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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-naphthopyranopyran-1,11(5H)-dione
Identifiers
CAS Number	167114-89-8
3D model (JSmol)	Interactive image
ChEBI	CHEBI:65435
ChEMBL	ChEMBL283509
ChemSpider	8430760
PubChem CID	10255275
CompTox Dashboard (EPA)	DTXSID401045615
InChI 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/s1Key: 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/s1Key: MIHBCQWIBJDVPX-JUDWXZBOBZ
SMILES C12CC3((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
Chemical formula	C₂₈H₃₂O₈
Molar mass	496.556 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

Arisugacin A is an orally active acetylcholinesterase inhibitor.

References

"KNApSAcK Metabolite Information - C00016246". www.knapsackfamily.com.
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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Acetylcholine metabolism and transport modulators

Enzyme
(modulators)

ChATTooltip Choline acetyltransferase

AChETooltip Acetylcholinesterase

BChETooltip Butyrylcholinesterase

Inhibitors: Affinine
Affinisine
Conodurine
Cymserine
Ladostigil
Profenamine (ethopropazine)
Rivastigmine
Tacrine
ZINC-12613047
Many of the other AChE inhibitors listed above

Transporter
(modulators)

CHTTooltip Choline transporter

Inhibitors: Hemicholinium-3 (hemicholine)
Triethylcholine

Enhancers: Coluracetam

VAChTTooltip Vesicular acetylcholine transporter

Inhibitors: Vesamicol

Release
(modulators)

SNAP-25Tooltip Synaptosomal-associated protein 25 inactivators: Botulinum toxin (A, C, E)

VAMPTooltip Vesicle-associated membrane protein inactivators: Botulinum toxin (B, D, F, G)

Others: Bungarotoxins (β-bungarotoxin, γ-bungarotoxin)

LPHNTooltip Latrophilin agonists: α-Latrotoxin

Others: Atracotoxins (e.g., robustoxin, versutoxin)
Crotoxin

See also: Receptor/signaling modulators; Muscarinic acetylcholine receptor modulators; Nicotinic acetylcholine receptor modulators

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