Record Information
Version1.0
Creation date2010-04-08 22:09:40 UTC
Update date2015-07-20 22:40:47 UTC
Primary IDFDB011479
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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).
CAS Number6035-40-1
Structure
Thumb
Synonyms
SynonymSource
(±)-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
(.+-.)-α-narcotinebiospider
(±) a-Narcotinedb_source
α-gnoscopinebiospider
DL-narcotinebiospider
Narcotine, (.+-.)-biospider
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
Chemical FormulaC22H23NO7
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
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
InChI KeyAKNNEGZIBPJZJG-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(OC)C2=C(C=C1)C(OC2=O)C1N(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 DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Role

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 230-233° (227-230°)DFC
Boiling PointNot Available
Experimental Water Solubility0.044 mg/mL at 20 oCSTEPHEN,H & STEPHEN,T (1963)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(±)-alpha-Narcotine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-0090000000-3c9ba32ffef0cb240424Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0010900000-cdd1247660f106a951f8Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0095100000-9600e118d85ae53c098bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0095000000-da9f07f22cfbc8de1589Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-05fr-0093000000-0bd2017e1bcc5746d029Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4i-0291000000-bbe1cf250f43716443dcSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4i-0590000000-a8e70dcad06bd7414fcbSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0000900000-c9769de8c704796705c7Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0229-0095800000-2c1c0615cb0341b18deeSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0079000000-a8be17dcb81cbaeb32b1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-05fr-0094000000-bf20e99af379ddfd1eb1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0291000000-7c2db78d383690296165Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-05fr-0394000000-4ff7d94b3c87b88e259fSpectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-0193000000-9ebb9c8bd7bea33e777cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0013900000-5b826e3916f6a190b5d4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03k9-0349500000-0a1171b8ad158af511deSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f96-1938000000-0226d383a4c62f6dd51aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0002900000-3e5155cb1df43a1ee339Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03yj-0009300000-554dd8c085d71b8e8c59Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0i6u-1109000000-3b5e0f2ae056ecae25b2Spectrum
NMRNot Available
ChemSpider ID4385
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID4544
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33441
CRC / DFC (Dictionary of Food Compounds) IDGPK99-U:GPL08-X
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
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
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference