Showing Compound Protopine (FDB023249)

Record Information

Version

1.0

Creation date

2011-09-21 00:26:55 UTC

Update date

2015-07-21 06:57:36 UTC

Primary ID

FDB023249

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Protopine

Description

Protopine, 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 Number

130-86-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
4,6,7,14-Tetrahydro-5-methyl-bis(1,3)benzodioxolo(4,5-c-5',6'-g)azecin-13(5H)-one	ChEBI
7-Methyl-6,8,9,16-tetrahydrobis[1,3]benzodioxolo[4,5-c:5',6'-g]azecin-15(7H)-one	ChEBI
Corydinine	ChEBI
Fumarine	ChEBI
Macleyine	ChEBI
Biflorine	HMDB
Hypercorine	HMDB
Protopin	HMDB
Protopine mesylate	MeSH, HMDB
Protopine hydrochloride	MeSH, HMDB

Predicted Properties

Property	Value	Source
Water Solubility	0.2 g/L	ALOGPS
logP	1.95	ALOGPS
logP	2.59	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	15.82	ChemAxon
pKa (Strongest Basic)	4.95	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	57.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	94.57 m³·mol⁻¹	ChemAxon
Polarizability	36.68 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C20H19NO5

IUPAC name

15-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 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 Key

GPTFURBXHJWNHR-UHFFFAOYSA-N

Isomeric SMILES

CN1CCC2=C(C=C3OCOC3=C2)C(=O)CC2=C(C1)C1=C(OCO1)C=C2

Average Molecular Weight

353.3686

Monoisotopic Molecular Weight

353.126322723

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.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Protopine alkaloids

Sub Class

Not Available

Direct Parent

Protopine 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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

dibenzazecine alkaloid (CHEBI:16415 )
Isoquinoline alkaloids (C05189 )
a small molecule (PROTOPINE )

Ontology

Disposition

Source:

Endogenous

Biological location:

Subcellular:

Organ and components:

Kidney

Role

Biological role:

Metabolite

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0002-2910000000-c237219498d206631a06	2014-09-20	View Spectrum
GC-MS	Protopine, 1 TMS, GC-MS Spectrum	splash10-004r-2931000000-d14db9f8fbba357a7cea	Spectrum
GC-MS	Protopine, non-derivatized, GC-MS Spectrum	splash10-004r-2931000000-d14db9f8fbba357a7cea	Spectrum
Predicted GC-MS	Protopine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00ri-2049000000-c70fb92c70c89eb31559	Spectrum
Predicted GC-MS	Protopine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protopine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0f79-0936000000-da2afff6dba215da666a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-0931000000-3ae8ba25a400b3cfc336	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0udi-0009000000-d474e4da85bfe6b8622e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0udi-0009000000-c77daec49f175e0080d3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0udi-0629000000-f410a01812829c61b1b5	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-0921000000-cb2a7100722bf81f462f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-0930000000-e740d177ef096526ca53	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-000j-0932000000-899dc6a90055430abee2	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0009000000-1833ae0a6ab82f156d51	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udr-0938000000-8a5ae3db2af3946a0e75	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0920000000-925c965ff2b76b30d02f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-0f79-0944000000-e1624142a49564f32b99	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-000i-0910000000-79485782e2b17a1fccef	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-000i-0931000000-a9d401bee935049397de	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-000i-0920000000-092e042fc79ca310c193	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-000i-0941000000-1fdf197d94d08c882c08	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0009000000-aab71a61504570b7beeb	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0udr-0928000000-60509c382ac86776f91c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0920000000-925c965ff2b76b30d02f	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0009000000-0089e0012db766e23529	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udj-0509000000-ed54f57036aee6ac913c	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004j-1900000000-e130dfa9e240571ed4e0	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-400e98b52794a7bf4fbd	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0009000000-71833c50697c0a4e532c	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002f-9658000000-c8824149cc8b247dcb6f	2016-08-03	View Spectrum

NMR

Type	Description		View

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

16415

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB03920

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound Protopine (FDB023249)

Structure for FDB023249 (Protopine)