[(3S,6R)-6-[(1R,3R,6S,7S,8R,11S,12S,14S,15R,16R)-14-hydroxy-7-(hydroxymethyl)-7,12,16-trimethyl-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-15-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]-2-methyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptan-3-yl] acetate

Details

• Internal ID: 09d6534a-e5a5-44d5-8d1c-c620dec9ba2d
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: [(3S,6R)-6-[(1R,3R,6S,7S,8R,11S,12S,14S,15R,16R)-14-hydroxy-7-(hydroxymethyl)-7,12,16-trimethyl-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-15-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]-2-methyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptan-3-yl] acetate
• SMILES (Canonical): CC(CCC(C(C)(C)OC1C(C(C(C(O1)CO)O)O)O)OC(=O)C)C2C(CC3(C2(CCC45C3CCC6C4(C5)CCC(C6(C)CO)OC7C(C(C(C(O7)CO)O)O)O)C)C)O
• SMILES (Isomeric): C[C@H](CC[C@@H](C(C)(C)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)OC(=O)C)[C@H]2[C@H](C[C@@]3([C@@]2(CC[C@@]45[C@H]3CC[C@@H]6[C@]4(C5)CC[C@@H]([C@]6(C)CO)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)C)C)O
• InChI: InChI=1S/C44H74O16/c1-21(8-11-28(56-22(2)48)39(3,4)60-38-36(55)34(53)32(51)25(18-46)58-38)30-23(49)16-42(7)27-10-9-26-40(5,20-47)29(59-37-35(54)33(52)31(50)24(17-45)57-37)12-13-43(26)19-44(27,43)15-14-41(30,42)6/h21,23-38,45-47,49-55H,8-20H2,1-7H3/t21-,23+,24-,25-,26+,27+,28+,29+,30+,31-,32-,33+,34+,35-,36-,37+,38+,40-,41-,42+,43-,44-/m1/s1
• InChI Key: GZXPRQBHVHIUNP-ZEQCLZRWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₄H₇₄O₁₆
• Molecular Weight: 859.00 g/mol
• Exact Mass: 858.49768627 g/mol
• Topological Polar Surface Area (TPSA): 266.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 0.50
• H-Bond Acceptor: 16
• H-Bond Donor: 10
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6078	60.78%
Caco-2	-	0.8870	88.70%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.6939	69.39%
OATP2B1 inhibitior	-	0.8743	87.43%
OATP1B1 inhibitior	+	0.8432	84.32%
OATP1B3 inhibitior	+	0.8998	89.98%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.6392	63.92%
P-glycoprotein inhibitior	+	0.7650	76.50%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.7231	72.31%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8746	87.46%
CYP3A4 inhibition	-	0.9251	92.51%
CYP2C9 inhibition	-	0.7950	79.50%
CYP2C19 inhibition	-	0.8502	85.02%
CYP2D6 inhibition	-	0.9519	95.19%
CYP1A2 inhibition	-	0.8924	89.24%
CYP2C8 inhibition	+	0.6104	61.04%
CYP inhibitory promiscuity	-	0.9717	97.17%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6989	69.89%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9073	90.73%
Skin irritation	-	0.6948	69.48%
Skin corrosion	-	0.9469	94.69%
Ames mutagenesis	-	0.6648	66.48%
Human Ether-a-go-go-Related Gene inhibition	+	0.7624	76.24%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.6308	63.08%
skin sensitisation	-	0.9134	91.34%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	+	0.5785	57.85%
Acute Oral Toxicity (c)	I	0.5431	54.31%
Estrogen receptor binding	+	0.7583	75.83%
Androgen receptor binding	+	0.7712	77.12%
Thyroid receptor binding	-	0.6027	60.27%
Glucocorticoid receptor binding	+	0.6728	67.28%
Aromatase binding	+	0.6539	65.39%
PPAR gamma	+	0.7586	75.86%
Honey bee toxicity	-	0.6589	65.89%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.8557	85.57%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.57%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.33%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.71%	94.45%
CHEMBL2581	P07339	Cathepsin D	95.80%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.34%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	94.79%	96.61%
CHEMBL220	P22303	Acetylcholinesterase	94.21%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.27%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.89%	89.00%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	90.08%	98.75%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	89.71%	100.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	89.52%	91.24%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	89.30%	82.50%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	88.54%	89.34%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	88.31%	96.21%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	87.57%	97.47%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.29%	96.77%
CHEMBL1937	Q92769	Histone deacetylase 2	86.79%	94.75%
CHEMBL237	P41145	Kappa opioid receptor	86.64%	98.10%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	86.20%	95.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.91%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.76%	97.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.31%	100.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	85.30%	100.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.26%	96.95%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.17%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.40%	93.56%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	83.68%	92.86%
CHEMBL5255	O00206	Toll-like receptor 4	83.59%	92.50%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.36%	93.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.31%	91.07%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	82.11%	92.88%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	81.88%	95.58%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.60%	95.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.40%	94.33%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	81.20%	92.78%
CHEMBL340	P08684	Cytochrome P450 3A4	80.93%	91.19%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.77%	85.14%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	80.06%	97.29%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.01%	92.62%

Plants that contains it

• Thalictrum fortunei

Cross-Links

• PubChem: 162992049
• LOTUS: LTS0254341
• wikiData: Q105024712