Record Information
Version1.0
Creation date2011-09-21 00:26:55 UTC
Update date2015-07-21 06:57:36 UTC
Primary IDFDB023249
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameProtopine
DescriptionProtopine, also known as corydinine or fumarine, belongs to the class of organic compounds known as protopine alkaloids. These are alkaloids with a structure based on a tricyclic protopine formed by oxidative ring fission of protoberberine N-metho salts. Protopine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make protopine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Protopine.
CAS Number130-86-9
Structure
Thumb
Synonyms
SynonymSource
4,6,7,14-Tetrahydro-5-methyl-bis(1,3)benzodioxolo(4,5-c-5',6'-g)azecin-13(5H)-oneChEBI
7-Methyl-6,8,9,16-tetrahydrobis[1,3]benzodioxolo[4,5-c:5',6'-g]azecin-15(7H)-oneChEBI
CorydinineChEBI
FumarineChEBI
MacleyineChEBI
BiflorineHMDB
HypercorineHMDB
ProtopinHMDB
Protopine mesylateMeSH, HMDB
Protopine hydrochlorideMeSH, HMDB
Predicted Properties
PropertyValueSource
Water Solubility0.2 g/LALOGPS
logP1.95ALOGPS
logP2.59ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)15.82ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area57.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity94.57 m³·mol⁻¹ChemAxon
Polarizability36.68 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H19NO5
IUPAC name15-methyl-7,9,19,21-tetraoxa-15-azapentacyclo[15.7.0.0⁴,¹².0⁶,¹⁰.0¹⁸,²²]tetracosa-1(17),4(12),5,10,18(22),23-hexaen-3-one
InChI IdentifierInChI=1S/C20H19NO5/c1-21-5-4-13-7-18-19(25-10-24-18)8-14(13)16(22)6-12-2-3-17-20(15(12)9-21)26-11-23-17/h2-3,7-8H,4-6,9-11H2,1H3
InChI KeyGPTFURBXHJWNHR-UHFFFAOYSA-N
Isomeric SMILESCN1CCC2=C(C=C3OCOC3=C2)C(=O)CC2=C(C1)C1=C(OCO1)C=C2
Average Molecular Weight353.3686
Monoisotopic Molecular Weight353.126322723
Classification
Description Belongs to the class of organic compounds known as protopine alkaloids. These are alkaloids with a structure based on a tricyclic protopine formed by oxidative ring fission of protoberberine N-metho salts.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassProtopine alkaloids
Sub ClassNot Available
Direct ParentProtopine alkaloids
Alternative Parents
Substituents
  • Protopine skeleton
  • Benzodioxole
  • Aryl ketone
  • Aryl alkyl ketone
  • Aralkylamine
  • Benzenoid
  • Ketone
  • Tertiary amine
  • Tertiary aliphatic amine
  • Acetal
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Amine
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
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
EI-MSMass Spectrum (Electron Ionization)splash10-0002-2910000000-c237219498d206631a06Spectrum
GC-MSProtopine, 1 TMS, GC-MS Spectrumsplash10-004r-2931000000-d14db9f8fbba357a7ceaSpectrum
GC-MSProtopine, non-derivatized, GC-MS Spectrumsplash10-004r-2931000000-d14db9f8fbba357a7ceaSpectrum
Predicted GC-MSProtopine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00ri-2049000000-c70fb92c70c89eb31559Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0f79-0936000000-da2afff6dba215da666aSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0931000000-3ae8ba25a400b3cfc336Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0009000000-d474e4da85bfe6b8622eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0009000000-c77daec49f175e0080d3Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0629000000-f410a01812829c61b1b5Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0921000000-cb2a7100722bf81f462fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0930000000-e740d177ef096526ca53Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-000j-0932000000-899dc6a90055430abee2Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0009000000-1833ae0a6ab82f156d51Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udr-0938000000-8a5ae3db2af3946a0e75Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0920000000-925c965ff2b76b30d02fSpectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0f79-0944000000-e1624142a49564f32b99Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0910000000-79485782e2b17a1fccefSpectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0931000000-a9d401bee935049397deSpectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0920000000-092e042fc79ca310c193Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0941000000-1fdf197d94d08c882c08Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-aab71a61504570b7beebSpectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0udr-0928000000-60509c382ac86776f91cSpectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000i-0920000000-925c965ff2b76b30d02fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-0089e0012db766e23529Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udj-0509000000-ed54f57036aee6ac913cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-1900000000-e130dfa9e240571ed4e0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-400e98b52794a7bf4fbdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0009000000-71833c50697c0a4e532cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9658000000-c8824149cc8b247dcb6fSpectrum
NMR
TypeDescriptionView
ChemSpider ID4799
ChEMBL IDCHEMBL453019
KEGG Compound IDC05189
Pubchem Compound ID4970
Pubchem Substance IDNot Available
ChEBI ID16415
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03920
CRC / DFC (Dictionary of Food Compounds) IDNot Available
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
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference