Seco Rapamycin (sodium salt)

Rapamycin (Cay-13346) is a natural macrolide immunosuppressant that activates mTORC1. Seco rapamycin (sodium salt) is a nonenzyme-dependent degradation product of rapamycin (Cay-13346) resulting from ester hydration followed by dehydration. It has less than 4% of the potency of rapamycin in a thymocyte proliferation assay. Rapamycin quickly degrades to two ring-opened products, including seco rapamycin, in the cytoplasm or in homogenates of Caco-2 cells. Like rapamycin, seco rapamycin is secreted from cells by P-glycoprotein and metabolized to a common dihydro species. While seco rapamycin poorly activates mTOR, it mimics rapamycin in its ability to inhibit the proteasome.Formal Name: [2R-[2alpha,2(S*),3alpha,6beta[2S*,3E,5E,7E,9S*,11R*,13R*,14R*,15E,7R*,19E,21R*,22(1S*,3R*,4R*)]]]-1-[oxo[tetrahydro-2-hydroxy-6-[14-hydroxy-22-(4-hydroxy-3methoxycyclohexyl)-2,13-dimethoxy-3,9,11,15,17,21-hexamethyl-12,18-dioxo-3,5,7,15,19-docosapentaenyl]-3-methyl-2H-pyran-2-yl]acetyl]-2-piperidinecarboxylic acid, monosodium salt. CAS Number: 148554-65-8. Molecular Formula: C51H78NO13 . Na. Formula Weight: 936.2. Purity: >85%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 30 mg/ml, DMSO: 25 mg/ml, Ethanol: 25 mg/ml, PBS (pH 7.2): 5 mg/ml. lambdamax: 277, 289 nm. SMILES: O[C@@H]1CC[C@@H](C[C@@H](C)/C=C/C([C@H](C)/C=C(C)/[C@@H](O)[C@@H](OC)C([C@H](C)C[C@H](C)/C=C/C=C/C=C([C@@H](OC)C[C@@H]2CC[C@@H](C)[C@](O)(C(C(N3CCCC[C@H]3C([O-])=O)=O)=O)O2)\C)=O)=O)C[C@H]1OC.[Na+]. InChi Code: InChI=1S/C51H79NO13.Na/c1-31(26-35(5)45(55)47(64-10)46(56)36(6)28-34(4)41(53)23-19-32(2)27-38-21-24-42(54)44(29-38)63-9)16-12-11-13-17-33(3)43(62-8)30-39-22-20-37(7)51(61,65-39)48(57)49(58)52-25-15-14-18-40(52)50(59)60,/h11-13,16-17,19,23,28,31-32,34-35,37-40,42-44,46-47,54,56,61H,14-15,18,20-22,24-27,29-30H2,1-10H3,(H,59,60),/q,+1/p-1/b13-11+,16-12+,23-19+,33-17+,36-28+,/t31-,32+,34-,35-,37-,38+,39+,40+,42-,43+,44-,46-,47+,51-,/m1./s1. InChi Key: DNMSBJYMPJMFNS-OWGFPTNRSA-M.