Acanthosessilioside C

Details

• Internal ID: 1990050c-935d-4842-8556-ff6870329e95
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,2R,5R,8R,9R,10S,11R,13R,14R,15R,17S,18S)-11,17-dihydroxy-8-(2-methoxy-2-oxoethyl)-1,2,6,6,9-pentamethyl-15-prop-1-en-2-yl-7-oxapentacyclo[11.7.0.02,10.05,9.014,18]icosane-18-carboxylate
• SMILES (Canonical): CC(=C)C1CC(C2(C1C3CC(C4C(C3(CC2)C)(CCC5C4(C(OC5(C)C)CC(=O)OC)C)C)O)C(=O)OC6C(C(C(C(O6)CO)O)O)O)O
• SMILES (Isomeric): CC(=C)[C@@H]1C[C@@H]([C@]2([C@H]1[C@H]3C[C@H]([C@H]4[C@]([C@@]3(CC2)C)(CC[C@@H]5[C@@]4([C@H](OC5(C)C)CC(=O)OC)C)C)O)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O
• InChI: InChI=1S/C37H58O12/c1-17(2)18-13-23(40)37(32(45)48-31-29(44)28(43)27(42)21(16-38)47-31)12-11-34(5)19(26(18)37)14-20(39)30-35(34,6)10-9-22-33(3,4)49-24(36(22,30)7)15-25(41)46-8/h18-24,26-31,38-40,42-44H,1,9-16H2,2-8H3/t18-,19+,20+,21+,22-,23-,24+,26+,27+,28-,29+,30-,31-,34+,35+,36+,37+/m0/s1
• InChI Key: PJRCJHUXBYLHNU-RWKILBRVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₅₈O₁₂
• Molecular Weight: 694.80 g/mol
• Exact Mass: 694.39282728 g/mol
• Topological Polar Surface Area (TPSA): 192.00 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 1.85
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

• ((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl) (1R,2R,5R,8R,9R,10S,11R,13R,14R,15R,17S,18S)-11,17-dihydroxy-8-(2-methoxy-2-oxoethyl)-1,2,6,6,9-pentamethyl-15-prop-1-en-2-yl-7-oxapentacyclo(11.7.0.02,10.05,9.014,18)icosane-18-carboxylate
• [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,2R,5R,8R,9R,10S,11R,13R,14R,15R,17S,18S)-11,17-dihydroxy-8-(2-methoxy-2-oxoethyl)-1,2,6,6,9-pentamethyl-15-prop-1-en-2-yl-7-oxapentacyclo[11.7.0.02,10.05,9.014,18]icosane-18-carboxylate
• RefChem:108706
• CHEMBL2063158

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8322	83.22%
Caco-2	-	0.8701	87.01%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.8003	80.03%
OATP2B1 inhibitior	-	0.8692	86.92%
OATP1B1 inhibitior	+	0.7824	78.24%
OATP1B3 inhibitior	+	0.9007	90.07%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6282	62.82%
BSEP inhibitior	-	0.7286	72.86%
P-glycoprotein inhibitior	+	0.7289	72.89%
P-glycoprotein substrate	+	0.6292	62.92%
CYP3A4 substrate	+	0.7344	73.44%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8681	86.81%
CYP3A4 inhibition	-	0.6622	66.22%
CYP2C9 inhibition	-	0.7784	77.84%
CYP2C19 inhibition	-	0.8879	88.79%
CYP2D6 inhibition	-	0.9387	93.87%
CYP1A2 inhibition	-	0.8914	89.14%
CYP2C8 inhibition	+	0.7258	72.58%
CYP inhibitory promiscuity	-	0.9394	93.94%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5695	56.95%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9137	91.37%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9351	93.51%
Ames mutagenesis	-	0.6670	66.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.6977	69.77%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.7602	76.02%
skin sensitisation	-	0.8927	89.27%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.5900	59.00%
Acute Oral Toxicity (c)	I	0.4695	46.95%
Estrogen receptor binding	+	0.6774	67.74%
Androgen receptor binding	+	0.7601	76.01%
Thyroid receptor binding	-	0.6051	60.51%
Glucocorticoid receptor binding	+	0.6507	65.07%
Aromatase binding	+	0.6565	65.65%
PPAR gamma	+	0.6970	69.70%
Honey bee toxicity	-	0.6251	62.51%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9736	97.36%

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	99.10%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	97.98%	96.61%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.95%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.22%	91.11%
CHEMBL233	P35372	Mu opioid receptor	95.69%	97.93%
CHEMBL4040	P28482	MAP kinase ERK2	95.62%	83.82%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	93.61%	91.24%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.37%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.96%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	90.24%	95.93%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	87.96%	95.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.72%	94.33%
CHEMBL5255	O00206	Toll-like receptor 4	87.51%	92.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.40%	100.00%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	87.05%	82.50%
CHEMBL259	P32245	Melanocortin receptor 4	86.98%	95.38%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.22%	97.25%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.95%	95.83%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	84.70%	97.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.68%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	84.62%	91.19%
CHEMBL237	P41145	Kappa opioid receptor	84.27%	98.10%
CHEMBL1871	P10275	Androgen Receptor	83.76%	96.43%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.92%	92.62%
CHEMBL3437	Q16853	Amine oxidase, copper containing	82.45%	94.00%
CHEMBL2996	Q05655	Protein kinase C delta	82.33%	97.79%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	82.18%	96.38%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	82.07%	95.71%
CHEMBL4072	P07858	Cathepsin B	81.95%	93.67%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.69%	97.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.43%	86.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.43%	91.07%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.39%	96.77%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.98%	97.28%
CHEMBL5028	O14672	ADAM10	80.77%	97.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.46%	95.89%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	80.29%	95.36%
CHEMBL2094135	Q96BI3	Gamma-secretase	80.09%	98.05%

Plants that contains it

• Eleutherococcus sessiliflorus

Cross-Links

• PubChem: 60155053
• LOTUS: LTS0240897
• wikiData: Q105210126