(−)-Calyculin A

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Formula C50H81N4O15P
IUPAC Name [(2r,3r,5r,7r,8s,9s)-2-[(1s,3s,4s,5r,6r,7e,9e,11e,13z)-14-cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyl-tetradeca-7,9,11,13-tetraenyl]-9-[(e)-3-[2-[(1s)-3-[[(2s,3s,4s)-4-(dimethylamino)-2,3-dihydroxy-5-methoxy-pentanoyl]amino]-1-methyl-propyl]oxazol-4-yl]allyl]-7-hydroxy-4,4,8-trimethyl-1,10-dioxaspiro[4.5]decan-3-yl] dihydrogen phosphate
Molecular Mass 1009.170 g·mol−1
Heat of Formation -3044.6 ± 16.7 kJ·mol−1
Dipole Moment 17.72 ± 1.08 D
Volume 1271.07 Å 3
Surface Area 832.7 Å 2
HOMO Energy -8.73 ± 0.55 eV
LUMO Energy -0.69 ± eV
Point Group Symmetry C1
Synonyms
  • [(2r,3r,5r,7s,8s,9r)-2-[(1s,3s,4s,5r,6r,7e,9e,11e,13z)-14-cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyl-tetradeca-7,9,11,13-tetraenyl]-7-[(e)-3-[2-[(1s)-3-[[(2s,3s,4s)-4-dimethylamino-2,3-dihydroxy-5-methoxy-pentanoyl]amino]-1-methyl-propyl]oxazol-4-yl]prop-2-enyl]-9-hydroxy-4,4,8-trimethyl-1,6-dioxaspiro[4.5]decan-3-yl] dihydrogen phosphate
  • [(2r,3r,5r,7s,8s,9r)-2-[(1s,3s,4s,5r,6r,7e,9e,11e,13z)-14-cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyl-tetradeca-7,9,11,13-tetraenyl]-7-[(e)-3-[2-[(2s)-4-[[(2s,3s,4s)-4-dimethylamino-2,3-dihydroxy-5-methoxy-pentanoyl]amino]butan-2-yl]-1,3-oxazol-4-yl]prop-2-enyl]-9-hydroxy-4,4,8-trimethyl-1,6-dioxaspiro[4.5]decan-3-yl] dihydrogen phosphate
  • [(2r,3r,5r,7s,8s,9r)-2-[(1s,3s,4s,5r,6r,7e,9e,11e,13z)-14-cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyltetradeca-7,9,11,13-tetraenyl]-7-[(e)-3-[2-[(1s)-3-[[(2s,3s,4s)-4-dimethylamino-2,3-dihydroxy-5-methoxy-1-oxopentyl]amino]-1-methylpropyl]-4-oxazolyl]prop-2-enyl]-9-hydroxy-4,4,8-trimethyl-1,6-dioxaspiro[4.5]decan-3-yl] dihydrogen phosphate
  • [(2r,3r,5r,7s,8s,9r)-2-[(1s,3s,4s,5r,6r,7e,9e,11e,13z)-14-cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyltetradeca-7,9,11,13-tetraenyl]-7-[(e)-3-[2-[(2s)-4-[[(2s,3s,4s)-4-dimethylamino-2,3-dihydroxy-5-methoxypentanoyl]amino]butan-2-yl]-1,3-oxazol-4-yl]prop-2-enyl]-9-hydroxy-4,4,8-trimethyl-1,6-dioxaspiro[4.5]decan-3-yl] dihydrogen phosphate
  • calyculin
  • calyculin a from discodermia calyx
  • l-ribonamide, n-((3s)-3-(4-((1e)-3-((2r,3r,5r,7s,8s,9r)-2-((1s,3s,4s,5r,6r,7e,9e,11e,13z)-14-cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyl-7,9,11,13-tetradecatetraenyl)-9-hydroxy-4,4,8-trimethyl-3-(phosphonooxy)-1,6-dioxaspiro(4.5)dec-7-yl)-1-propenyl)-2-oxazolyl)butyl)-4-deoxy-4-(dimethylamino)-5-o-methyl-
InChIKey FKAWLXNLHHIHLA-YCBIHMBMSA-N
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