3beta-[[6-O-[3-(3,5-Dimethoxy-4-hydroxyphenyl)propenoyl]-beta-D-glucopyranosyl]oxy]-14-hydroxy-5alpha-card-20(22)-enolide

Details

• Internal ID: f86b0d9c-2a2f-4148-8e26-cf0e698f4e89
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: [(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[[(3S,5S,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]oxan-2-yl]methyl (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
• SMILES (Canonical): CC12CCC(CC1CCC3C2CCC4(C3(CCC4C5=CC(=O)OC5)O)C)OC6C(C(C(C(O6)COC(=O)C=CC7=CC(=C(C(=C7)OC)O)OC)O)O)O
• SMILES (Isomeric): C[C@]12CC[C@@H](C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@@]3(CC[C@@H]4C5=CC(=O)OC5)O)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)COC(=O)/C=C/C7=CC(=C(C(=C7)OC)O)OC)O)O)O
• InChI: InChI=1S/C40H54O13/c1-38-12-9-24(18-23(38)6-7-27-26(38)10-13-39(2)25(11-14-40(27,39)47)22-17-32(42)50-19-22)52-37-36(46)35(45)34(44)30(53-37)20-51-31(41)8-5-21-15-28(48-3)33(43)29(16-21)49-4/h5,8,15-17,23-27,30,34-37,43-47H,6-7,9-14,18-20H2,1-4H3/b8-5+/t23-,24-,25+,26-,27+,30+,34+,35-,36+,37+,38-,39+,40-/m0/s1
• InChI Key: UMPSALOXRRADAP-JCBIKUBLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₅₄O₁₃
• Molecular Weight: 742.80 g/mol
• Exact Mass: 742.35644177 g/mol
• Topological Polar Surface Area (TPSA): 191.00 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.42
• H-Bond Acceptor: 13
• H-Bond Donor: 5
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9122	91.22%
Caco-2	-	0.8790	87.90%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7644	76.44%
OATP2B1 inhibitior	-	0.8683	86.83%
OATP1B1 inhibitior	+	0.8646	86.46%
OATP1B3 inhibitior	+	0.9462	94.62%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9024	90.24%
P-glycoprotein inhibitior	+	0.7336	73.36%
P-glycoprotein substrate	+	0.7481	74.81%
CYP3A4 substrate	+	0.7387	73.87%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8811	88.11%
CYP3A4 inhibition	-	0.8488	84.88%
CYP2C9 inhibition	-	0.8648	86.48%
CYP2C19 inhibition	-	0.8763	87.63%
CYP2D6 inhibition	-	0.9354	93.54%
CYP1A2 inhibition	-	0.8175	81.75%
CYP2C8 inhibition	+	0.6692	66.92%
CYP inhibitory promiscuity	-	0.8948	89.48%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5612	56.12%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9164	91.64%
Skin irritation	-	0.7069	70.69%
Skin corrosion	-	0.9431	94.31%
Ames mutagenesis	-	0.6970	69.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.6910	69.10%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	-	0.7250	72.50%
skin sensitisation	-	0.8901	89.01%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.9582	95.82%
Acute Oral Toxicity (c)	I	0.5933	59.33%
Estrogen receptor binding	+	0.8611	86.11%
Androgen receptor binding	+	0.8037	80.37%
Thyroid receptor binding	-	0.5439	54.39%
Glucocorticoid receptor binding	+	0.6765	67.65%
Aromatase binding	+	0.6929	69.29%
PPAR gamma	+	0.7553	75.53%
Honey bee toxicity	-	0.6647	66.47%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9907	99.07%

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	99.75%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.50%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.05%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.42%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.12%	85.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	97.02%	96.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.74%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.66%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.22%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.92%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	93.89%	92.94%
CHEMBL5255	O00206	Toll-like receptor 4	92.97%	92.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.97%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.85%	95.89%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.60%	96.77%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.44%	92.62%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.29%	94.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.11%	96.21%
CHEMBL1871	P10275	Androgen Receptor	84.22%	96.43%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.02%	90.71%
CHEMBL4208	P20618	Proteasome component C5	82.51%	90.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.41%	97.36%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.31%	94.00%
CHEMBL226	P30542	Adenosine A1 receptor	81.29%	95.93%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	80.53%	98.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.07%	97.14%

Plants that contains it

• Anemone narcissiflora
• Asclepias curassavica
• Hyperbaena columbica
• Viburnum lantanoides

Cross-Links

• PubChem: 101676218
• NPASS: NPC107295
• LOTUS: LTS0159289
• wikiData: Q105275652