Lanatoside B

Details

• Internal ID: 63ec9cca-8c84-4e8a-bfd2-42bc918276c5
• 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,13R,14S,16S,17R)-14,16-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-2-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-4-yl] acetate
• SMILES (Canonical): CC1C(C(CC(O1)OC2CCC3(C(C2)CCC4C3CCC5(C4(CC(C5C6=CC(=O)OC6)O)O)C)C)O)OC7CC(C(C(O7)C)OC8CC(C(C(O8)C)OC9C(C(C(C(O9)CO)O)O)O)OC(=O)C)O
• SMILES (Isomeric): C[C@@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2CC[C@]3([C@@H](C2)CC[C@@H]4[C@@H]3CC[C@]5([C@@]4(C[C@@H]([C@@H]5C6=CC(=O)OC6)O)O)C)C)O)O[C@H]7C[C@@H]([C@@H]([C@H](O7)C)O[C@H]8C[C@@H]([C@@H]([C@H](O8)C)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)OC(=O)C)O
• InChI: InChI=1S/C49H76O20/c1-21-43(67-37-16-31(53)44(22(2)62-37)68-38-17-33(64-24(4)51)45(23(3)63-38)69-46-42(58)41(57)40(56)34(19-50)66-46)30(52)15-36(61-21)65-27-9-11-47(5)26(14-27)7-8-29-28(47)10-12-48(6)39(25-13-35(55)60-20-25)32(54)18-49(29,48)59/h13,21-23,26-34,36-46,50,52-54,56-59H,7-12,14-20H2,1-6H3/t21-,22-,23-,26-,27+,28+,29-,30+,31+,32+,33+,34-,36+,37+,38+,39+,40-,41+,42-,43-,44-,45-,46+,47+,48-,49+/m1/s1
• InChI Key: XVAPNQFQPDAROQ-CAPSWCROSA-N
• Popularity: 30 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₉H₇₆O₂₀
• Molecular Weight: 985.10 g/mol
• Exact Mass: 984.49299481 g/mol
• Topological Polar Surface Area (TPSA): 288.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 0.61
• H-Bond Acceptor: 20
• H-Bond Donor: 8
• Rotatable Bonds: 11

Synonyms

• Digilanide B
• Digilanid B
• 17575-21-2
• Lanatosid B [German]
• NSC 7535
• EINECS 241-545-6
• BRN 0078394
• Lanatosid B
• UNII-3822U6I4Z0
• 3822U6I4Z0
• 3-((O-beta-D-Glucopyranosyl-(1-4)-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)-14,16-dihydroxycard-20(22)-enolide (3beta,5beta,16beta)-
• Card-20(22)-enolide, 3-((O-beta-D-glucopyranosyl-(1-4)-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)-14,16-dihydroxy-, (3beta,5beta,16beta)-
• 5-18-04-00388 (Beilstein Handbook Reference)
• NSC-7535
• LANATOSIDE B [MI]
• (3beta,5beta,16beta)-3-{[beta-D-glucopyranosyl-(1->4)-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
• Card-20(22)-enolide, 3-[(O-.beta.-D-glucopyranosyl-(1.fwdarw.4)-O-3-O-acetyl-2,6-dideoxy-.beta.-D-ribo-hexopyranosyl-(1.fwdarw.4)-O-2,6-dideoxy-.beta.-D-ribo-hexopyranosyl-(1.fwdarw.4)-2,6-dideoxy-.beta.-D-ribo-hexopyranosyl)oxy]-14,16-dihydroxy-, (3.beta.,5.beta.,16.beta.)-
• MFCD00016800
• STL565780
• AKOS032437831
• LS-87551
• Q27256727

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8036	80.36%
Caco-2	-	0.8791	87.91%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8375	83.75%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9171	91.71%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9502	95.02%
P-glycoprotein inhibitior	+	0.7438	74.38%
P-glycoprotein substrate	+	0.7971	79.71%
CYP3A4 substrate	+	0.7354	73.54%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9029	90.29%
CYP3A4 inhibition	-	0.8550	85.50%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9340	93.40%
CYP2D6 inhibition	-	0.9458	94.58%
CYP1A2 inhibition	-	0.9232	92.32%
CYP2C8 inhibition	+	0.4466	44.66%
CYP inhibitory promiscuity	-	0.9425	94.25%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5614	56.14%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9088	90.88%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9387	93.87%
Ames mutagenesis	-	0.5093	50.93%
Human Ether-a-go-go-Related Gene inhibition	+	0.8436	84.36%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.5641	56.41%
skin sensitisation	-	0.9286	92.86%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.8558	85.58%
Acute Oral Toxicity (c)	I	0.8759	87.59%
Estrogen receptor binding	+	0.8905	89.05%
Androgen receptor binding	+	0.8112	81.12%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.7780	77.80%
Aromatase binding	+	0.7084	70.84%
PPAR gamma	+	0.8708	87.08%
Honey bee toxicity	-	0.5993	59.93%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9628	96.28%

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	98.53%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.50%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.00%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.83%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.97%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.64%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.27%	86.33%
CHEMBL2581	P07339	Cathepsin D	90.29%	98.95%
CHEMBL220	P22303	Acetylcholinesterase	89.28%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.20%	97.25%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	87.94%	94.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.39%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.09%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.73%	94.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.57%	94.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.99%	96.21%
CHEMBL5255	O00206	Toll-like receptor 4	84.89%	92.50%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	83.42%	94.62%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	83.18%	97.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.31%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.78%	95.56%
CHEMBL5028	O14672	ADAM10	81.61%	97.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.18%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	80.10%	91.19%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.09%	96.77%

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: 72604
• NPASS: NPC60056
• LOTUS: LTS0146711
• wikiData: Q27256727