[(2S,3R,4S,5R)-2-[(2S,3R,4S,5S)-3-acetyloxy-2-[[(3S,8R,9S,10R,13S,14S,16S,17S)-3,17-dihydroxy-10,13-dimethyl-17-[(2S)-6-methyl-3-oxoheptan-2-yl]-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-16-yl]oxy]-5-hydroxyoxan-4-yl]oxy-4,5-dihydroxyoxan-3-yl] (E)-3-phenylprop-2-enoate

Details

• Internal ID: c20db215-b0b0-485f-a228-c6f37b0f5dc0
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: [(2S,3R,4S,5R)-2-[(2S,3R,4S,5S)-3-acetyloxy-2-[[(3S,8R,9S,10R,13S,14S,16S,17S)-3,17-dihydroxy-10,13-dimethyl-17-[(2S)-6-methyl-3-oxoheptan-2-yl]-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-16-yl]oxy]-5-hydroxyoxan-4-yl]oxy-4,5-dihydroxyoxan-3-yl] (E)-3-phenylprop-2-enoate
• SMILES (Canonical): CC(C)CCC(=O)C(C)C1(C(CC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)OC5C(C(C(CO5)O)OC6C(C(C(CO6)O)O)OC(=O)C=CC7=CC=CC=C7)OC(=O)C)O
• SMILES (Isomeric): C[C@H](C(=O)CCC(C)C)[C@]1([C@H](C[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C)O[C@H]5[C@@H]([C@H]([C@H](CO5)O)O[C@H]6[C@@H]([C@H]([C@@H](CO6)O)O)OC(=O)/C=C/C7=CC=CC=C7)OC(=O)C)O
• InChI: InChI=1S/C48H68O14/c1-26(2)12-16-35(51)27(3)48(56)38(23-34-32-15-14-30-22-31(50)18-20-46(30,5)33(32)19-21-47(34,48)6)60-45-43(59-28(4)49)41(37(53)25-58-45)62-44-42(40(55)36(52)24-57-44)61-39(54)17-13-29-10-8-7-9-11-29/h7-11,13-14,17,26-27,31-34,36-38,40-45,50,52-53,55-56H,12,15-16,18-25H2,1-6H3/b17-13+/t27-,31+,32-,33+,34+,36-,37+,38+,40+,41+,42-,43-,44+,45+,46+,47+,48-/m1/s1
• InChI Key: QWBUTRPXIJIBDK-GARMIUHUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₆₈O₁₄
• Molecular Weight: 869.00 g/mol
• Exact Mass: 868.46090684 g/mol
• Topological Polar Surface Area (TPSA): 208.00 Ų
• XlogP: 4.80
• Atomic LogP (AlogP): 4.42
• H-Bond Acceptor: 14
• H-Bond Donor: 5
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9324	93.24%
Caco-2	-	0.8734	87.34%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.8834	88.34%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8335	83.35%
OATP1B3 inhibitior	+	0.8012	80.12%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7026	70.26%
BSEP inhibitior	+	0.9419	94.19%
P-glycoprotein inhibitior	+	0.7534	75.34%
P-glycoprotein substrate	+	0.7733	77.33%
CYP3A4 substrate	+	0.7544	75.44%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8919	89.19%
CYP3A4 inhibition	-	0.6971	69.71%
CYP2C9 inhibition	-	0.8001	80.01%
CYP2C19 inhibition	-	0.8748	87.48%
CYP2D6 inhibition	-	0.9345	93.45%
CYP1A2 inhibition	-	0.8089	80.89%
CYP2C8 inhibition	+	0.8289	82.89%
CYP inhibitory promiscuity	-	0.9445	94.45%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5359	53.59%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.9086	90.86%
Skin irritation	-	0.5439	54.39%
Skin corrosion	-	0.9444	94.44%
Ames mutagenesis	-	0.5878	58.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.6764	67.64%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.8914	89.14%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.9222	92.22%
Acute Oral Toxicity (c)	I	0.4791	47.91%
Estrogen receptor binding	+	0.8229	82.29%
Androgen receptor binding	+	0.7649	76.49%
Thyroid receptor binding	+	0.5818	58.18%
Glucocorticoid receptor binding	+	0.7535	75.35%
Aromatase binding	+	0.5462	54.62%
PPAR gamma	+	0.8053	80.53%
Honey bee toxicity	-	0.6322	63.22%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.6045	60.45%
Fish aquatic toxicity	+	0.9930	99.30%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.16%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.55%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.50%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.82%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.59%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.57%	96.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	95.55%	94.62%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	95.35%	94.08%
CHEMBL226	P30542	Adenosine A1 receptor	93.48%	95.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.84%	89.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	90.07%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.94%	94.45%
CHEMBL5028	O14672	ADAM10	89.92%	97.50%
CHEMBL3359	P21462	Formyl peptide receptor 1	89.18%	93.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.52%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	88.26%	90.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.36%	95.50%
CHEMBL2179	P04062	Beta-glucocerebrosidase	86.35%	85.31%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.66%	82.69%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.98%	97.14%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	84.51%	94.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.34%	99.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.96%	97.25%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	83.86%	89.67%
CHEMBL2959	Q08881	Tyrosine-protein kinase ITK/TSK	83.83%	95.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.69%	91.07%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.58%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.89%	100.00%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	82.63%	89.44%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.53%	93.99%
CHEMBL340	P08684	Cytochrome P450 3A4	82.23%	91.19%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.09%	93.00%
CHEMBL325	Q13547	Histone deacetylase 1	81.67%	95.92%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.03%	95.71%
CHEMBL1914	P06276	Butyrylcholinesterase	80.74%	95.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.08%	92.62%

Plants that contains it

• Harungana madagascariensis
• Ornithogalum saundersiae

Cross-Links

• PubChem: 101504648
• LOTUS: LTS0210621
• wikiData: Q105218090