(2S,3R,4R,5R,6S)-2-[(2S,3R,4S,5R)-2-[[(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-9,14-dihydroxy-7,7,12,16-tetramethyl-15-[(2R,5S)-2-methyl-5-[2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropan-2-yl]oxolan-2-yl]-6-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]oxy]-4,5-dihydroxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol

Details

• Internal ID: 7afa91f0-b365-45c9-b80e-91333634a8f2
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (2S,3R,4R,5R,6S)-2-[(2S,3R,4S,5R)-2-[[(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-9,14-dihydroxy-7,7,12,16-tetramethyl-15-[(2R,5S)-2-methyl-5-[2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropan-2-yl]oxolan-2-yl]-6-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]oxy]-4,5-dihydroxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(COC2OC3CCC45CC46CCC7(C(C(CC7(C6CC(C5C3(C)C)O)C)O)C8(CCC(O8)C(C)(C)OC9C(C(C(C(O9)CO)O)O)O)C)C)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H](CO[C@H]2O[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)O)[C@]8(CC[C@H](O8)C(C)(C)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)C)C)O)O)O)O)O
• InChI: InChI=1S/C47H78O18/c1-20-28(52)31(55)33(57)38(60-20)63-35-29(53)23(51)18-59-40(35)62-26-10-12-47-19-46(47)14-13-43(6)37(22(50)16-44(43,7)25(46)15-21(49)36(47)41(26,2)3)45(8)11-9-27(64-45)42(4,5)65-39-34(58)32(56)30(54)24(17-48)61-39/h20-40,48-58H,9-19H2,1-8H3/t20-,21-,22-,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: AFDAWVKSWHBRTN-MYIHITSNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₇H₇₈O₁₈
• Molecular Weight: 931.10 g/mol
• Exact Mass: 930.51881563 g/mol
• Topological Polar Surface Area (TPSA): 287.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): -0.42
• H-Bond Acceptor: 18
• H-Bond Donor: 11
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6581	65.81%
Caco-2	-	0.8861	88.61%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6782	67.82%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8227	82.27%
OATP1B3 inhibitior	+	0.9422	94.22%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.4556	45.56%
P-glycoprotein inhibitior	+	0.7499	74.99%
P-glycoprotein substrate	+	0.5712	57.12%
CYP3A4 substrate	+	0.7363	73.63%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8237	82.37%
CYP3A4 inhibition	-	0.8783	87.83%
CYP2C9 inhibition	-	0.8009	80.09%
CYP2C19 inhibition	-	0.8368	83.68%
CYP2D6 inhibition	-	0.9401	94.01%
CYP1A2 inhibition	-	0.8971	89.71%
CYP2C8 inhibition	+	0.7134	71.34%
CYP inhibitory promiscuity	-	0.9329	93.29%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6399	63.99%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.9040	90.40%
Skin irritation	-	0.7237	72.37%
Skin corrosion	-	0.9438	94.38%
Ames mutagenesis	-	0.6370	63.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7632	76.32%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.5783	57.83%
skin sensitisation	-	0.9098	90.98%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.9612	96.12%
Acute Oral Toxicity (c)	I	0.6658	66.58%
Estrogen receptor binding	+	0.7547	75.47%
Androgen receptor binding	+	0.7571	75.71%
Thyroid receptor binding	-	0.5332	53.32%
Glucocorticoid receptor binding	+	0.6874	68.74%
Aromatase binding	+	0.6585	65.85%
PPAR gamma	+	0.7719	77.19%
Honey bee toxicity	-	0.6115	61.15%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.8633	86.33%

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	99.29%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.03%	91.11%
CHEMBL218	P21554	Cannabinoid CB1 receptor	96.94%	96.61%
CHEMBL226	P30542	Adenosine A1 receptor	95.83%	95.93%
CHEMBL240	Q12809	HERG	95.83%	89.76%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.41%	97.09%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	93.81%	97.31%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.62%	96.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.93%	97.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.78%	86.33%
CHEMBL1914	P06276	Butyrylcholinesterase	89.98%	95.00%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	89.34%	95.58%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.95%	89.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	87.80%	96.21%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	86.85%	100.00%
CHEMBL259	P32245	Melanocortin receptor 4	86.83%	95.38%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	85.77%	97.86%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.62%	96.77%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.54%	97.14%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.37%	92.94%
CHEMBL3589	P55263	Adenosine kinase	85.24%	98.05%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.69%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.98%	95.50%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	83.27%	91.03%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	83.15%	90.24%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.54%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.42%	95.89%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	80.81%	98.75%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	80.77%	92.86%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	80.13%	92.88%

Plants that contains it

• Astragalus ernestii

Cross-Links

• PubChem: 162957634
• LOTUS: LTS0036485
• wikiData: Q104911016