(1S,3R,6S,8R,11S,12S,14R,15S,16R)-7,7,12,16-tetramethyl-6-(methylamino)-15-[(1S)-1-(methylamino)ethyl]pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-14-ol

• ChemBase ID: 73022
• Molecular Formular: C26H46N2O
• Molecular Mass: 402.65624
• Monoisotopic Mass: 402.3610141
• SMILES: C1[C@@H](C([C@H]2[C@]3(C1)[C@]1([C@@H](CC2)[C@]2([C@](CC1)([C@H]([C@@H](C2)O)[C@H](C)NC)C)C)C3)(C)C)NC
• Canonical SMILES: CN[C@H]([C@H]1[C@H](O)C[C@@]2([C@]1(C)CC[C@@]13[C@H]2CC[C@@H]2[C@]3(C1)CC[C@@H](C2(C)C)NC)C)C
• InChI: InChI=1S/C26H46N2O/c1-16(27-6)21-17(29)14-24(5)19-9-8-18-22(2,3)20(28-7)10-11-25(18)15-26(19,25)13-12-23(21,24)4/h16-21,27-29H,8-15H2,1-7H3/t16-,17+,18-,19-,20-,21-,23+,24-,25+,26-/m0/s1
• InChIKey: GMNAPBAUIVITMI-ABNIRSKTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3R,6S,8R,11S,12S,14R,15S,16R)-7,7,12,16-tetramethyl-6-(methylamino)-15-[(1S)-1-(methylamino)ethyl]pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-14-ol
• IUPAC Traditional name: (1S,3R,6S,8R,11S,12S,14R,15S,16R)-7,7,12,16-tetramethyl-6-(methylamino)-15-[(1S)-1-(methylamino)ethyl]pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-14-ol
• Synonyms: Bebuxine; Cyclovirobuxine; Cyclovirobuxine D; NSC 91722; Cyclovirobuxin D(Bebuxine)

Database IDs

• CAS Number: 860-79-7
• PubChem SID: 162037942
• PubChem CID: 260439

CALCULATED PROPERTIES

• Acid pKa: 14.865901
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -2.9480493
• LogD (pH = 7.4): -2.2235258
• Log P: 3.5204458
• Molar Refractivity: 119.7864 cm^3
• Polarizability: 48.67277 Å^3
• Polar Surface Area: 44.29 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S2402

Research Area: Cardiovascular Disease
Biological Activity:
Cyclovirobuxine D (bebuxine; Cyclovirobuxine) is an active compound extracted from Buxus microphylla, which has been used for treating acute myocardial ischemia. Cyclovirobuxine D (bebuxine; Cyclovirobuxine) significantly increased cardiomyocytes viability injured by oxidation or hypoxia. It significantly reduced the infarct size induced by ligating the coronary artery in rats, and the effect was almost abolished by glibenclamide, a blocker of ATP sensitive potassium channel, but it was not influenced by cyclooxygenase-2 inhibitor celecoxib or estrogen receptor antagonist tamoxifen. In addition, cyclovirobuxine D (bebuxine; Cyclovirobuxine) significantly protected rat aorta endothelial cells against hypoxia and enhanced nitric oxide (NO) release from endothelial cells, which was inhibited by nitric oxide synthase (NOS) inhibitor N-nitro-l-arginine methyl ester (L-NAME). Furthermore, cyclovirobuxine D (bebuxine; Cyclovirobuxine) significantly decreased the weight of venous thrombus in rats. [1][2]

REFERENCES

• Grossini E et al. Life Sci. 1999;65(5):PL59-65.