alpha-Acetyldigoxin

Details

• Internal ID: 7b38274d-6fdf-412e-8884-0ed4ba259286
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: [(2R,3R,4S,6S)-6-[(2R,3S,4S,6S)-6-[(2R,3S,4S,6R)-6-[[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-12,14-dihydroxy-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]-4-hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2-methyloxan-3-yl]oxy-3-hydroxy-2-methyloxan-4-yl] acetate
• SMILES (Canonical): CC1C(C(CC(O1)OC2C(OC(CC2O)OC3C(OC(CC3O)OC4CCC5(C(C4)CCC6C5CC(C7(C6(CCC7C8=CC(=O)OC8)O)C)O)C)C)C)OC(=O)C)O
• SMILES (Isomeric): C[C@@H]1[C@H]([C@H](C[C@@H](O1)O[C@@H]2[C@H](O[C@H](C[C@@H]2O)O[C@@H]3[C@H](O[C@H](C[C@@H]3O)O[C@H]4CC[C@]5([C@@H](C4)CC[C@@H]6[C@@H]5C[C@H]([C@]7([C@@]6(CC[C@@H]7C8=CC(=O)OC8)O)C)O)C)C)C)OC(=O)C)O
• InChI: InChI=1S/C43H66O15/c1-20-38(49)32(55-23(4)44)18-37(52-20)58-40-22(3)54-36(17-31(40)46)57-39-21(2)53-35(16-30(39)45)56-26-9-11-41(5)25(14-26)7-8-28-29(41)15-33(47)42(6)27(10-12-43(28,42)50)24-13-34(48)51-19-24/h13,20-22,25-33,35-40,45-47,49-50H,7-12,14-19H2,1-6H3/t20-,21-,22-,25-,26+,27-,28-,29+,30+,31+,32+,33-,35+,36+,37+,38-,39-,40-,41+,42+,43+/m1/s1
• InChI Key: HWKJSYYYURVNQU-DXJNJSHLSA-N
• Popularity: 93 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₆₆O₁₅
• Molecular Weight: 823.00 g/mol
• Exact Mass: 822.44017139 g/mol
• Topological Polar Surface Area (TPSA): 209.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.79
• H-Bond Acceptor: 15
• H-Bond Donor: 5
• Rotatable Bonds: 8

Synonyms

• Acetyldigoxin
• 5511-98-8
• Lanatilin
• Sandolanid
• Digoxin, 3'''-acetate
• Lanadigin
• .alpha.-acetyldigoxin
• Q28IFH7A50
• Desglucolanatoside C
• 3'''-Acetyldigoxin
• alpha-Acetyl Digoxin
• Digorid A
• (2R,3R,4S,6S)-6-(((2R,3S,4S,6S)-6-(((2R,3S,4S,6R)-6-(((3S,5R,8R,9S,10S,12R,13S,14S,17R)-12,14-dihydroxy-10,13-dimethyl-17-(5-oxo-2,5-dihydrofuran-3-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)-4-hydroxy-2-methyltetrahydro-2H-pyran-3-yl)oxy)-4-hydroxy-2-methyltetrahydro-2H-pyran-3-yl)oxy)-3-hydroxy-2-methyltetrahydro-2H-pyran-4-yl acetate
• Acetyl-digoxin-alpha
• UNII-Q28IFH7A50
• -cetyl Digoxin
• Cedigossima (TN)
• EINECS 226-855-1
• Digoxin, acetate, alpha-
• Digoxigenin + zuckerkette wie bie acetyl-digitoxin A
• ACETYLDIGOXIN [WHO-DD]
• SCHEMBL4436090
• CHEMBL2074725
• NIOSH/OE1750000
• DTXSID00203630
• Digoxigenin + zuckerkette wie bie acetyl-digitoxin A [German]
• .ALPHA.-ACETYLDIGOXIN [MI]
• AKOS015969734
• DB13691
• DIGOXIN IMPURITY I [EP IMPURITY]
• OE17500000
• C22189
• D07555
• [(2R,3R,4S,6S)-6-[(2R,3S,4S,6S)-6-[(2R,3S,4S,6R)-6-[[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-12,14-dihydroxy-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]-4-hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2-methyloxan-3-yl]oxy-3-hydroxy-2-methyloxan-4-yl] acetate
• 3.BETA.-((3-O-ACETYL-2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL-(1->4)-2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL-(1->4)-2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL)OXY)-12.BETA.,14-DIHYDROXY-5.BETA.-CARD-20(22)-ENOLIDE
• Card-20(22)-enolide, 3-((O-3-O-acetyl-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)-12,14-dihydroxy-, (3beta,5beta,12beta)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9526	95.26%
Caco-2	-	0.9021	90.21%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8370	83.70%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9418	94.18%
OATP1B3 inhibitior	+	0.9614	96.14%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8614	86.14%
BSEP inhibitior	+	0.9601	96.01%
P-glycoprotein inhibitior	+	0.7417	74.17%
P-glycoprotein substrate	+	0.9283	92.83%
CYP3A4 substrate	+	0.6561	65.61%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9074	90.74%
CYP3A4 inhibition	-	0.8663	86.63%
CYP2C9 inhibition	-	0.9108	91.08%
CYP2C19 inhibition	-	0.9544	95.44%
CYP2D6 inhibition	-	0.9487	94.87%
CYP1A2 inhibition	-	0.9373	93.73%
CYP2C8 inhibition	-	0.9390	93.90%
CYP inhibitory promiscuity	-	0.9166	91.66%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5225	52.25%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9306	93.06%
Skin irritation	+	0.5370	53.70%
Skin corrosion	-	0.9326	93.26%
Ames mutagenesis	+	0.5176	51.76%
Human Ether-a-go-go-Related Gene inhibition	+	0.8279	82.79%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.9173	91.73%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.8315	83.15%
Acute Oral Toxicity (c)	I	0.8792	87.92%
Estrogen receptor binding	+	0.8770	87.70%
Androgen receptor binding	+	0.8473	84.73%
Thyroid receptor binding	-	0.6850	68.50%
Glucocorticoid receptor binding	+	0.7199	71.99%
Aromatase binding	+	0.7553	75.53%
PPAR gamma	+	0.7932	79.32%
Honey bee toxicity	-	0.6788	67.88%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9802	98.02%

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	98.78%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.94%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.73%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.12%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.38%	94.45%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	94.16%	82.69%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.78%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.15%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.72%	89.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.80%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.74%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.38%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.63%	99.23%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.71%	94.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.28%	92.94%
CHEMBL340	P08684	Cytochrome P450 3A4	83.82%	91.19%
CHEMBL2581	P07339	Cathepsin D	82.51%	98.95%
CHEMBL5028	O14672	ADAM10	82.39%	97.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.34%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	80.87%	92.50%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	80.32%	81.11%

Plants that contains it

• Digitalis grandiflora
• Digitalis lanata

Cross-Links

• PubChem: 11765960
• LOTUS: LTS0264855
• wikiData: Q104252849