Information on EC 3.1.1.7 - acetylcholinesterase

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The expected taxonomic range for this enzyme is: Eukaryota

EC NUMBER
COMMENTARY hide
3.1.1.7
-
RECOMMENDED NAME
GeneOntology No.
acetylcholinesterase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
acetylcholine + H2O = choline + acetate
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hydrolysis of carboxylic ester
-
-
-
-
transacetylation
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Glycerophospholipid metabolism
-
-
SYSTEMATIC NAME
IUBMB Comments
acetylcholine acetylhydrolase
Acts on a variety of acetic esters; also catalyses transacetylations.
CAS REGISTRY NUMBER
COMMENTARY hide
9000-81-1
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
yellow fever mosquito
-
-
Manually annotated by BRENDA team
razorbill
-
-
Manually annotated by BRENDA team
cotton aphid
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
German cockroach
-
-
Manually annotated by BRENDA team
peacock bass
-
-
Manually annotated by BRENDA team
Bedbug
-
-
Manually annotated by BRENDA team
Bedbug
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Hong Kong oyster
-
-
Manually annotated by BRENDA team
cat flea
UniProt
Manually annotated by BRENDA team
Nothern house mosquito
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
strain MH19
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
cotton aphid
-
-
Manually annotated by BRENDA team
Atlantic puffin
-
-
Manually annotated by BRENDA team
lizard
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
blood-sucking stomach worm of domestic animals
-
-
Manually annotated by BRENDA team
multi-colored Asian ladybird beetle
-
-
Manually annotated by BRENDA team
eight different Egyptian strains EA2, EB6, EB7, EG7, EG8, EG9, EK1 and EK2, different isozymes, i.e. AChE1A, isozyme pattern
-
-
Manually annotated by BRENDA team
strain 105
-
-
Manually annotated by BRENDA team
strain 105
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
Australian sheep blowfly
UniProt
Manually annotated by BRENDA team
sea urchins collected from St. Joseph Bay, Florida in May of 2006
-
-
Manually annotated by BRENDA team
siratro
-
-
Manually annotated by BRENDA team
mussel
-
-
Manually annotated by BRENDA team
mussel
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
strains susceptible and resistant to carbamate and organophosphorus insecticides
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
American cockroach
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
SwissProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
Torpedo californica
flour beetle
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
common guillemot
-
-
Manually annotated by BRENDA team
desert cobra
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
-
Alzheimer's disease, a neurodegenerative disease characterized by a low concentration of acetylcholine in the hippocampus and cortex, is the leading cause of dementia among older people
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2,6-dichloro-3'-methylindophenylacetate + H2O
2,6-dichloro-3'-methylindophenol + acetate
show the reaction diagram
2,6-dichlorophenolindophenylacetate + H2O
2,6-dichlorophenolindophenol + acetate
show the reaction diagram
2-methoxyacetylthiocholine + H2O
thiocholine + 2-methoxyacetate
show the reaction diagram
3',5'-dichloro-2'-methylindophenylacetate + H2O
3',5'-dichloro-2'-methylindophenol + acetate
show the reaction diagram
-
weak substrate
-
?
3',5'-dichlorophenolindophenylacetate + H2O
3',5'-dichlorophenolindophenol + acetate
show the reaction diagram
-
weak substrate
-
?
3-(acetamido)-N,N,N-trimethylanilinium + H2O
?
show the reaction diagram
-
slow hydrolysis
-
-
?
3-(acetamido)-N,N,N-trimethylanilinum + H2O
?
show the reaction diagram
-
ATMA
-
?
3-methylbutyrylthiocholine + H2O
thiocholine + 3-methylbutyrate
show the reaction diagram
acetyl(beta-methyl)thiocholine iodide + H2O
1-methyl(thio)choline iodide + acetate
show the reaction diagram
-
-
-
-
?
acetyl-(beta-methyl)thiocholine + H2O
(beta-methyl)thiocholine + acetate
show the reaction diagram
-
-
-
?
acetyl-(beta-methyl)thiocholine iodide + H2O
acetate + methylthiocholine iodide
show the reaction diagram
-
-
-
-
?
acetyl-beta-methyl-thiocholine + H2O
beta-methyl-thiocholine + acetate
show the reaction diagram
-
-
-
?
acetyl-beta-methylcholine + H2O
methylcholine + acetate
show the reaction diagram
-
-
-
?
