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Arisugacin A

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Arisugacin A
Names
Preferred IUPAC name
(4aR,6aR,12aS,12bS)-9-(3,4-Dimethoxyphenyl)-4a,12a-dihydroxy-4,4,6a,12b-tetramethyl-4a,6,6a,12,12a,12b-hexahydro-4H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-1,11(5H)-dione
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
  • InChI=1S/C28H32O8/c1-24(2)10-9-22(29)26(4)27(24,31)12-11-25(3)28(26,32)15-17-20(36-25)14-19(35-23(17)30)16-7-8-18(33-5)21(13-16)34-6/h7-10,13-14,31-32H,11-12,15H2,1-6H3/t25-,26+,27-,28-/m1/s1
    Key: MIHBCQWIBJDVPX-JUDWXZBOSA-N
  • InChI=1/C28H32O8/c1-24(2)10-9-22(29)26(4)27(24,31)12-11-25(3)28(26,32)15-17-20(36-25)14-19(35-23(17)30)16-7-8-18(33-5)21(13-16)34-6/h7-10,13-14,31-32H,11-12,15H2,1-6H3/t25-,26+,27-,28-/m1/s1
    Key: MIHBCQWIBJDVPX-JUDWXZBOBZ
  • C[C@@]12CC[C@@]3([C@@]([C@]1(CC4=C(O2)C=C(OC4=O)C5=CC(=C(C=C5)OC)OC)O)(C(=O)C=CC3(C)C)C)O
Properties
C28H32O8
Molar mass 496.556 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Arisugacin A is an orally active acetylcholinesterase inhibitor.[2]

References

[edit]
  1. ^ "KNApSAcK Metabolite Information - C00016246". www.knapsackfamily.com.
  2. ^ Sunazuka, T; Handa, M; Nagai, K; Shirahata, T; Harigaya, Y; Otoguro, K; Kuwajima, I; Omura, S (2002). "The first total synthesis of (+/-)-arisugacin A, a potent, orally bioavailable inhibitor of acetylcholinesterase". Organic Letters. 4 (3): 367–9. doi:10.1021/ol017046x. PMID 11820881.



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