Calphostin C

Calphostin C is a natural chemical compound. It is one of the calphostins, isolated from the fungus Cladosporium cladosporioides.[1][2] Calphostin C is a potent inhibitor of protein kinase C (PKC).

Calphostin C
Names
IUPAC name
[(2R)-1-[3,10-dihydroxy-12-[(2R)-2-(4-hydroxyphenoxy)carbonyloxypropyl]-2,6,7,11-tetramethoxy-4,9-dioxoperylen-1-yl]propan-2-yl] benzoate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C44H38O14/c1-20(56-43(50)22-10-8-7-9-11-22)16-25-31-32-26(17-21(2)57-44(51)58-24-14-12-23(45)13-15-24)42(55-6)40(49)34-28(47)19-30(53-4)36(38(32)34)35-29(52-3)18-27(46)33(37(31)35)39(48)41(25)54-5/h7-15,18-21,45,48-49H,16-17H2,1-6H3/t20-,21-/m1/s1 ☒N
    Key: LSUTUUOITDQYNO-NHCUHLMSSA-N ☒N
  • InChI=1/C44H38O14/c1-20(56-43(50)22-10-8-7-9-11-22)16-25-31-32-26(17-21(2)57-44(51)58-24-14-12-23(45)13-15-24)42(55-6)40(49)34-28(47)19-30(53-4)36(38(32)34)35-29(52-3)18-27(46)33(37(31)35)39(48)41(25)54-5/h7-15,18-21,45,48-49H,16-17H2,1-6H3/t20-,21-/m1/s1
    Key: LSUTUUOITDQYNO-NHCUHLMSBH
  • C[C@H](CC1=C(C(=C2C(=O)C=C(C3=C4C(=CC(=O)C5=C(C(=C(C(=C45)C1=C32)C[C@@H](C)OC(=O)OC6=CC=C(C=C6)O)OC)O)OC)OC)O)OC)OC(=O)C7=CC=CC=C7
Properties
C44H38O14
Molar mass 790.774 g·mol−1
Appearance red to brown powder
log P 7.65
Acidity (pKa) 5.46
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

References
  1. Kobayashi, E; Ando, K; Nakano, H; Iida, T; Ohno, H; Morimoto, M; Tamaoki, T (1989). "Calphostins (UCN-1028), novel and specific inhibitors of protein kinase C. I. Fermentation, isolation, physico-chemical properties and biological activities". J. Antibiot. 42 (10): 1470–1474. doi:10.7164/antibiotics.42.1470. PMID 2478514.
  2. Iida, T; Kobayashi, E; Yoshida, M; Sano, H (1989). "Calphostins, novel and specific inhibitors of protein kinase C. II. Chemical structures". J. Antibiot. 42 (10): 1475–1481. doi:10.7164/antibiotics.42.1475. PMID 2478515.

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