acetyl-beta-methylthiocholine + H2O
? + acetate
show the reaction diagram
-
-
-
-
?
acetyl-beta-methylthiocholine + H2O
beta-methylthiocholine + acetate
show the reaction diagram
-
-
-
?
acetyl-homo-thiocholine + H2O
?
show the reaction diagram
acetyl-[beta-methyl]thiocholine + H2O
acetate + [beta-methyl]thiocholine
show the reaction diagram
acetylcholine + H2O
?
show the reaction diagram
acetylcholine + H2O
acetate + choline
show the reaction diagram
acetylcholine + H2O
choline + acetate
show the reaction diagram
acetylcholine chloride + H2O
acetate + choline chloride
show the reaction diagram
-
-
-
-
?
acetylcholine chloride + H2O
choline chloride + acetate
show the reaction diagram
-
-
-
-
?
acetylcholine iodide + H2O
acetate + choline iodide
show the reaction diagram
acetylthiocholine + H2O
acetate + thiocholine
show the reaction diagram
acetylthiocholine + H2O
thiocholine + acetate
show the reaction diagram
acetylthiocholine chloride + H2O
acetate + thiocholine chloride
show the reaction diagram
-
-
-
-
?
acetylthiocholine chloride + H2O
thiocholine chloride + acetate
show the reaction diagram
-
-
-
-
?
acetylthiocholine iodide + H2O
acetate + thiocholine iodide
show the reaction diagram
acetylthiocholine iodide + H2O
thiocholine + acetate
show the reaction diagram
acetylthiocholine iodide + H2O
thiocholine iodide + acetate
show the reaction diagram
alkyl methylphosphonfluoridate + H2O
?
show the reaction diagram
-
oxime-assisted catalysis of organophosphates by AChE, mechanism, reaction system, overview
-
-
?
alpha-naphthyl acetate + H2O
alpha-naphthol + acetate
show the reaction diagram
alpha-naphthyl acetate + H2O
naphthol + acetate
show the reaction diagram
-
-
-
-
?
aryl-acyl-amides + H2O
?
show the reaction diagram
benzoylthiocholine + H2O
thiocholine + benzoate
show the reaction diagram
benzoylthiocholine iodide + H2O
thiocholine iodide + benzoate
show the reaction diagram
-
22.2% activity compared to acetylthiocholine
-
-
?
butylthiocholine + H2O
thiocholine + butanol
show the reaction diagram
butyrylthiocholine + H2O
butyrate + thiocholine
show the reaction diagram
butyrylthiocholine + H2O
thiocholine + butanoate
show the reaction diagram
butyrylthiocholine + H2O
thiocholine + butyrate
show the reaction diagram
butyrylthiocholine iodide + H2O
thiocholine iodide + butyrate
show the reaction diagram
carbachol + H2O
?
show the reaction diagram
-
slow hydrolysis
-
-
?
cyclopentylcarbonylthiocholine + H2O
thiocholine + cyclopentanecarboxylate
show the reaction diagram
cyclopropylcarbonylthiocholine + H2O
thiocholine + cyclopropanecarboxylate
show the reaction diagram
diisopropyl phosphofluoridate + H2O
?
show the reaction diagram
echothiophate + H2O
?
show the reaction diagram
edrophonium chloride + H2O
?
show the reaction diagram
-
-
-
-
?
hexanoylthiocholine + H2O
thiocholine + hexanoate
show the reaction diagram
indophenylacetate + H2O
indophenol + acetate
show the reaction diagram
isobutyrylthiocholine + H2O
thiocholine + isobutyrate
show the reaction diagram
Leu + Arg
Tyr + Gly
show the reaction diagram
-
-
-
?
