methyl (4S,5E,6S)-5-ethylidene-4-[2-[[(1S,2R,3S,5S)-3-[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-5-[(2S)-1-hydroxypropan-2-yl]-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: 2fc83633-aac8-4f3c-b2f3-c7aecfd23ba9
• 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-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-4-yl]acetyl]oxy-5-[(2S)-1-hydroxypropan-2-yl]-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(C)CO)OC(=O)CC4C(=COC(C4=CC)OC5C(C(C(C(O5)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)OC(=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)C
• InChI: InChI=1S/C44H64O23/c1-7-20-23(26(39(56)58-5)16-61-41(20)66-43-37(54)35(52)33(50)29(13-46)64-43)10-31(48)60-15-25-19(4)28(9-22(25)18(3)12-45)63-32(49)11-24-21(8-2)42(62-17-27(24)40(57)59-6)67-44-38(55)36(53)34(51)30(14-47)65-44/h7-8,16-19,22-25,28-30,33-38,41-47,50-55H,9-15H2,1-6H3/b20-7+,21-8+/t18-,19-,22+,23+,24+,25-,28+,29-,30-,33-,34-,35+,36+,37-,38-,41+,42+,43+,44+/m1/s1
• InChI Key: PEVWIGNKOSRYCF-KABYCWAOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₄H₆₄O₂₃
• Molecular Weight: 961.00 g/mol
• Exact Mass: 960.38383828 g/mol
• Topological Polar Surface Area (TPSA): 343.00 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): -2.29
• H-Bond Acceptor: 23
• H-Bond Donor: 9
• Rotatable Bonds: 17

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	-	0.8660	86.60%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7953	79.53%
OATP2B1 inhibitior	-	0.8647	86.47%
OATP1B1 inhibitior	+	0.7362	73.62%
OATP1B3 inhibitior	+	0.9308	93.08%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9575	95.75%
P-glycoprotein inhibitior	+	0.7426	74.26%
P-glycoprotein substrate	+	0.6271	62.71%
CYP3A4 substrate	+	0.6876	68.76%
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	+	0.6343	63.43%
CYP inhibitory promiscuity	-	0.9299	92.99%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7158	71.58%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.9018	90.18%
Skin irritation	-	0.7666	76.66%
Skin corrosion	-	0.9593	95.93%
Ames mutagenesis	+	0.5346	53.46%
Human Ether-a-go-go-Related Gene inhibition	+	0.7260	72.60%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.7477	74.77%
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	-	0.6344	63.44%
Acute Oral Toxicity (c)	III	0.5273	52.73%
Estrogen receptor binding	+	0.8002	80.02%
Androgen receptor binding	+	0.6926	69.26%
Thyroid receptor binding	+	0.5506	55.06%
Glucocorticoid receptor binding	+	0.7590	75.90%
Aromatase binding	+	0.5633	56.33%
PPAR gamma	+	0.7745	77.45%
Honey bee toxicity	-	0.7078	70.78%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
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	98.45%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.19%	91.11%
CHEMBL2581	P07339	Cathepsin D	89.84%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.03%	97.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.54%	96.00%
CHEMBL2996	Q05655	Protein kinase C delta	88.54%	97.79%
CHEMBL3401	O75469	Pregnane X receptor	87.19%	94.73%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	86.01%	95.83%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.89%	94.45%
CHEMBL5028	O14672	ADAM10	85.46%	97.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.16%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.93%	99.17%
CHEMBL340	P08684	Cytochrome P450 3A4	83.38%	91.19%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.08%	86.92%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.70%	89.00%
CHEMBL221	P23219	Cyclooxygenase-1	81.51%	90.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.47%	95.89%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.22%	94.33%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	81.15%	94.80%
CHEMBL5255	O00206	Toll-like receptor 4	80.50%	92.50%
CHEMBL2243	O00519	Anandamide amidohydrolase	80.16%	97.53%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.03%	96.90%

Plants that contains it

• Jasminum nudiflorum

Cross-Links

• PubChem: 163030880
• LOTUS: LTS0002041
• wikiData: Q105207429