Digoxigenin

Details

• Internal ID: 26ae823d-c434-46ee-8c9d-88ad843d681a
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives
• IUPAC Name: 3-[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-3,12,14-trihydroxy-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(CC1CCC3C2CC(C4(C3(CCC4C5=CC(=O)OC5)O)C)O)O
• SMILES (Isomeric): C[C@]12CC[C@@H](C[C@H]1CC[C@@H]3[C@@H]2C[C@H]([C@]4([C@@]3(CC[C@@H]4C5=CC(=O)OC5)O)C)O)O
• InChI: InChI=1S/C23H34O5/c1-21-7-5-15(24)10-14(21)3-4-17-18(21)11-19(25)22(2)16(6-8-23(17,22)27)13-9-20(26)28-12-13/h9,14-19,24-25,27H,3-8,10-12H2,1-2H3/t14-,15+,16-,17-,18+,19-,21+,22+,23+/m1/s1
• InChI Key: SHIBSTMRCDJXLN-KCZCNTNESA-N
• Popularity: 10,238 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₄O₅
• Molecular Weight: 390.50 g/mol
• Exact Mass: 390.24062418 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 2.58
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• 1672-46-4
• Lanadigenin
• Digoxigenine
• CHEBI:42098
• HSDB 7108
• NQ1SX9LNAU
• UNII-NQ1SX9LNAU
• EINECS 216-806-2
• BRN 0096479
• DTXSID6051778
• Card-20(22)-enolide, 3,12,14-trihydroxy-, (3beta,5beta,12beta)-
• 3-beta,12-beta,14-Trihydroxy-card-20(22)-enolide
• 3-beta,12,14-Trioxy-digen-(20:22)-olid [German]
• 3-beta,12,14-Trioxy-carden-(20:22)-olid [German]
• 3beta,12beta,14-Trihydroxy-5beta,20(22)-cardenolide
• Cardogenen-(20:22)-triol-(3-beta,12,14) [German]
• (3beta,5beta,12beta)-3,12,14-Trihydroxycard-20(22)-enolide
• 3-beta,12,14-Trioxy-carden-(20:22)-olid
• 3-beta,12,14-Trioxy-digen-(20:22)-olid
• delta-sup(20:22)-3-beta,12-beta,14,21-Tetrahydroxynorcholenic acid lactone
• 3-[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-3,12,14-trihydroxy-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
• 4-((3S,5R,8R,9S,10S,12R,13S,14S,17R)-3,12,14-trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)furan-2(5H)-one
• 5-18-04-00380 (Beilstein Handbook Reference)
• CARDOGENEN-(20:22)-TRIOL-(3-beta,12,14)
• 3beta,12beta,14-trihydroxy-5beta-card-20(22)-enolide
• Card-20(22)-enolide, 3,12,14-trihydroxy-, (3ss,5ss,12ss)-
• 3beta,12beta,14beta,21-Tetrahydroxy-20(22)-norcholenic acid lactone
• 5-beta-CARD-20(22)-ENOLIDE, 3-beta,12-beta,14-TRIHYDROXY-
• Card-20(22)-enolide, 3,12,14-trihydroxy-, (3-beta,5-beta,12-beta)-
• SR-01000841253
• Lanadigigenin
• 1lke
• CAS-1672-46-4
• 4j8t
• 4j9a
• DIGOXIGENIN [MI]
• Prestwick0_000883
• Prestwick1_000883
• Prestwick2_000883
• Prestwick3_000883
• DIGOXIGENIN [HSDB]
• bmse000735
• Epitope ID:180303
• CHEMBL1153
• SCHEMBL21105
• BSPBio_000666
• MLS002154050
• SPBio_002885
• BPBio1_000734
• Digoxigenin, analytical standard
• DTXCID9030333
• Card-20(22)-enolide, 3,12,14-trihydroxy-, (3.beta.,5.beta.,12.beta.)-
• SHIBSTMRCDJXLN-KCZCNTNESA-N
• BDBM225707
• CS337
• HMS1570B08
• HMS2097B08
• HMS2233P09
• HMS3714B08
• HY-B1025
• Tox21_303893
• LMST01120008
• AKOS015915909
• CCG-220883
• CS-4542
• DB03671
• DIGOXIN IMPURITY C [EP IMPURITY]
• NCGC00017309-03
• NCGC00142481-02
• NCGC00357149-01
• AS-79043
• LS-52505
• SMR001233370
• AB00513944
• F85214
• AB00513944_05
• A937306
• Q420728
• 5beta,20(22)-Cardenolide-3beta,12beta,14-triol
• J-010346
• SR-01000841253-2
• SR-01000841253-3
• BRD-K18619710-001-03-7
• Digoxigenin, European Pharmacopoeia (EP) Reference Standard
• (3-beta,5-beta,12-beta)-3,12,14-Trihydroxycard-20(22)-enolide
• 5.beta.-Card-20(22)-enolide, 3.beta.,12.beta.,14-trihydroxy-
• Card-20(22)-enolida, 3,12,14-trihidroxi-, (3?,5?,12?)-
• 3.BETA.,12.BETA.,14-TRIHYDROXY-5.BETA.-CARD-20(22)-ENOLIDE
• Card-20(22)-enolide, 3,12,14-trihydroxy-, (3.beta.,5.beta,12.beta.)-
