4-[(1S,2S,5S,7R,10R,11S,13S,14R,15R)-5,11,13-trihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]-2,5-dihydrofuran-2-one

• ChemBase ID: 107646
• Molecular Formular: C23H34O5
• Molecular Mass: 390.51306
• Monoisotopic Mass: 390.24062419
• SMILES: O=C1OCC(=C1)[C@@H]1[C@@]2([C@](O)(C[C@@H]1O)[C@@H]1CC[C@@H]3C[C@@H](O)CC[C@]3(C)[C@H]1CC2)C
• Canonical SMILES: O[C@H]1CC[C@]2([C@@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@]1(O)C[C@@H]([C@@H]2C1=CC(=O)OC1)O)C)C
• InChI: InChI=1S/C23H34O5/c1-21-7-5-15(24)10-14(21)3-4-17-16(21)6-8-22(2)20(13-9-19(26)28-12-13)18(25)11-23(17,22)27/h9,14-18,20,24-25,27H,3-8,10-12H2,1-2H3/t14-,15+,16+,17-,18+,20+,21+,22-,23+/m1/s1
• InChIKey: PVAMXWLZJKTXFW-VQMOFDJESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1S,2S,5S,7R,10R,11S,13S,14R,15R)-5,11,13-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]-2,5-dihydrofuran-2-one; 4-[(1S,2S,5S,7R,10R,11S,13S,14R,15R)-5,11,13-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0?,?.0??,??]heptadecan-14-yl]-2,5-dihydrofuran-2-one
• IUPAC Traditional name: gitoxigenin
• Synonyms: 16β-Hydroxydigitoxigenin; 3β,14,16β,21-Tetrahydroxy-20(22)-norcholenic acid lactone; 3β,14,16β-Trihydroxy-5β,20(22)-cardenolide; 5β,20(22)-Cardenolide-3β,14,16β-triol; Gitoxigenin; GITOXIGENIN

Database IDs

• CAS Number: 545-26-6
• EC Number: 208-886-2
• MDL Number: MFCD00021174
• Beilstein Number: 96483
• PubChem SID: 162095452
• PubChem CID: 348482

CALCULATED PROPERTIES

• Acid pKa: 6.8310256
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 1.666012
• LogD (pH = 7.4): 1.0149335
• Log P: 1.6857958
• Molar Refractivity: 105.1895 cm^3
• Polarizability: 41.84968 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: ~230 °C
• Optical Rotation: [α]20/D +30±2°, c = 1% in methanol

Safety Information

• RTECS: FH5391000
• European Hazard Symbols: Toxic (T)
• UN Number: 1544
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1
• Risk Statements: 23/24/25
• Safety Statements: 36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H331
• GHS Precautionary statements: P261-P280-P301 + P310-P311
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 1544 6.1/PG 1

Product Information

• Purity: ≥98.0% (HPLC)
• Empirical Formula (Hill Notation): C23H34O5
• Classification: Rare Genuine Natural Compounds

DETAILS

MP Biomedicals - 05204447

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 48940

Biochem/physiol Actions
Structure-activity relationships for 16β-substituted digitoxigenins as inhibitors of Na+/K+ ATPases.1