Leu + Met
substance P
show the reaction diagram
-
-
-
?
methylthiocholine + H2O
thiocholine + methanol
show the reaction diagram
neuropeptides + H2O
?
show the reaction diagram
paraoxon + H2O
?
show the reaction diagram
pentanoylthiocholine + H2O
thiocholine + pentanoate
show the reaction diagram
Phe + Leu
Gly + Gly + Gly
show the reaction diagram
-
-
-
?
phenylacetylthiocholine + H2O
thiocholine + phenylacetate
show the reaction diagram
pivaloylthiocholine + H2O
thiocholine + pivalate
show the reaction diagram
propionylcholine chloride + H2O
choline chloride + propionate
show the reaction diagram
-
-
-
-
?
propionylthiocholine + H2O
propanoate + thiocholine
show the reaction diagram
propionylthiocholine + H2O
thiocholine + propionate
show the reaction diagram
propionylthiocholine chloride + H2O
thiocholine chloride + propionate
show the reaction diagram
-
-
-
-
?
propionylthiocholine iodide + H2O
thiocholine iodide + propionate
show the reaction diagram
propylthiocholine + H2O
thiocholine + propanol
show the reaction diagram
S-acetylthiocholine + H2O
acetate + thiocholine
show the reaction diagram
S-acetylthiocholine iodide + H2O
acetate + thiocholine iodide
show the reaction diagram
S-butyrylthiocholine + H2O
thiocholine + butyrate
show the reaction diagram
S-butyrylthiocholine iodide + H2O
thiocholine iodide + butyrate
show the reaction diagram
-
-
-
-
?
succinyldicholine + H2O
2 choline + succinate
show the reaction diagram
-
-
-
-
?
[leu5] enkephalin + H2O
Tyr + Leu
show the reaction diagram
-
-
-
?
[met5] enkephalins + H2O
Tyr + Met
show the reaction diagram
-
-
-
?
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
acetylcholine + H2O
?
show the reaction diagram
acetylcholine + H2O
acetate + choline
show the reaction diagram
acetylcholine + H2O
choline + acetate
show the reaction diagram
acetylcholine chloride + H2O
choline chloride + acetate
show the reaction diagram
-
-
-
-
?
acetylthiocholine + H2O
acetate + thiocholine
show the reaction diagram
acetylthiocholine + H2O
thiocholine + acetate
show the reaction diagram
neuropeptides + H2O
?
show the reaction diagram
additional information
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
aluminium chloride
-
activates the enzyme in vitro and in vivo after oral treatment
ammonium sulfate
-
activates optimally at 0.2 M
Iron
-
in vitro, iron promotes a significant increase in AChE activity in brain (52%) and liver (53%) at the higher concentration (2.6 mM). In vivo, a significant increase in enzyme activity is observed in the presence of 15 mg/l in both, brain (62%) and liver tissue (70%)
additional information
-
AchE is not affected by Ca2+
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(+)-(1R,3R,6S)-9-benzyl-3-fluoro-2,4-dioxa-9-aza-3-phosphadecalin 3-oxide
-
-
(+)-(1R,3S,6S)-9-benzyl-3-fluoro-2,4-dioxa-9-aza-3-phosphadecalin 3-oxide
-
-
(+)-(1S,3R,6S)-9-benzyl-3-fluoro-2,4-dioxa-9-aza-3-phosphadecalin 3-oxide
-
-
(+)-(1S,3S,6S)-9-benzyl-3-fluoro-2,4-dioxa-9-aza-3-phosphadecalin 3-oxide
-
-
(+)-2-carene
-
50% inhibition at 0.90 mM
(+)-3-carene
-
50% inhibition at 0.20 mM
(+)-7-deoxy-O6-buxafurandiene
-
isolated from Buxus hyrcana
(+)-alpha-pinene
-
50% inhibition at 0.4 mM
(+)-benzoylbuxidienine
-
isolated from Buxus hyrcana
(+)-borneol
-
1 mM, 22.2% inhibition
(+)-buxapapillinine
-
isolated from Buxus hyrcana
(+)-buxaquamarine
-
isolated from Buxus hyrcana
(+)-Camphor
-
1 mM, 26.4% inhibition
(+)-cis-verbenol
-
1 mM, 17.7% inhibition
-
(+)-fenchol
-
1 mM, 37.7% inhibition
(+)-fenchone
-
1 mM, 23.3 inhibition
(+)-haemanthamine
-
-
(+)-huperzine A
Torpedo californica
-
synthetic enantiomer of the anti-Alzheimer drug (-)-huperzine A and of its natural homologue (-)-huperzine B, interacts with the anionic subsite of the active site
(+)-irehine
-
isolated from Buxus hyrcana
(+)-limonene
-
