methyl (4S,5E,6S)-5-ethylidene-4-[2-[[(1S,2R,3S,5S)-3-hydroxy-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: 14d5b81f-fe1a-4749-b0ed-f3cf2c28e726
• 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-hydroxy-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)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](C)CO)O)C
• InChI: InChI=1S/C27H42O13/c1-5-14-16(7-21(31)37-10-17-13(3)19(30)6-15(17)12(2)8-28)18(25(35)36-4)11-38-26(14)40-27-24(34)23(33)22(32)20(9-29)39-27/h5,11-13,15-17,19-20,22-24,26-30,32-34H,6-10H2,1-4H3/b14-5+/t12-,13-,15+,16+,17-,19+,20-,22-,23+,24-,26+,27+/m1/s1
• InChI Key: XNIRCYGLGZSLPW-DEDXPKGASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₂O₁₃
• Molecular Weight: 574.60 g/mol
• Exact Mass: 574.26254139 g/mol
• Topological Polar Surface Area (TPSA): 202.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -1.03
• H-Bond Acceptor: 13
• 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	-	0.6005	60.05%
Caco-2	-	0.8690	86.90%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7567	75.67%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.6954	69.54%
OATP1B3 inhibitior	+	0.9375	93.75%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6712	67.12%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	+	0.5836	58.36%
CYP3A4 substrate	+	0.6744	67.44%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8894	88.94%
CYP3A4 inhibition	-	0.8198	81.98%
CYP2C9 inhibition	-	0.9113	91.13%
CYP2C19 inhibition	-	0.8896	88.96%
CYP2D6 inhibition	-	0.9267	92.67%
CYP1A2 inhibition	-	0.9073	90.73%
CYP2C8 inhibition	+	0.5736	57.36%
CYP inhibitory promiscuity	-	0.9654	96.54%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7224	72.24%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9281	92.81%
Skin irritation	-	0.7407	74.07%
Skin corrosion	-	0.9570	95.70%
Ames mutagenesis	+	0.5346	53.46%
Human Ether-a-go-go-Related Gene inhibition	-	0.3922	39.22%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.7352	73.52%
skin sensitisation	-	0.9044	90.44%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.7499	74.99%
Acute Oral Toxicity (c)	III	0.5290	52.90%
Estrogen receptor binding	+	0.7332	73.32%
Androgen receptor binding	+	0.5633	56.33%
Thyroid receptor binding	-	0.5853	58.53%
Glucocorticoid receptor binding	+	0.6857	68.57%
Aromatase binding	+	0.5430	54.30%
PPAR gamma	+	0.6104	61.04%
Honey bee toxicity	-	0.7159	71.59%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.9160	91.60%

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	98.24%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.24%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.97%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.37%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	88.88%	94.73%
CHEMBL2581	P07339	Cathepsin D	88.55%	98.95%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	88.01%	95.83%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.49%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.83%	99.17%
CHEMBL2996	Q05655	Protein kinase C delta	86.08%	97.79%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.74%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	85.62%	91.19%
CHEMBL1951	P21397	Monoamine oxidase A	83.80%	91.49%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	83.49%	80.33%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.35%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.10%	85.14%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	83.09%	94.80%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.99%	86.92%
CHEMBL5028	O14672	ADAM10	82.14%	97.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.55%	95.89%
CHEMBL2179	P04062	Beta-glucocerebrosidase	81.16%	85.31%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.97%	95.89%
CHEMBL2243	O00519	Anandamide amidohydrolase	80.54%	97.53%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.14%	96.90%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.05%	94.33%

Plants that contains it

• Jasminum nudiflorum

Cross-Links

• PubChem: 162953628
• LOTUS: LTS0252608
• wikiData: Q105331689