Noscapine
(3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3H-2-benzofuran-1-one
Molecular Identity
Noscapine
(3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3H-2-benzofuran-1-one
PubChem CID: 275196
(-)-noscapine is 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. It has a role as an antineoplastic agent, an antitussive, an apoptosis inducer and a plant metabolite. It is a benzylisoquinoline alkaloid, an organic heterotricyclic compound, an organic heterobicyclic compound, an aromatic ether, a tertiary amino compound, an isobenzofuranone and a cyclic acetal. It is functionally related to a (-)-noscapine hemiacetal.
2D Structure
Properties
C22H23NO7
Molecular Formula
413.40
Molecular Weight
g/mol
413.1475
Exact Mass
Da
2.7
XLogP
Drug-like (Lipinski: < 5)
75.7
TPSA
Good oral absorption (< 140 A²)
0
H-Bond Donors
8
H-Bond Acceptors
647
Complexity
SMILES
Canonical SMILES
SMILES: CN1CCC2=CC3=C(C(=C2C1C4C5=C(C(=C(C=C5)OC)OC)C(=O)O4)OC)OCO3Isomeric SMILES
SMILES: CN1CCC2=CC3=C(C(=C2[C@@H]1[C@@H]4C5=C(C(=C(C=C5)OC)OC)C(=O)O4)OC)OCO3Synonyms(20)
noscapine128-62-1NARCOTINETusscapineMethoxyhydrastineTerbenolCoscopinNarcomprenNarcosineVadebexNoscapalinLongatinOpianine(-)-NarcotineNarcotin
Data from PubChem (NCBI)
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Drug Network
Trials and conditions connected to Noscapine
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