CHEBI:73237 - (−)-noscapine

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ChEBI Name (−)-noscapine
ChEBI ID CHEBI:73237
ChEBI ASCII Name (-)-noscapine
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Steve Jupe
Secondary ChEBI IDs CHEBI:10321
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Formula C22H23NO7
Net Charge 0
Average Mass 413.421
Monoisotopic Mass 413.147
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
SMILES C1N([C@@](C2=C(C1)C=C3OCOC3=C2OC)([H])[C@@]4(C=5C=CC(=C(C5C(O4)=O)OC)OC)[H])C
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (−)-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 Sources
noscapina ChemIDplus
noscapine ChemIDplus
noscapine WHO MedNet
noscapinum ChemIDplus
Synonyms Sources
(−)-α-narcotine HMDB
(−)-narcotine ChemIDplus
alpha-Narcotine KEGG COMPOUND
noscapine UniProt
Manual Xrefs Databases
1973 DrugCentral
C00001891 KNApSAcK
C09592 KEGG COMPOUND
CPD-14834 MetaCyc
D01036 KEGG DRUG
HMDB0033439 HMDB
LSM-3997 LINCS
Noscapine Wikipedia
View more database links
Registry Numbers Types Sources
128-62-1 CAS Registry Number KEGG COMPOUND
128-62-1 CAS Registry Number ChemIDplus
128-62-1 CAS Registry Number NIST Chemistry WebBook
99933 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
22079300 PubMed citation Europe PMC
22546556 PubMed citation Europe PMC
22653730 PubMed citation Europe PMC
22671862 PubMed citation Europe PMC
22733149 PubMed citation Europe PMC
22848370 PubMed citation Europe PMC
22935070 PubMed citation Europe PMC
23117045 PubMed citation Europe PMC
Last Modified
20 August 2018