Digitoxigenin

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	4d1ac629-1fae-4e9d-a9fa-9a40bfd8fea1
Taxonomy	Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives
IUPAC Name	3-[(3S,5R,8R,9S,10S,13R,14S,17R)-3,14-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)	CC12CCC(CC1CCC3C2CCC4(C3(CCC4C5=CC(=O)OC5)O)C)O
SMILES (Isomeric)	C[C@]12CC[C@@H](C[C@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@@]3(CC[C@@H]4C5=CC(=O)OC5)O)C)O
InChI	InChI=1S/C23H34O4/c1-21-8-5-16(24)12-15(21)3-4-19-18(21)6-9-22(2)17(7-10-23(19,22)26)14-11-20(25)27-13-14/h11,15-19,24,26H,3-10,12-13H2,1-2H3/t15-,16+,17-,18+,19-,21+,22-,23+/m1/s1
InChI Key	XZTUSOXSLKTKJQ-CESUGQOBSA-N
Popularity	1,540 references in papers

Physical and Chemical Properties

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Molecular Formula	C₂₃H₃₄O₄
Molecular Weight	374.50 g/mol
Exact Mass	374.24570956 g/mol
Topological Polar Surface Area (TPSA)	66.80 Å²
XlogP	2.60
Atomic LogP (AlogP)	3.60
H-Bond Acceptor	4
H-Bond Donor	2
Rotatable Bonds	1

Synonyms

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143-62-4

Cerberigenin

Echujetin

Thevetigenin

Evonogenin

Digitoxigenine

MLS002153810

3-[(3S,5R,8R,9S,10S,13R,14S,17R)-3,14-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

UNII-S63WOD4VOL

S63WOD4VOL

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	+	0.9945	99.45%
Caco-2	+	0.5900	59.00%
Blood Brain Barrier	-	0.6645	66.45%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8605	86.05%
OATP2B1 inhibitior	-	0.7300	73.00%
OATP1B1 inhibitior	+	0.9251	92.51%
OATP1B3 inhibitior	+	0.9667	96.67%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6493	64.93%
BSEP inhibitior	+	0.8300	83.00%
P-glycoprotein inhibitior	-	0.8811	88.11%
P-glycoprotein substrate	+	0.7446	74.46%
CYP3A4 substrate	+	0.6852	68.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9060	90.60%
CYP3A4 inhibition	-	0.6717	67.17%
CYP2C9 inhibition	-	0.9355	93.55%
CYP2C19 inhibition	-	0.9237	92.37%
CYP2D6 inhibition	-	0.9253	92.53%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.8743	87.43%
CYP inhibitory promiscuity	-	0.8681	86.81%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5341	53.41%
Eye corrosion	-	0.9925	99.25%
Eye irritation	-	0.9561	95.61%
Skin irritation	-	0.5148	51.48%
Skin corrosion	-	0.9425	94.25%
Ames mutagenesis	-	0.6424	64.24%
Human Ether-a-go-go-Related Gene inhibition	-	0.4684	46.84%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.5127	51.27%
skin sensitisation	-	0.8671	86.71%
Respiratory toxicity	+	0.9222	92.22%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.6990	69.90%
Acute Oral Toxicity (c)	III	0.4005	40.05%
Estrogen receptor binding	+	0.9180	91.80%
Androgen receptor binding	+	0.8593	85.93%
Thyroid receptor binding	+	0.5761	57.61%
Glucocorticoid receptor binding	+	0.8863	88.63%
Aromatase binding	+	0.7039	70.39%
PPAR gamma	-	0.5323	53.23%
Honey bee toxicity	-	0.7636	76.36%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9922	99.22%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4096	P04637	Cellular tumor antigen p53	158.5 nM	Potency	via Super-PRED
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	251.2 nM	Potency	via Super-PRED
CHEMBL1293277	O15118	Niemann-Pick C1 protein	1258.9 nM	Potency	via CMAUP
CHEMBL2362980	Q06710	Paired box protein Pax-8	1380 nM	AC50	via CMAUP
CHEMBL2933	P54707	Potassium-transporting ATPase alpha chain 2	80 nM	IC50	PMID: 9685243
CHEMBL1293235	P02545	Prelamin-A/C	17.8 nM	Potency	via Super-PRED
CHEMBL1293294	P51151	Ras-related protein Rab-9A	1258.9 nM	Potency	via CMAUP
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	794.3 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	95.90%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.56%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	94.85%	82.69%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.07%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.03%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.23%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.62%	97.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.22%	96.77%
CHEMBL1871	P10275	Androgen Receptor	88.42%	96.43%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	87.15%	93.04%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.00%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.50%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.50%	99.23%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	82.81%	81.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.89%	97.25%

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

Angelica archangelica

Asclepias curassavica

Beaumontia grandiflora

Calotropis gigantea

Cirsium dipsacolepis

Cocculus diversifolius

Crinum kirkii

Cryptostegia madagascariensis

Cytisus scoparius

Digitalis ciliata