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

Details

• Internal ID: e64ed37e-d982-462e-8867-6795926c7022
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: methyl (3R,4aS,6S,7R,7aS)-6-[(2S,3R,4S)-3-ethenyl-4-[2-(oxiran-2-yl)ethyl]-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carbonyl]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)C3=COC(C(C3CCC4CO4)C=C)OC5C(C(C(C(O5)CO)O)O)O
• SMILES (Isomeric): C[C@H]1[C@H](C[C@H]2[C@@H]1CO[C@H](C2C(=O)OC)O)OC(=O)C3=CO[C@H]([C@@H]([C@@H]3CCC4CO4)C=C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
• InChI: InChI=1S/C29H42O14/c1-4-14-15(6-5-13-9-38-13)18(11-40-28(14)43-29-24(33)23(32)22(31)20(8-30)42-29)25(34)41-19-7-16-17(12(19)2)10-39-27(36)21(16)26(35)37-3/h4,11-17,19-24,27-33,36H,1,5-10H2,2-3H3/t12-,13?,14-,15+,16+,17-,19+,20-,21?,22-,23+,24-,27-,28+,29+/m1/s1
• InChI Key: JVJDFEQEXIIQNC-CCNWUNFJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₂O₁₄
• Molecular Weight: 614.60 g/mol
• Exact Mass: 614.25745601 g/mol
• Topological Polar Surface Area (TPSA): 203.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): -1.04
• H-Bond Acceptor: 14
• H-Bond Donor: 5
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4818	48.18%
Caco-2	-	0.8662	86.62%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.7790	77.90%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7572	75.72%
OATP1B3 inhibitior	+	0.9465	94.65%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.6145	61.45%
P-glycoprotein inhibitior	-	0.4507	45.07%
P-glycoprotein substrate	+	0.6468	64.68%
CYP3A4 substrate	+	0.7132	71.32%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8784	87.84%
CYP3A4 inhibition	-	0.8620	86.20%
CYP2C9 inhibition	-	0.8779	87.79%
CYP2C19 inhibition	-	0.8397	83.97%
CYP2D6 inhibition	-	0.9084	90.84%
CYP1A2 inhibition	-	0.8137	81.37%
CYP2C8 inhibition	+	0.7221	72.21%
CYP inhibitory promiscuity	-	0.9276	92.76%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7387	73.87%
Eye corrosion	-	0.9849	98.49%
Eye irritation	-	0.9353	93.53%
Skin irritation	-	0.7095	70.95%
Skin corrosion	-	0.9388	93.88%
Ames mutagenesis	-	0.5169	51.69%
Human Ether-a-go-go-Related Gene inhibition	+	0.6765	67.65%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.8614	86.14%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.7715	77.15%
Acute Oral Toxicity (c)	III	0.4153	41.53%
Estrogen receptor binding	+	0.7753	77.53%
Androgen receptor binding	+	0.6053	60.53%
Thyroid receptor binding	-	0.5806	58.06%
Glucocorticoid receptor binding	+	0.5769	57.69%
Aromatase binding	+	0.5579	55.79%
PPAR gamma	+	0.6140	61.40%
Honey bee toxicity	-	0.6857	68.57%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9346	93.46%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.74%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.45%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	90.51%	90.17%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	90.30%	91.24%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.57%	99.17%
CHEMBL220	P22303	Acetylcholinesterase	87.43%	94.45%
CHEMBL2581	P07339	Cathepsin D	87.38%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.59%	96.00%
CHEMBL2243	O00519	Anandamide amidohydrolase	85.50%	97.53%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.31%	86.33%
CHEMBL4208	P20618	Proteasome component C5	83.63%	90.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.56%	95.83%
CHEMBL340	P08684	Cytochrome P450 3A4	83.48%	91.19%
CHEMBL5028	O14672	ADAM10	83.35%	97.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.67%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.96%	89.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.59%	94.33%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.15%	95.50%
CHEMBL3401	O75469	Pregnane X receptor	81.06%	94.73%
CHEMBL2996	Q05655	Protein kinase C delta	80.78%	97.79%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.59%	91.07%

Plants that contains it

• Dipsacus laciniatus

Cross-Links

• PubChem: 122228282
• LOTUS: LTS0251082
• wikiData: Q105135772