Synonyms: ISIS 301012 parent acid | isis-301012 | Kynamro®
mipomersen is an approved drug (FDA (2013))
Compound class:
Nucleic acid
Comment: Mipomersen is a synthetic phosphorothioate antisense oligonucleotide (ASO) that is designed to block production of apolipoprotein B as a mechanism to reduce levels of very low-density lipoprotein (vLDL) and LDL. It is formulated as a sodium adduct for clinical administration.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors
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160
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Hydrogen bond donors
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26
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Rotatable bonds
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156
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Topological polar surface area
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3334.68
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Molecular weight
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7152.94
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XLogP
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-19.15
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No. Lipinski's rules broken
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3
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SMILES / InChI / InChIKey
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Canonical SMILES
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COCCOC1C(SP(=O)(OCC2OC(CC2SP(=O)(OCC2OC(CC2SP(=O)(OCC2OC(CC2SP(=O)(OCC2OC(CC2SP(=O)(OCC2OC(CC2SP(=O)(OCC2OC(CC2SP(=O)(OCC2OC(CC2SP(=O)(OCC2OC(CC2SP(=O)(OCC2OC(CC2SP(=O)(OCC2OC(CC2SP(=O)(OCC2OC(C(C2SP(=O)(OCC2OC(C(C2SP(=O)(OCC2OC(C(C2SP(=O)(OCC2OC(C(C2SP(=O)(OCC2OC(C(C2O)OCCOC)n2cc(C)c(nc2=O)N)[O-])OCCOC)n2cc(C)c(nc2=O)N)[O-])OCCOC)n2cnc3c2ncnc3N)[O-])OCCOC)n2cc(C)c(nc2=O)N)[O-])OCCOC)n2cnc3c2nc(N)[nH]c3=O)[O-])n2cc(C)c(nc2=O)N)[O-])n2cc(C)c(=O)[nH]c2=O)[O-])n2cc(C)c(=O)[nH]c2=O)[O-])n2cc(C)c(nc2=O)N)[O-])n2cnc3c2nc(N)[nH]c3=O)[O-])n2cc(C)c(=O)[nH]c2=O)[O-])n2cc(C)c(nc2=O)N)[O-])n2cc(C)c(=O)[nH]c2=O)[O-])n2cnc3c2nc(N)[nH]c3=O)[O-])n2cnc3c2ncnc3N)[O-])C(OC1n1cc(C)c(nc1=O)N)COP(=O)(SC1C(COP(=O)(SC2C(COP(=O)(SC3C(COP(=O)(SC4C(CO)OC(C4OCCOC)n4cnc5c4nc(N)[nH]c5=O)[O-])OC(C3OCCOC)n3cc(C)c(nc3=O)N)[O-])OC(C2OCCOC)n2cc(C)c(nc2=O)N)[O-])OC(C1OCCOC)n1cc(C)c(=O)[nH]c1=O)[O-]
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Isomeric SMILES
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COCCO[C@@H]1[C@H](SP(=O)(OC[C@H]2O[C@H](C[C@@H]2SP(=O)(OC[C@H]2O[C@H](C[C@@H]2SP(=O)(OC[C@H]2O[C@H](C[C@@H]2SP(=O)(OC[C@H]2O[C@H](C[C@@H]2SP(=O)(OC[C@H]2O[C@H](C[C@@H]2SP(=O)(OC[C@H]2O[C@H](C[C@@H]2SP(=O)(OC[C@H]2O[C@H](C[C@@H]2SP(=O)(OC[C@H]2O[C@H](C[C@@H]2SP(=O)(OC[C@H]2O[C@H](C[C@@H]2SP(=O)(OC[C@H]2O[C@H](C[C@@H]2SP(=O)(OC[C@H]2O[C@H]([C@@H]([C@@H]2SP(=O)(OC[C@@H]2O[C@@H]([C@H]([C@H]2SP(=O)(OC[C@@H]2O[C@@H]([C@H]([C@H]2SP(=O)(OC[C@@H]2O[C@@H]([C@H]([C@H]2SP(=O)(OC[C@@H]2O[C@@H]([C@H]([C@H]2O)OCCOC)n2cc(C)c(nc2=O)N)[O-])OCCOC)n2cc(C)c(nc2=O)N)[O-])OCCOC)n2cnc3c2ncnc3N)[O-])OCCOC)n2cc(C)c(nc2=O)N)[O-])OCCOC)n2cnc3c2nc(N)[nH]c3=O)[O-])n2cc(C)c(nc2=O)N)[O-])n2cc(C)c(=O)[nH]c2=O)[O-])n2cc(C)c(=O)[nH]c2=O)[O-])n2cc(C)c(nc2=O)N)[O-])n2cnc3c2nc(N)[nH]c3=O)[O-])n2cc(C)c(=O)[nH]c2=O)[O-])n2cc(C)c(nc2=O)N)[O-])n2cc(C)c(=O)[nH]c2=O)[O-])n2cnc3c2nc(N)[nH]c3=O)[O-])n2cnc3c2ncnc3N)[O-])[C@H](O[C@H]1n1cc(C)c(nc1=O)N)COP(=O)(S[C@@H]1[C@@H](COP(=O)(S[C@@H]2[C@@H](COP(=O)(S[C@@H]3[C@@H](COP(=O)(S[C@@H]4[C@@H](CO)O[C@H]([C@@H]4OCCOC)n4cnc5c4nc(N)[nH]c5=O)[O-])O[C@H]([C@@H]3OCCOC)n3cc(C)c(nc3=O)N)[O-])O[C@H]([C@@H]2OCCOC)n2cc(C)c(nc2=O)N)[O-])O[C@H]([C@@H]1OCCOC)n1cc(C)c(=O)[nH]c1=O)[O-]
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InChI Key
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TZRFSLHOCZEXCC-HIVFKXHNSA-A
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