(3alpha,5beta,12beta)-3,12,14-Trihydroxycard-20(22)-enolide

Details

• Internal ID: 6ca5cba9-b19d-4fec-a807-43a739942b5c
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives
• IUPAC Name: 3-(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): CC12CCC(CC1CCC3C2CC(C4(C3(CCC4C5=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
• InChI Key: SHIBSTMRCDJXLN-UHFFFAOYSA-N
• Popularity: 1 reference 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

Synonyms

• (3alpha,5beta,12beta)-3,12,14-Trihydroxycard-20(22)-enolide
• 465-14-5
• Spectrum_000743
• SpecPlus_000208
• 3,12,14-Trihydroxycard-20(22)-enolide
• Spectrum4_001416
• Spectrum5_000212
• KBioGR_001832
• KBioSS_001223
• DivK1c_006304
• SCHEMBL4994463
• KBio1_001248
• KBio2_001223
• KBio2_003791
• KBio2_006359
• DTXSID30859669
• CHEBI:181806
• SHIBSTMRCDJXLN-UHFFFAOYSA-N
• AKOS025247981
• 3-(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
• VS-12310
• FT-0603569
• SW197220-3
• 3-.beta.,12,14-Trioxy-carden-(20:22)-olid
• 3-.beta.,12,14-Trioxy-digen-(20:22)-olid
• Cardogenen-(20:22)-triol-(3.beta.,12,14)
• 3-.beta.,12-.beta.,14-Trihydroxy-card-20(22)-enolide
• 3,12,14-Trihydroxycard-20(22)-enolide-, (3.beta.,12.beta.)-
• 5-.beta.-Card-20(22)-enolide, 3-.beta.,12-.beta.,14-trihydroxy-
• .delta.(20:22)-3-.beta.,12-.beta.,14,21-Tetrahydroxynorcholenic acid lactone
• Card-20(22)-enolide, 3,12,14-trihydroxy-, (3.beta.,5.beta.,12.beta.)-
• 3-(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-uran-5-one

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	631 nM	Potency	via Super-PRED
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	15.8 nM	Potency	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	223.9 nM	Potency	via Super-PRED
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	0.1 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	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

• Asclepias syriaca

Cross-Links

• PubChem: 608640
• LOTUS: LTS0204440
• wikiData: Q105252990