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CAS 159351-88-9

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31-O-Methylrapamycin

Description:
31-O-Methylrapamycin, with the CAS number 159351-88-9, is a derivative of rapamycin, a macrolide compound originally discovered as an antifungal agent. This substance exhibits immunosuppressive properties, making it significant in the field of transplant medicine and autoimmune disease treatment. Structurally, it features a methoxy group at the 31-position of the rapamycin molecule, which alters its pharmacological profile and enhances its bioactivity. The compound functions primarily as an inhibitor of the mammalian target of rapamycin (mTOR), a crucial regulator of cell growth, proliferation, and survival. This inhibition can lead to reduced cell proliferation and has implications in cancer therapy and age-related diseases. Additionally, 31-O-Methylrapamycin may exhibit improved solubility and stability compared to its parent compound, potentially leading to better therapeutic outcomes. As with other rapamycin derivatives, its use is associated with a range of biological effects, including modulation of immune responses and potential anti-cancer activities, making it a subject of ongoing research in pharmacology and medicinal chemistry.
Formula:C52H81NO13
InChI:InChI=1S/C52H81NO13/c1-31-17-13-12-14-18-32(2)43(61-8)29-39-22-20-37(7)52(60,66-39)49(57)50(58)53-24-16-15-19-40(53)51(59)65-44(34(4)27-38-21-23-41(54)45(28-38)62-9)30-42(55)33(3)26-36(6)47(63-10)48(64-11)46(56)35(5)25-31/h12-14,17-18,26,31,33-35,37-41,43-45,47-48,54,60H,15-16,19-25,27-30H2,1-11H3/b14-12+,17-13+,32-18+,36-26+/t31-,33-,34-,35-,37-,38+,39+,40+,41-,43+,44+,45-,47-,48+,52-/m1/s1
InChI key:InChIKey=TXZXMCLTSBPVQD-JQEUAWNDSA-N
SMILES:O=C1N2[C@](C(=O)O[C@]([C@@H](C[C@H]3C[C@@H](OC)[C@H](O)CC3)C)(CC(=O)[C@H](C)/C=C(\C)/[C@@H](OC)[C@@H](OC)C(=O)[C@H](C)C[C@H](C)\C=C\C=C\C=C(/C)\[C@@H](OC)C[C@]4(O[C@@](O)(C1=O)[C@H](C)CC4)[H])[H])(CCCC2)[H]
Synonyms:
  • 28-O-Methylrapamycin
  • Rapamycin, 31-O-methyl-
  • 23,27-Epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclohentriacontine, rapamycin deriv.
  • 31-O-Methylrapamycin
  • Rapamycin Impurity 13
  • 28-O-Methyl-rapaMycin
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