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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-13 07:14:09 UTC
Update Date2020-02-26 21:24:50 UTC
HMDB IDHMDB0003920
Secondary Accession Numbers
  • HMDB03920
Metabolite Identification
Common 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 is a strong basic compound (based on its pKa). Protopine is a potentially toxic compound. Protopine is a benzylisoquinoline alkaloid occurring in opium poppy, Corydalis tubers and other plants of the family papaveraceae, like Fumaria officinalis.
Structure
Data?1582752290
Synonyms
ValueSource
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 mesylateHMDB
Protopine hydrochlorideHMDB
Chemical FormulaC20H19NO5
Average Molecular Weight353.3686
Monoisotopic Molecular Weight353.126322723
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
Traditional Nameprotopine
CAS Registry Number130-86-9
SMILES
CN1CCC2=C(C=C3OCOC3=C2)C(=O)CC2=C(C1)C1=C(OCO1)C=C2
InChI Identifier
InChI=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
Chemical Taxonomy
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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point208 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-004r-2931000000-d14db9f8fbba357a7ceaSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004r-2931000000-d14db9f8fbba357a7ceaSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ri-2049000000-c70fb92c70c89eb31559Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0f79-0936000000-da2afff6dba215da666aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0931000000-3ae8ba25a400b3cfc336Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0009000000-d474e4da85bfe6b8622eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0009000000-c77daec49f175e0080d3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0629000000-f410a01812829c61b1b5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0921000000-cb2a7100722bf81f462fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0930000000-e740d177ef096526ca53Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-000j-0932000000-899dc6a90055430abee2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0009000000-1833ae0a6ab82f156d51Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udr-0938000000-8a5ae3db2af3946a0e75Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0920000000-925c965ff2b76b30d02fSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0f79-0944000000-e1624142a49564f32b99Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-0089e0012db766e23529Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udj-0509000000-ed54f57036aee6ac913cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-1900000000-e130dfa9e240571ed4e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-400e98b52794a7bf4fbdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0009000000-71833c50697c0a4e532cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9658000000-c8824149cc8b247dcb6fSpectrum
MSMass Spectrum (Electron Ionization)splash10-0002-2910000000-c237219498d206631a06Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue Locations
  • Kidney
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 IDFDB023249
KNApSAcK IDC00001906
Chemspider ID4799
KEGG Compound IDC05189
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkProtopine
METLIN ID6988
PubChem Compound4970
PDB IDNot Available
ChEBI ID16415
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceRueffer, M.; Zenk, M. H. Enzymatic formation of protopines by a microsomal cytochrome P-450 system of Corydalis vaginans. Tetrahedron Letters (1987), 28(44), 5307-10.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Paul LD, Maurer HH: Studies on the metabolism and toxicological detection of the Eschscholtzia californica alkaloids californine and protopine in urine using gas chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jun 5;789(1):43-57. [PubMed:12726842 ]
  2. Wynne PM, Vine JH, Amiet RG: Protopine alkaloids in horse urine. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Nov 5;811(1):85-91. [PubMed:15458726 ]
  3. Jiang B, Cao K, Wang R: Inhibitory effect of protopine on K(ATP) channel subunits expressed in HEK-293 cells. Eur J Pharmacol. 2004 Dec 15;506(2):93-100. [PubMed:15588728 ]