3,5,14-trihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carboxaldehyde

Details

• Internal ID: 545d3b5e-4744-45db-866a-daec60172174
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives
• IUPAC Name: 3,5,14-trihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
• SMILES (Canonical): CC12CCC3C(C1(CCC2C4=CC(=O)OC4)O)CCC5(C3(CCC(C5)O)C=O)O
• SMILES (Isomeric): CC12CCC3C(C1(CCC2C4=CC(=O)OC4)O)CCC5(C3(CCC(C5)O)C=O)O
• InChI: InChI=1S/C23H32O6/c1-20-6-3-17-18(4-8-22(27)11-15(25)2-7-21(17,22)13-24)23(20,28)9-5-16(20)14-10-19(26)29-12-14/h10,13,15-18,25,27-28H,2-9,11-12H2,1H3
• InChI Key: ODJLBQGVINUMMR-UHFFFAOYSA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₂O₆
• Molecular Weight: 404.50 g/mol
• Exact Mass: 404.21988874 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 0.60

Synonyms

• 3,5,14-trihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
• 3,5,14-Trihydroxy-19-oxocard-20(22)-enolide
• Cymarigenen
• SMR001565512
• Strophantidine
• 3,5,14-trihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carboxaldehyde
• Antibiotic XS-89
• XS-89
• 5.beta.-Hydroxy-19-oxodigitoxigenin
• Strophanthidin, >=90%
• cid_5303
• 3beta,5,14-Trihydroxy-19-oxo-5beta,20(22)-cardenolide
• 5.beta.-Card-20(22)-enolide, 3.beta.,5,14-trihydroxy-19-oxo-
• CHEMBL368773
• BDBM97176
• DTXSID60871536
• CHEBI:131147
• ODJLBQGVINUMMR-UHFFFAOYSA-N
• NCGC00485220-01
• FT-0631291
• BRD-A84066268-001-01-2
• BRD-A84066268-001-02-0
• BRD-A84066268-001-03-8
• Q27224933
• 19-Oxo-cardogenen-(20:22)-triol-(3-.beta.,5,14)
• 3-.beta.,5,14-Trioxy-19-oxo-carden-(20:22)-olid
• 3-.beta.,5,14-Trioxy-19-oxo-digen-(20:22)-olid
• 3.beta.,5,14-Trihydroxy-19-oxo-5.beta.-card-20(22)-enolide
• Card-20(22)-enolide, 3,5,14-trihydroxy-19-oxo-, (3.beta.,5.beta.)-
• 13-methyl-3,5,14-tris(oxidanyl)-17-(5-oxidanylidene-2H-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
• 3,5,14-trihydroxy-17-(5-keto-2H-furan-3-yl)-13-methyl-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4096	P04637	Cellular tumor antigen p53	501.2 nM; 501.2 nM	Potency; Potency	via Super-PRED; via Super-PRED
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	501.2 nM	Potency	via Super-PRED
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	25.1 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1994	P08235	Mineralocorticoid receptor	95.91%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.88%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.88%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.04%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.25%	94.45%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	91.80%	82.69%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.15%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.80%	97.09%
CHEMBL4208	P20618	Proteasome component C5	85.73%	90.00%
CHEMBL1871	P10275	Androgen Receptor	85.31%	96.43%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.26%	95.89%
CHEMBL3492	P49721	Proteasome Macropain subunit	83.95%	90.24%
CHEMBL2581	P07339	Cathepsin D	82.15%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.69%	97.25%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.59%	93.40%
CHEMBL226	P30542	Adenosine A1 receptor	81.54%	95.93%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.39%	93.04%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.24%	97.14%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.86%	97.28%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	80.43%	94.78%

Plants that contains it

• Adonis aestivalis
• Antiaris toxicaria
• Apocynum androsaemifolium
• Corchorus capsularis
• Corchorus olitorius
• Descurainia sophia
• Erysimum cheiranthoides
• Erysimum leptophyllum
• Erysimum pulchellum

Cross-Links

• PubChem: 5303
• LOTUS: LTS0262470
• wikiData: Q27224933