.9622	96.22%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6762	67.62%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.7167	71.67%
skin sensitisation	-	0.9165	91.65%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.6528	65.28%
Acute Oral Toxicity (c)	III	0.6173	61.73%
Estrogen receptor binding	+	0.7769	77.69%
Androgen receptor binding	+	0.6290	62.90%
Thyroid receptor binding	-	0.5134	51.34%
Glucocorticoid receptor binding	+	0.7176	71.76%
Aromatase binding	+	0.6050	60.50%
PPAR gamma	+	0.6780	67.80%
Honey bee toxicity	-	0.7232	72.32%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9098	90.98%

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	96.63%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	95.63%	94.73%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.77%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.27%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.09%	94.45%
CHEMBL2581	P07339	Cathepsin D	90.55%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.47%	99.17%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	86.61%	96.90%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.04%	86.33%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	83.63%	89.67%
CHEMBL2996	Q05655	Protein kinase C delta	83.33%	97.79%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.15%	89.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.31%	94.33%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.02%	90.71%
CHEMBL5255	O00206	Toll-like receptor 4	80.94%	92.50%

Plants that contains it

• Jasminum polyanthum

Cross-Links

• PubChem: 163103549
• LOTUS: LTS0011002
• wikiData: Q104938972