isolated from the ethanolic extract from the fruits of Pimpinella anisoides
(+)-O6-buxafurandiene
-
isolated from Buxus hyrcana
(+)-sabinene
-
isolated from the ethanolic extract from the fruits of Pimpinella anisoides
(+)-tabun
(+)-trans-myrtanol
-
1 mM, 37.15% inhibition
(-)-(1R,3R,6R)-9-benzyl-3-fluoro-2,4-dioxa-9-aza-3-phosphadecalin 3-oxide
-
-
(-)-(1R,3S,6R)-9-benzyl-3-fluoro-2,4-dioxa-9-aza-3-phosphadecalin 3-oxide
-
-
(-)-(1S,3R,6R)-9-benzyl-3-fluoro-2,4-dioxa-9-aza-3-phosphadecalin 3-oxide
-
-
(-)-(1S,3S,6R)-9-benzyl-3-fluoro-2,4-dioxa-9-aza-3-phosphadecalin 3-oxide
-
-
(-)-10,10-dimethylhuperzine A
-
-
(-)-3-O-acetyl-spectaline
-
isolated from flowers of Senna spectabilis
(-)-alpha-pinene
-
50% inhibition at 0.44 mM
(-)-beta-pinene
-
1 mM, 48.5% inhibition
(-)-borneol
-
1 mM, 22.6% inhibition
(-)-Camphor
-
1 mM, 21.2% inhibition
(-)-fenchone
-
1 mM, 28.2% inhibition
(-)-galanthamine
-
isolated from Galanthus woronowii
(-)-huperzine A
Torpedo californica
-
anti-Alzheimer drug
(-)-huperzine B
Torpedo californica
-
-
(-)-myrtenol
-
1 mM, 15.0% inhibition
(-)-phenserine
-
-
(-)-S-3-[1-(dimethylamino)ethyl]phenol
Torpedo californica
-
competitive reversible inhibitor
(-)-spectaline
-
isolated from flowers of Senna spectabilis
(-)-tabun
(-)-trans-myrtanol
-
1 mM, 37.4% inhibition
(-)-verbenone
-
1 mM, 12.6% inhibition
(1alpha,3beta,22R)-stigmast-5-ene-1,3,22-triol
-
i.e. haloxysterol A, isolated from Haloxylon recurvum
(1alpha,3beta,22R)-stigmasta-4,6-diene-1,3,22-triol
-
i.e. haloxysterol B, isolated from Haloxylon recurvum
(1alpha,3beta,5alpha,6beta,22R)-stigmastane-1,3,5,6,22-pentol
-
i.e. haloxysterol D, isolated from Haloxylon recurvum
(1S,2R)-N-(1-benzyl-2-hydroxy-3-(S)-[2-(1-benzylpiperidin-4-yl)ethylamino]-propyl)-5-nitro-N'-[(R)-1-phenylethyl]isophthalamide
-
-
(1S,2R)-N-(1-benzyl-2-hydroxy-3-(S)-[2-(1-benzylpiperidin-4-yl)ethylamino]-propyl)-5-[methyl(methylsulfonyl)-amino]-N'-[(R)-1-(4-fluorophenyl)ethyl]isophthalamide
-
-
(1S,2R)-N-(1-benzyl-2-hydroxy-3-(S)-[2-(1-benzylpiperidin-4-yl)ethylamino]-propyl)-5-[methyl(methylsulfonyl)amino]-N-[(R)-1-phenylethyl]isophthalamide
-
shows inhibitory effects on beta amyloid production of amyloid precursor protein-transfected HEK293 cells and mild protective effect against hydrogen peroxide-induced cell injury
(1S,2R)-N-(1-benzyl-2-hydroxy-3-(S)-[2-(1-benzylpiperidin-4-yl)ethylamino]-propyl)-N',N'-dipropyl-5-nitroisophthalamide
-
-
(1S,2R)-N-(1-benzyl-2-hydroxy-3-(S)-[2-(1-benzylpiperidin-4-yl)ethylamino]-propyl)-N',N'-dipropyl-5-[methyl(methylsulfonyl)amino]isophthalamide
-
-
(1S,2R)-N-(1-benzyl-2-hydroxy-3-(S)-[2-(1-benzylpiperidin-4-yl)ethylamino]-propyl)-N',N'-dipropylisophthalamide
-
-
(1S,2R)-N-(1-benzyl-2-hydroxy-3-(S)-[2-(1-benzylpiperidin-4-yl)ethylamino]-propyl)-N'-[(R)-1-(4-fluorophenyl)ethyl]-5-nitroisophthalamide
-
-
(1S,2R)-N-(1-benzyl-2-hydroxy-3-(S)-[2-(1-benzylpiperidin-4-yl)ethylamino]-propyl)-N'-[(R)-1-(4-fluorophenyl)ethyl]-isophthalamide
-
-
(1S,2R)-N-(1-benzyl-2-hydroxy-3-(S)-[2-(1-benzylpiperidin-4-yl)ethylamino]-propyl)-N'-[(R)-1-phenylethyl]isophthalamide
-
-
(1S,2S,11bS)-4-[2-(acetyloxy)ethyl]-5-methyl-1,2,3,4,4a,5,6,11b-octahydro[1,3]dioxolo[4,5-j]phenanthridine-1,2-diyl diacetate
-
-
(1S,2S,11bS)-4-[2-(acetyloxy)ethyl]-5-methyl-1,2,4a,5,6,11b-hexahydro[1,3]dioxolo[4,5-j]phenanthridine-1,2-diyl diacetate
-
-
(2-methoxy-7-methyl-2-oxido-2,3,4,5-tetrahydro-1,2-oxaphosphepin-6-yl)methanol
-
-
(22R)-22-hydroxystigmasta-4,9(11)-dien-3-one
-
i.e. haloxysterol C, isolated from Haloxylon recurvum
(24S)-ethylcholesta-7,9(11),22(E)-triene-3beta-ol
-
isolated from Haloxylon recurvum
(2E)-1,3-diphenylprop-2-en-1-one
-
-
(2E)-1-(5-chloro-2-hydroxyphenyl)-3-(4-chlorophenyl)prop-2-en-1-one
-
-
(2E)-3-(2-hydroxyphenyl)-1-phenylprop-2-en-1-one
-
-
(2E)-3-(3,4-dimethoxyphenyl)-1-phenylprop-2-en-1-one
