[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,4S,5R,9R,10S,11S,13S,14S,16S)-16-hydroxy-13-(hydroxymethyl)-5,9-dimethyl-12-oxapentacyclo[11.2.1.111,14.01,10.04,9]heptadecane-5-carboxylate

Details

• Internal ID: 36ab04cc-41ba-4d76-945a-44d62b4d1906
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: [(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,4S,5R,9R,10S,11S,13S,14S,16S)-16-hydroxy-13-(hydroxymethyl)-5,9-dimethyl-12-oxapentacyclo[11.2.1.111,14.01,10.04,9]heptadecane-5-carboxylate
• SMILES (Canonical): CC12CCCC(C1CCC34C2C5CC(C3)C(C4O)(O5)CO)(C)C(=O)OC6C(C(C(C(O6)CO)O)O)O
• SMILES (Isomeric): C[C@@]12CCC[C@@]([C@H]1CC[C@]34[C@H]2[C@@H]5C[C@H](C3)[C@]([C@H]4O)(O5)CO)(C)C(=O)O[C@@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
• InChI: InChI=1S/C26H40O10/c1-23-5-3-6-24(2,22(33)35-20-18(31)17(30)16(29)14(10-27)34-20)15(23)4-7-25-9-12-8-13(19(23)25)36-26(12,11-28)21(25)32/h12-21,27-32H,3-11H2,1-2H3/t12-,13+,14-,15+,16-,17+,18-,19+,20-,21+,23-,24-,25-,26-/m1/s1
• InChI Key: WHWKRKUTKZNNOI-GXKQNQNISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₄₀O₁₀
• Molecular Weight: 512.60 g/mol
• Exact Mass: 512.26214747 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): -0.55
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5000	50.00%
Caco-2	-	0.8317	83.17%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7561	75.61%
OATP2B1 inhibitior	-	0.7209	72.09%
OATP1B1 inhibitior	+	0.8420	84.20%
OATP1B3 inhibitior	+	0.9532	95.32%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.7871	78.71%
P-glycoprotein inhibitior	-	0.5966	59.66%
P-glycoprotein substrate	-	0.6891	68.91%
CYP3A4 substrate	+	0.7033	70.33%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8383	83.83%
CYP3A4 inhibition	-	0.9556	95.56%
CYP2C9 inhibition	-	0.8980	89.80%
CYP2C19 inhibition	-	0.8427	84.27%
CYP2D6 inhibition	-	0.9505	95.05%
CYP1A2 inhibition	-	0.8942	89.42%
CYP2C8 inhibition	+	0.4781	47.81%
CYP inhibitory promiscuity	-	0.9454	94.54%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6759	67.59%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9585	95.85%
Skin irritation	-	0.7206	72.06%
Skin corrosion	-	0.9454	94.54%
Ames mutagenesis	-	0.6837	68.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.3798	37.98%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	-	0.7852	78.52%
skin sensitisation	-	0.9361	93.61%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.7528	75.28%
Acute Oral Toxicity (c)	I	0.6047	60.47%
Estrogen receptor binding	+	0.6591	65.91%
Androgen receptor binding	+	0.6468	64.68%
Thyroid receptor binding	-	0.5319	53.19%
Glucocorticoid receptor binding	+	0.6560	65.60%
Aromatase binding	+	0.7076	70.76%
PPAR gamma	-	0.5114	51.14%
Honey bee toxicity	-	0.7380	73.80%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.8890	88.90%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL218	P21554	Cannabinoid CB1 receptor	98.63%	96.61%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.55%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.06%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.26%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.62%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.73%	97.09%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	91.37%	91.24%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	90.80%	95.50%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	89.82%	96.21%
CHEMBL5255	O00206	Toll-like receptor 4	89.78%	92.50%
CHEMBL237	P41145	Kappa opioid receptor	89.60%	98.10%
CHEMBL226	P30542	Adenosine A1 receptor	89.17%	95.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.52%	95.89%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.28%	96.77%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.14%	95.83%
CHEMBL259	P32245	Melanocortin receptor 4	83.39%	95.38%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.43%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.59%	92.62%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.31%	94.33%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.89%	100.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.53%	86.92%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.20%	93.04%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.19%	97.14%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	80.18%	97.86%

Plants that contains it

• Adenostemma lavenia

Cross-Links

• PubChem: 163195642
• LOTUS: LTS0140026
• wikiData: Q105306044