3-[(3S,5R,10S,13R,14S,17R)-3-[(2R,5S)-3,5-dihydroxy-4-methoxy-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

Details

• Internal ID: feb1eb80-86fd-45f9-a6aa-992594a550ca
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: 3-[(3S,5R,10S,13R,14S,17R)-3-[(2R,5S)-3,5-dihydroxy-4-methoxy-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(C(C(O1)OC2CCC3(C(C2)CCC4C3CCC5(C4(CC(C5C6=CC(=O)OC6)O)O)C)C)O)OC)O
• SMILES (Isomeric): CC1[C@@H](C(C([C@@H](O1)O[C@H]2CC[C@]3([C@@H](C2)CCC4C3CC[C@]5([C@@]4(CC([C@@H]5C6=CC(=O)OC6)O)O)C)C)O)OC)O
• InChI: InChI=1S/C30H46O9/c1-15-24(33)26(36-4)25(34)27(38-15)39-18-7-9-28(2)17(12-18)5-6-20-19(28)8-10-29(3)23(16-11-22(32)37-14-16)21(31)13-30(20,29)35/h11,15,17-21,23-27,31,33-35H,5-10,12-14H2,1-4H3/t15?,17-,18+,19?,20?,21?,23+,24+,25?,26?,27+,28+,29-,30+/m1/s1
• InChI Key: CPFNIKYEDJFRAT-RHZHZRSRSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₆O₉
• Molecular Weight: 550.70 g/mol
• Exact Mass: 550.31418304 g/mol
• Topological Polar Surface Area (TPSA): 135.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 2.08
• H-Bond Acceptor: 9
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

• Strospesid [German]
• 595-21-1
• Gitoxogenin-D-digitalosid [German]
• Desgluco-digitalinum verum [German]
• EINECS 209-859-8
• DTXSID90974903
• 3-[(6-deoxy-3-O-methylhexopyranosyl)oxy]-14,16-dihydroxycard-20(22)-enolide
• 5-beta-Card-20(22)-enolide, 3-beta-((6-deoxy-3-O-methyl-D-galactopyranosyl)oxy)-14,16-dihydroxy-
• LS-52333

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9583	95.83%
Caco-2	-	0.8297	82.97%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7896	78.96%
OATP2B1 inhibitior	-	0.5936	59.36%
OATP1B1 inhibitior	+	0.9289	92.89%
OATP1B3 inhibitior	+	0.9683	96.83%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6013	60.13%
P-glycoprotein inhibitior	-	0.4437	44.37%
P-glycoprotein substrate	+	0.7580	75.80%
CYP3A4 substrate	+	0.7219	72.19%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9037	90.37%
CYP3A4 inhibition	-	0.8949	89.49%
CYP2C9 inhibition	-	0.9092	90.92%
CYP2C19 inhibition	-	0.9351	93.51%
CYP2D6 inhibition	-	0.9376	93.76%
CYP1A2 inhibition	-	0.9214	92.14%
CYP2C8 inhibition	-	0.6983	69.83%
CYP inhibitory promiscuity	-	0.8900	89.00%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5406	54.06%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9376	93.76%
Skin irritation	-	0.5363	53.63%
Skin corrosion	-	0.9392	93.92%
Ames mutagenesis	-	0.6193	61.93%
Human Ether-a-go-go-Related Gene inhibition	+	0.7311	73.11%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.6942	69.42%
skin sensitisation	-	0.9064	90.64%
Respiratory toxicity	+	0.9111	91.11%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.8029	80.29%
Acute Oral Toxicity (c)	I	0.7811	78.11%
Estrogen receptor binding	+	0.7363	73.63%
Androgen receptor binding	+	0.8015	80.15%
Thyroid receptor binding	-	0.6247	62.47%
Glucocorticoid receptor binding	+	0.6949	69.49%
Aromatase binding	+	0.6915	69.15%
PPAR gamma	+	0.5465	54.65%
Honey bee toxicity	-	0.6558	65.58%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.9474	94.74%

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	97.42%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.37%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.21%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.10%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.80%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.08%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.37%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.51%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.24%	95.89%
CHEMBL1871	P10275	Androgen Receptor	89.32%	96.43%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.94%	92.94%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.07%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.88%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.13%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.12%	89.00%
CHEMBL2581	P07339	Cathepsin D	85.34%	98.95%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.11%	82.69%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.97%	99.23%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	81.31%	94.78%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.15%	93.04%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.60%	91.07%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.59%	97.36%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.54%	97.14%
CHEMBL5255	O00206	Toll-like receptor 4	80.28%	92.50%

Plants that contains it

• Digitalis lanata
• Digitalis purpurea

Cross-Links

• PubChem: 11680
• NPASS: NPC143309