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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:10:24 UTC
Update Date2022-03-07 02:53:42 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
Data?1563862406
Synonyms
ValueSource
(-)-NarcotineChEBI
alpha-NarcotineChEBI
NoscapinaChEBI
NoscapineChEBI
NoscapinumChEBI
a-NarcotineGenerator
Α-narcotineGenerator
(-)-a-NarcotineGenerator
(-)-Α-narcotineGenerator
CapvalMeSH
Capval tropfenMeSH
Embonate, noscapine hydrogenMeSH
Hydrochloride, noscapineMeSH
Hydrogen embonate, noscapineMeSH
Librochin prikkelhoestMeSH
NarcotineMeSH
NoscapectMeSH
Noscapine hydrochlorideMeSH
Noscapine hydrogen embonateMeSH
Tropfen, capvalMeSH
TuscalmanMeSH
Prikkelhoest, librochinMeSH
(-)-alpha-NarcotineChEBI
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
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

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point176 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.3 mg/mL at 30 °CNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+195.60231661259
DarkChem[M-H]-191.39231661259
DeepCCS[M-2H]-216.44330932474
DeepCCS[M+Na]+191.86930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(-)-alpha-Narcotine[H][C@@]1(OC(=O)C2=C1C=CC(OC)=C2OC)[C@]1([H])N(C)CCC2=CC3=C(OCO3)C(OC)=C124578.9Standard polar33892256
(-)-alpha-Narcotine[H][C@@]1(OC(=O)C2=C1C=CC(OC)=C2OC)[C@]1([H])N(C)CCC2=CC3=C(OCO3)C(OC)=C123142.6Standard non polar33892256
(-)-alpha-Narcotine[H][C@@]1(OC(=O)C2=C1C=CC(OC)=C2OC)[C@]1([H])N(C)CCC2=CC3=C(OCO3)C(OC)=C123128.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (-)-alpha-Narcotine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0090000000-32e92f98445c85eff9932017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-alpha-Narcotine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-alpha-Narcotine DI-ESI-qTof , Positive-QTOFsplash10-00di-0090000000-d382091e1ec4d8b38b312017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-alpha-Narcotine Linear Ion Trap , positive-QTOFsplash10-00di-0092000000-b90243e40af9870ee7a72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-alpha-Narcotine Linear Ion Trap , positive-QTOFsplash10-00di-0091000000-a54e072ef1d92f81334d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-alpha-Narcotine Linear Ion Trap , positive-QTOFsplash10-00di-0091000000-fce496b34ef93b8f503f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-alpha-Narcotine Linear Ion Trap , positive-QTOFsplash10-0ab9-0040900000-47e532749f5b8ffb3ccc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-alpha-Narcotine Linear Ion Trap , positive-QTOFsplash10-00di-0002900000-254fac469b3a082493192017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-alpha-Narcotine , positive-QTOFsplash10-00di-0494000000-cb9d8aed31ebc22f9c222017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-alpha-Narcotine 15V, Positive-QTOFsplash10-03k9-0062900000-bf0cf5fac123965ac7b12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-alpha-Narcotine 35V, Positive-QTOFsplash10-00di-0089300000-86a4acdf0e1666ee2f5d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-alpha-Narcotine 30V, Positive-QTOFsplash10-00di-0097000000-3dc8b045aeb87b81f4882021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-alpha-Narcotine 20V, Positive-QTOFsplash10-00di-0096200000-0e46351b9e099dd035ff2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-alpha-Narcotine 30V, Positive-QTOFsplash10-00di-0097000000-2c38fbf5a5a8273cb5622021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-alpha-Narcotine 15V, Positive-QTOFsplash10-03k9-0062900000-d48438307b64d04a27212021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-alpha-Narcotine 10V, Positive-QTOFsplash10-03di-0010900000-a69d344c6c2917e1894f2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-alpha-Narcotine 10V, Positive-QTOFsplash10-03di-0013900000-5b826e3916f6a190b5d42016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-alpha-Narcotine 20V, Positive-QTOFsplash10-03k9-0349500000-0a1171b8ad158af511de2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-alpha-Narcotine 40V, Positive-QTOFsplash10-0f96-1938000000-0226d383a4c62f6dd51a2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-alpha-Narcotine 10V, Negative-QTOFsplash10-03di-0002900000-3e5155cb1df43a1ee3392016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-alpha-Narcotine 20V, Negative-QTOFsplash10-03yj-0009300000-554dd8c085d71b8e8c592016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-alpha-Narcotine 40V, Negative-QTOFsplash10-0i6u-1109000000-3b5e0f2ae056ecae25b22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-alpha-Narcotine 10V, Negative-QTOFsplash10-03di-0000900000-3a2b668bf2dbd5c6416c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-alpha-Narcotine 20V, Negative-QTOFsplash10-03di-0007900000-6699c8e8d0e97bb3ffff2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-alpha-Narcotine 40V, Negative-QTOFsplash10-01ot-0549100000-6e0506ecee44b088751b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-alpha-Narcotine 10V, Positive-QTOFsplash10-03di-0010900000-def7e1eece373bfc3cb72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-alpha-Narcotine 20V, Positive-QTOFsplash10-03di-0031900000-3d606db82b215faa9e7e2021-09-25Wishart LabView Spectrum
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 IDDB06174
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1142581
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.. .