Digitalinum verum monoacetate

Details

• Internal ID: 3c82c75d-c1c6-41e7-bee2-e9c43a8e092e
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: [(2R,3S,4S,6R)-6-[(2R,3R,4S,6S)-4-[(2R,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-6-[[(3S,5R,8R,9S,10S,13R,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]-2-methyloxan-3-yl]oxy-4-hydroxy-2-methyloxan-3-yl] acetate
• SMILES (Canonical): CC1C(C(CC(O1)OC2CC(OC(C2OC3CC(C(C(O3)C)OC(=O)C)O)C)OC4CCC5(C(C4)CCC6C5CCC7(C6(CCC7C8=CC(=O)OC8)O)C)C)O)O
• SMILES (Isomeric): C[C@@H]1[C@H]([C@H](C[C@H](O1)O[C@H]2C[C@H](O[C@@H]([C@H]2O[C@@H]3C[C@@H]([C@@H]([C@H](O3)C)OC(=O)C)O)C)O[C@H]4CC[C@]5([C@@H](C4)CC[C@@H]6[C@@H]5CC[C@]7(C6(CC[C@@H]7C8=CC(=O)OC8)O)C)C)O)O
• InChI: InChI=1S/C43H66O14/c1-21-38(48)31(45)17-35(51-21)56-33-19-37(53-23(3)40(33)57-36-18-32(46)39(22(2)52-36)54-24(4)44)55-27-9-12-41(5)26(16-27)7-8-30-29(41)10-13-42(6)28(11-14-43(30,42)49)25-15-34(47)50-20-25/h15,21-23,26-33,35-40,45-46,48-49H,7-14,16-20H2,1-6H3/t21-,22-,23-,26-,27+,28-,29+,30-,31+,32+,33+,35-,36-,37-,38-,39-,40-,41+,42-,43?/m1/s1
• InChI Key: YTOYNGLDTBVTJA-MLRICCPWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₆₆O₁₄
• Molecular Weight: 807.00 g/mol
• Exact Mass: 806.44525677 g/mol
• Topological Polar Surface Area (TPSA): 189.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 3.82
• H-Bond Acceptor: 14
• H-Bond Donor: 4
• Rotatable Bonds: 8

Synonyms

• Digitoxin, monoacetate
• EINECS 246-942-8
• 3-((O-2,6-Dideoxy-beta-D-ribo-hexopyranosyl-(1-4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy)-14-hydroxycard-20(22)-enolide monoacetate, (3beta,5beta)-
• Card-20(22)-enolide, 3-((O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1.4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1.4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy)-14-hydroxy-, monoacetate, (3beta,5beta)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9551	95.51%
Caco-2	-	0.8795	87.95%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	+	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8783	87.83%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9298	92.98%
OATP1B3 inhibitior	+	0.9509	95.09%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9384	93.84%
P-glycoprotein inhibitior	+	0.7625	76.25%
P-glycoprotein substrate	+	0.9189	91.89%
CYP3A4 substrate	+	0.7065	70.65%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9053	90.53%
CYP3A4 inhibition	-	0.8598	85.98%
CYP2C9 inhibition	-	0.9008	90.08%
CYP2C19 inhibition	-	0.9395	93.95%
CYP2D6 inhibition	-	0.9508	95.08%
CYP1A2 inhibition	-	0.9063	90.63%
CYP2C8 inhibition	-	0.8220	82.20%
CYP inhibitory promiscuity	-	0.9585	95.85%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4953	49.53%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.9207	92.07%
Skin irritation	+	0.5744	57.44%
Skin corrosion	-	0.9325	93.25%
Ames mutagenesis	-	0.6070	60.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7617	76.17%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.8075	80.75%
skin sensitisation	-	0.9129	91.29%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.8487	84.87%
Acute Oral Toxicity (c)	I	0.8720	87.20%
Estrogen receptor binding	+	0.8370	83.70%
Androgen receptor binding	+	0.8503	85.03%
Thyroid receptor binding	-	0.6264	62.64%
Glucocorticoid receptor binding	+	0.7070	70.70%
Aromatase binding	+	0.7010	70.10%
PPAR gamma	+	0.7462	74.62%
Honey bee toxicity	-	0.6286	62.86%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9856	98.56%

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	97.95%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.88%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.74%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.70%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	96.30%	82.69%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.07%	85.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.03%	96.77%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	91.79%	81.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.78%	97.09%
CHEMBL2581	P07339	Cathepsin D	90.63%	98.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.17%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.61%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.34%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.81%	89.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	86.16%	89.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.89%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.78%	95.56%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.28%	94.33%
CHEMBL340	P08684	Cytochrome P450 3A4	83.58%	91.19%
CHEMBL5255	O00206	Toll-like receptor 4	83.57%	92.50%
CHEMBL4040	P28482	MAP kinase ERK2	83.26%	83.82%
CHEMBL5028	O14672	ADAM10	82.39%	97.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.33%	97.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.25%	94.00%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.92%	100.00%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.50%	97.33%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	80.14%	94.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.02%	97.25%

Plants that contains it

• Solidago rugosa

Cross-Links

• PubChem: 3035155
• LOTUS: LTS0250176
• wikiData: Q105361799