(2S,3R,4S,5R)-2-[[(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-14-hydroxy-15-[(2R,5S)-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]oxane-3,4,5-triol

Details

• Internal ID: ffd0183b-cd49-46f2-93ae-c5705a2f1af3
• 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)-14-hydroxy-15-[(2R,5S)-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]oxane-3,4,5-triol
• SMILES (Canonical): CC1(C(CCC23C1C(CC4C2(C3)CCC5(C4(CC(C5C6(CCC(O6)C(C)(C)O)C)O)C)C)OC7C(C(C(CO7)O)O)O)OC8C(C(C(CO8)O)O)O)C
• SMILES (Isomeric): C[C@]12CC[C@@]34C[C@@]35CC[C@@H](C([C@@H]5[C@H](C[C@H]4[C@@]1(C[C@@H]([C@@H]2[C@]6(CC[C@H](O6)C(C)(C)O)C)O)C)O[C@H]7[C@@H]([C@H]([C@@H](CO7)O)O)O)(C)C)O[C@H]8[C@@H]([C@H]([C@@H](CO8)O)O)O
• InChI: InChI=1S/C40H66O13/c1-34(2)24(52-33-29(47)27(45)21(43)17-50-33)9-11-40-18-39(40)13-12-36(5)30(38(7)10-8-25(53-38)35(3,4)48)19(41)15-37(36,6)23(39)14-22(31(34)40)51-32-28(46)26(44)20(42)16-49-32/h19-33,41-48H,8-18H2,1-7H3/t19-,20+,21+,22-,23-,24-,25-,26-,27-,28+,29+,30-,31-,32-,33-,36+,37-,38+,39-,40+/m0/s1
• InChI Key: NPKUPKNGMRUMDI-WZQGUIJMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₆₆O₁₃
• Molecular Weight: 754.90 g/mol
• Exact Mass: 754.45034216 g/mol
• Topological Polar Surface Area (TPSA): 208.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 1.36
• H-Bond Acceptor: 13
• H-Bond Donor: 8
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7397	73.97%
Caco-2	-	0.8638	86.38%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6908	69.08%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8699	86.99%
OATP1B3 inhibitior	+	0.9414	94.14%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.7772	77.72%
P-glycoprotein inhibitior	+	0.7511	75.11%
P-glycoprotein substrate	-	0.5241	52.41%
CYP3A4 substrate	+	0.7191	71.91%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8303	83.03%
CYP3A4 inhibition	-	0.9079	90.79%
CYP2C9 inhibition	-	0.8168	81.68%
CYP2C19 inhibition	-	0.8275	82.75%
CYP2D6 inhibition	-	0.9394	93.94%
CYP1A2 inhibition	-	0.8964	89.64%
CYP2C8 inhibition	+	0.6613	66.13%
CYP inhibitory promiscuity	-	0.9535	95.35%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6068	60.68%
Eye corrosion	-	0.9876	98.76%
Eye irritation	-	0.9080	90.80%
Skin irritation	-	0.7319	73.19%
Skin corrosion	-	0.9401	94.01%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7247	72.47%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.6466	64.66%
skin sensitisation	-	0.8969	89.69%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.9324	93.24%
Acute Oral Toxicity (c)	I	0.6064	60.64%
Estrogen receptor binding	+	0.5498	54.98%
Androgen receptor binding	+	0.7385	73.85%
Thyroid receptor binding	-	0.5845	58.45%
Glucocorticoid receptor binding	+	0.6078	60.78%
Aromatase binding	+	0.6626	66.26%
PPAR gamma	+	0.6802	68.02%
Honey bee toxicity	-	0.6302	63.02%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9139	91.39%

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	97.94%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.65%	97.25%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	93.94%	83.57%
CHEMBL284	P27487	Dipeptidyl peptidase IV	91.28%	95.69%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.27%	97.09%
CHEMBL259	P32245	Melanocortin receptor 4	90.94%	95.38%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	90.07%	96.77%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.94%	92.94%
CHEMBL240	Q12809	HERG	89.30%	89.76%
CHEMBL204	P00734	Thrombin	88.55%	96.01%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	88.15%	100.00%
CHEMBL1914	P06276	Butyrylcholinesterase	88.04%	95.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.91%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.65%	96.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.05%	96.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.98%	100.00%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	85.91%	92.88%
CHEMBL218	P21554	Cannabinoid CB1 receptor	85.77%	96.61%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.23%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.18%	97.14%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	84.85%	95.58%
CHEMBL1871	P10275	Androgen Receptor	84.11%	96.43%
CHEMBL4302	P08183	P-glycoprotein 1	83.91%	92.98%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.60%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.96%	89.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.51%	92.62%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.88%	91.07%
CHEMBL1977	P11473	Vitamin D receptor	80.85%	99.43%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.35%	94.62%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	80.05%	91.03%

Plants that contains it

• Astragalus condensatus
• Astragalus dissectus
• Astragalus exilis
• Astragalus flexus
• Astragalus kahiricus
• Astragalus melanophrurius
• Astragalus sieversianus
• Euphorbia glareosa

Cross-Links

• PubChem: 102069296
• LOTUS: LTS0030719
• wikiData: Q105183106