12beta,14,19-Trihydroxy-3beta-[4-O-(beta-D-glucopyranosyl)-6-deoxy-beta-D-allopyranosyloxy]-5alpha-card-20(22)-enolide

Details

• Internal ID: 26f9bfd3-6c5b-4728-92f4-09ef8e6b5eaf
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: 3-[(3S,5S,8R,9S,10R,12R,13S,14S,17R)-3-[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-12,14-dihydroxy-10-(hydroxymethyl)-13-methyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2CCC3(C(C2)CCC4C3CC(C5(C4(CCC5C6=CC(=O)OC6)O)C)O)CO)O)O)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]3C[C@H]([C@]5([C@@]4(CC[C@@H]5C6=CC(=O)OC6)O)C)O)CO)O)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O
• InChI: InChI=1S/C35H54O15/c1-15-30(50-32-28(43)26(41)25(40)22(12-36)49-32)27(42)29(44)31(47-15)48-18-5-7-34(14-37)17(10-18)3-4-20-21(34)11-23(38)33(2)19(6-8-35(20,33)45)16-9-24(39)46-13-16/h9,15,17-23,25-32,36-38,40-45H,3-8,10-14H2,1-2H3/t15-,17+,18+,19-,20-,21+,22-,23-,25-,26+,27+,28-,29-,30-,31+,32+,33+,34-,35+/m1/s1
• InChI Key: WUDWVYDGLPDSHP-AWPOJWOVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₅₄O₁₅
• Molecular Weight: 714.80 g/mol
• Exact Mass: 714.34627101 g/mol
• Topological Polar Surface Area (TPSA): 245.00 Ų
• XlogP: -2.40
• Atomic LogP (AlogP): -1.78
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7905	79.05%
Caco-2	-	0.8876	88.76%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8521	85.21%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9194	91.94%
OATP1B3 inhibitior	+	0.9521	95.21%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.5539	55.39%
P-glycoprotein inhibitior	+	0.6550	65.50%
P-glycoprotein substrate	+	0.7259	72.59%
CYP3A4 substrate	+	0.6907	69.07%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9010	90.10%
CYP3A4 inhibition	-	0.9516	95.16%
CYP2C9 inhibition	-	0.9310	93.10%
CYP2C19 inhibition	-	0.9254	92.54%
CYP2D6 inhibition	-	0.9192	91.92%
CYP1A2 inhibition	-	0.9043	90.43%
CYP2C8 inhibition	-	0.6613	66.13%
CYP inhibitory promiscuity	-	0.9136	91.36%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6262	62.62%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9257	92.57%
Skin irritation	-	0.6105	61.05%
Skin corrosion	-	0.9410	94.10%
Ames mutagenesis	-	0.5579	55.79%
Human Ether-a-go-go-Related Gene inhibition	+	0.8410	84.10%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.9048	90.48%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.6507	65.07%
Acute Oral Toxicity (c)	I	0.7772	77.72%
Estrogen receptor binding	+	0.8121	81.21%
Androgen receptor binding	+	0.8141	81.41%
Thyroid receptor binding	-	0.6563	65.63%
Glucocorticoid receptor binding	-	0.4707	47.07%
Aromatase binding	+	0.6881	68.81%
PPAR gamma	+	0.6870	68.70%
Honey bee toxicity	-	0.6564	65.64%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9023	90.23%

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	99.02%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.72%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.88%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.28%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.16%	97.25%
CHEMBL1937	Q92769	Histone deacetylase 2	92.89%	94.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.67%	86.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	90.95%	96.77%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.39%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.78%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.26%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.00%	97.36%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.00%	95.89%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	85.80%	92.32%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.07%	94.00%
CHEMBL226	P30542	Adenosine A1 receptor	84.92%	95.93%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.82%	82.69%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.74%	94.45%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.46%	96.21%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.12%	95.89%
CHEMBL2581	P07339	Cathepsin D	82.85%	98.95%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.81%	92.94%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.70%	96.00%
CHEMBL5255	O00206	Toll-like receptor 4	82.65%	92.50%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	82.56%	98.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.57%	91.24%

Plants that contains it

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

Cross-Links

• PubChem: 11765396
• NPASS: NPC93973
• LOTUS: LTS0239564
• wikiData: Q105312993