4-[(1S,2S,5S,7R,10R,11S,14R,15R)-5,11-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2,5-dihydrofuran-2-one

• ChemBase ID: 107780
• Molecular Formular: C23H34O4
• Molecular Mass: 374.51366
• Monoisotopic Mass: 374.24570957
• SMILES: C[C@]12CC[C@H](O)C[C@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@H](CC[C@]12O)C1=CC(=O)OC1
• Canonical SMILES: O[C@H]1CC[C@]2([C@@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@]1(O)CC[C@@H]2C1=CC(=O)OC1)C)C
• 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
• InChIKey: XZTUSOXSLKTKJQ-CESUGQOBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1S,2S,5S,7R,10R,11S,14R,15R)-5,11-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2,5-dihydrofuran-2-one; 4-[(1S,2S,5S,7R,10R,11S,14R,15R)-5,11-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]-2,5-dihydrofuran-2-one
• IUPAC Traditional name: 4-[(1S,2S,5S,7R,10R,11S,14R,15R)-5,11-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]-2,5-dihydrofuran-2-one; digitoxigenin
• Synonyms: 3β,14-Dihydroxy-5β,20(22)-cardenolide; 3,14,21-Trihydroxy-20(22)-norcholenic acid lactone; 5β,20(22)-Cardenolide-3β,14-diol; Digitoxigenin; (+)-Digitoxigenin; Thevetigenin; Cerberigenin; Echujetin; DIGITOXIGENIN; Digitoxigenin; 洋地黄毒苷配基; (+)-毛地黄毒苷配基; 3,14,21-三羟基-20(22)-去甲胆烯酸内酯; 3β,14-二羟基-5β,20(22)-卡烯内酯; 5β,20(22)-卡烯内酯-3β,14-二醇; 洋地黄毒苷配基

Database IDs

• CAS Number: 143-62-4
• EC Number: 205-603-4
• MDL Number: MFCD00003687
• Beilstein Number: 95448
• PubChem SID: 24894291; 24863063; 162095458
• PubChem CID: 4369270

CALCULATED PROPERTIES

• Acid pKa: 7.1826363
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.0584373
• LogD (pH = 7.4): 2.645005
• Log P: 3.0673547
• Molar Refractivity: 103.6406 cm^3
• Polarizability: 41.212856 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 253 °C(lit.); 253-255 °C (dec.)(lit.)
• Optical Rotation: [α]20/D +14.5±2°, c = 1% in methanol; [α]20/D +16.9°, c = 1.3 in methanol

Safety Information

• RTECS: FH4975000
• European Hazard Symbols: Toxic (T)
• UN Number: 3462
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300
• GHS Precautionary statements: P264-P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 3462 6.1/PG 2

Pharmacology Properties

• Gene Information: rat ... Atp1a1(24211)
• Mechanism of Action: Na-K-Atpase inhibitor

Product Information

• Purity: ≥99.0% (HPLC); 98%
• Grade: puriss.
• Description: non-ionic
• Biological Source: Isol. from Digitalis lanata, Pachycarpus schinzianus, Gongronema gazense and others
• Application(s): Cardiotonic agent
• Empirical Formula (Hill Notation): C23H34O4

DETAILS

MP Biomedicals - 05205013

MP Biomedicals Rare Chemical collection

Sigma Aldrich - D103209

Packaging
100 mg in glass bottle

REFERENCES

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 1063A, (ir)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 605A; 605B, (nmr)
• Fritsch, W. et al., Annalen, 1974, 621-629, (Digitoxigenin, synth)
• Yoshii, E. et al., Chem. Pharm. Bull., 1975, 23, 2496-2506, (Digitoxigenin, synth)
• Welzel, P. et al., Annalen, 1982, 2119-2134, (Digitoxigenin, synth)
• Milkova, T. et al., Tet. Lett., 1982, 23, 413-414, (Digitoxigenin, synth)
• Wicha, J. et al., J.C.S. Perkin 1, 1985, 1601-1605, (Digitoxigenin, synth)