(3beta,5beta,16beta)-3-((6-Deoxy-4-O-beta-D-glucopyranosyl-3-O-methyl-beta-D-galactopyranosyl)oxy)-14,16-dihydroxycard-20(22)-enolide 16-formate

Details

• Internal ID: d30e5fdd-d292-4f21-96a0-4e9b53585bf3
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: [(3S,5R,8R,9S,10S,13R,14S,16S,17R)-14-hydroxy-3-[(2R,3R,4R,5S,6R)-3-hydroxy-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-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-16-yl] formate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2CCC3(C(C2)CCC4C3CCC5(C4(CC(C5C6=CC(=O)OC6)OC=O)O)C)C)O)OC)OC7C(C(C(C(O7)CO)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@H]2CC[C@]3([C@@H](C2)CC[C@@H]4[C@@H]3CC[C@]5([C@@]4(C[C@@H]([C@@H]5C6=CC(=O)OC6)OC=O)O)C)C)O)OC)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O
• InChI: InChI=1S/C37H56O15/c1-17-31(52-33-29(43)28(42)27(41)24(14-38)51-33)32(46-4)30(44)34(49-17)50-20-7-9-35(2)19(12-20)5-6-22-21(35)8-10-36(3)26(18-11-25(40)47-15-18)23(48-16-39)13-37(22,36)45/h11,16-17,19-24,26-34,38,41-45H,5-10,12-15H2,1-4H3/t17-,19-,20+,21+,22-,23+,24-,26+,27-,28+,29-,30-,31+,32-,33+,34+,35+,36-,37+/m1/s1
• InChI Key: SVNMSAUVRSRHGA-UUXWYOJBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₅₆O₁₅
• Molecular Weight: 740.80 g/mol
• Exact Mass: 740.36192108 g/mol
• Topological Polar Surface Area (TPSA): 220.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): 0.09
• H-Bond Acceptor: 15
• H-Bond Donor: 6
• Rotatable Bonds: 9

Synonyms

• EINECS 227-879-5
• 6022-99-7
• (3beta,5beta,16beta)-3-((6-Deoxy-4-O-beta-D-glucopyranosyl-3-O-methyl-beta-D-galactopyranosyl)oxy)-14,16-dihydroxycard-20(22)-enolide 16-formate
• DTXSID90975637
• 3-[(6-Deoxy-4-O-hexopyranosyl-3-O-methylhexopyranosyl)oxy]-16-(formyloxy)-14-hydroxycard-20(22)-enolide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7964	79.64%
Caco-2	-	0.8877	88.77%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8047	80.47%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8930	89.30%
OATP1B3 inhibitior	+	0.9615	96.15%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7453	74.53%
P-glycoprotein inhibitior	+	0.7233	72.33%
P-glycoprotein substrate	+	0.7317	73.17%
CYP3A4 substrate	+	0.7356	73.56%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8999	89.99%
CYP3A4 inhibition	-	0.8841	88.41%
CYP2C9 inhibition	-	0.9054	90.54%
CYP2C19 inhibition	-	0.9238	92.38%
CYP2D6 inhibition	-	0.9467	94.67%
CYP1A2 inhibition	-	0.9221	92.21%
CYP2C8 inhibition	+	0.5872	58.72%
CYP inhibitory promiscuity	-	0.9513	95.13%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5527	55.27%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9231	92.31%
Skin irritation	-	0.5611	56.11%
Skin corrosion	-	0.9387	93.87%
Ames mutagenesis	-	0.5793	57.93%
Human Ether-a-go-go-Related Gene inhibition	+	0.7810	78.10%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.6467	64.67%
skin sensitisation	-	0.9209	92.09%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.8301	83.01%
Acute Oral Toxicity (c)	I	0.8305	83.05%
Estrogen receptor binding	+	0.8020	80.20%
Androgen receptor binding	+	0.8030	80.30%
Thyroid receptor binding	-	0.6588	65.88%
Glucocorticoid receptor binding	+	0.6685	66.85%
Aromatase binding	+	0.6946	69.46%
PPAR gamma	+	0.7292	72.92%
Honey bee toxicity	-	0.5836	58.36%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9314	93.14%

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	98.69%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.67%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.83%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.10%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.43%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.54%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.28%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.87%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.70%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.29%	94.45%
CHEMBL1937	Q92769	Histone deacetylase 2	85.43%	94.75%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.34%	92.94%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.86%	96.00%
CHEMBL1871	P10275	Androgen Receptor	84.80%	96.43%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.42%	89.00%
CHEMBL2581	P07339	Cathepsin D	84.03%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.96%	94.00%
CHEMBL226	P30542	Adenosine A1 receptor	83.47%	95.93%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.54%	95.89%
CHEMBL4208	P20618	Proteasome component C5	82.26%	90.00%
CHEMBL5255	O00206	Toll-like receptor 4	81.79%	92.50%
CHEMBL3492	P49721	Proteasome Macropain subunit	80.80%	90.24%

Plants that contains it

• Digitalis cariensis
• Digitalis lanata

Cross-Links

• PubChem: 3083927
• LOTUS: LTS0008146
• wikiData: Q82960302