methyl (5E)-5-ethylidene-4-propyl-6-[(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate

Details

• Internal ID: 8684f8f0-cb02-43cc-a0ec-6fa7f6d46430
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: methyl (5E)-5-ethylidene-4-propyl-6-[(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
• SMILES (Canonical): CCCC1C(=COC(C1=CC)OC2C(C(C(C(O2)CO)O)O)O)C(=O)OC
• SMILES (Isomeric): CCCC\1C(=COC(/C1=C/C)O[C@H]2[C@H]([C@H]([C@H]([C@H](O2)CO)O)O)O)C(=O)OC
• InChI: InChI=1S/C18H28O9/c1-4-6-10-9(5-2)17(25-8-11(10)16(23)24-3)27-18-15(22)14(21)13(20)12(7-19)26-18/h5,8,10,12-15,17-22H,4,6-7H2,1-3H3/b9-5+/t10?,12-,13+,14+,15+,17?,18+/m1/s1
• InChI Key: SDKGJLREAMABGO-BSXPSEOHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₈O₉
• Molecular Weight: 388.40 g/mol
• Exact Mass: 388.17333247 g/mol
• Topological Polar Surface Area (TPSA): 135.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): -0.42
• H-Bond Acceptor: 9
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6333	63.33%
Caco-2	-	0.7853	78.53%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7899	78.99%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7410	74.10%
OATP1B3 inhibitior	+	0.9084	90.84%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.7012	70.12%
P-glycoprotein inhibitior	-	0.8518	85.18%
P-glycoprotein substrate	-	0.6896	68.96%
CYP3A4 substrate	+	0.5895	58.95%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8741	87.41%
CYP3A4 inhibition	-	0.8718	87.18%
CYP2C9 inhibition	-	0.8322	83.22%
CYP2C19 inhibition	-	0.7809	78.09%
CYP2D6 inhibition	-	0.9030	90.30%
CYP1A2 inhibition	-	0.8809	88.09%
CYP2C8 inhibition	+	0.4769	47.69%
CYP inhibitory promiscuity	-	0.7857	78.57%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6751	67.51%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9728	97.28%
Skin irritation	-	0.7695	76.95%
Skin corrosion	-	0.9563	95.63%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5255	52.55%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.8091	80.91%
skin sensitisation	-	0.8754	87.54%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.5595	55.95%
Acute Oral Toxicity (c)	III	0.6922	69.22%
Estrogen receptor binding	+	0.6070	60.70%
Androgen receptor binding	-	0.5309	53.09%
Thyroid receptor binding	-	0.5098	50.98%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.7437	74.37%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.8370	83.70%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	-	0.4255	42.55%

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	95.13%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.53%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.15%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	90.42%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.46%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.36%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.89%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.48%	86.92%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.83%	95.83%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.83%	94.33%

Plants that contains it

• Ligustrum lucidum

Cross-Links

• PubChem: 11968803
• NPASS: NPC158300