-
-
(2E)-3-(3-hydroxyphenyl)-1-phenylprop-2-en-1-one
-
-
(2E)-3-(4-hydroxyphenyl)-1-phenylprop-2-en-1-one
-
-
(2E)-3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one
-
-
(3,4-dimethoxyphenyl)(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)methanol
-
-
(3,4-dimethoxyphenyl)-(4-([(2-dimethylaminoethyl)-methylamino]methyl)phenyl)-methanone
-
-
(3,4-dimethoxyphenyl)-(4-([(2-methoxybenzyl)methylamino]methyl)phenyl)-methanone
-
-
(3,4-dimethoxyphenyl)-(4-([methyl-(3-methylbenzyl)amino]methyl)phenyl)methanone
-
-
(3,4-dimethoxyphenyl)-(4-([methyl-(3-nitrobenzyl)amino]methyl)phenyl)methanone
-
-
(3,4-dimethoxyphenyl)-(4-morpholin-4-ylmethylphenyl)methanone
-
-
(3,4-dimethoxyphenyl)-(4-[(methylprop-2-ynylamino)-methyl]phenyl)methanone
-
-
(3,4-dimethoxyphenyl)-{4-[(ethylpropylamino)methyl]phenyl}methanone
-
-
(3aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo(2,3-b)indol-5-yl (2-methylphenyl)carbamate
-
50% inhibition at 10 nM
(3aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo(2,3-b)indol-5-yl (4-isopropylphenyl)carbamate
-
50% inhibition at 760 nM
(3aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo(2,3-b)indol-5-yl ethylcarbamate
-
50% inhibition at 94 nM
(3aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo(2,3-b)indol-5-yl methylcarbamate
-
50% inhibition at 28 nM
(3aR)-3a,8-dimethyl-3,3a,8,8a-tetrahydro-2H-furo(2,3-b)indol-5-yl (2-methylphenyl)carbamate
-
50% inhibition at 13 nM
(3aR)-3a,8-dimethyl-3,3a,8,8a-tetrahydro-2H-furo(2,3-b)indol-5-yl (4-isopropylphenyl)carbamate
-
50% inhibition at 3860 nM
(3aR)-3a,8-dimethyl-3,3a,8,8a-tetrahydro-2H-furo(2,3-b)indol-5-yl ethylcarbamate
-
50% inhibition at 82 nM
(3aR)-3a,8-dimethyl-3,3a,8,8a-tetrahydro-2H-furo(2,3-b)indol-5-yl methylcarbamate
-
50% inhibition at 27 nM
(3aS,8aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl (2,3-dimethylphenyl)carbamate
-
-
(3aS,8aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl (2,4,6-trimethylphenyl)carbamate
-
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(3aS,8aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl (2,4-dimethylphenyl)carbamate
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(3aS,8aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl (2,5-dimethylphenyl)carbamate
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(3aS,8aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl (2,6-dimethylphenyl)carbamate
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(3aS,8aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl (2-ethylphenyl)carbamate
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(3aS,8aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl (3,4-dimethylphenyl)carbamate
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(3aS,8aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl (3-methylphenyl)carbamate
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(3aS,8aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl (4-methylphenyl)carbamate
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(3beta,4beta,5beta,6beta,8xi,9xi,14xi,17xi,22R)-4,28-dihydroxy-3-methoxy-1,26-dioxo-5,6:22,26-diepoxyergost-24-en-19-oic acid
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(3beta,4beta,5beta,6beta,8xi,9xi,14xi,17xi,22R)-4,28-dihydroxy-3-methoxy-5,6:22,26-diepoxyergost-24-ene-1,26-dione
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(3beta,4beta,6beta,8xi,9xi,14xi,17xi,22R)-4,6,27-trihydroxy-3-methoxy-22,26-epoxyergost-24-ene-1,26-dione
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(3E)-3-([4-[2-(diethylamino)ethoxy]phenyl]methylidene)-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one
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(3E)-3-([4-[3-(diethylamino)propoxy]phenyl]methylidene)-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one
