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

Details

• Internal ID: 845eaab9-6722-4115-b1e9-2bc003d28c66
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: [(2R,3R,4S,5S,6R)-2-[[(1S,3R,6S,8S,9S,11R,12S,14S,15R,16R)-9,14-dihydroxy-15-[(2R,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-6-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] acetate
• SMILES (Canonical): CC(=O)OC1C(C(C(OC1OC2CCC34CC35CCC6(C(C(CC6(C5CC(C4C2(C)C)O)C)O)C7(CCC(O7)C(C)(C)O)C)C)CO)O)O
• SMILES (Isomeric): CC(=O)O[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1O[C@H]2CC[C@]34C[C@]35CC[C@@]6([C@H]([C@H](C[C@]6([C@H]5C[C@@H]([C@@H]4C2(C)C)O)C)O)[C@]7(CC[C@H](O7)C(C)(C)O)C)C)CO)O)O
• InChI: InChI=1S/C38H62O11/c1-19(40)46-28-27(44)26(43)22(17-39)47-31(28)48-24-10-12-38-18-37(38)14-13-34(6)30(36(8)11-9-25(49-36)33(4,5)45)21(42)16-35(34,7)23(37)15-20(41)29(38)32(24,2)3/h20-31,39,41-45H,9-18H2,1-8H3/t20-,21-,22+,23+,24-,25-,26+,27-,28+,29+,30-,31-,34+,35-,36+,37-,38+/m0/s1
• InChI Key: BPCILTNDGJOSHT-GPWWGNELSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₆₂O₁₁
• Molecular Weight: 694.90 g/mol
• Exact Mass: 694.42921279 g/mol
• Topological Polar Surface Area (TPSA): 175.00 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 2.83
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7975	79.75%
Caco-2	-	0.8644	86.44%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7697	76.97%
OATP2B1 inhibitior	-	0.7304	73.04%
OATP1B1 inhibitior	+	0.7994	79.94%
OATP1B3 inhibitior	+	0.9313	93.13%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7287	72.87%
BSEP inhibitior	-	0.8072	80.72%
P-glycoprotein inhibitior	+	0.7710	77.10%
P-glycoprotein substrate	-	0.5595	55.95%
CYP3A4 substrate	+	0.7336	73.36%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8835	88.35%
CYP3A4 inhibition	-	0.7581	75.81%
CYP2C9 inhibition	-	0.7687	76.87%
CYP2C19 inhibition	-	0.8741	87.41%
CYP2D6 inhibition	-	0.9432	94.32%
CYP1A2 inhibition	-	0.8914	89.14%
CYP2C8 inhibition	+	0.5987	59.87%
CYP inhibitory promiscuity	-	0.9309	93.09%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6640	66.40%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9122	91.22%
Skin irritation	-	0.6681	66.81%
Skin corrosion	-	0.9391	93.91%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7295	72.95%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.6374	63.74%
skin sensitisation	-	0.9090	90.90%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.8656	86.56%
Acute Oral Toxicity (c)	I	0.5727	57.27%
Estrogen receptor binding	+	0.5390	53.90%
Androgen receptor binding	+	0.7512	75.12%
Thyroid receptor binding	-	0.5924	59.24%
Glucocorticoid receptor binding	+	0.6666	66.66%
Aromatase binding	+	0.6971	69.71%
PPAR gamma	+	0.6752	67.52%
Honey bee toxicity	-	0.6427	64.27%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9205	92.05%

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	98.58%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.78%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.91%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.97%	94.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	94.85%	96.95%
CHEMBL218	P21554	Cannabinoid CB1 receptor	91.78%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.53%	97.09%
CHEMBL204	P00734	Thrombin	91.00%	96.01%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	90.52%	96.77%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	90.46%	96.21%
CHEMBL2996	Q05655	Protein kinase C delta	90.04%	97.79%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.86%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.99%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.97%	95.50%
CHEMBL340	P08684	Cytochrome P450 3A4	85.74%	91.19%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	85.25%	89.34%
CHEMBL5255	O00206	Toll-like receptor 4	85.08%	92.50%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	84.90%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.72%	86.33%
CHEMBL259	P32245	Melanocortin receptor 4	84.14%	95.38%
CHEMBL2581	P07339	Cathepsin D	84.05%	98.95%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	83.36%	82.50%
CHEMBL2413	P32246	C-C chemokine receptor type 1	83.24%	89.50%
CHEMBL226	P30542	Adenosine A1 receptor	83.04%	95.93%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.50%	93.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.44%	95.89%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.17%	91.24%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.65%	92.62%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.60%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.55%	91.07%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	80.46%	95.36%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.42%	93.04%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.03%	95.89%
CHEMBL1914	P06276	Butyrylcholinesterase	80.00%	95.00%

Plants that contains it

• Astragalus verrucosus

Cross-Links

• PubChem: 162868789
• LOTUS: LTS0052723
• wikiData: Q104941484