Record Information |
---|
Version | 1.0 |
---|
Creation date | 2010-04-08 22:09:40 UTC |
---|
Update date | 2019-11-26 03:04:58 UTC |
---|
Primary ID | FDB011478 |
---|
Secondary Accession Numbers | Not Available |
---|
Chemical Information |
---|
FooDB Name | Narcotoline |
---|
Description | Alkaloid from straw of Papaver somniferum (opium poppy)
Narcotoline is an opiate alkaloid chemically related to noscapine. It binds to the same receptors in the brain as noscapine to act as an antitussive, and has also been used in tissue culture media. It can be obtained from the opium poppy Papaver somniferum. It is present at much higher levels in strains used for culinary purposes (poppyseed production) than in high-morphine strains used for opium production. Narcotoline is found in opium poppy. |
---|
CAS Number | 521-40-4 |
---|
Structure | |
---|
Synonyms | |
---|
Predicted Properties | |
---|
Chemical Formula | C21H21NO7 |
---|
IUPAC name | 3-{4-hydroxy-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl}-6,7-dimethoxy-1,3-dihydro-2-benzofuran-1-one |
---|
InChI Identifier | InChI=1S/C21H21NO7/c1-22-7-6-10-8-13-20(28-9-27-13)17(23)14(10)16(22)18-11-4-5-12(25-2)19(26-3)15(11)21(24)29-18/h4-5,8,16,18,23H,6-7,9H2,1-3H3 |
---|
InChI Key | LMGZCSKYOKDBES-UHFFFAOYSA-N |
---|
Isomeric SMILES | COC1=C(OC)C2=C(C=C1)C(OC2=O)C1N(C)CCC2=CC3=C(OCO3)C(O)=C12 |
---|
Average Molecular Weight | 399.3939 |
---|
Monoisotopic Molecular Weight | 399.131802031 |
---|
Classification |
---|
Description | Belongs to the class of organic compounds known as phthalide isoquinolines. These are organic compounds with a structure characterized by an isoquinoline moiety linked to phthalide. |
---|
Kingdom | Organic compounds |
---|
Super Class | Alkaloids and derivatives |
---|
Class | Phthalide isoquinolines |
---|
Sub Class | Not Available |
---|
Direct Parent | Phthalide isoquinolines |
---|
Alternative Parents | |
---|
Substituents | - Phthalide isoquinoline
- Phthalide
- Isobenzofuranone
- Benzofuranone
- Tetrahydroisoquinoline
- Benzodioxole
- Isocoumaran
- Anisole
- Alkyl aryl ether
- 1-hydroxy-4-unsubstituted benzenoid
- Aralkylamine
- Benzenoid
- Amino acid or derivatives
- Tertiary aliphatic amine
- Carboxylic acid ester
- Tertiary amine
- Lactone
- Acetal
- Carboxylic acid derivative
- Oxacycle
- Ether
- Azacycle
- Monocarboxylic acid or derivatives
- Organoheterocyclic compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Amine
- Organic oxygen compound
- Organopnictogen compound
- Organonitrogen compound
- Organooxygen compound
- Organic oxide
- Aromatic heteropolycyclic compound
|
---|
Molecular Framework | Aromatic heteropolycyclic compounds |
---|
External Descriptors | Not Available |
---|
Ontology |
---|
|
Disposition | Route of exposure: Source: Biological location: |
---|
Role | Biological role: |
---|
Physico-Chemical Properties |
---|
Physico-Chemical Properties - Experimental | |
---|
Spectra |
---|
Spectra | |
---|
EI-MS/GC-MS | Type | Description | Splash Key | View |
---|
Predicted GC-MS | Narcotoline, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0a4i-0090000000-8d36861fe0a3f59dbd49 | Spectrum | Predicted GC-MS | Narcotoline, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-004i-0090000000-83da6a230540709d25ed | Spectrum | Predicted GC-MS | Narcotoline, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
|
---|
MS/MS | Type | Description | Splash Key | View |
---|
Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0012900000-eb91c9a66be98f3a0e6a | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0zfr-0439500000-73d8dce5952ad6dabd42 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-004i-1913000000-f9a62eb623879958a12a | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0009000000-46306f2e15cf4d8ab386 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000t-0009000000-4f29fdfaf4b68c9a4380 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0f7a-4149000000-ae5a71e7bcc549404f18 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0009000000-493e5720e60337ba3deb | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-0009000000-78f035578ab74eed99fa | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0lxw-0529000000-1cb32954177b072022c8 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0010900000-00307be5f0edf24e3e7d | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-0021900000-5a924610ef954314a386 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0690-0977000000-146ce1b694343cd559a7 | 2021-09-25 | View Spectrum |
|
---|
NMR | Not Available |
---|
External Links |
---|
ChemSpider ID | 2736756 |
---|
ChEMBL ID | Not Available |
---|
KEGG Compound ID | C09593 |
---|
Pubchem Compound ID | 3496496 |
---|
Pubchem Substance ID | Not Available |
---|
ChEBI ID | Not Available |
---|
Phenol-Explorer ID | Not Available |
---|
DrugBank ID | Not Available |
---|
HMDB ID | HMDB33440 |
---|
CRC / DFC (Dictionary of Food Compounds) ID | GPK99-U:GPL03-S |
---|
EAFUS ID | Not Available |
---|
Dr. Duke ID | Not Available |
---|
BIGG ID | Not Available |
---|
KNApSAcK ID | C00001892 |
---|
HET ID | Not Available |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | Not Available |
---|
Flavornet ID | Not Available |
---|
GoodScent ID | Not Available |
---|
SuperScent ID | Not Available |
---|
Wikipedia ID | Narcotoline |
---|
Phenol-Explorer Metabolite ID | Not Available |
---|
Duplicate IDS | Not Available |
---|
Old DFC IDS | Not Available |
---|
Associated Foods |
---|
|
Biological Effects and Interactions |
---|
Health Effects / Bioactivities | Not Available |
---|
Enzymes | Not Available |
---|
Pathways | Not Available |
---|
Metabolism | Not Available |
---|
Biosynthesis | Not Available |
---|
Organoleptic Properties |
---|
Flavours | Not Available |
---|
Files |
---|
MSDS | Not Available |
---|
References |
---|
Synthesis Reference | Not Available |
---|
General Reference | Not Available |
---|
Content Reference | — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
|
---|