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(3E)-3-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one
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(3E)-3-[(4-[2-[diethenyl(methylidene)-l5-azanyl]ethoxy]phenyl)methylidene]-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one
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(3E)-3-[(4-[3-[diethenyl(methylidene)-l5-azanyl]propoxy]phenyl)methylidene]-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one
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(3R,4aS,9bS)-9-(chloromethyl)-9b-[2-[(ethoxycarbonyl)(methyl)amino]ethyl]-6-methoxy-3,4,4a,9b-tetrahydrodibenzo[b,d]furan-3-yl ethyl carbonate
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(3R,5aR)-3-methoxy-1-methyl-4,5,5a,6-tetrahydro-3H,8H-furo[3,4-e][1,2]oxaphosphepin-8-one 3-oxide
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a diastereoisomeric bicyclic phosphonate analogue
(3S,5aR)-3-methoxy-1-methyl-4,5,5a,6-tetrahydro-3H,8H-furo[3,4-e][1,2]oxaphosphepin-8-one 3-oxide
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a diastereoisomeric bicyclic phosphonate analogue
(4-([benzyl-(2-dimethylaminoethyl)amino]methyl)-phenyl)-(3,4-dimethoxyphenyl)methanone
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(4-([benzyl-(2-hydroxyethyl)amino]methyl)phenyl)-(3,4-dimethoxyphenyl)methanone
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(4-bromobenzoyl)phosphoramidic dichloride
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(4-chlorobenzoyl)phosphoramidic dichloride
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(4-methylbenzoyl)phosphoramidic dichloride
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(4-[(benzylethylamino)methyl]phenyl)-(3,4-dimethoxyphenyl)methanone
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(4-[(benzylmethylamino)methyl]phenyl)-(3,4-dimethoxyphenyl)methanone
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(4-[(benzylmethylamino)methyl]phenyl)-(3-fluoro-4-methoxyphenyl)methanone
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(4-[(benzylmethylamino)methyl]phenyl)-(4-methoxyphenyl)methanone
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(4-[(benzylmethylamino)methyl]phenyl)naphthalen-2-yl-methanone
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(4-[3-(benzylmethylamino)propenyl]phenyl)-(3,4-dimethoxyphenyl)methanone
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(4aS,6R,8aS)-3-methoxy-11-methyl-5,6,10,11,13,14-hexahydro-4aH,9H-[1]benzofuro[3a,3,2-gh][3,4]benzoxazonin-6-ol
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(4aS,6R,8aS)-3-methoxy-11-[8-[(4aS,6R,8aS)-3-methoxy-6-methyl-5,6,9,10-tetrahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-11(12H)-yl]octyl]-5,6,9,10,11,12-hexahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-6-ol
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(4aS,6R,8aS)-3-[[12-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)dodecyl]oxy]-6-hydroxy-11-methyl-5,6,9,10-tetrahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-11-ium
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(4aS,6R,8aS)-3-[[8-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)octyl]oxy]-6-hydroxy-11-methyl-5,6,9,10-tetrahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-11-ium
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(4aS,6R,8aS)-6-hydroxy-3-methoxy-11-[10-[(4aS,6R,8aS)-3-methoxy-6-methyl-5,6,9,10-tetrahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-11(12H)-yl]decyl]-5,6,9,10-tetrahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-11-ium
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(4aS,6R,8aS)-6-hydroxy-3-methoxy-11-[8-[(4aS,6R,8aS)-3-methoxy-6-methyl-5,6,9,10-tetrahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-11(12H)-yl]octyl]-5,6,9,10-tetrahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-11-ium