• delta-20:22-3-beta,12-beta,14,21-tetrahydroxynorcholenic acid lactone
• delta-20:22-3beta,12beta,14,21-tetrahydroxynorcholenic acid lactone
• 4-((3S,8R,9S,10S,12R,13S,14S,17R)-3,12,14-trihydroxy-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	+	0.9875	98.75%
Caco-2	-	0.5413	54.13%
Blood Brain Barrier	-	0.6189	61.89%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8004	80.04%
OATP2B1 inhibitior	-	0.7268	72.68%
OATP1B1 inhibitior	+	0.9350	93.50%
OATP1B3 inhibitior	+	0.9615	96.15%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7493	74.93%
BSEP inhibitior	+	0.8186	81.86%
P-glycoprotein inhibitior	-	0.8715	87.15%
P-glycoprotein substrate	+	0.9249	92.49%
CYP3A4 substrate	+	0.6476	64.76%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9060	90.60%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	-	0.9099	90.99%
CYP2C19 inhibition	-	0.9256	92.56%
CYP2D6 inhibition	-	0.9362	93.62%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	-	0.9460	94.60%
CYP inhibitory promiscuity	-	0.8702	87.02%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5443	54.43%
Eye corrosion	-	0.9913	99.13%
Eye irritation	-	0.9557	95.57%
Skin irritation	-	0.5181	51.81%
Skin corrosion	-	0.9360	93.60%
Ames mutagenesis	-	0.5449	54.49%
Human Ether-a-go-go-Related Gene inhibition	-	0.4793	47.93%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.5123	51.23%
skin sensitisation	-	0.8828	88.28%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.6568	65.68%
Acute Oral Toxicity (c)	I	0.5853	58.53%
Estrogen receptor binding	+	0.9076	90.76%
Androgen receptor binding	+	0.8387	83.87%
Thyroid receptor binding	+	0.5645	56.45%
Glucocorticoid receptor binding	+	0.8547	85.47%
Aromatase binding	+	0.7212	72.12%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.8085	80.85%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9889	98.89%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4096	P04637	Cellular tumor antigen p53	1995.3 nM; 631 nM; 631 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via Super-PRED
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	15.8 nM	Potency	via Super-PRED
CHEMBL1293277	O15118	Niemann-Pick C1 protein	3981.1 nM	Potency	via CMAUP
CHEMBL2362980	Q06710	Paired box protein Pax-8	2350 nM	AC50	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	223.9 nM	Potency	via Super-PRED
CHEMBL1293294	P51151	Ras-related protein Rab-9A	2511.9 nM	Potency	via CMAUP
CHEMBL2073690	Q6ZQN7	Solute carrier organic anion transporter family member 4C1	490 nM	IC50	PMID: 14993604
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	0.1 nM; 0.1 nM	Potency; Potency	via Super-PRED; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.01%	91.11%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	95.08%	82.69%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.07%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.59%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.04%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.63%	97.09%
CHEMBL1871	P10275	Androgen Receptor	89.38%	96.43%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.97%	94.45%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.98%	96.77%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.73%	93.04%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.21%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.91%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.51%	86.33%
CHEMBL3038469	P24941	CDK2/Cyclin A	81.62%	91.38%

Plants that contains it

• Digitalis lanata
• Digitalis purpurea

Cross-Links

• PubChem: 15478
• NPASS: NPC189588
• ChEMBL: CHEMBL1153
• LOTUS: LTS0074709
• wikiData: Q420728