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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:10:24 UTC
Update Date2018-03-12 22:00:12 UTC
HMDB IDHMDB0033439
Secondary Accession Numbers
  • HMDB33439
Metabolite Identification
Common Name(-)-alpha-Narcotine
Description(-)-alpha-Narcotine is found in opium poppy. (-)-alpha-Narcotine is an alkaloid 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. (Wikipedia).
Structure
Thumb
Synonyms
ValueSource
(-)-alpha-NarcotineChEBI
(-)-NarcotineChEBI
alpha-NarcotineChEBI
NoscapinaChEBI
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
Chemical FormulaC22H23NO7
Average Molecular Weight413.4205
Monoisotopic Molecular Weight413.147452095
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
Traditional Namenoscapine
CAS Registry Number128-62-1
SMILES
[H][C@@]1(OC(=O)C2=C1C=CC(OC)=C2OC)[C@]1([H])N(C)CCC2=CC3=C(OCO3)C(OC)=C12
InChI Identifier
InChI=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
Chemical Taxonomy
DescriptionThis compound 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
  • Benzylisoquinoline
  • Tetrahydroisoquinoline
  • Phthalide
  • Benzofuranone
  • Benzodioxole
  • Anisole
  • Aralkylamine
  • Alkyl aryl ether
  • Benzenoid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point176 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.3 mg/mL at 30 °CNot Available
LogPNot AvailableNot Available
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
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0090000000-32e92f98445c85eff993View in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-00di-0090000000-d382091e1ec4d8b38b31View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00di-0092000000-b90243e40af9870ee7a7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00di-0091000000-a54e072ef1d92f81334dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00di-0091000000-fce496b34ef93b8f503fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0ab9-0040900000-47e532749f5b8ffb3cccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00di-0002900000-254fac469b3a08249319View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-0494000000-cb9d8aed31ebc22f9c22View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0013900000-5b826e3916f6a190b5d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03k9-0349500000-0a1171b8ad158af511deView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f96-1938000000-0226d383a4c62f6dd51aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0002900000-3e5155cb1df43a1ee339View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03yj-0009300000-554dd8c085d71b8e8c59View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0i6u-1109000000-3b5e0f2ae056ecae25b2View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011477
KNApSAcK IDC00001891
Chemspider ID242139
KEGG Compound IDC09592
BioCyc IDCPD-14834
BiGG IDNot Available
Wikipedia LinkNoscapine
METLIN IDNot Available
PubChem Compound275196
PDB IDNot Available
ChEBI ID73237
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .