Deacetyllanatoside B

Details

• Internal ID: 64e1fb2d-17a2-4f96-97d9-216be747b0ba
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: 3-[(3S,5R,8R,9S,10S,13R,16S,17R)-3-[(2S,4S,5R,6R)-5-[(2R,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-4-[(2R,4S,5R,6R)-5-hydroxy-6-methyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-14,16-dihydroxy-10,13-dimethyl-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(CC(O1)OC2C(OC(CC2OC3CC(C(C(O3)C)O)OC4C(C(C(C(O4)CO)O)O)O)OC5CCC6(C(C5)CCC7C6CCC8(C7(CC(C8C9=CC(=O)OC9)O)O)C)C)C)O)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[C@@H]3C[C@@H]([C@@H]([C@H](O3)C)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O[C@H]5CC[C@]6([C@@H](C5)CC[C@@H]7[C@@H]6CC[C@]8(C7(C[C@@H]([C@@H]8C9=CC(=O)OC9)O)O)C)C)C)O)O
• InChI: InChI=1S/C47H74O19/c1-20-38(52)28(49)14-34(59-20)66-43-22(3)61-35(16-31(43)63-36-15-30(39(53)21(2)60-36)64-44-42(56)41(55)40(54)32(18-48)65-44)62-25-8-10-45(4)24(13-25)6-7-27-26(45)9-11-46(5)37(23-12-33(51)58-19-23)29(50)17-47(27,46)57/h12,20-22,24-32,34-44,48-50,52-57H,6-11,13-19H2,1-5H3/t20-,21-,22-,24-,25+,26+,27-,28+,29+,30+,31+,32-,34-,35-,36-,37+,38-,39-,40-,41+,42-,43-,44-,45+,46-,47?/m1/s1
• InChI Key: XBTFSPYPZZJUIG-LAFKWZLNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₇H₇₄O₁₉
• Molecular Weight: 943.10 g/mol
• Exact Mass: 942.48243013 g/mol
• Topological Polar Surface Area (TPSA): 282.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): 0.04
• H-Bond Acceptor: 19
• H-Bond Donor: 9
• Rotatable Bonds: 10

Synonyms

• Purpurea glycoside B
• Desacetyllanatoside B
• Lanatoside B, deacetyl-
• Purpureaglykosid B [German]
• Glucogitoxin
• Desacetyl-lanatosid B [German]
• EINECS 243-373-7
• BRN 0078185
• 5-beta-Card-20(22)-enolide, 3-beta-((O-beta-glucopyranosyl-(1-4)-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-beta-dihydroxy-
• Purpureaglykosid B
• Purpurea glycoside B (Glucogitoxin)
• LS-52467

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8285	82.85%
Caco-2	-	0.8869	88.69%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8184	81.84%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9043	90.43%
OATP1B3 inhibitior	+	0.9329	93.29%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8267	82.67%
P-glycoprotein inhibitior	+	0.7450	74.50%
P-glycoprotein substrate	+	0.7981	79.81%
CYP3A4 substrate	+	0.7271	72.71%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9010	90.10%
CYP3A4 inhibition	-	0.9194	91.94%
CYP2C9 inhibition	-	0.9182	91.82%
CYP2C19 inhibition	-	0.9284	92.84%
CYP2D6 inhibition	-	0.9380	93.80%
CYP1A2 inhibition	-	0.9197	91.97%
CYP2C8 inhibition	-	0.5874	58.74%
CYP inhibitory promiscuity	-	0.9237	92.37%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5893	58.93%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.9148	91.48%
Skin irritation	-	0.5142	51.42%
Skin corrosion	-	0.9440	94.40%
Ames mutagenesis	-	0.5570	55.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7746	77.46%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.5965	59.65%
skin sensitisation	-	0.9231	92.31%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.8936	89.36%
Acute Oral Toxicity (c)	I	0.8499	84.99%
Estrogen receptor binding	+	0.8489	84.89%
Androgen receptor binding	+	0.8183	81.83%
Thyroid receptor binding	-	0.5628	56.28%
Glucocorticoid receptor binding	+	0.7161	71.61%
Aromatase binding	+	0.6878	68.78%
PPAR gamma	+	0.7899	78.99%
Honey bee toxicity	-	0.6099	60.99%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9475	94.75%

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	97.87%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.52%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.61%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.53%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.38%	97.25%
CHEMBL220	P22303	Acetylcholinesterase	92.49%	94.45%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.92%	96.21%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.44%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.93%	85.14%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	89.36%	97.33%
CHEMBL2581	P07339	Cathepsin D	89.32%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.38%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.47%	94.45%
CHEMBL1871	P10275	Androgen Receptor	85.74%	96.43%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.69%	94.00%
CHEMBL226	P30542	Adenosine A1 receptor	84.28%	95.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.35%	95.56%
CHEMBL5255	O00206	Toll-like receptor 4	83.26%	92.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.81%	89.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.31%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.25%	92.94%

Plants that contains it

• Digitalis lanata
• Digitalis purpurea

Cross-Links

• PubChem: 197988
• NPASS: NPC53288
• LOTUS: LTS0107429
• wikiData: Q104252838