Record Information
Version1.0
Creation date2010-04-08 22:09:40 UTC
Update date2018-05-29 00:52:32 UTC
Primary IDFDB011477
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(-)-alpha-Narcotine
DescriptionAlkaloid from Papaver somniferum (opium poppy) Noscapine (also known as Narcotine, Nectodon, Nospen, and Anarcotine) is a benzylisoquinoline alkaloid from plants of the Papaveraceae family, without significant painkilling properties. This agent is primarily used for its antitussive (cough-suppressing) effects. It has also been shown to have anticancer activity. (-)-alpha-Narcotine is found in opium poppy.
CAS Number128-62-1
Structure
Thumb
Synonyms
SynonymSource
(-)-alpha-NarcotineChEBI
(-)-NarcotineChEBI
alpha-NarcotineChEBI
NoscapinaChEBI
NoscapineChEBI
NoscapinumChEBI
(-)-a-NarcotineGenerator
(-)-Α-narcotineGenerator
a-NarcotineGenerator
Α-narcotineGenerator
CapvalHMDB
CoscopinHMDB
L-alpha-NarcotineHMDB
LongatinHMDB
LyobexHMDB
MethoxyhydrastineHMDB
NarcomprenHMDB
NarcosineHMDB
NarcotinHMDB
NarcotussinHMDB
NarkotinHMDB
NectadonHMDB
NicolaneHMDB
NipaxonHMDB
NoscapalHMDB
NoscapalinHMDB
NoscapinHMDB
Noscapine (JP15/usp/inn)HMDB
NoscopineHMDB
O-MethylnarcotolineHMDB
OpianHMDB
OpianinHMDB
OpianineHMDB
TerbenolHMDB
TusscapineHMDB
VadebexHMDB
Librochin prikkelhoestMeSH
NarcotineMeSH
NoscapectMeSH
Noscapine hydrogen embonateMeSH
Embonate, noscapine hydrogenMeSH
Tropfen, capvalMeSH
TuscalmanMeSH
Capval tropfenMeSH
Hydrochloride, noscapineMeSH
Hydrogen embonate, noscapineMeSH
Noscapine hydrochlorideMeSH
Prikkelhoest, librochinMeSH
(-)-α-narcotineGenerator
α-Narcotinebiospider
L-α-Narcotinebiospider
Noscapine (JP15/USP/INN)biospider
o-Methylnarcotolinebiospider
α-narcotineGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.18 g/LALOGPS
logP2ALOGPS
logP2.58ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)14.59ChemAxon
pKa (Strongest Basic)6.44ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area75.69 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity107.08 m³·mol⁻¹ChemAxon
Polarizability42.19 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC22H23NO7
IUPAC name(3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-1,3-dihydro-2-benzofuran-1-one
InChI IdentifierInChI=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
InChI KeyAKNNEGZIBPJZJG-MSOLQXFVSA-N
Isomeric SMILES[H][C@@]1(OC(=O)C2=C1C=CC(OC)=C2OC)[C@]1([H])N(C)CCC2=CC3=C(OCO3)C(OC)=C12
Average Molecular Weight413.4205
Monoisotopic Molecular Weight413.147452095
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
  • Isobenzofuranone
  • Benzofuranone
  • Tetrahydroisoquinoline
  • Phthalide
  • Benzodioxole
  • Isocoumaran
  • Anisole
  • Alkyl aryl ether
  • Aralkylamine
  • Benzenoid
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Lactone
  • Tertiary aliphatic amine
  • Tertiary amine
  • 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 Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 63.92%; H 5.61%; N 3.39%; O 27.09%DFC
Melting PointMp 176°DFC
Boiling PointNot Available
Experimental Water Solubility0.3 mg/mL at 30 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -200 (CHCl3)DFC
Spectroscopic UV Data309 (e 4900) (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0090000000-32e92f98445c85eff993JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-00di-0090000000-d382091e1ec4d8b38b31JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00di-0092000000-b90243e40af9870ee7a7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00di-0091000000-a54e072ef1d92f81334dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00di-0091000000-fce496b34ef93b8f503fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0ab9-0040900000-47e532749f5b8ffb3cccJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00di-0002900000-254fac469b3a08249319JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-0494000000-cb9d8aed31ebc22f9c22JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0013900000-5b826e3916f6a190b5d4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03k9-0349500000-0a1171b8ad158af511deJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f96-1938000000-0226d383a4c62f6dd51aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0002900000-3e5155cb1df43a1ee339JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03yj-0009300000-554dd8c085d71b8e8c59JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0i6u-1109000000-3b5e0f2ae056ecae25b2JSpectraViewer
ChemSpider ID242139
ChEMBL IDCHEMBL364713
KEGG Compound IDC09592
Pubchem Compound ID275196
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33439
CRC / DFC (Dictionary of Food Compounds) IDGPK99-U:GPL01-Q
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00001891
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNoscapine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
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.