methyl (4R,4aS,6S,7R,7aS)-6-[2-[3-ethenyl-5-methoxycarbonyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]acetyl]oxy-3-hydroxy-7-methyl-1,3,4,4a,5,6,7,7a-octahydrocyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: c1084ef1-5626-494b-a55f-d4ae9693fef5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: methyl (4R,4aS,6S,7R,7aS)-6-[2-[3-ethenyl-5-methoxycarbonyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]acetyl]oxy-3-hydroxy-7-methyl-1,3,4,4a,5,6,7,7a-octahydrocyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): CC1C(CC2C1COC(C2C(=O)OC)O)OC(=O)CC3C(C(OC=C3C(=O)OC)OC4C(C(C(C(O4)CO)O)O)O)C=C
• SMILES (Isomeric): C[C@H]1[C@H](C[C@H]2[C@@H]1COC([C@@H]2C(=O)OC)O)OC(=O)CC3C(C(OC=C3C(=O)OC)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C=C
• InChI: InChI=1S/C28H40O15/c1-5-12-13(7-19(30)41-17-6-14-15(11(17)2)9-39-26(36)20(14)25(35)38-4)16(24(34)37-3)10-40-27(12)43-28-23(33)22(32)21(31)18(8-29)42-28/h5,10-15,17-18,20-23,26-29,31-33,36H,1,6-9H2,2-4H3/t11-,12?,13?,14+,15-,17+,18-,20+,21-,22+,23-,26?,27?,28+/m1/s1
• InChI Key: FLVLFJQOHKWOAZ-LICRRKAHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₀O₁₅
• Molecular Weight: 616.60 g/mol
• Exact Mass: 616.23672056 g/mol
• Topological Polar Surface Area (TPSA): 217.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -1.65
• H-Bond Acceptor: 15
• H-Bond Donor: 5
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4610	46.10%
Caco-2	-	0.8739	87.39%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.7162	71.62%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7427	74.27%
OATP1B3 inhibitior	+	0.9377	93.77%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.6086	60.86%
P-glycoprotein inhibitior	+	0.5825	58.25%
P-glycoprotein substrate	+	0.6334	63.34%
CYP3A4 substrate	+	0.7132	71.32%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8802	88.02%
CYP3A4 inhibition	-	0.8415	84.15%
CYP2C9 inhibition	-	0.9177	91.77%
CYP2C19 inhibition	-	0.8703	87.03%
CYP2D6 inhibition	-	0.9334	93.34%
CYP1A2 inhibition	-	0.8867	88.67%
CYP2C8 inhibition	+	0.6736	67.36%
CYP inhibitory promiscuity	-	0.9296	92.96%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7401	74.01%
Eye corrosion	-	0.9870	98.70%
Eye irritation	-	0.9278	92.78%
Skin irritation	-	0.7193	71.93%
Skin corrosion	-	0.9485	94.85%
Ames mutagenesis	-	0.5123	51.23%
Human Ether-a-go-go-Related Gene inhibition	+	0.6809	68.09%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.8718	87.18%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.6123	61.23%
Acute Oral Toxicity (c)	III	0.4595	45.95%
Estrogen receptor binding	+	0.7334	73.34%
Androgen receptor binding	+	0.5783	57.83%
Thyroid receptor binding	-	0.5663	56.63%
Glucocorticoid receptor binding	+	0.5647	56.47%
Aromatase binding	+	0.5589	55.89%
PPAR gamma	+	0.6034	60.34%
Honey bee toxicity	-	0.6671	66.71%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.9522	95.22%

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	97.85%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.60%	91.11%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	90.59%	91.24%
CHEMBL221	P23219	Cyclooxygenase-1	89.59%	90.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.00%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.62%	86.33%
CHEMBL5028	O14672	ADAM10	85.87%	97.50%
CHEMBL4208	P20618	Proteasome component C5	85.65%	90.00%
CHEMBL2581	P07339	Cathepsin D	85.48%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	85.26%	91.19%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.20%	89.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.47%	95.83%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.90%	96.00%
CHEMBL2243	O00519	Anandamide amidohydrolase	82.13%	97.53%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.87%	94.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.28%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.23%	100.00%

Plants that contains it

• Loasa acerifolia

Cross-Links

• PubChem: 100989554
• LOTUS: LTS0044038
• wikiData: Q104392949