Digilanide C, deacetyl-

Details

• Internal ID: 161c266e-0beb-486d-b270-9505e3766212
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: 3-[12,14-dihydroxy-3-[4-hydroxy-5-[4-hydroxy-5-[4-hydroxy-6-methyl-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-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)OC2CCC3(C(C2)CCC4C3CC(C5(C4(CCC5C6=CC(=O)OC6)O)C)O)C)O)OC7CC(C(C(O7)C)OC8CC(C(C(O8)C)OC9C(C(C(C(O9)CO)O)O)O)O)O
• SMILES (Isomeric): CC1C(C(CC(O1)OC2CCC3(C(C2)CCC4C3CC(C5(C4(CCC5C6=CC(=O)OC6)O)C)O)C)O)OC7CC(C(C(O7)C)OC8CC(C(C(O8)C)OC9C(C(C(C(O9)CO)O)O)O)O)O
• InChI: InChI=1S/C47H74O19/c1-20-41(64-36-16-30(50)42(21(2)60-36)65-37-17-31(51)43(22(3)61-37)66-44-40(56)39(55)38(54)32(18-48)63-44)29(49)15-35(59-20)62-25-8-10-45(4)24(13-25)6-7-27-28(45)14-33(52)46(5)26(9-11-47(27,46)57)23-12-34(53)58-19-23/h12,20-22,24-33,35-44,48-52,54-57H,6-11,13-19H2,1-5H3
• InChI Key: OBATZBGFDSVCJD-UHFFFAOYSA-N
• Popularity: 1 reference 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: -0.30
• Atomic LogP (AlogP): 0.04
• H-Bond Acceptor: 19
• H-Bond Donor: 9
• Rotatable Bonds: 10

Synonyms

• Deacetyl-lanatoside C
• NCGC00159441-02
• Digilanide C, deacetyl-
• DTXSID30860210
• NSC-7531
• FT-0775994
• 3-{[Hexopyranosyl-(1->4)-2,6-dideoxyhexopyranosyl-(1->4)-2,6-dideoxyhexopyranosyl-(1->4)-2,6-dideoxyhexopyranosyl]oxy}-12,14-dihydroxycard-20(22)-enolide
• 4-(12,14-dihydroxy-3-((4-hydroxy-5-((4-hydroxy-5-((4-hydroxy-6-methyl-5-((3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yl)oxy)tetrahydro-2h-pyran-2-yl)oxy)-6-methyltetrahydro-2h-pyran-2-yl)oxy)-6-methyltetrahydro-2h-pyran-2-yl)oxy)-10,13-dimethylhexadecahydro-1h-cyclopenta[a]phenanthren-17-yl)furan-2(5h)-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8285	82.85%
Caco-2	-	0.8928	89.28%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.8184	81.84%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9392	93.92%
OATP1B3 inhibitior	+	0.9329	93.29%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9224	92.24%
P-glycoprotein inhibitior	+	0.7405	74.05%
P-glycoprotein substrate	+	0.8636	86.36%
CYP3A4 substrate	+	0.6562	65.62%
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	-	0.9124	91.24%
CYP inhibitory promiscuity	-	0.9237	92.37%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5893	58.93%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.9189	91.89%
Skin irritation	-	0.5142	51.42%
Skin corrosion	-	0.9440	94.40%
Ames mutagenesis	-	0.5179	51.79%
Human Ether-a-go-go-Related Gene inhibition	+	0.8939	89.39%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.9231	92.31%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.8759	87.59%
Acute Oral Toxicity (c)	I	0.8499	84.99%
Estrogen receptor binding	+	0.8906	89.06%
Androgen receptor binding	+	0.8503	85.03%
Thyroid receptor binding	-	0.5755	57.55%
Glucocorticoid receptor binding	+	0.7524	75.24%
Aromatase binding	+	0.7708	77.08%
PPAR gamma	+	0.8274	82.74%
Honey bee toxicity	-	0.6604	66.04%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9475	94.75%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293224	P10636	Microtubule-associated protein tau	79.4 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.90%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.18%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.76%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.41%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.32%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.28%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.31%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.71%	95.56%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	87.26%	96.21%
CHEMBL226	P30542	Adenosine A1 receptor	87.22%	95.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.13%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.91%	89.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.27%	96.77%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.13%	96.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.07%	94.33%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.99%	97.36%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.51%	94.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.26%	82.69%
CHEMBL1871	P10275	Androgen Receptor	82.20%	96.43%
CHEMBL2581	P07339	Cathepsin D	81.68%	98.95%
CHEMBL1937	Q92769	Histone deacetylase 2	81.56%	94.75%
CHEMBL5255	O00206	Toll-like receptor 4	81.36%	92.50%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	80.91%	92.32%

Plants that contains it

• Digitalis lanata
• Digitalis purpurea

Cross-Links

• PubChem: 2996
• NPASS: NPC97027
• LOTUS: LTS0219378
• wikiData: Q105188919