[(2S,3R,4S,5R)-4,5-dihydroxy-2-[[(3S,5R,6S,8R,9R,10S,13R,14S,16S,17R)-16-hydroxy-17-[(2R,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,9,10,13,14-hexamethyl-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,5,6,7,8,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-yl]oxy]oxan-3-yl] acetate

Details

• Internal ID: 25567b2c-6153-40cb-bff0-0da84910a296
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: [(2S,3R,4S,5R)-4,5-dihydroxy-2-[[(3S,5R,6S,8R,9R,10S,13R,14S,16S,17R)-16-hydroxy-17-[(2R,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,9,10,13,14-hexamethyl-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,5,6,7,8,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-yl]oxy]oxan-3-yl] acetate
• InChI: InChI=1S/C44H74O15/c1-21(46)55-33-29(49)23(48)20-54-37(33)58-27-11-13-41(7)35(38(27,2)3)24(56-36-32(52)31(51)30(50)25(19-45)57-36)17-26-40(41,6)15-16-42(8)34(22(47)18-43(26,42)9)44(10)14-12-28(59-44)39(4,5)53/h22-37,45,47-53H,11-20H2,1-10H3/t22-,23+,24-,25+,26+,27-,28-,29-,30+,31-,32+,33+,34-,35-,36+,37-,40+,41-,42+,43-,44+/m0/s1
• InChI Key: HAHQAWFCXTWTAV-HNKFYAGMSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₄H₇₄O₁₅
• Molecular Weight: 843.00 g/mol
• Exact Mass: 842.50277165 g/mol
• Topological Polar Surface Area (TPSA): 234.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 1.93
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7220	72.20%
Caco-2	-	0.8792	87.92%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.8105	81.05%
OATP2B1 inhibitior	-	0.8736	87.36%
OATP1B1 inhibitior	+	0.8261	82.61%
OATP1B3 inhibitior	+	0.9285	92.85%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7037	70.37%
BSEP inhibitior	-	0.5503	55.03%
P-glycoprotein inhibitior	+	0.7754	77.54%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.7449	74.49%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8898	88.98%
CYP3A4 inhibition	-	0.8813	88.13%
CYP2C9 inhibition	-	0.8806	88.06%
CYP2C19 inhibition	-	0.9007	90.07%
CYP2D6 inhibition	-	0.9508	95.08%
CYP1A2 inhibition	-	0.9311	93.11%
CYP2C8 inhibition	+	0.6750	67.50%
CYP inhibitory promiscuity	-	0.9547	95.47%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6382	63.82%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9067	90.67%
Skin irritation	-	0.6858	68.58%
Skin corrosion	-	0.9474	94.74%
Ames mutagenesis	-	0.5870	58.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7638	76.38%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.6509	65.09%
skin sensitisation	-	0.9310	93.10%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.8921	89.21%
Acute Oral Toxicity (c)	I	0.7095	70.95%
Estrogen receptor binding	+	0.6613	66.13%
Androgen receptor binding	+	0.7279	72.79%
Thyroid receptor binding	-	0.5773	57.73%
Glucocorticoid receptor binding	+	0.7216	72.16%
Aromatase binding	+	0.6840	68.40%
PPAR gamma	+	0.7622	76.22%
Honey bee toxicity	-	0.6021	60.21%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.8887	88.87%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1914	P06276	Butyrylcholinesterase	97.87%	95.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.36%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.91%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.63%	96.09%
CHEMBL220	P22303	Acetylcholinesterase	95.21%	94.45%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.62%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.97%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	90.83%	96.61%
CHEMBL259	P32245	Melanocortin receptor 4	90.69%	95.38%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.38%	86.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.94%	96.77%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	88.73%	91.24%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	86.85%	100.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	86.17%	97.28%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	85.89%	82.50%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.83%	93.04%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.61%	100.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.55%	96.21%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.38%	95.50%
CHEMBL2581	P07339	Cathepsin D	83.92%	98.95%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.79%	91.07%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.52%	92.62%
CHEMBL5255	O00206	Toll-like receptor 4	83.32%	92.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.29%	89.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.20%	97.14%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.95%	96.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.68%	95.89%
CHEMBL2996	Q05655	Protein kinase C delta	82.67%	97.79%
CHEMBL340	P08684	Cytochrome P450 3A4	82.54%	91.19%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.00%	94.00%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.95%	97.33%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.64%	95.71%

Plants that contains it

• Astragalus sieversianus

Cross-Links

• PubChem: 163046430
• LOTUS: LTS0254785
• wikiData: Q105024886