Acetylgitoxin-alpha [German]

Details

• Internal ID: 2fd40ce5-a661-4bc1-a5c3-25cced7bb817
• 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,16R,17R)-3-[(2S,4S,5R,6R)-4,5-bis[[(2R,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy]-6-methyloxan-2-yl]oxy-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-16-yl] acetate
• SMILES (Canonical): CC1C(C(CC(O1)OC2CC(OC(C2OC3CC(C(C(O3)C)O)O)C)OC4CCC5(C(C4)CCC6C5CCC7(C6(CC(C7C8=CC(=O)OC8)OC(=O)C)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)O)O)C)O[C@H]4CC[C@]5([C@@H](C4)CC[C@@H]6[C@@H]5CC[C@]7(C6(C[C@H]([C@@H]7C8=CC(=O)OC8)OC(=O)C)O)C)C)O)O
• InChI: InChI=1S/C43H66O15/c1-20-38(48)29(45)15-34(52-20)57-31-17-36(54-22(3)40(31)58-35-16-30(46)39(49)21(2)53-35)56-26-9-11-41(5)25(14-26)7-8-28-27(41)10-12-42(6)37(24-13-33(47)51-19-24)32(55-23(4)44)18-43(28,42)50/h13,20-22,25-32,34-40,45-46,48-50H,7-12,14-19H2,1-6H3/t20-,21-,22-,25-,26+,27+,28-,29+,30+,31+,32-,34-,35-,36-,37+,38-,39-,40-,41+,42-,43?/m1/s1
• InChI Key: SZHBGTRKQDNXNC-RIYHBKJUSA-N
• Popularity: 1 reference 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: 1.60
• Atomic LogP (AlogP): 2.79
• H-Bond Acceptor: 15
• H-Bond Donor: 5
• Rotatable Bonds: 8

Synonyms

• alpha-Acetylgitoxin
• Gitoxigenin + zuckerkette wie bei acetyl-digitoxin-alpha [German]
• 29362-48-9
• 5-beta-Card-20(22)-enolide, 3-beta-((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)-14,16-alpha-dihydroxy-, 16-acetate
• Gitoxigenin + zuckerkette wie bei acetyl-digitoxin-alpha

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9551	95.51%
Caco-2	-	0.8830	88.30%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8783	87.83%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9278	92.78%
OATP1B3 inhibitior	+	0.9509	95.09%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8881	88.81%
P-glycoprotein inhibitior	+	0.7549	75.49%
P-glycoprotein substrate	+	0.8696	86.96%
CYP3A4 substrate	+	0.7218	72.18%
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	-	0.6937	69.37%
CYP inhibitory promiscuity	-	0.9585	95.85%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4953	49.53%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.9183	91.83%
Skin irritation	+	0.5744	57.44%
Skin corrosion	-	0.9325	93.25%
Ames mutagenesis	-	0.5770	57.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.6687	66.87%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.6717	67.17%
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	-	0.7839	78.39%
Acute Oral Toxicity (c)	I	0.8720	87.20%
Estrogen receptor binding	+	0.8315	83.15%
Androgen receptor binding	+	0.8154	81.54%
Thyroid receptor binding	-	0.6207	62.07%
Glucocorticoid receptor binding	+	0.6992	69.92%
Aromatase binding	+	0.6981	69.81%
PPAR gamma	+	0.7684	76.84%
Honey bee toxicity	-	0.6225	62.25%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
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
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.88%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.81%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.65%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.85%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.07%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.57%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.80%	85.14%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	90.54%	82.69%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.41%	86.33%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	87.83%	81.11%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.09%	92.94%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.93%	96.77%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.60%	89.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.92%	94.33%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	85.70%	97.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.55%	99.23%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.31%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	84.42%	92.50%
CHEMBL4208	P20618	Proteasome component C5	84.41%	90.00%
CHEMBL5028	O14672	ADAM10	82.86%	97.50%
CHEMBL2581	P07339	Cathepsin D	82.60%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	81.69%	91.19%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.61%	94.00%

Plants that contains it

• Digitalis lanata

Cross-Links

• PubChem: 207215
• LOTUS: LTS0150400
• wikiData: Q104252840