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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 07:14:09 UTC
Update Date2021-10-13 04:42:32 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 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. Protopine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Protopine.
Structure
Data?1594319783
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 mesylateMeSH, HMDB
Protopine hydrochlorideMeSH, HMDB
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

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point208 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.82 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.2 g/LALOGPS
logP10(1.95) g/LALOGPS
logP10(2.59) g/LChemAxon
logS10(-3.2) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+183.34131661259
DarkChem[M-H]-182.09131661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ProtopineCN1CCC2=C(C=C3OCOC3=C2)C(=O)CC2=C(C1)C1=C(OCO1)C=C24343.4Standard polar33892256
ProtopineCN1CCC2=C(C=C3OCOC3=C2)C(=O)CC2=C(C1)C1=C(OCO1)C=C22758.5Standard non polar33892256
ProtopineCN1CCC2=C(C=C3OCOC3=C2)C(=O)CC2=C(C1)C1=C(OCO1)C=C23013.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Protopine GC-MS (1 TMS)splash10-004r-2931000000-d14db9f8fbba357a7cea2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Protopine GC-MS (Non-derivatized)splash10-004r-2931000000-d14db9f8fbba357a7cea2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Protopine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ri-2049000000-c70fb92c70c89eb315592017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Protopine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Protopine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0002-2910000000-c237219498d206631a062014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Protopine LC-ESI-QQ , positive-QTOFsplash10-0f79-0936000000-da2afff6dba215da666a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Protopine LC-ESI-QQ , positive-QTOFsplash10-000i-0931000000-3ae8ba25a400b3cfc3362017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Protopine LC-ESI-QQ , positive-QTOFsplash10-0udi-0009000000-d474e4da85bfe6b8622e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Protopine LC-ESI-QQ , positive-QTOFsplash10-0udi-0009000000-c77daec49f175e0080d32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Protopine LC-ESI-QQ , positive-QTOFsplash10-0udi-0629000000-f410a01812829c61b1b52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Protopine LC-ESI-QQ , positive-QTOFsplash10-000i-0921000000-cb2a7100722bf81f462f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Protopine LC-ESI-QQ , positive-QTOFsplash10-000i-0930000000-e740d177ef096526ca532017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Protopine LC-ESI-IT , positive-QTOFsplash10-000j-0932000000-899dc6a90055430abee22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Protopine LC-ESI-QTOF , positive-QTOFsplash10-0udi-0009000000-1833ae0a6ab82f156d512017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Protopine LC-ESI-QTOF , positive-QTOFsplash10-0udr-0938000000-8a5ae3db2af3946a0e752017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Protopine LC-ESI-QTOF , positive-QTOFsplash10-000i-0920000000-925c965ff2b76b30d02f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Protopine , positive-QTOFsplash10-0f79-0944000000-e1624142a49564f32b992017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Protopine 6V, Positive-QTOFsplash10-000i-0910000000-79485782e2b17a1fccef2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Protopine 6V, Positive-QTOFsplash10-000i-0931000000-a9d401bee935049397de2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Protopine 6V, Positive-QTOFsplash10-000i-0920000000-092e042fc79ca310c1932021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Protopine 6V, Positive-QTOFsplash10-000i-0941000000-1fdf197d94d08c882c082021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Protopine 10V, Positive-QTOFsplash10-0udi-0009000000-aab71a61504570b7beeb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Protopine 20V, Positive-QTOFsplash10-0udr-0928000000-60509c382ac86776f91c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Protopine 40V, Positive-QTOFsplash10-000i-0920000000-925c965ff2b76b30d02f2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protopine 10V, Positive-QTOFsplash10-0udi-0009000000-0089e0012db766e235292016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protopine 20V, Positive-QTOFsplash10-0udj-0509000000-ed54f57036aee6ac913c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protopine 40V, Positive-QTOFsplash10-004j-1900000000-e130dfa9e240571ed4e02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protopine 10V, Negative-QTOFsplash10-0udi-0009000000-400e98b52794a7bf4fbd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protopine 20V, Negative-QTOFsplash10-0udi-0009000000-71833c50697c0a4e532c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protopine 40V, Negative-QTOFsplash10-002f-9658000000-c8824149cc8b247dcb6f2016-08-03Wishart LabView Spectrum
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
FooDB IDFDB023249
KNApSAcK IDC00001906
Chemspider ID4799
KEGG Compound IDC05189
BioCyc IDPROTOPINE
BiGG IDNot Available
Wikipedia LinkProtopine
METLIN ID6988
PubChem Compound4970
PDB IDNot Available
ChEBI ID16415
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1836891
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 ]