askendoside B

Details

• Internal ID: fdf63b62-d972-4c45-a7fc-fd35598f56b1
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: [(2S,3R,4S,5R)-5-hydroxy-2-[[(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-14-hydroxy-15-[(2R,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-6-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]oxy]-3-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-4-yl] acetate
• SMILES (Canonical): CC(=O)OC1C(COC(C1OC2C(C(C(CO2)O)O)O)OC3CCC45CC46CCC7(C(C(CC7(C6CC(C5C3(C)C)OC8C(C(C(CO8)O)O)O)C)O)C9(CCC(O9)C(C)(C)O)C)C)O
• SMILES (Isomeric): CC(=O)O[C@H]1[C@@H](CO[C@H]([C@@H]1O[C@H]2[C@@H]([C@H]([C@H](CO2)O)O)O)O[C@H]3CC[C@]45C[C@]46CC[C@@]7([C@H]([C@H](C[C@]7([C@@H]6C[C@@H]([C@H]5C3(C)C)O[C@H]8[C@@H]([C@H]([C@@H](CO8)O)O)O)C)O)[C@]9(CC[C@@H](O9)C(C)(C)O)C)C)O
• InChI: InChI=1S/C47H76O18/c1-21(48)61-34-25(52)19-60-40(35(34)64-39-33(56)31(54)24(51)18-59-39)63-28-10-12-47-20-46(47)14-13-43(6)36(45(8)11-9-29(65-45)42(4,5)57)22(49)16-44(43,7)27(46)15-26(37(47)41(28,2)3)62-38-32(55)30(53)23(50)17-58-38/h22-40,49-57H,9-20H2,1-8H3/t22-,23+,24-,25+,26-,27-,28-,29+,30-,31-,32+,33+,34-,35+,36-,37-,38-,39-,40-,43+,44-,45+,46-,47+/m0/s1
• InChI Key: BTTRQTJYXLOSMR-WEWBRACISA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₇H₇₆O₁₈
• Molecular Weight: 929.10 g/mol
• Exact Mass: 928.50316557 g/mol
• Topological Polar Surface Area (TPSA): 273.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 0.40
• H-Bond Acceptor: 18
• H-Bond Donor: 9
• Rotatable Bonds: 9

Synonyms

• CHEMBL411981
• BDBM50176699

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7990	79.90%
Caco-2	-	0.8845	88.45%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7663	76.63%
OATP2B1 inhibitior	-	0.8769	87.69%
OATP1B1 inhibitior	+	0.8429	84.29%
OATP1B3 inhibitior	+	0.9420	94.20%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7787	77.87%
BSEP inhibitior	+	0.6364	63.64%
P-glycoprotein inhibitior	+	0.7628	76.28%
P-glycoprotein substrate	+	0.5607	56.07%
CYP3A4 substrate	+	0.7437	74.37%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8849	88.49%
CYP3A4 inhibition	-	0.8546	85.46%
CYP2C9 inhibition	-	0.8174	81.74%
CYP2C19 inhibition	-	0.8361	83.61%
CYP2D6 inhibition	-	0.9423	94.23%
CYP1A2 inhibition	-	0.9036	90.36%
CYP2C8 inhibition	+	0.6858	68.58%
CYP inhibitory promiscuity	-	0.9633	96.33%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6192	61.92%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.9056	90.56%
Skin irritation	-	0.7109	71.09%
Skin corrosion	-	0.9370	93.70%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6813	68.13%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.8966	89.66%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.8582	85.82%
Acute Oral Toxicity (c)	I	0.5902	59.02%
Estrogen receptor binding	+	0.7610	76.10%
Androgen receptor binding	+	0.7421	74.21%
Thyroid receptor binding	-	0.5449	54.49%
Glucocorticoid receptor binding	+	0.7122	71.22%
Aromatase binding	+	0.6692	66.92%
PPAR gamma	+	0.7778	77.78%
Honey bee toxicity	-	0.5837	58.37%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9389	93.89%

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	97.64%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.55%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.83%	96.77%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.80%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.90%	96.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	91.57%	96.95%
CHEMBL340	P08684	Cytochrome P450 3A4	91.52%	91.19%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	90.92%	83.57%
CHEMBL204	P00734	Thrombin	90.76%	96.01%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.10%	89.00%
CHEMBL259	P32245	Melanocortin receptor 4	89.80%	95.38%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	86.22%	94.62%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.17%	97.14%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.86%	91.24%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	85.59%	95.71%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	85.15%	95.58%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.10%	86.33%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.69%	95.71%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.63%	82.69%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.60%	100.00%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	84.48%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.12%	85.14%
CHEMBL284	P27487	Dipeptidyl peptidase IV	83.78%	95.69%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.66%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.09%	95.89%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	83.05%	97.21%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.98%	91.07%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.52%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.38%	92.62%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	81.71%	92.88%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.68%	97.09%
CHEMBL2581	P07339	Cathepsin D	81.40%	98.95%
CHEMBL1914	P06276	Butyrylcholinesterase	81.39%	95.00%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	81.29%	82.50%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	80.83%	91.03%

Plants that contains it

• Astragalus taschkendicus

Cross-Links

• PubChem: 44406305
• LOTUS: LTS0259167
• wikiData: Q104945859