Digitalin

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	d7467238-08ca-4b81-89f3-b4ddd37d5e41
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,14S,16S,17R)-14,16-dihydroxy-3-[(2R,3R,4R,5S,6R)-3-hydroxy-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-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(C(C(O1)OC2CCC3(C(C2)CCC4C3CCC5(C4(CC(C5C6=CC(=O)OC6)O)O)C)C)O)OC)OC7C(C(C(C(O7)CO)O)O)O
SMILES (Isomeric)	C[C@@H]1[C@@H]([C@@H]([C@H]([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)OC)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O
InChI	InChI=1S/C36H56O14/c1-16-30(50-32-28(42)27(41)26(40)23(14-37)49-32)31(45-4)29(43)33(47-16)48-19-7-9-34(2)18(12-19)5-6-21-20(34)8-10-35(3)25(17-11-24(39)46-15-17)22(38)13-36(21,35)44/h11,16,18-23,25-33,37-38,40-44H,5-10,12-15H2,1-4H3/t16-,18-,19+,20+,21-,22+,23-,25+,26-,27+,28-,29-,30+,31-,32+,33+,34+,35-,36+/m1/s1
InChI Key	CKNOLMVLQUPVMU-YMMLYESFSA-N
Popularity	723 references in papers

Physical and Chemical Properties

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Molecular Formula	C₃₆H₅₆O₁₄
Molecular Weight	712.80 g/mol
Exact Mass	712.36700646 g/mol
Topological Polar Surface Area (TPSA)	214.00 Å²
XlogP	-0.30
Atomic LogP (AlogP)	-0.09
H-Bond Acceptor	14
H-Bond Donor	7
Rotatable Bonds	7

Synonyms

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Glucostrospeside

Diginorgin

Digitalum verum

Digitalinum true

752-61-4

Digitalin (glycoside)

Schmiedebergs digitalin

Gitoxigenin-glucodigitalosid

UNII-Q15ECE254B

Q15ECE254B

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8177	81.77%
Caco-2	-	0.8845	88.45%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7900	79.00%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9043	90.43%
OATP1B3 inhibitior	+	0.9487	94.87%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.4859	48.59%
P-glycoprotein inhibitior	+	0.7064	70.64%
P-glycoprotein substrate	+	0.6936	69.36%
CYP3A4 substrate	+	0.7322	73.22%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9002	90.02%
CYP3A4 inhibition	-	0.9358	93.58%
CYP2C9 inhibition	-	0.9140	91.40%
CYP2C19 inhibition	-	0.9183	91.83%
CYP2D6 inhibition	-	0.9397	93.97%
CYP1A2 inhibition	-	0.9208	92.08%
CYP2C8 inhibition	+	0.4494	44.94%
CYP inhibitory promiscuity	-	0.9347	93.47%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5835	58.35%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9255	92.55%
Skin irritation	-	0.5686	56.86%
Skin corrosion	-	0.9432	94.32%
Ames mutagenesis	-	0.6293	62.93%
Human Ether-a-go-go-Related Gene inhibition	+	0.8000	80.00%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.6266	62.66%
skin sensitisation	-	0.9154	91.54%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.8521	85.21%
Acute Oral Toxicity (c)	I	0.7685	76.85%
Estrogen receptor binding	+	0.7873	78.73%
Androgen receptor binding	+	0.8082	80.82%
Thyroid receptor binding	-	0.7002	70.02%
Glucocorticoid receptor binding	+	0.6087	60.87%
Aromatase binding	+	0.6936	69.36%
PPAR gamma	+	0.6914	69.14%
Honey bee toxicity	-	0.6112	61.12%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9043	90.43%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
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	98.41%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.37%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.31%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.61%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.99%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.77%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.76%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.42%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.29%	95.89%
CHEMBL2581	P07339	Cathepsin D	88.60%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.00%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.39%	95.56%
CHEMBL1871	P10275	Androgen Receptor	85.21%	96.43%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.58%	89.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	84.34%	97.36%
CHEMBL1937	Q92769	Histone deacetylase 2	84.02%	94.75%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.65%	92.94%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.15%	96.21%
CHEMBL226	P30542	Adenosine A1 receptor	82.24%	95.93%
CHEMBL5255	O00206	Toll-like receptor 4	81.51%	92.50%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.87%	93.04%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.73%	100.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.29%	96.00%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Aconitum brevicalcaratum

Ammodendron conollyi

Begonia glabra

Cirsium dipsacolepis

Cocculus diversifolius

Cordyline fruticosa

Crinum kirkii

Cryptostegia grandiflora

Cytisus scoparius

Digitalis purpurea

Erysimum repandum

Heliomeris longifolia var. annua