methyl (4S,5E,6S)-5-ethylidene-4-[2-[[(1S,2R,3S,5S)-3-[2-[(2S,3E,4S)-3-ethylidene-5-methoxycarbonyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-4-yl]acetyl]oxy-2-methyl-5-[(2R)-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropan-2-yl]cyclopentyl]methoxy]-2-oxoethyl]-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate

Details

• Internal ID: 0c06bc65-a28d-4617-a2f4-57a6e60cd09c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: methyl (4S,5E,6S)-5-ethylidene-4-[2-[[(1S,2R,3S,5S)-3-[2-[(2S,3E,4S)-3-ethylidene-5-methoxycarbonyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-4-yl]acetyl]oxy-2-methyl-5-[(2R)-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropan-2-yl]cyclopentyl]methoxy]-2-oxoethyl]-6-[(2R,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)OCC3C(C(CC3C(C)COC4C(C(C(C(O4)CO)O)O)O)OC(=O)CC5C(=COC(C5=CC)OC6C(C(C(C(O6)CO)O)O)O)C(=O)OC)C
• 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)OC[C@@H]3[C@H]([C@H](C[C@H]3[C@@H](C)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OC(=O)C[C@@H]\5C(=CO[C@H](/C5=C/C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C(=O)OC)C
• InChI: InChI=1S/C50H74O28/c1-7-21-24(27(44(65)67-5)17-71-46(21)77-49-42(63)39(60)36(57)31(13-52)75-49)10-33(54)69-16-26-20(4)29(9-23(26)19(3)15-70-48-41(62)38(59)35(56)30(12-51)74-48)73-34(55)11-25-22(8-2)47(72-18-28(25)45(66)68-6)78-50-43(64)40(61)37(58)32(14-53)76-50/h7-8,17-20,23-26,29-32,35-43,46-53,56-64H,9-16H2,1-6H3/b21-7+,22-8+/t19-,20+,23-,24-,25-,26+,29-,30+,31+,32+,35+,36+,37+,38-,39-,40-,41+,42+,43+,46-,47-,48+,49-,50-/m0/s1
• InChI Key: IVSNJPCWTDNKHQ-UKPWFQCWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₀H₇₄O₂₈
• Molecular Weight: 1123.10 g/mol
• Exact Mass: 1122.43666170 g/mol
• Topological Polar Surface Area (TPSA): 422.00 Ų
• XlogP: -3.60
• Atomic LogP (AlogP): -4.47
• H-Bond Acceptor: 28
• H-Bond Donor: 12
• Rotatable Bonds: 20

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6425	64.25%
Caco-2	-	0.8650	86.50%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7953	79.53%
OATP2B1 inhibitior	-	0.8667	86.67%
OATP1B1 inhibitior	+	0.7444	74.44%
OATP1B3 inhibitior	+	0.9308	93.08%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9359	93.59%
P-glycoprotein inhibitior	+	0.7444	74.44%
P-glycoprotein substrate	+	0.6641	66.41%
CYP3A4 substrate	+	0.6971	69.71%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8894	88.94%
CYP3A4 inhibition	-	0.8532	85.32%
CYP2C9 inhibition	-	0.8960	89.60%
CYP2C19 inhibition	-	0.8687	86.87%
CYP2D6 inhibition	-	0.9237	92.37%
CYP1A2 inhibition	-	0.8951	89.51%
CYP2C8 inhibition	+	0.6610	66.10%
CYP inhibitory promiscuity	-	0.9299	92.99%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7158	71.58%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.8996	89.96%
Skin irritation	-	0.7666	76.66%
Skin corrosion	-	0.9593	95.93%
Ames mutagenesis	+	0.5655	56.55%
Human Ether-a-go-go-Related Gene inhibition	+	0.7484	74.84%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.7102	71.02%
skin sensitisation	-	0.9046	90.46%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.6809	68.09%
Acute Oral Toxicity (c)	III	0.5273	52.73%
Estrogen receptor binding	+	0.8077	80.77%
Androgen receptor binding	+	0.7117	71.17%
Thyroid receptor binding	+	0.6130	61.30%
Glucocorticoid receptor binding	+	0.7855	78.55%
Aromatase binding	+	0.5642	56.42%
PPAR gamma	+	0.7870	78.70%
Honey bee toxicity	-	0.6919	69.19%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.9428	94.28%

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	98.63%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.50%	91.11%
CHEMBL2581	P07339	Cathepsin D	90.90%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.74%	96.00%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	88.86%	95.17%
CHEMBL2996	Q05655	Protein kinase C delta	88.83%	97.79%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.55%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	87.71%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.13%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	85.93%	90.17%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.63%	95.83%
CHEMBL5028	O14672	ADAM10	85.46%	97.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.59%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.03%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.94%	89.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.45%	86.92%
CHEMBL5255	O00206	Toll-like receptor 4	82.26%	92.50%
CHEMBL340	P08684	Cytochrome P450 3A4	81.87%	91.19%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.22%	94.33%
CHEMBL2179	P04062	Beta-glucocerebrosidase	80.79%	85.31%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.00%	94.80%

Plants that contains it

• Jasminum nudiflorum

Cross-Links

• PubChem: 102510589
• LOTUS: LTS0011645
• wikiData: Q105121271