methyl 2-[(1S,2S,4aR,5R,8S,8aS)-1,5,8-trihydroxy-4a-methyl-8-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]prop-2-enoate

Details

• Internal ID: 567f50c7-05a4-4bd0-a940-600ddc40374b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: methyl 2-[(1S,2S,4aR,5R,8S,8aS)-1,5,8-trihydroxy-4a-methyl-8-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]prop-2-enoate
• SMILES (Canonical): CC12CCC(C(C1C(CCC2O)(COC3C(C(C(C(O3)CO)O)O)O)O)O)C(=C)C(=O)OC
• SMILES (Isomeric): C[C@@]12CC[C@H]([C@@H]([C@H]1[C@@](CC[C@H]2O)(CO[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O)C(=C)C(=O)OC
• InChI: InChI=1S/C22H36O11/c1-10(19(29)31-3)11-4-6-21(2)13(24)5-7-22(30,18(21)14(11)25)9-32-20-17(28)16(27)15(26)12(8-23)33-20/h11-18,20,23-28,30H,1,4-9H2,2-3H3/t11-,12+,13+,14-,15+,16-,17+,18+,20+,21-,22+/m0/s1
• InChI Key: DZHUNUYNXHZANA-XPBNFJSVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₆O₁₁
• Molecular Weight: 476.50 g/mol
• Exact Mass: 476.22576196 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -2.19
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6769	67.69%
Caco-2	-	0.8254	82.54%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7561	75.61%
OATP2B1 inhibitior	-	0.7204	72.04%
OATP1B1 inhibitior	+	0.8929	89.29%
OATP1B3 inhibitior	+	0.8695	86.95%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7569	75.69%
BSEP inhibitior	-	0.7857	78.57%
P-glycoprotein inhibitior	-	0.7067	70.67%
P-glycoprotein substrate	-	0.7944	79.44%
CYP3A4 substrate	+	0.6910	69.10%
CYP2C9 substrate	-	0.8032	80.32%
CYP2D6 substrate	-	0.8774	87.74%
CYP3A4 inhibition	-	0.8781	87.81%
CYP2C9 inhibition	-	0.8936	89.36%
CYP2C19 inhibition	-	0.8226	82.26%
CYP2D6 inhibition	-	0.9307	93.07%
CYP1A2 inhibition	-	0.8132	81.32%
CYP2C8 inhibition	-	0.6019	60.19%
CYP inhibitory promiscuity	-	0.9615	96.15%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7406	74.06%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9541	95.41%
Skin irritation	-	0.6392	63.92%
Skin corrosion	-	0.9463	94.63%
Ames mutagenesis	-	0.7454	74.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.6701	67.01%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.6976	69.76%
skin sensitisation	-	0.8844	88.44%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.6358	63.58%
Acute Oral Toxicity (c)	III	0.5414	54.14%
Estrogen receptor binding	+	0.7190	71.90%
Androgen receptor binding	+	0.6446	64.46%
Thyroid receptor binding	-	0.5320	53.20%
Glucocorticoid receptor binding	+	0.5972	59.72%
Aromatase binding	+	0.6552	65.52%
PPAR gamma	+	0.6898	68.98%
Honey bee toxicity	-	0.7521	75.21%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	+	0.9297	92.97%

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	97.79%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.97%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.98%	94.45%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	89.91%	91.24%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	88.55%	94.33%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.26%	96.61%
CHEMBL4040	P28482	MAP kinase ERK2	88.01%	83.82%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.35%	97.09%
CHEMBL5028	O14672	ADAM10	86.18%	97.50%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.73%	95.50%
CHEMBL5255	O00206	Toll-like receptor 4	83.87%	92.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.83%	100.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.64%	95.83%
CHEMBL220	P22303	Acetylcholinesterase	83.54%	94.45%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.02%	96.21%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	82.24%	89.05%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.57%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.29%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.06%	95.89%
CHEMBL221	P23219	Cyclooxygenase-1	80.94%	90.17%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	80.62%	96.38%
CHEMBL233	P35372	Mu opioid receptor	80.49%	97.93%

Plants that contains it

• Ixeris repens

Cross-Links

• PubChem: 163028455
• LOTUS: LTS0240032
• wikiData: Q104991809