[(3R,4S,5R,6S)-5-acetyloxy-4-hydroxy-6-[[(3S,5R,6S,8R,9R,10S,13R,14S,16S,17R)-16-hydroxy-17-[(2R,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,9,10,13,14-hexamethyl-6-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-1,2,3,5,6,7,8,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-yl]oxy]oxan-3-yl] acetate

Details

• Internal ID: f981a692-610a-4368-815c-4cbd70beee82
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: [(3R,4S,5R,6S)-5-acetyloxy-4-hydroxy-6-[[(3S,5R,6S,8R,9R,10S,13R,14S,16S,17R)-16-hydroxy-17-[(2R,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,9,10,13,14-hexamethyl-6-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-1,2,3,5,6,7,8,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-yl]oxy]oxan-3-yl] acetate
• SMILES (Canonical): CC(=O)OC1COC(C(C1O)OC(=O)C)OC2CCC3(C(C2(C)C)C(CC4C3(CCC5(C4(CC(C5C6(CCC(O6)C(C)(C)O)C)O)C)C)C)OC7C(C(C(CO7)O)O)O)C
• SMILES (Isomeric): CC(=O)O[C@@H]1CO[C@H]([C@@H]([C@H]1O)OC(=O)C)O[C@H]2CC[C@]3([C@H](C2(C)C)[C@H](C[C@@H]4[C@]3(CC[C@]5([C@]4(C[C@@H]([C@@H]5[C@]6(CC[C@H](O6)C(C)(C)O)C)O)C)C)C)O[C@H]7[C@@H]([C@H]([C@@H](CO7)O)O)O)C
• InChI: InChI=1S/C45H74O15/c1-22(46)56-27-21-55-38(34(32(27)51)57-23(2)47)59-29-12-14-42(8)36(39(29,3)4)26(58-37-33(52)31(50)25(49)20-54-37)18-28-41(42,7)16-17-43(9)35(24(48)19-44(28,43)10)45(11)15-13-30(60-45)40(5,6)53/h24-38,48-53H,12-21H2,1-11H3/t24-,25+,26-,27+,28+,29-,30-,31-,32-,33+,34+,35-,36-,37-,38-,41+,42-,43+,44-,45+/m0/s1
• InChI Key: ZZBMDTNGBMRRFC-ITXIXRAFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₅H₇₄O₁₅
• Molecular Weight: 855.10 g/mol
• Exact Mass: 854.50277165 g/mol
• Topological Polar Surface Area (TPSA): 220.00 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.14
• H-Bond Acceptor: 15
• H-Bond Donor: 6
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7585	75.85%
Caco-2	-	0.8776	87.76%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8371	83.71%
OATP2B1 inhibitior	-	0.8766	87.66%
OATP1B1 inhibitior	+	0.8526	85.26%
OATP1B3 inhibitior	+	0.9415	94.15%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7787	77.87%
BSEP inhibitior	+	0.7317	73.17%
P-glycoprotein inhibitior	+	0.7744	77.44%
P-glycoprotein substrate	+	0.5646	56.46%
CYP3A4 substrate	+	0.7447	74.47%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8916	89.16%
CYP3A4 inhibition	-	0.8860	88.60%
CYP2C9 inhibition	-	0.8891	88.91%
CYP2C19 inhibition	-	0.8996	89.96%
CYP2D6 inhibition	-	0.9557	95.57%
CYP1A2 inhibition	-	0.9398	93.98%
CYP2C8 inhibition	+	0.6823	68.23%
CYP inhibitory promiscuity	-	0.9795	97.95%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5940	59.40%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9054	90.54%
Skin irritation	-	0.6931	69.31%
Skin corrosion	-	0.9307	93.07%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6771	67.71%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.9217	92.17%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.8551	85.51%
Acute Oral Toxicity (c)	I	0.6885	68.85%
Estrogen receptor binding	+	0.7100	71.00%
Androgen receptor binding	+	0.7244	72.44%
Thyroid receptor binding	-	0.5640	56.40%
Glucocorticoid receptor binding	+	0.7717	77.17%
Aromatase binding	+	0.6776	67.76%
PPAR gamma	+	0.7845	78.45%
Honey bee toxicity	-	0.6073	60.73%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9509	95.09%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1914	P06276	Butyrylcholinesterase	98.92%	95.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.65%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.62%	94.45%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	92.88%	96.77%
CHEMBL259	P32245	Melanocortin receptor 4	92.04%	95.38%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.02%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.74%	96.09%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	89.51%	91.07%
CHEMBL2179	P04062	Beta-glucocerebrosidase	88.65%	85.31%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.50%	89.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.24%	92.94%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.13%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.98%	97.09%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.60%	93.04%
CHEMBL3922	P50579	Methionine aminopeptidase 2	85.28%	97.28%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.26%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.13%	95.89%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.65%	82.69%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.18%	92.62%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	83.17%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	83.09%	91.19%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	82.78%	82.50%
CHEMBL1871	P10275	Androgen Receptor	82.53%	96.43%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.91%	86.33%
CHEMBL2581	P07339	Cathepsin D	81.56%	98.95%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	81.04%	89.05%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.02%	95.71%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	80.92%	95.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.47%	99.23%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.47%	97.33%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.14%	100.00%

Plants that contains it

• Astragalus sieversianus

Cross-Links

• PubChem: 162983419
• LOTUS: LTS0003066
• wikiData: Q105386654