(−)-noscapine
CHEBI:73237 EXACT SEEDED cytotoxicenzyme inhibitor
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.
Structure
| Standard InChIKey | AKNNEGZIBPJZJG-MSOLQXFVSA-N |
|---|---|
| SMILES | CN1CCC2=CC3=C(C(=C2[C@@H]1[C@@H]4C5=C(C(=C(C=C5)OC)OC)C(=O)O4)OC)OCO3 |
| Stereochemistry | fully defined |
| Cross-references | pubchem:275196 |
Filing pathway
Alkaloids — computed by NPClassifier npclassifier.gnps2.org@2026-09-07, which is why it is pinned rather than recomputed. The gene cluster's asserted class is other, from MIBiG.
Producer organisms 1
A claim that this taxon makes the compound. The basis says what the evidence addressed — a knockout and a database assertion are not the same claim.
| Taxon | Basis | Cluster | Evidence |
|---|---|---|---|
| Papaver somniferum NCBITaxon:3469 |
SOURCE_ASSERTION | mibig:BGC0001325 | DOI:10.1371/journal.pone.0017733 |
Occurrences 25
Somebody found the compound in this organism and cited it. That is not a claim that the organism makes it, and nothing here promotes one to the other.
| Taxon | Source | Reference |
|---|---|---|
| Corydalis heterocarpa var. japonica NCBITaxon:1030657 |
LOTUS | DOI:10.1002/ARDP.19873200805 |
| Papaver pseudo-orientale NCBITaxon:215228 |
LOTUS | DOI:10.1016/S0031-9422(00)81705-7 |
| Papaver setigerum NCBITaxon:215229 |
LOTUS | DOI:10.1055/S-2007-969106 |
| Papaver orientale NCBITaxon:22694 |
LOTUS | DOI:10.1016/S0031-9422(00)81705-7 |
| Papaver fugax NCBITaxon:3117443 |
LOTUS | DOI:10.1016/S0031-9422(00)81705-7 |
| Papaver rhoeas NCBITaxon:33128 |
LOTUS | DOI:10.1055/S-2006-960934 |
| Papaver oreophilum NCBITaxon:3736021 |
LOTUS | DOI:10.1021/NP070099O |
| Roemeria carica NCBITaxon:3736784 |
LOTUS | DOI:10.3987/R-1986-05-1227 |
| Corydalis ochotensis NCBITaxon:38907 |
LOTUS | DOI:10.1002/ARDP.19873200805 |
| Corydalis solida NCBITaxon:38914 |
LOTUS | DOI:10.1139/V69-178 |
| Corydalis ophiocarpa NCBITaxon:38929 |
LOTUS | DOI:10.1002/ARDP.19873200805 |
| Papaver somniferum NCBITaxon:3469 |
LOTUS | DOI:10.1002/PCA.2800020205 |
| Papaver somniferum NCBITaxon:3469 |
LOTUS | DOI:10.1016/0305-1978(88)90092-0 |
| Papaver somniferum NCBITaxon:3469 |
LOTUS | DOI:10.1016/0379-0738(94)90219-4 |
| Papaver somniferum NCBITaxon:3469 |
LOTUS | DOI:10.1016/0731-7085(95)01574-4 |
| Papaver somniferum NCBITaxon:3469 |
LOTUS | DOI:10.1016/S0021-9673(00)94605-3 |
| Papaver somniferum NCBITaxon:3469 |
LOTUS | DOI:10.1016/S0031-9422(00)88047-4 |
| Papaver somniferum NCBITaxon:3469 |
LOTUS | DOI:10.1016/S0031-9422(99)00420-3 |
| Papaver somniferum NCBITaxon:3469 |
LOTUS | DOI:10.1055/S-2006-957966 |
| Papaver somniferum NCBITaxon:3469 |
LOTUS | DOI:10.1055/S-2006-959739 |
| Papaver somniferum NCBITaxon:3469 |
LOTUS | DOI:10.1055/S-2007-969106 |
| Papaver somniferum NCBITaxon:3469 |
LOTUS | DOI:10.1055/S-2007-969109 |
| Papaver somniferum NCBITaxon:3469 |
LOTUS | DOI:10.1073/PNAS.95.4.1601 |
| Papaver somniferum NCBITaxon:3469 |
LOTUS | DOI:10.1126/SCIENCE.1220757 |
| Papaver somniferum NCBITaxon:3469 |
LOTUS | DOI:10.1515/ZNC-1984-9-1004 |
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0001325 | Papaver somniferum NCBITaxon:3469 |
CLUSTER_UNSTATED | genbank:MIBIG.BGC0001325.1 |
A locus claim and a taxon claim are different questions. Heterologous expression settles the first and leaves the second where the isolation report left it.
