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

Details

• Internal ID: 195e87fd-3802-4208-a634-95358eda4759
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: methyl (4S,5E,6S)-5-ethylidene-4-[2-[[(1S,2R,3R,5R)-5-[(2R)-1-[2-[(2S,3E,4S)-3-ethylidene-5-methoxycarbonyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-4-yl]acetyl]oxy-3-hydroxypropan-2-yl]-3-hydroxy-2-methylcyclopentyl]methoxy]-2-oxoethyl]-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)OCC3C(C(CC3C(CO)COC(=O)CC4C(=COC(C4=CC)OC5C(C(C(C(O5)CO)O)O)O)C(=O)OC)O)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](CO)COC(=O)C[C@@H]\4C(=CO[C@H](/C4=C/C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C(=O)OC)O)C
• InChI: InChI=1S/C44H64O24/c1-6-20-23(26(39(57)59-4)16-63-41(20)67-43-37(55)35(53)33(51)29(12-46)65-43)9-31(49)61-14-19(11-45)22-8-28(48)18(3)25(22)15-62-32(50)10-24-21(7-2)42(64-17-27(24)40(58)60-5)68-44-38(56)36(54)34(52)30(13-47)66-44/h6-7,16-19,22-25,28-30,33-38,41-48,51-56H,8-15H2,1-5H3/b20-6+,21-7+/t18-,19-,22+,23+,24+,25-,28-,29-,30-,33-,34-,35+,36+,37-,38-,41+,42+,43+,44+/m1/s1
• InChI Key: DHWFTDJZMBRGBH-ZLKZLVTFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₄H₆₄O₂₄
• Molecular Weight: 977.00 g/mol
• Exact Mass: 976.37875290 g/mol
• Topological Polar Surface Area (TPSA): 363.00 Ų
• XlogP: -3.20
• Atomic LogP (AlogP): -3.32
• H-Bond Acceptor: 24
• H-Bond Donor: 10
• Rotatable Bonds: 18

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6606	66.06%
Caco-2	-	0.8640	86.40%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7657	76.57%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7119	71.19%
OATP1B3 inhibitior	+	0.9430	94.30%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9362	93.62%
P-glycoprotein inhibitior	+	0.7430	74.30%
P-glycoprotein substrate	+	0.6458	64.58%
CYP3A4 substrate	+	0.6845	68.45%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8894	88.94%
CYP3A4 inhibition	-	0.8738	87.38%
CYP2C9 inhibition	-	0.9172	91.72%
CYP2C19 inhibition	-	0.8969	89.69%
CYP2D6 inhibition	-	0.9197	91.97%
CYP1A2 inhibition	-	0.9133	91.33%
CYP2C8 inhibition	+	0.6202	62.02%
CYP inhibitory promiscuity	-	0.9617	96.17%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7408	74.08%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9013	90.13%
Skin irritation	-	0.7558	75.58%
Skin corrosion	-	0.9564	95.64%
Ames mutagenesis	+	0.5446	54.46%
Human Ether-a-go-go-Related Gene inhibition	+	0.7786	77.86%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.7102	71.02%
skin sensitisation	-	0.8963	89.63%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.7606	76.06%
Acute Oral Toxicity (c)	III	0.5140	51.40%
Estrogen receptor binding	+	0.7820	78.20%
Androgen receptor binding	+	0.6955	69.55%
Thyroid receptor binding	+	0.5814	58.14%
Glucocorticoid receptor binding	+	0.7597	75.97%
Aromatase binding	+	0.5475	54.75%
PPAR gamma	+	0.7936	79.36%
Honey bee toxicity	-	0.7005	70.05%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.8439	84.39%

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	98.34%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.29%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	91.79%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.71%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.05%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	89.41%	94.73%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	88.83%	95.83%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.48%	96.00%
CHEMBL340	P08684	Cytochrome P450 3A4	88.04%	91.19%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.58%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.65%	89.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.33%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.22%	86.33%
CHEMBL2581	P07339	Cathepsin D	84.41%	98.95%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	84.33%	80.33%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	84.16%	94.80%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.55%	85.14%
CHEMBL5028	O14672	ADAM10	81.49%	97.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.09%	94.33%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	81.07%	95.64%
CHEMBL5255	O00206	Toll-like receptor 4	80.85%	92.50%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.77%	96.90%
CHEMBL2996	Q05655	Protein kinase C delta	80.67%	97.79%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.40%	95.89%

Plants that contains it

• Jasminum sambac

Cross-Links

• PubChem: 163187710
• LOTUS: LTS0008366
• wikiData: Q104980942