3,14-Dihydroxycard-20(22)-enolide
Basic information
- CAS
466-09-1- Standard SMILES
CC12CCC(O)CC1CCC1C2CCC2(C)C(C3=CC(=O)OC3)CCC12O- InChIKey
XZTUSOXSLKTKJQ-UHFFFAOYSA-N- Molecular formula
- C23H34O4
- Average molar mass
- 374.5 g/mol
- Monoisotopic mass
- 374.24570956
Overview
digitoxigenin has been reported in Nerium oleander, Digitalis lanata, and other organisms with data available.
Names & identifiers
- Preferred name
- 3,14-Dihydroxycard-20(22)-enolide
- IUPAC
- 3-(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
- English name
- Uzarigenin
- Molecular formula
- C23H34O4
- Molecular weight
- 374.51
Names & synonyms
3-(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-one3,14-Dihydroxycard-20(22)-enolide3-(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-oneRefChem:269790NSC2772905.alpha.-Card-20(22)-enolide,14-dihydroxy-MLS002701726Card-20(22)-enolide,14-dihydroxy-, (3.beta.,5.alpha.)-NSC4078065alpha-Card-20(22)-enolide,14-dihydroxy-SCHEMBL1152954XZTUSOXSLKTKJQ-UHFFFAOYSA-N
Show more names
OsinUZARIGENINODORIGENIN B3-beta-14-beta-5-allo-cardenolid3β,14-Dihydroxy-5α-card-20(22)-enolideCard-20(22)-enolide,3,14-dihydroxy-, (3b,5a)-Card-20(22)-enolide, 3,14-dihydroxy-, (3β,5α)-3-beta,14-dihydroxy-5-alpha-card-20(22)-enolide
NSC119993NSC224424UZARIGENIN B614014K070AKOS032948827NSC-224424LS-15019NCI60_002256NCI60_003892
Properties
Computed structural properties
- XLogP
- 2.6
- Topological polar surface area
- 66.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 1
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 686
Experimental & physicochemical properties
LogP2.64
Physicochemical properties
- Melting point
- 240 · 240-256°
- alpha
- 20 · D20 +10.5° (c = 1.056 in alc)
- Boiling point
- 549.3 · 549.3±50.0 °C(Predicted)
- Density
- 1.231 · 1.231±0.06 g/cm3(Predicted)
- pka
- 14.93 · 14.93±0.70(Predicted)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 9 ZR7LI283 · K9ZR7LI283
- Toxicity
- 1379 ug/kg · LDLo intravenous in cat: 1379ug/kg
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Toxicity
- LDLo intravenous in cat: 1379ug/kg
Chemistry & industry
Applications
UsesUzarigenin (NSC 119993; NSC 277290; Odorigeni) is a carnolide can be isolated from Pergularia tomentosa and exhibits antiproliferative activity. Uzarigenin resists the proliferation of PC3 cells, HeLa cells, Calu-1 cells, MCF-7 cells and U251MG cells, with IC50 values of 0.3 μM, 3.0 μM, 8.0 μM, 6.0 μM and 6.0 μM respectively[1].
Related reactions
0 records
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Compound notes
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