5-[(1S,2S,5S,7R,10R,11S,14S,15R)-5,11-dihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]-2H-pyran-2-one

• ChemBase ID: 104154
• Molecular Formular: C24H34O4
• Molecular Mass: 386.52436
• Monoisotopic Mass: 386.24570957
• SMILES: O=c1occ(cc1)[C@@H]1[C@@]2(C)CC[C@@H]3[C@@]4(C)CC[C@H](O)C[C@H]4CC[C@H]3[C@@]2(O)CC1
• 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]2c1ccc(=O)oc1)C)C
• InChI: InChI=1S/C24H34O4/c1-22-10-7-17(25)13-16(22)4-5-20-19(22)8-11-23(2)18(9-12-24(20,23)27)15-3-6-21(26)28-14-15/h3,6,14,16-20,25,27H,4-5,7-13H2,1-2H3/t16-,17+,18-,19+,20-,22+,23-,24+/m1/s1
• InChIKey: QEEBRPGZBVVINN-BMPKRDENSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(1S,2S,5S,7R,10R,11S,14S,15R)-5,11-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]-2H-pyran-2-one; 5-[(1S,2S,5S,7R,10R,11S,14S,15R)-5,11-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2H-pyran-2-one
• IUPAC Traditional name: bufalin
• Synonyms: 3β,14-Dihydroxy-5β,20(22)-bufadienolide; 5β,20(22)-Bufadienolide-3β,14-diol; Bufalin; (3β,5β)-3,14-Dihydroxy-bufa-20,22-dienolide; 3β,14-dihydroxy-5β-Bufa-20,22-dienolide; 5 β,20[22]-Bufadienolide-3β,14-diol; 3β,14-Dihydroxy-5 β,20[22]-bufadienolide; BUFALIN

Database IDs

• CAS Number: 465-21-4
• MDL Number: MFCD00056525
• PubChem SID: 162092776; 24891509
• PubChem CID: 9547215

CALCULATED PROPERTIES

• Acid pKa: 18.296396
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.2767599
• LogD (pH = 7.4): 3.2767615
• Log P: 3.2767615
• Molar Refractivity: 108.4887 cm^3
• Polarizability: 42.809875 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: 2-8°C, Desiccate
• RTECS: EI2962500
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 3462
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 28
• Safety Statements: 28-36/37-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300
• GHS Precautionary statements: P264-P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3462 6.1/PG 2
• Storage Temperature: 2-8°C

DETAILS

MP Biomedicals - 02154903

(5β,20[22]-Bufadienolide-3β,14-diol; 3β,14-Dihydroxy-5β,20[22]-bufadienolide) Crystalline

Toronto Research Chemicals - B689510

A bufadienolide derivative, cardiac steroid, a component of bufadienolides present in the traditional Chinese medicine Chan'su, used therapeutically for the treatment of heart disease, also has been reported as a protective factor in many tumors.

REFERENCES

• Wang, B., et al.: Biol. Pharm. Bull., 34, 967 (2011)
• Song, C., et al.: Xiandai Zhongliu Yixue, 18, 1863, 2010.