(-)-noscapineImported
A benzylisoquinoline alkaloid that is 1,2,3,4-tetrahydroisoquinoline which is substituted by a 4,5-dimethoxy-3-oxo-1,3-dihydro-2-benzofuran-1-yl group at position 1, a methylenedioxy group at positions 6-7 and a methoxy group at position 8. Obtained from plants of the Papaveraceae family, it lacks significant painkilling properties and is primarily used for its antitussive (cough-suppressing) effects.
Defined bychebi
Also appears indron
Exact Synonyms
(3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-2-benzofuran-1(3H)-one
Related Synonyms
(-)-alpha-narcotine
(-)-narcotine
alpha-Narcotine
noscapina
noscapine
noscapinum
class Information
charge
0
formula
C22H23NO7
has_alternative_id
has_dbxref
- CAS:128-62-1
- Drug_Central:1973
- HMDB:HMDB0033439
- KEGG:C09592
- KEGG:D01036
- KNApSAcK:C00001891
- LINCS:LSM-3997
- MetaCyc:CPD-14834
- PMID:22079300
- PMID:22546556
- PMID:22653730
- PMID:22671862
- PMID:22733149
- PMID:22848370
- PMID:22935070
- PMID:23117045
- Reaxys:99933
- Wikipedia:Noscapine
has_obo_namespace
chebi_ontology
inchi
InChI=1S/C22H23NO7/c1-23-8-7-11-9-14-20(29-10-28-14)21(27-4)15(11)17(23)18-12-5-6-13(25-2)19(26-3)16(12)22(24)30-18/h5-6,9,17-18H,7-8,10H2,1-4H3/t17-,18+/m1/s1
inchikey
AKNNEGZIBPJZJG-MSOLQXFVSA-N
in_subset
mass
413.421
monoisotopicmass
413.14745
smiles
C1N([C@@](C2=C(C1)C=C3OCOC3=C2OC)([H])[C@@]4(C=5C=CC(=C(C5C(O4)=O)OC)OC)[H])C
class Relations
Subclass of
- benzylisoquinoline alkaloidchebi
- organic heterotricyclic compoundchebi
- organic heterobicyclic compoundchebi
- aromatic etherchebi
- tertiary amino compoundchebi
- isobenzofuranonechebi
- cyclic acetalchebi
- has rolerosomeantineoplastic agentchebi
- has rolerosomeantitussivechebi
- has rolerosomeapoptosis inducerchebi
- has rolerosomeplant metabolitechebi
- has functional parentsome(-)-noscapine hemiacetalchebi