Record Information
Version1.0
Creation date2010-04-08 22:09:40 UTC
Update date2019-11-26 03:04:58 UTC
Primary IDFDB011478
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNarcotoline
DescriptionAlkaloid 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 Number521-40-4
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.46 g/LALOGPS
logP1.98ALOGPS
logP1.42ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)6.1ChemAxon
pKa (Strongest Basic)10.31ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area86.69 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity102.59 m³·mol⁻¹ChemAxon
Polarizability40.42 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H21NO7
IUPAC name3-{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 IdentifierInChI=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 KeyLMGZCSKYOKDBES-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(OC)C2=C(C=C1)C(OC2=O)C1N(C)CCC2=CC3=C(OCO3)C(O)=C12
Average Molecular Weight399.3939
Monoisotopic Molecular Weight399.131802031
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.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassPhthalide isoquinolines
Sub ClassNot Available
Direct ParentPhthalide 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 FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot 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
TypeDescriptionSplash KeyView
Predicted GC-MSNarcotoline, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-0090000000-8d36861fe0a3f59dbd49Spectrum
Predicted GC-MSNarcotoline, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-0090000000-83da6a230540709d25edSpectrum
Predicted GC-MSNarcotoline, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0012900000-eb91c9a66be98f3a0e6a2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zfr-0439500000-73d8dce5952ad6dabd422015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-1913000000-f9a62eb623879958a12a2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-46306f2e15cf4d8ab3862015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000t-0009000000-4f29fdfaf4b68c9a43802015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f7a-4149000000-ae5a71e7bcc549404f182015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-493e5720e60337ba3deb2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-78f035578ab74eed99fa2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0lxw-0529000000-1cb32954177b072022c82021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0010900000-00307be5f0edf24e3e7d2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0021900000-5a924610ef954314a3862021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0690-0977000000-146ce1b694343cd559a72021-09-25View Spectrum
NMRNot Available
ChemSpider ID2736756
ChEMBL IDNot Available
KEGG Compound IDC09593
Pubchem Compound ID3496496
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33440
CRC / DFC (Dictionary of Food Compounds) IDGPK99-U:GPL03-S
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00001892
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNarcotoline
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.