Showing metabocard for Protopine (BMDB0003920)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:06:36 UTC
Update Date2020-05-11 20:15:12 UTC
BMDB IDBMDB0003920
Secondary Accession Numbers
  • BMDB03920
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. Based on a literature review a significant number of articles have been published on Protopine.
Structure
Thumb
MOLSDFPDBSMILESInChI
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
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point208 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-004r-2931000000-d14db9f8fbba357a7ceaView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004r-2931000000-d14db9f8fbba357a7ceaView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ri-2049000000-c70fb92c70c89eb31559View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0f79-0936000000-da2afff6dba215da666aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0931000000-3ae8ba25a400b3cfc336View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0009000000-d474e4da85bfe6b8622eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0009000000-c77daec49f175e0080d3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0629000000-f410a01812829c61b1b5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0921000000-cb2a7100722bf81f462fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0930000000-e740d177ef096526ca53View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-000j-0932000000-899dc6a90055430abee2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0009000000-1833ae0a6ab82f156d51View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udr-0938000000-8a5ae3db2af3946a0e75View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0920000000-925c965ff2b76b30d02fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0f79-0944000000-e1624142a49564f32b99View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0910000000-79485782e2b17a1fccefView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0931000000-a9d401bee935049397deView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0920000000-092e042fc79ca310c193View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0941000000-1fdf197d94d08c882c08View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-aab71a61504570b7beebView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0udr-0928000000-60509c382ac86776f91cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000i-0920000000-925c965ff2b76b30d02fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-0089e0012db766e23529View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udj-0509000000-ed54f57036aee6ac913cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-1900000000-e130dfa9e240571ed4e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-400e98b52794a7bf4fbdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0009000000-71833c50697c0a4e532cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9658000000-c8824149cc8b247dcb6fView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0002-2910000000-c237219498d206631a06View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen Locations
  • Kidney
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0003920
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
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)Not Available
General ReferencesNot Available