Acetyldigitoxin

Details

• Internal ID: b79985b4-dc56-4219-9f0e-5d0844c1f0a9
• 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)-3-hydroxy-6-[(2R,3S,4S,6S)-4-hydroxy-6-[(2R,3S,4S,6R)-4-hydroxy-6-[[(3S,5R,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]-2-methyloxan-3-yl]oxy-2-methyloxan-3-yl]oxy-2-methyloxan-4-yl] acetate
• InChI: InChI=1S/C43H66O14/c1-21-38(48)33(54-24(4)44)19-37(51-21)57-40-23(3)53-36(18-32(40)46)56-39-22(2)52-35(17-31(39)45)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: HPMZBILYSWLILX-UMDUKNJSSA-N
• Popularity: 139 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

• 1111-39-3
• alpha-Acetyldigitoxin
• Desglucolanatoside A
• Acylanid
• Acetildigitoxina
• Acetyldiginatin
• alpha-Monoacetyldigitoxin
• Acetyldigitoxinum
• Acetyl-digitoxin-alpha
• Digitoxin 3'''-acetate
• acetyldigitoxine
• 0ZV4Q4L2FU
• CHEBI:53773
• [(2R,3R,4S,6S)-3-hydroxy-6-[(2R,3S,4S,6S)-4-hydroxy-6-[(2R,3S,4S,6R)-4-hydroxy-6-[[(3S,5R,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]-2-methyloxan-3-yl]oxy-2-methyloxan-3-yl]oxy-2-methyloxan-4-yl] acetate
• DTXSID6022551
• acetildigitossina
• ((2R,3R,4S,6S)-3-hydroxy-6-((2R,3S,4S,6S)-4-hydroxy-6-((2R,3S,4S,6R)-4-hydroxy-6-(((3S,5R,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)-2-methyloxan-3-yl)oxy-2-methyloxan-3-yl)oxy-2-methyloxan-4-yl) acetate
• (2R,3R,4S,6S)-3-hydroxy-6-(((2R,3S,4S,6S)-4-hydroxy-6-(((2R,3S,4S,6R)-4-hydroxy-6-(((1S,2S,5S,7R,10R,11S,14R,15R)-11-hydroxy-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo(8.7.0.0^(2,7).0^(11,15))heptadecan-5-yl)oxy)-2-methyloxan-3-yl)oxy)-2-methyloxan-3-yl)oxy)-2-methyloxan-4-yl acetate
• (2R,3R,4S,6S)-3-hydroxy-6-{[(2R,3S,4S,6S)-4-hydroxy-6-{[(2R,3S,4S,6R)-4-hydroxy-6-{[(1S,2S,5S,7R,10R,11S,14R,15R)-11-hydroxy-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxy}-2-methyloxan-3-yl]oxy}-2-methyloxan-3-yl]oxy}-2-methyloxan-4-yl acetate
• alpha Acetyldigitoxin
• Acetyldigitoxins alpha-
• RefChem:57137
• C01AA01
• C01AA02
• DTXCID001473935
• (3beta,5beta)-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)-14-hydroxycard-20(22)-enolide
• 214-178-4
• Acylanide
• Acetyldigitoxin [INN]
• 3'''-O-acetyldigitoxin
• alpha-Acetylgitaloxin
• Acetyldigitoxin (INN)
• 25395-32-8
• Acetyldigitoxins .alpha.-form
• (3beta,5beta)-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)-14-hydroxycard-20(22)-enolide
• Acedigal
• Adicin
• Digitoxin, 3'''-acetate
• Acylanid (TN)
• Acetyldigitoxinum [INN-Latin]
• alpha-Acetyldigitoxins
• Acetildigitoxina [INN-Spanish]
• Digitoxin, alpha-acetyl-
• Acetyldigitoxin [INN:NF]
• UNII-0ZV4Q4L2FU
• Acetyldigitoxins
• EINECS 214-178-4
• BRN 0077291
• Digitoxin, acetate, alpha-
• SCHEMBL309649
• GTPL6794
• orb1698769
• ACETYLDIGITOXIN [MART.]
• ACETYLDIGITOXIN [WHO-DD]
• CHEMBL3545057
• HPMZBILYSWLILX-UMDUKNJSSA-N
• GLXC-23122
• (2R,3R,4S,6S)-6-{[(2R,3S,4S,6S)-6-{[(2R,3S,4S,6R)-6-{[(1R,3aS,3bR,5aR,7S,9aS,9bS,11aR)-3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2,5-dihydrofuran-3-yl)-hexadecahydro-1H-cyclopenta[a]phenanthren-7-yl]oxy}-4-hydroxy-2-methyloxan-3-yl]oxy}-4-hydroxy-2-methyloxan-3
• ACETYLDIGITOXIN [ORANGE BOOK]
• MFCD00151402
• AKOS040750096
• DB00511
• (3beta,5beta)-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)-14-hydroxycard-20(22)-enolide
• (3beta,5beta)-3-{[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}-14-hydroxycard-20(22)-enolide
• 3beta-[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-hexopyranosyloxy]-14-hydroxy-5beta-card-20(22)-enolide
• DA-60729
• HY-16022
• ACETYLDIGITOXINS .ALPHA.-FORM [MI]
• CS-0006116
• NS00023555
• C22191
• D06881
• EN300-24432971
