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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
Thumb
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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
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
Predicted Chromatographic Properties
Spectra
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)Not Available
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 ]