CHEBI:73237 - (−)-noscapine

ChEBI IDCHEBI:73237
ChEBI Name(−)-noscapine
Stars
ASCII Name(-)-noscapine
DefinitionA 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.
Secondary ChEBI IDCHEBI:10321
Last Modified20 August 2018
Submittersjupe
DownloadsMolfile
FormulaC22H23NO7
Net Charge0
Average Mass413.426
Monoisotopic Mass413.14745
SMILES[H][C@]1([C@@]2([H])c3c(cc4c(c3OC)OCO4)CCN2C)OC(=O)c2c1ccc(OC)c2OC
InChIInChI=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
InChIKeyAKNNEGZIBPJZJG-MSOLQXFVSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Applications:
antitussive  An agent that suppresses cough. Antitussives have a central or a peripheral action on the cough reflex, or a combination of both. Compare with expectorants, which are considered to increase the volume of secretions in the respiratory tract, so facilitating their removal by ciliary action and coughing, and mucolytics, which decrease the viscosity of mucus, facilitating its removal by ciliary action and expectoration.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
(−)-noscapine (CHEBI:73237) has functional parent (−)-noscapine hemiacetal (CHEBI:141667)
(−)-noscapine (CHEBI:73237) has role antineoplastic agent (CHEBI:35610)
(−)-noscapine (CHEBI:73237) has role antitussive (CHEBI:51177)
(−)-noscapine (CHEBI:73237) has role apoptosis inducer (CHEBI:68495)
(−)-noscapine (CHEBI:73237) has role plant metabolite (CHEBI:76924)
(−)-noscapine (CHEBI:73237) is a aromatic ether (CHEBI:35618)
(−)-noscapine (CHEBI:73237) is a benzylisoquinoline alkaloid (CHEBI:22750)
(−)-noscapine (CHEBI:73237) is a cyclic acetal (CHEBI:59770)
(−)-noscapine (CHEBI:73237) is a isobenzofuranone (CHEBI:55372)
(−)-noscapine (CHEBI:73237) is a organic heterobicyclic compound (CHEBI:27171)
(−)-noscapine (CHEBI:73237) is a organic heterotricyclic compound (CHEBI:26979)
(−)-noscapine (CHEBI:73237) is a tertiary amino compound (CHEBI:50996)
IUPAC Name 
(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
INNs  Source
noscapinumChemIDplus
noscapineChemIDplus
noscapineWHO MedNet
noscapinaChemIDplus
Synonyms  Source
alpha-NarcotineKEGG COMPOUND
(−)-α-narcotineHMDB
(−)-narcotineChemIDplus
UniProt Name  Source
noscapineUniProt
Manual XrefsDatabases
D01036KEGG DRUG
C09592KEGG COMPOUND
HMDB0033439HMDB
CPD-14834MetaCyc
NoscapineWikipedia
C00001891KNApSAcK
LSM-3997LINCS
1973DrugCentral
Registry NumbersSources
Reaxys:99933Reaxys
CAS:128-62-1KEGG COMPOUND
CAS:128-62-1ChemIDplus
CAS:128-62-1NIST Chemistry WebBook
Citations