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Hibarimicinone is an organic atropisomeric small molecule, derived from , which are isolated from the microbial culture strain of from the region of Japan. Analysis of the bacteria identified a new class of molecule containing a dimeric-tetracyclic polyketide backbone, which are now known as the hibarimicins. Hibarimicinone and its derivatives were initially extracted for their potential inhibitory properties of various protein kinases, such as calmodulin-dependent protein kinase III (CAMKIII), protein kinase A (PKA), protein kinase C (PKC), and protein tyrosine kinase (PTK). The atropisomerism that the hibarimicin family possess arises from the hindered rotation about the biaryl axis connecting to the two monomers, with steric hindrance imposed by the four ortho substituents. The absolu

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  • Hibarimicinone (en)
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  • Hibarimicinone is an organic atropisomeric small molecule, derived from , which are isolated from the microbial culture strain of from the region of Japan. Analysis of the bacteria identified a new class of molecule containing a dimeric-tetracyclic polyketide backbone, which are now known as the hibarimicins. Hibarimicinone and its derivatives were initially extracted for their potential inhibitory properties of various protein kinases, such as calmodulin-dependent protein kinase III (CAMKIII), protein kinase A (PKA), protein kinase C (PKC), and protein tyrosine kinase (PTK). The atropisomerism that the hibarimicin family possess arises from the hindered rotation about the biaryl axis connecting to the two monomers, with steric hindrance imposed by the four ortho substituents. The absolu (en)
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  • Hibarimicinone (en)
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  • Hibarimicinone (en)
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  • http://commons.wikimedia.org/wiki/Special:FilePath/Hibarimicinone.svg
  • http://commons.wikimedia.org/wiki/Special:FilePath/Hibarimicinone_Biosynthesis.svg
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  • Hibarimicinone.svg (en)
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  • Hibarimicinone is an organic atropisomeric small molecule, derived from , which are isolated from the microbial culture strain of from the region of Japan. Analysis of the bacteria identified a new class of molecule containing a dimeric-tetracyclic polyketide backbone, which are now known as the hibarimicins. Hibarimicinone and its derivatives were initially extracted for their potential inhibitory properties of various protein kinases, such as calmodulin-dependent protein kinase III (CAMKIII), protein kinase A (PKA), protein kinase C (PKC), and protein tyrosine kinase (PTK). The atropisomerism that the hibarimicin family possess arises from the hindered rotation about the biaryl axis connecting to the two monomers, with steric hindrance imposed by the four ortho substituents. The absolute configuration around the axis was elucidated by Romaine et al., utilizing a C2-symmetric shunt metabolite HMP-Y6, a glycosylated structural analogue of hibarimicinone, in tandem with biomimetic homocoupling.Recent work by multiple groups have shown the total synthesis of hibarimicinone and its derivatives. (en)
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IUPAC name
  • (2R,5S,6R,7S,8S,9S)-15-[(6aR,7S,8R,9S,10S,10aS)-1,7,8,9,10,10a,12-Heptahydroxy-3,4-dimethoxy-11-oxo-10-propyl-6,6a,7,8,9,10,10a,11-octahydro-2-tetracenyl]-5,6,7,9,12,19-hexahydroxy-16-methoxy-4-propyl ;-3-oxapentacyclo[9.8.0.02,8.04,9.013,18]nonadeca-1(11),12,15,18-tetraene-10,14,17-trione (en)
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