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(4aS,6R,8aS)-6-hydroxy-3-methyl-11-(10-phenyldecyl)-5,6,9,10-tetrahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-11-ium
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(4aS,6R,8aS)-6-hydroxy-3-methyl-11-(8-phenyloctyl)-5,6,9,10-tetrahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-11-ium
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(4beta,5beta,6beta,8xi,9xi,14xi,17xi,22R)-4,27-dihydroxy-5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione
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(5alpha,6alpha,7alpha,8xi,9xi,14xi,17xi,22R)-5-hydroxy-20-methyl-6,7:22,26-diepoxyergosta-2,24-diene-1,26-dione
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(6,7-dimethoxyisoquinolin-1-yl)(2-methoxyphenyl)methanol
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(6,7-dimethoxyisoquinolin-1-yl)(3,4-dimethoxyphenyl)methanol
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(6,7-dimethoxyisoquinolin-1-yl)(3,4-dimethoxyphenyl)methanone
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(7S,9R)-ar-turmerol
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a synthetic bisabolane-type sesquiterpenoid derivative
(7S,9R)-dihydro-arturmerol
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a synthetic bisabolane-type sesquiterpenoid derivative
(7S,9S)-arturmerol
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a synthetic bisabolane-type sesquiterpenoid derivative
(7S,9S)-dihydro-ar-turmerol
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a synthetic bisabolane-type sesquiterpenoid derivative
(8Z)-5,6-dihydro-8H-isoquino[1,2b]quinazolin-8-imine
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(E)-1-(2,4-dichlorobenzyl)-4-((2-oxoindolin-3-ylidene)methyl)pyridinium chloride
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(E)-1-(2,6-dichlorobenzyl)-4-((2-oxoindolin-3-ylidene)methyl)pyridinium chloride
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(E)-1-(2-bromobenzyl)-4-((2-oxoindolin-3-ylidene)methyl)pyridinium chloride
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(E)-1-(2-chloro-6-fluorobenzyl)-4-((2-oxoindolin-3-ylidene)methyl)pyridinium chloride
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(E)-1-(2-chlorobenzyl)-4-((2-oxoindolin-3-ylidene)methyl)pyridinium chloride
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(E)-1-(2-fluorobenzyl)-4-((2-oxoindolin-3-ylidene)methyl)pyridinium chloride
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(E)-1-(2-methylbenzyl)-4-((2-oxoindolin-3-ylidene)methyl)pyridinium chloride
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(E)-1-(2-nitrobenzyl)-4-((2-oxoindolin-3-ylidene)methyl)pyridinium bromide
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(E)-1-(3,4-dichlorobenzyl)-4-((2-oxoindolin-3-ylidene)methyl)pyridinium chloride
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(E)-1-(3-bromobenzyl)-4-((2-oxoindolin-3-ylidene)methyl)pyridinium chloride
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(E)-1-(3-chlorobenzyl)-4-((2-oxoindolin-3-ylidene)methyl)pyridinium bromide
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(E)-1-(3-fluorobenzyl)-4-((2-oxoindolin-3-ylidene)methyl)pyridinium chloride
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(E)-1-(3-methoxylbenzyl)-4-((2-oxoindolin-3-ylidene)methyl)pyridinium chloride
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(E)-1-(3-methylbenzyl)-4-((2-oxoindolin-3-ylidene)methyl)pyridinium chloride
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(E)-1-(4-bromobenzyl)-4-((2-oxoindolin-3-ylidene)methyl)pyridinium chloride
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(E)-1-(4-chlorobenzyl)-4-((2-oxoindolin-3-ylidene)methyl)pyridinium chloride
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