[(1S,6S,8R,11S,17S,18R,19R,21S)-21-(2-hydroxypropan-2-yl)-1,3,12,12,17-pentamethyl-11-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-20,24-dioxaheptacyclo[19.2.1.02,19.03,17.06,8.06,16.08,13]tetracosan-18-yl] acetate

Details

• Internal ID: c6a2b5bb-c73d-4364-b141-8451b83e7b0d
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: [(1S,6S,8R,11S,17S,18R,19R,21S)-21-(2-hydroxypropan-2-yl)-1,3,12,12,17-pentamethyl-11-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-20,24-dioxaheptacyclo[19.2.1.02,19.03,17.06,8.06,16.08,13]tetracosan-18-yl] acetate
• SMILES (Canonical): CC(=O)OC1C2C(C3(C1(C4CCC5C(C(CCC56C4(C6)CC3)OC7C(C(C(CO7)O)O)O)(C)C)C)C)C8(CCC(O2)(O8)C(C)(C)O)C
• SMILES (Isomeric): CC(=O)O[C@H]1[C@H]2C([C@@]3(CC[C@](O2)(O3)C(C)(C)O)C)C4([C@@]1(C5CCC6[C@@]7([C@]5(C7)CC4)CC[C@@H](C6(C)C)O[C@H]8[C@@H]([C@H]([C@@H](CO8)O)O)O)C)C
• InChI: InChI=1S/C37H58O10/c1-19(38)44-28-26-27(33(7)14-16-37(46-26,47-33)31(4,5)42)32(6)13-15-36-18-35(36)12-11-23(45-29-25(41)24(40)20(39)17-43-29)30(2,3)21(35)9-10-22(36)34(28,32)8/h20-29,39-42H,9-18H2,1-8H3/t20-,21?,22?,23+,24+,25-,26-,27?,28+,29+,32?,33+,34-,35-,36+,37+/m1/s1
• InChI Key: WNDAONQOFISAOL-PFUKGYBLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₅₈O₁₀
• Molecular Weight: 662.80 g/mol
• Exact Mass: 662.40299804 g/mol
• Topological Polar Surface Area (TPSA): 144.00 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 3.84
• H-Bond Acceptor: 10
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8059	80.59%
Caco-2	-	0.8471	84.71%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7464	74.64%
OATP2B1 inhibitior	-	0.7205	72.05%
OATP1B1 inhibitior	+	0.8396	83.96%
OATP1B3 inhibitior	+	0.9334	93.34%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.4648	46.48%
P-glycoprotein inhibitior	+	0.7515	75.15%
P-glycoprotein substrate	+	0.5058	50.58%
CYP3A4 substrate	+	0.7260	72.60%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8794	87.94%
CYP3A4 inhibition	-	0.8545	85.45%
CYP2C9 inhibition	-	0.7963	79.63%
CYP2C19 inhibition	-	0.8638	86.38%
CYP2D6 inhibition	-	0.9430	94.30%
CYP1A2 inhibition	-	0.8662	86.62%
CYP2C8 inhibition	+	0.7172	71.72%
CYP inhibitory promiscuity	-	0.9663	96.63%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6383	63.83%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9133	91.33%
Skin irritation	-	0.6519	65.19%
Skin corrosion	-	0.9323	93.23%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3978	39.78%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.6591	65.91%
skin sensitisation	-	0.8895	88.95%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.5696	56.96%
Acute Oral Toxicity (c)	I	0.4074	40.74%
Estrogen receptor binding	+	0.5683	56.83%
Androgen receptor binding	+	0.7445	74.45%
Thyroid receptor binding	-	0.5713	57.13%
Glucocorticoid receptor binding	+	0.6454	64.54%
Aromatase binding	+	0.6781	67.81%
PPAR gamma	+	0.6846	68.46%
Honey bee toxicity	-	0.6514	65.14%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9378	93.78%

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	98.55%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.92%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.73%	96.77%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.80%	96.09%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	93.51%	98.75%
CHEMBL2581	P07339	Cathepsin D	93.41%	98.95%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	91.70%	97.14%
CHEMBL204	P00734	Thrombin	90.83%	96.01%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	90.80%	89.34%
CHEMBL340	P08684	Cytochrome P450 3A4	90.33%	91.19%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	89.58%	95.71%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.33%	96.61%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	87.34%	87.67%
CHEMBL2413	P32246	C-C chemokine receptor type 1	87.08%	89.50%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	87.03%	91.03%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	86.99%	95.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.71%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.63%	97.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.49%	82.69%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.43%	91.07%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	86.42%	82.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.88%	89.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.56%	92.94%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	84.95%	100.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	84.93%	97.28%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.16%	100.00%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	83.20%	97.47%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.61%	100.00%
CHEMBL3474	P14555	Phospholipase A2 group IIA	82.56%	94.05%
CHEMBL5028	O14672	ADAM10	82.47%	97.50%
CHEMBL259	P32245	Melanocortin receptor 4	81.99%	95.38%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	81.89%	92.88%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.45%	95.89%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	81.36%	94.62%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.16%	92.62%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.75%	93.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.41%	86.33%

Plants that contains it

• Beesia calthifolia

Cross-Links

• PubChem: 24893576
• NPASS: NPC107144