20(R),24(S)-epoxycycloartane-3beta,6alpha,16beta,25-tetraol-3beta-O-D-(2-O-acetyl)-xylopyranoside

Details

• Internal ID: 96328e5e-e379-4eac-97bd-69d89fd61d11
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: [(2S,3R,4S,5R)-2-[[(1S,3R,6S,8R,9S,11S,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-dihydroxyoxan-3-yl] acetate
• SMILES (Canonical): CC(=O)OC1C(C(COC1OC2CCC34CC35CCC6(C(C(CC6(C5CC(C4C2(C)C)O)C)O)C7(CCC(O7)C(C)(C)O)C)C)O)O
• SMILES (Isomeric): CC(=O)O[C@@H]1[C@H]([C@@H](CO[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)O)O
• InChI: InChI=1S/C37H60O10/c1-19(38)45-27-26(42)22(41)17-44-30(27)46-24-10-12-37-18-36(37)14-13-33(6)29(35(8)11-9-25(47-35)32(4,5)43)21(40)16-34(33,7)23(36)15-20(39)28(37)31(24,2)3/h20-30,39-43H,9-18H2,1-8H3/t20-,21-,22+,23-,24-,25-,26-,27+,28-,29-,30-,33+,34-,35+,36-,37+/m0/s1
• InChI Key: KILZIJKCZIGLFJ-HQIOABIXSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₆₀O₁₀
• Molecular Weight: 664.90 g/mol
• Exact Mass: 664.41864811 g/mol
• Topological Polar Surface Area (TPSA): 155.00 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 3.47
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

• 20(R),24(S)-epoxycycloartane-3beta,6alpha,16beta,25-tetraol-3beta-O-D-(2-O-acetyl)-xylopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9271	92.71%
Caco-2	-	0.8576	85.76%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8234	82.34%
OATP2B1 inhibitior	-	0.7249	72.49%
OATP1B1 inhibitior	+	0.8284	82.84%
OATP1B3 inhibitior	+	0.8970	89.70%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8537	85.37%
BSEP inhibitior	-	0.7835	78.35%
P-glycoprotein inhibitior	+	0.7716	77.16%
P-glycoprotein substrate	+	0.5240	52.40%
CYP3A4 substrate	+	0.7362	73.62%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8849	88.49%
CYP3A4 inhibition	-	0.7974	79.74%
CYP2C9 inhibition	-	0.7927	79.27%
CYP2C19 inhibition	-	0.8422	84.22%
CYP2D6 inhibition	-	0.9469	94.69%
CYP1A2 inhibition	-	0.8540	85.40%
CYP2C8 inhibition	+	0.6241	62.41%
CYP inhibitory promiscuity	-	0.9611	96.11%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6094	60.94%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9147	91.47%
Skin irritation	-	0.6682	66.82%
Skin corrosion	-	0.9357	93.57%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6983	69.83%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.6448	64.48%
skin sensitisation	-	0.8950	89.50%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.8937	89.37%
Acute Oral Toxicity (c)	I	0.5298	52.98%
Estrogen receptor binding	+	0.5385	53.85%
Androgen receptor binding	+	0.7408	74.08%
Thyroid receptor binding	-	0.5912	59.12%
Glucocorticoid receptor binding	+	0.6731	67.31%
Aromatase binding	+	0.7118	71.18%
PPAR gamma	+	0.6559	65.59%
Honey bee toxicity	-	0.6317	63.17%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9593	95.93%

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	98.43%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.57%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	96.47%	96.77%
CHEMBL204	P00734	Thrombin	96.22%	96.01%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.12%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.87%	96.09%
CHEMBL1914	P06276	Butyrylcholinesterase	92.44%	95.00%
CHEMBL284	P27487	Dipeptidyl peptidase IV	91.21%	95.69%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.84%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	90.57%	91.19%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	90.11%	96.95%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	90.00%	82.69%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.38%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.46%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.83%	91.07%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.90%	97.14%
CHEMBL259	P32245	Melanocortin receptor 4	83.76%	95.38%
CHEMBL2179	P04062	Beta-glucocerebrosidase	83.44%	85.31%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.37%	92.94%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	82.90%	100.00%
CHEMBL1871	P10275	Androgen Receptor	82.24%	96.43%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	82.15%	95.71%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	82.09%	92.88%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.83%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.27%	86.33%
CHEMBL2581	P07339	Cathepsin D	81.18%	98.95%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	81.11%	85.30%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.30%	95.89%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	80.23%	82.50%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.04%	89.50%

Plants that contains it

• Astragalus exilis
• Astragalus galegiformis

Cross-Links

• PubChem: 13996714
• LOTUS: LTS0002174
• wikiData: Q105141585