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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:10:32 UTC
Update Date2019-07-23 06:13:26 UTC
HMDB IDHMDB0033441
Secondary Accession Numbers
  • HMDB33441
Metabolite Identification
Common Name(±)-alpha-Narcotine
Description(±)-alpha-Narcotine, also known as a-gnoscopine or (+/-)-noscapine, 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 (±)-alpha-Narcotine is a very strong basic compound (based on its pKa).
Structure
Data?1563862406
Synonyms
ValueSource
(±)-a-narcotineGenerator
(±)-α-narcotineGenerator
(+/-)-noscapineHMDB
(+/-) a-narcotineHMDB
(.+-.)-alpha-narcotineHMDB
(.+-.)-narcotineHMDB
a-GnoscopineHMDB
alpha-GnoscopineHMDB
DL-NarcotineHMDB
GnoscopineHMDB
Berna brand OF noscapine hydrochlorideHMDB
Dreluso brand OF noscapineHMDB
Embonate, noscapine hydrogenHMDB
Librochin prikkelhoestHMDB
Noscapine dreluso brandHMDB
Tropfen, capvalHMDB
TuscalmanHMDB
Boots brand OF noscapine hydrochlorideHMDB
Byk brand OF noscapine hydrochlorideHMDB
Dreluso brand OF noscapine hydrochlorideHMDB
NoscapectHMDB
NoscapineHMDB
Noscapine hydrogen embonateHMDB
Capval tropfenHMDB
Hydrochloride, noscapineHMDB
CapvalHMDB
Hydrogen embonate, noscapineHMDB
Noscapine hydrochlorideHMDB
Prikkelhoest, librochinHMDB
NarcotineMeSH
Chemical FormulaC22H23NO7
Average Molecular Weight413.4205
Monoisotopic Molecular Weight413.147452095
IUPAC Name6,7-dimethoxy-3-{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 Number6035-40-1
SMILES
COC1=C(OC)C2=C(C=C1)C(OC2=O)C1N(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
InChI KeyAKNNEGZIBPJZJG-UHFFFAOYSA-N
Chemical Taxonomy
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 DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point230 - 233 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.044 mg/mL at 20 °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
Polarizability42.34 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0090000000-3c9ba32ffef0cb240424Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0010900000-cdd1247660f106a951f8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0095100000-9600e118d85ae53c098bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0095000000-da9f07f22cfbc8de1589Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-05fr-0093000000-0bd2017e1bcc5746d029Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4i-0291000000-bbe1cf250f43716443dcSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4i-0590000000-a8e70dcad06bd7414fcbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0000900000-c9769de8c704796705c7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0229-0095800000-2c1c0615cb0341b18deeSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0079000000-a8be17dcb81cbaeb32b1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-05fr-0094000000-bf20e99af379ddfd1eb1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0291000000-7c2db78d383690296165Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-05fr-0394000000-4ff7d94b3c87b88e259fSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-0193000000-9ebb9c8bd7bea33e777cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0013900000-5b826e3916f6a190b5d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03k9-0349500000-0a1171b8ad158af511deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f96-1938000000-0226d383a4c62f6dd51aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0002900000-3e5155cb1df43a1ee339Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03yj-0009300000-554dd8c085d71b8e8c59Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0i6u-1109000000-3b5e0f2ae056ecae25b2Spectrum
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
FooDB IDFDB011479
KNApSAcK IDNot Available
Chemspider ID4385
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound4544
PDB IDNot Available
ChEBI ID110185
Food Biomarker OntologyNot Available
VMH IDNot Available
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.. .