Bioactivities 25
| Assay | Result | Reference |
|---|---|---|
| A CellTox Green Cytotoxicity Assay to monitor cytotoxicity in HepG2 cells - 32 hour | 26.8325 uM | pubchem.aid:1224883 |
| A CellTox Green Cytotoxicity Assay to monitor cytotoxicity in HepG2 cells - 40 hour | 26.8325 uM | pubchem.aid:1224879 |
| A quantitative high throughput screen for small molecules that induce DNA re-replication in SW480 colon adenocarcinoma cells. | 29.0929 uM | pubchem.aid:624297 |
| A quantitative high throughput screen for small molecules that induce DNA re-replication in SW480 colon adenocarcinoma cells. | 23.1093 uM | pubchem.aid:624297 |
| Caspase-3/7 induction in CHO-K1 cells by small molecules, qHTS cell viability counter screen | 13.3332 uM | pubchem.aid:1346979 |
| Caspase-3/7 induction in HepG2 cells by small molecules, qHTS cell viability counter screen | 14.9601 uM | pubchem.aid:1346981 |
| Cellular viability qHTS for adrenocortical cancer (ACC) cell line NCI-H295R | 29.0929 uM | pubchem.aid:1963990 |
| Cellular viability qHTS for adrenocortical cancer (ACC) cell line SW-13 | 23.1093 uM | pubchem.aid:1963989 |
| Cellular viability qHTS for anaplastic thyroid cancer (ATC) cell line 8505C | 23.0153 uM | pubchem.aid:2202553 |
| Cytochrome P450 Family 2 Subfamily C Member 19 (CYP2C19) small molecule antagonists: luciferase reporter qHTS assay | 1.3803 uM | pubchem.aid:1671197 |
| Cytochrome P450 Family 2 Subfamily C Member 19 (CYP2C19) small molecule antagonists: luciferase reporter qHTS assay | 1.3803 uM | pubchem.aid:1671197 |
| Cytochrome P450 Family 2 Subfamily C Member 9 (CYP2C9) small molecule antagonists: luciferase reporter qHTS assay | 0.8709 uM | pubchem.aid:1671198 |
| Cytochrome P450 Family 2 Subfamily C Member 9 (CYP2C9) small molecule antagonists: luciferase reporter qHTS assay | 0.8709 uM | pubchem.aid:1671198 |
| Cytochrome P450 Family 2 Subfamily D Member 6 (CYP2D6) small molecule antagonists: luciferase reporter qHTS assay | 10.964 uM | pubchem.aid:1671196 |
| Cytochrome P450 Family 2 Subfamily D Member 6 (CYP2D6) small molecule antagonists: luciferase reporter qHTS assay | 10.964 uM | pubchem.aid:1671196 |
| Cytochrome P450 Family 3 Subfamily A Member 4 (CYP3A4) small molecule antagonists: luciferase reporter qHTS assay | 0.6918 uM | pubchem.aid:1671201 |
| Cytochrome P450 Family 3 Subfamily A Member 4 (CYP3A4) small molecule antagonists: luciferase reporter qHTS assay | 0.6918 uM | pubchem.aid:1671201 |
| Cytochrome P450 family 2 subfamily C member 9 (CYP2C9) small molecule antagonists: luciferase cell-based qHTS assay | 0.1096 uM | pubchem.aid:1645842 |
| Cytochrome P450 family 2 subfamily D member 6 (CYP2D6) small molecule antagonists: luciferase cell-based qHTS assay | 4.8975 uM | pubchem.aid:1645840 |
| Cytochrome P450 family 3 subfamily A member 4 (CYP3A4) small molecule antagonists: luciferase cell-based qHTS assay | 0.4365 uM | pubchem.aid:1645841 |
| Cytochrome P450 family 3 subfamily A member 7 (CYP3A7) small molecule antagonists: luciferase cell-based qHTS assay | 0.389 uM | pubchem.aid:1963596 |
| Cytochrome P450 family 3 subfamily A member 7 (CYP3A7) small molecule antagonists: luciferase cell-based qHTS assay | 0.389 uM | pubchem.aid:1963596 |
| GF-AFC viability counterscreen for inhibitors of alpha-synuclein gene (SNCA) expression | 5.6234 uM | pubchem.aid:1671193 |
| Human pregnane X receptor (PXR) activation by small molecules, qHTS assay | 22.3872 uM | pubchem.aid:1346985 |
| Human pregnane X receptor (PXR) small molecule agonists, qHTS assay | 11.8832 uM | pubchem.aid:1346982 |
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0001325 | MIBIG | 3 |
| CHEBI:73237 | CHEBI | 3-star |
This page is generated from data/natural_products/alkaloids/noscapine.yaml, which is generated from the committed inventories. Neither is edited by hand.