Purpurea glycoside A

Details

• Internal ID: 6ebb4591-46ce-4d18-8d79-c2a413b1897f
• 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,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-hydroxy-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(CCC8C9=CC(=O)OC9)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(CC[C@@H]8C9=CC(=O)OC9)O)C)C)C)O)O
• InChI: InChI=1S/C47H74O18/c1-21-38(51)30(49)16-35(58-21)65-43-23(3)60-36(18-32(43)62-37-17-31(39(52)22(2)59-37)63-44-42(55)41(54)40(53)33(19-48)64-44)61-26-8-11-45(4)25(15-26)6-7-29-28(45)9-12-46(5)27(10-13-47(29,46)56)24-14-34(50)57-20-24/h14,21-23,25-33,35-44,48-49,51-56H,6-13,15-20H2,1-5H3/t21-,22-,23-,25-,26+,27-,28+,29-,30+,31+,32+,33-,35-,36-,37-,38-,39-,40-,41+,42-,43-,44-,45+,46-,47?/m1/s1
• InChI Key: WJOCFXCSQDOQQR-MIKBVDKDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₇H₇₄O₁₈
• Molecular Weight: 927.10 g/mol
• Exact Mass: 926.48751551 g/mol
• Topological Polar Surface Area (TPSA): 262.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.07
• H-Bond Acceptor: 18
• H-Bond Donor: 8
• Rotatable Bonds: 10

Synonyms

• Purpureaglykosid A [German]
• Desacetyldigilanide A
• Lanatoside A, deacetyl-
• Glucodigitoxin
• Desacetyl-lanatosid A [German]
• EINECS 243-374-2
• BRN 0078127
• Purpureaglykosid A
• Desacetyl-lanatosid A
• 5-beta-Card-20(22)-enolide, 3-beta-((O-beta-D-glucopyranosyl-(1-4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-4)-O-2,6-dideoxy-beta-D-hexopyranosyl-(1-4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy)-14-hydroxy-
• Purpurea glycoside A (Glucodigitoxin)
• LS-52468

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8285	82.85%
Caco-2	-	0.8866	88.66%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8184	81.84%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9113	91.13%
OATP1B3 inhibitior	+	0.9329	93.29%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8462	84.62%
P-glycoprotein inhibitior	+	0.7457	74.57%
P-glycoprotein substrate	+	0.8382	83.82%
CYP3A4 substrate	+	0.7135	71.35%
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	-	0.6711	67.11%
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	-	0.9169	91.69%
Skin irritation	-	0.5142	51.42%
Skin corrosion	-	0.9440	94.40%
Ames mutagenesis	-	0.6224	62.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.7989	79.89%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.7700	77.00%
skin sensitisation	-	0.9231	92.31%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.9078	90.78%
Acute Oral Toxicity (c)	I	0.8499	84.99%
Estrogen receptor binding	+	0.8413	84.13%
Androgen receptor binding	+	0.8382	83.82%
Thyroid receptor binding	-	0.5768	57.68%
Glucocorticoid receptor binding	+	0.6994	69.94%
Aromatase binding	+	0.7051	70.51%
PPAR gamma	+	0.7828	78.28%
Honey bee toxicity	-	0.6191	61.91%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.63%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.11%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.60%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.09%	97.09%
CHEMBL4040	P28482	MAP kinase ERK2	94.51%	83.82%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.05%	85.14%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	90.80%	96.21%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.28%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.89%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.33%	94.45%
CHEMBL2581	P07339	Cathepsin D	87.70%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	87.14%	95.93%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.97%	94.00%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	86.66%	97.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.58%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.99%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.61%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.46%	92.94%
CHEMBL5255	O00206	Toll-like receptor 4	83.66%	92.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.73%	94.33%
CHEMBL1871	P10275	Androgen Receptor	82.71%	96.43%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.05%	96.77%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.09%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.07%	89.00%

Plants that contains it

• Digitalis ciliata
• Digitalis lanata
• Digitalis obscura
• Digitalis purpurea

Cross-Links

• PubChem: 197989
• NPASS: NPC55777
• LOTUS: LTS0038112
• wikiData: Q104252835