• (2R,3R,4S,6S)-6-{[(2R,3S,4S,6S)-6-{[(2R,3S,4S,6R)-6-{[(1R,3aS,3bR,5aR,7S,9aS,9bS,11aR)-3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2,5-dihydrofuran-3-yl)-hexadecahydro-1H-cyclopenta[a]phenanthren-7-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.,5.BETA.)-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)-14-HYDROXYCARD-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)-14-hydroxy-, (3beta,5beta)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9774	97.74%
Caco-2	-	0.8970	89.70%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.8143	81.43%
Subcellular localzation	Mitochondria	0.8739	87.39%
OATP2B1 inhibitior	-	0.8838	88.38%
OATP1B1 inhibitior	+	0.9365	93.65%
OATP1B3 inhibitior	+	0.9511	95.11%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8364	83.64%
BSEP inhibitior	+	0.9395	93.95%
P-glycoprotein inhibitior	+	0.7448	74.48%
P-glycoprotein substrate	+	0.9094	90.94%
CYP3A4 substrate	+	0.7008	70.08%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9074	90.74%
CYP3A4 inhibition	-	0.8311	83.11%
CYP2C9 inhibition	-	0.9065	90.65%
CYP2C19 inhibition	-	0.9516	95.16%
CYP2D6 inhibition	-	0.9544	95.44%
CYP1A2 inhibition	-	0.9105	91.05%
CYP2C8 inhibition	-	0.8211	82.11%
CYP inhibitory promiscuity	-	0.9302	93.02%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4706	47.06%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.9313	93.13%
Skin irritation	+	0.5726	57.26%
Skin corrosion	-	0.9346	93.46%
Ames mutagenesis	-	0.5070	50.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.8242	82.42%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.8375	83.75%
skin sensitisation	-	0.9196	91.96%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.8401	84.01%
Acute Oral Toxicity (c)	I	0.9011	90.11%
Estrogen receptor binding	+	0.8704	87.04%
Androgen receptor binding	+	0.8479	84.79%
Thyroid receptor binding	-	0.7189	71.89%
Glucocorticoid receptor binding	+	0.7009	70.09%
Aromatase binding	+	0.7476	74.76%
PPAR gamma	+	0.7781	77.81%
Honey bee toxicity	-	0.6446	64.46%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9839	98.39%

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	98.86%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.22%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.50%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.97%	94.45%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	95.06%	82.69%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.56%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.22%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.91%	86.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.38%	96.77%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	89.93%	81.11%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.43%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.23%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.81%	89.00%
CHEMBL2581	P07339	Cathepsin D	85.89%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.85%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.59%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.31%	94.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.17%	94.33%
CHEMBL340	P08684	Cytochrome P450 3A4	82.68%	91.19%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.47%	95.89%
CHEMBL5028	O14672	ADAM10	82.43%	97.50%
CHEMBL5255	O00206	Toll-like receptor 4	82.19%	92.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.59%	97.14%

Plants that contains it

• Begonia glabra
• Cordyline fruticosa
• Digitalis grandiflora
• Digitalis lanata
• Digitalis purpurea
• Erysimum repandum
• Hemerocallis fulva
• Karpatiosorbus latifolia
• Luffa aegyptiaca
• Phoenix canariensis
• Rubus coreanus
• Strychnos splendens

Cross-Links

• PubChem: 5284512
• NPASS: NPC41586
• LOTUS: LTS0012015
• wikiData: Q4673299