Physicochemical Properties
| Molecular Formula | C32H43N5O4 |
| Molecular Weight | 561.71 |
| Exact Mass | 561.332 |
| Elemental Analysis | C, 68.42; H, 7.72; N, 12.47; O, 11.39 |
| CAS # | 1071992-81-8 |
| Related CAS # | 1071992-81-8 |
| PubChem CID | 25173585 |
| Appearance | White to off-white solid |
| LogP | 4.647 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 9 |
| Heavy Atom Count | 41 |
| Complexity | 920 |
| Defined Atom Stereocenter Count | 4 |
| SMILES | O=C1[C@H](CN(C(CC(C)C)=O)CC[C@H]2CC[C@@H](C(NCC3=CC=CC=C3C3C=CC=CC=3)=O)N21)NC([C@H](C)NC)=O |
| InChi Key | SZVCBOBNBHXZKC-MZRLSVQCSA-N |
| InChi Code | InChI=1S/C32H43N5O4/c1-21(2)18-29(38)36-17-16-25-14-15-28(37(25)32(41)27(20-36)35-30(39)22(3)33-4)31(40)34-19-24-12-8-9-13-26(24)23-10-6-5-7-11-23/h5-13,21-22,25,27-28,33H,14-20H2,1-4H3,(H,34,40)(H,35,39)/t22-,25+,27-,28-/m0/s1 |
| Chemical Name | (5S,8S,10aR)-5-[[(2S)-2-(methylamino)propanoyl]amino]-3-(3-methylbutanoyl)-6-oxo-N-[(2-phenylphenyl)methyl]-1,2,4,5,8,9,10,10a-octahydropyrrolo[1,2-a][1,5]diazocine-8-carboxamide |
| Synonyms | SM433; SM 433; SM-433; UNII-DH7Q8HYP47; DH7Q8HYP47 |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | SM-433, a Smac mimetic, function as inhibitor of inhibitor of apoptosis proteins (IAPs). XIAP BIR3 protein exhibits strong binding affinity for SM-433 with an IC50<1 μM [1]. |
| ln Vitro | SM-433 demonstrates strong inhibitory action on SK-OV-3 ovarian cancer cells and MDA-MB -2131 human breast cancer cells (IC50 <10 μM, respectively) [1]. |
| References |
[1]. Diazo bicyclic smac mimetics and the uses thereof. WO2008128171A2. |
| Additional Infomation | See also: Xevinapant (annotation moved to). |
Solubility Data
| Solubility (In Vitro) | DMSO: ~160 mg/mL (~284.8 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 4 mg/mL (7.12 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 40.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 4 mg/mL (7.12 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 40.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 4 mg/mL (7.12 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 40.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.7803 mL | 8.9014 mL | 17.8028 mL | |
| 5 mM | 0.3561 mL | 1.7803 mL | 3.5606 mL | |
| 10 mM | 0.1780 mL | 0.8901 mL | 1.7803 mL |