[(3S,4S,5R,6S)-4-acetyloxy-6-[[(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-15-[(2R,5S)-5,6-dihydroxy-6-methylheptan-2-yl]-14-hydroxy-7,7,12,16-tetramethyl-9-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]oxy]-5-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl] acetate

Details

• Internal ID: db6d5dff-8b5d-4aab-892b-991765b92058
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: [(3S,4S,5R,6S)-4-acetyloxy-6-[[(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-15-[(2R,5S)-5,6-dihydroxy-6-methylheptan-2-yl]-14-hydroxy-7,7,12,16-tetramethyl-9-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]oxy]-5-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl] acetate
• SMILES (Canonical): CC(CCC(C(C)(C)O)O)C1C(CC2(C1(CCC34C2CC(C5C3(C4)CCC(C5(C)C)OC6C(C(C(CO6)OC(=O)C)OC(=O)C)OC7C(C(C(CO7)O)O)O)OC8C(C(C(C(O8)CO)O)O)O)C)C)O
• SMILES (Isomeric): C[C@H](CC[C@@H](C(C)(C)O)O)[C@H]1[C@H](C[C@@]2([C@@]1(CC[C@]34[C@H]2C[C@@H]([C@@H]5[C@]3(C4)CC[C@@H](C5(C)C)O[C@H]6[C@@H]([C@H]([C@H](CO6)OC(=O)C)OC(=O)C)O[C@H]7[C@@H]([C@H]([C@H](CO7)O)O)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)C)C)O
• InChI: InChI=1S/C50H82O20/c1-22(10-11-31(56)46(6,7)62)33-25(54)17-48(9)30-16-27(67-43-38(61)36(59)35(58)28(18-51)68-43)41-45(4,5)32(12-13-50(41)21-49(30,50)15-14-47(33,48)8)69-44-40(70-42-37(60)34(57)26(55)19-63-42)39(66-24(3)53)29(20-64-44)65-23(2)52/h22,25-44,51,54-62H,10-21H2,1-9H3/t22-,25+,26+,27+,28-,29+,30+,31+,32+,33+,34+,35-,36+,37-,38-,39+,40-,41+,42+,43-,44+,47-,48+,49+,50-/m1/s1
• InChI Key: PUHROWQRRBNZOO-FBKHTRAVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₀H₈₂O₂₀
• Molecular Weight: 1003.20 g/mol
• Exact Mass: 1002.53994500 g/mol
• Topological Polar Surface Area (TPSA): 310.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 0.17
• H-Bond Acceptor: 20
• H-Bond Donor: 10
• Rotatable Bonds: 14

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5583	55.83%
Caco-2	-	0.8806	88.06%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7272	72.72%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8070	80.70%
OATP1B3 inhibitior	+	0.9129	91.29%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	+	0.8922	89.22%
P-glycoprotein inhibitior	+	0.7589	75.89%
P-glycoprotein substrate	+	0.6480	64.80%
CYP3A4 substrate	+	0.7452	74.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8804	88.04%
CYP3A4 inhibition	-	0.8492	84.92%
CYP2C9 inhibition	-	0.7876	78.76%
CYP2C19 inhibition	-	0.8640	86.40%
CYP2D6 inhibition	-	0.9553	95.53%
CYP1A2 inhibition	-	0.9034	90.34%
CYP2C8 inhibition	+	0.7071	70.71%
CYP inhibitory promiscuity	-	0.9765	97.65%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6966	69.66%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9037	90.37%
Skin irritation	-	0.6943	69.43%
Skin corrosion	-	0.9413	94.13%
Ames mutagenesis	-	0.6048	60.48%
Human Ether-a-go-go-Related Gene inhibition	+	0.7477	74.77%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.6815	68.15%
skin sensitisation	-	0.9222	92.22%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.8777	87.77%
Acute Oral Toxicity (c)	I	0.5104	51.04%
Estrogen receptor binding	+	0.7977	79.77%
Androgen receptor binding	+	0.7398	73.98%
Thyroid receptor binding	-	0.5115	51.15%
Glucocorticoid receptor binding	+	0.7524	75.24%
Aromatase binding	+	0.6464	64.64%
PPAR gamma	+	0.8065	80.65%
Honey bee toxicity	-	0.5812	58.12%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.8965	89.65%

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	99.35%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.04%	91.11%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	97.12%	95.58%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.03%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.01%	96.09%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	95.73%	91.24%
CHEMBL2581	P07339	Cathepsin D	94.60%	98.95%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	92.93%	92.88%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	92.37%	96.47%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.90%	97.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.15%	96.77%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	90.71%	98.75%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	89.83%	82.50%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.39%	85.14%
CHEMBL284	P27487	Dipeptidyl peptidase IV	88.70%	95.69%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	88.70%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.47%	97.14%
CHEMBL340	P08684	Cytochrome P450 3A4	88.36%	91.19%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.10%	89.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.87%	91.07%
CHEMBL2007625	O75874	Isocitrate dehydrogenase [NADP] cytoplasmic	87.85%	99.00%
CHEMBL2996	Q05655	Protein kinase C delta	87.50%	97.79%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	87.24%	97.29%
CHEMBL218	P21554	Cannabinoid CB1 receptor	87.14%	96.61%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	87.07%	100.00%
CHEMBL237	P41145	Kappa opioid receptor	86.72%	98.10%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	86.15%	95.71%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	85.89%	95.71%
CHEMBL1937	Q92769	Histone deacetylase 2	85.62%	94.75%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.05%	100.00%
CHEMBL2095194	P08709	Coagulation factor VII/tissue factor	84.80%	99.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.71%	100.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.60%	94.33%
CHEMBL2413	P32246	C-C chemokine receptor type 1	84.14%	89.50%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	84.03%	95.17%
CHEMBL226	P30542	Adenosine A1 receptor	83.93%	95.93%
CHEMBL5255	O00206	Toll-like receptor 4	83.31%	92.50%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.22%	96.21%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.12%	95.89%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.48%	97.21%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.43%	96.95%
CHEMBL4105786	P41182	B-cell lymphoma 6 protein	82.12%	92.86%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.78%	96.00%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	81.68%	90.24%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	81.61%	91.03%
CHEMBL2514	O95665	Neurotensin receptor 2	81.46%	100.00%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	81.39%	92.86%
CHEMBL4581	P52732	Kinesin-like protein 1	81.30%	93.18%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.06%	86.33%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	80.94%	94.08%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.92%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.51%	92.62%

Plants that contains it

• Astragalus icmadophilus

Cross-Links

• PubChem: 101514266
• LOTUS: LTS0107474
• wikiData: Q105215099