ChemSpider 2D Image | (−)-calyculin A | C50H81N4O15P

(−)-calyculin A

  • Molecular FormulaC50H81N4O15P
  • Average mass1009.170 Da
  • Monoisotopic mass1008.543579 Da
  • ChemSpider ID4470862
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 15 of 15 defined stereocentres

More details:

Featured data source

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

(−)-calyculin A
(2R,3R,5R,7S,8S,9R)-2-[(1S,3S,4S,5R,6R,7E,9E,11E,13Z)-14-Cyan-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyl-7,9,11,13-tetradecatetraen-1-yl]-7-[(2E)-3-{2-[(2S)-4-{[(2S,3S,4S)-4-(dimethylamino)-2,3-di hydroxy-5-methoxypentanoyl]amino}-2-butanyl]-1,3-oxazol-4-yl}-2-propen-1-yl]-9-hydroxy-4,4,8-trimethyl-1,6-dioxaspiro[4.5]dec-3-yldihydrogenphosphat [German] [ACD/IUPAC Name]
(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-tetradecatetraen-1-yl]-7-[(2E)-3-{2-[(2S)-4-{[(2S,3S,4S)-4-(dimethylamino)-2,3-d ihydroxy-5-methoxypentanoyl]amino}-2-butanyl]-1,3-oxazol-4-yl}-2-propen-1-yl]-9-hydroxy-4,4,8-trimethyl-1,6-dioxaspiro[4.5]dec-3-yl dihydrogen phosphate [ACD/IUPAC Name]
(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-tetraen-1-yl]-7-[(2E)-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-en-1-yl]-9-hydroxy-4,4,8-trimethyl-1,6-dioxaspiro[4.5]dec-3-yl dihydrogen phosphate (non-preferred name)
101932-71-2 [RN]
Calyculin A
Dihydrogénophosphate de (2R,3R,5R,7S,8S,9R)-2-[(1S,3S,4S,5R,6R,7E,9E,11E,13Z)-14-cyano-3,5-dihydroxy-1-méthoxy-4,6,8,9,13-pentaméthyl-7,9,11,13-tétradécatétraén-1-yl]-7-[(2E)-3-{2-[(2S)-4-{[(2S,3S,4S) -4-(diméthylamino)-2,3-dihydroxy-5-méthoxypentanoyl]amino}-2-butanyl]-1,3-oxazol-4-yl}-2-propén-1-yl]-9-hydroxy-4,4,8-triméthyl-1,6-dioxaspiro[4.5]déc-3-yle [French] [ACD/IUPAC Name]
(-)-Calyculin A
[101932-71-2] [RN]

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

4903216 [DBID]
21279_FLUKA [DBID]
UN3462 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Bio Activity:

      Calyculin A is a potent inhibitor of the catalytic subunit of type-2A phosphatase, with IC50 values of 0.5 to 1 nM. ;Target: protein phosphataseCalyculin A induces contraction in smooth muscle fibers. With the catalytic subunit of protein phosphatase type-1, calyculin A is an effective inhibitor , IC50 values for calyculin A is about 2 nM and. The endogenous phosphatase of smooth muscle myosin B was inhibited by calyculin A with IC50 values of 0.3 to 0.7 nM for calyculin A. The partially purified catalytic subunit from myosin B had IC50 values of 0.7 nM for calyculin A. MedChem Express HY-18983
      Enzymes Tocris Bioscience 1336
      Phosphatases Tocris Bioscience 1336
      Potent and selective cell-permeable inhibitor of protein phosphatase 1 (IC50 = 0.3 - 0.7 nM) and protein phosphatase 2A (IC50 = 0.5 - 1 nM). Displays > 10,000,000-fold selectivity over PP2B and PP2C. Tocris Bioscience 1336
      Protein phosphatase 1 and 2A inhibitor Tocris Bioscience 1336
      Protein Ser/Thr Phosphatases Tocris Bioscience 1336

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.3±0.1 g/cm3
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction: 1.570
Molar Refractivity: 262.9±0.4 cm3
#H bond acceptors: 19
#H bond donors: 8
#Freely Rotating Bonds: 27
#Rule of 5 Violations: 3
ACD/LogP: 3.06
ACD/LogD (pH 5.5): -0.57
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -1.48
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 297 Å2
Polarizability: 104.2±0.5 10-24cm3
Surface Tension: 60.0±5.0 dyne/cm
Molar Volume: 801.0±5.0 cm3

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