methyl 2-[1,7-dihydroxy-4a,8-dimethyl-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,5,6,7,8,8a-octahydro-1H-naphthalen-2-yl]prop-2-enoate

Details

• Internal ID: a6f4356d-76a5-453a-947c-ba35c8ea2459
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: methyl 2-[1,7-dihydroxy-4a,8-dimethyl-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,5,6,7,8,8a-octahydro-1H-naphthalen-2-yl]prop-2-enoate
• SMILES (Canonical): CC1C(CC(C2(C1C(C(CC2)C(=C)C(=O)OC)O)C)OC3C(C(C(C(O3)CO)O)O)O)O
• SMILES (Isomeric): CC1C(CC(C2(C1C(C(CC2)C(=C)C(=O)OC)O)C)OC3C(C(C(C(O3)CO)O)O)O)O
• InChI: InChI=1S/C22H36O10/c1-9(20(29)30-4)11-5-6-22(3)14(7-12(24)10(2)15(22)16(11)25)32-21-19(28)18(27)17(26)13(8-23)31-21/h10-19,21,23-28H,1,5-8H2,2-4H3
• InChI Key: UIUPSHYSTLJURC-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₆O₁₀
• Molecular Weight: 460.50 g/mol
• Exact Mass: 460.23084734 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -1.31
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7666	76.66%
Caco-2	-	0.8140	81.40%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7403	74.03%
OATP2B1 inhibitior	-	0.8615	86.15%
OATP1B1 inhibitior	+	0.8442	84.42%
OATP1B3 inhibitior	+	0.8202	82.02%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.7292	72.92%
BSEP inhibitior	-	0.9037	90.37%
P-glycoprotein inhibitior	-	0.6923	69.23%
P-glycoprotein substrate	-	0.7806	78.06%
CYP3A4 substrate	+	0.6928	69.28%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8716	87.16%
CYP3A4 inhibition	-	0.7941	79.41%
CYP2C9 inhibition	-	0.8537	85.37%
CYP2C19 inhibition	-	0.8174	81.74%
CYP2D6 inhibition	-	0.9452	94.52%
CYP1A2 inhibition	-	0.7756	77.56%
CYP2C8 inhibition	-	0.6955	69.55%
CYP inhibitory promiscuity	-	0.9542	95.42%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7518	75.18%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9692	96.92%
Skin irritation	-	0.5532	55.32%
Skin corrosion	-	0.9487	94.87%
Ames mutagenesis	-	0.7379	73.79%
Human Ether-a-go-go-Related Gene inhibition	+	0.6484	64.84%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.7022	70.22%
skin sensitisation	-	0.8936	89.36%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.5919	59.19%
Acute Oral Toxicity (c)	III	0.5391	53.91%
Estrogen receptor binding	+	0.6950	69.50%
Androgen receptor binding	+	0.5713	57.13%
Thyroid receptor binding	-	0.5402	54.02%
Glucocorticoid receptor binding	+	0.5558	55.58%
Aromatase binding	+	0.6292	62.92%
PPAR gamma	+	0.7096	70.96%
Honey bee toxicity	-	0.7238	72.38%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9422	94.22%

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	97.37%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.01%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	93.05%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.34%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.11%	85.14%
CHEMBL237	P41145	Kappa opioid receptor	85.94%	98.10%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.66%	94.33%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	84.29%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.88%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	83.84%	91.19%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	83.71%	96.47%
CHEMBL5255	O00206	Toll-like receptor 4	83.39%	92.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.36%	91.24%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.35%	95.83%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.26%	94.45%
CHEMBL220	P22303	Acetylcholinesterase	82.80%	94.45%
CHEMBL5028	O14672	ADAM10	82.70%	97.50%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.59%	96.21%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.51%	89.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.68%	89.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.45%	91.07%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.15%	97.25%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.70%	92.62%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.59%	95.50%

Plants that contains it

• Taraxacum erythrospermum

Cross-Links

• PubChem: 162952384
• LOTUS: LTS0159964
• wikiData: Q105273606