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ChEBI
> Main
CHEBI:76923 - cyclanoline
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ChEBI Ontology
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ChEBI Name
cyclanoline
ChEBI ID
CHEBI:76923
Definition
A charged berberine alkaloid obtained by
N
-methylation of (
S
)-scoulerine.
Stars
This entity has been manually annotated by the ChEBI Team.
Submitter
KAX
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Read full article at Wikipedia
Formula
C20H24NO4
Net Charge
+1
Average Mass
342.40830
Monoisotopic Mass
342.16998
InChI
InChI=1S/C20H23NO4/c1-
21-
7-
6-
13-
9-
19(25-
3)
17(22)
10-
14(13)
16(21)
8-
12-
4-
5-
18(24-
2)
20(23)
15(12)
11-
21/h4-
5,9-
10,16H,6-
8,11H2,1-
3H3,(H-
,22,23)
/p+1/t16-
,21-
/m0/s1
InChIKey
LKLWVKCEYSPQHL-KKSFZXQISA-O
SMILES
COc1ccc2C[C@H]3c4cc(O)c(OC)cc4CC[N@@+]3(C)Cc2c1O
Roles Classification
Biological Role
(s):
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
EC 3.1.1.7 (acetylcholinesterase) inhibitor
An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via
alkaloid
)
View more via ChEBI Ontology
ChEBI Ontology
Outgoing
cyclanoline (
CHEBI:76923
)
has functional parent
(
S
)-scoulerine (
CHEBI:17129
)
cyclanoline (
CHEBI:76923
)
has role
EC 3.1.1.7 (acetylcholinesterase) inhibitor (
CHEBI:38462
)
cyclanoline (
CHEBI:76923
)
has role
plant metabolite (
CHEBI:76924
)
cyclanoline (
CHEBI:76923
)
is a
berberine alkaloid (
CHEBI:22754
)
cyclanoline (
CHEBI:76923
)
is a
quaternary ammonium ion (
CHEBI:35267
)
IUPAC Name
(7
S
,13a
S
)-
2,9-
dihydroxy-
3,10-
dimethoxy-
7-
methyl-
5,8,13,13a-
tetrahydro-
6
H
-
isoquinolino[3,2-
a
]isoquinolinium
Synonyms
Sources
(
S
)-
cis
-
N
-methylscoulerine
UniProt
(
S
,
S
)-
N
-methylscoulerine
ChEBI
Cissamine
ChemIDplus
Manual Xrefs
Databases
CN1500486
Patent
Cyclanoline
Wikipedia
View more database links
Registry Numbers
Types
Sources
1555524
Reaxys Registry Number
Reaxys
18556-27-9
CAS Registry Number
ChemIDplus
Citations
Types
Sources
10726860
PubMed citation
Europe PMC
14236247
PubMed citation
Europe PMC
15802807
PubMed citation
Europe PMC
16640839
PubMed citation
Europe PMC
19624470
PubMed citation
SUBMITTER
Last Modified
21 January 2014