AFCDB: alpha-Allocryptopine (FDB005759)

Record Information

Version

1.0

Creation date

2010-04-08 22:06:50 UTC

Update date

2019-11-26 03:00:45 UTC

Primary ID

FDB005759

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

alpha-Allocryptopine

Description

Alpha-allocryptopine, also known as alpha-fagarine or beta-homochelidonine, is a member of the class of compounds known as protopine alkaloids. Protopine alkaloids are alkaloids with a structure based on a tricyclic protopine formed by oxidative ring fission of protoberberine N-metho salts. Alpha-allocryptopine is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Alpha-allocryptopine can be found in barley, which makes alpha-allocryptopine a potential biomarker for the consumption of this food product.

CAS Number

485-91-6

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.051 g/L	ALOGPS
logP	2.38	ALOGPS
logP	2.65	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	15.98	ChemAxon
pKa (Strongest Basic)	5.01	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	2	ChemAxon
Refractivity	101.73 m³·mol⁻¹	ChemAxon
Polarizability	39.23 Å³	ChemAxon
Number of Rings	4	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

C21H23NO5

IUPAC name

7,8-dimethoxy-11-methyl-17,19-dioxa-11-azatetracyclo[12.7.0.0⁴,⁹.0¹⁶,²⁰]henicosa-1(14),4(9),5,7,15,20-hexaen-2-one

InChI Identifier

InChI=1S/C21H23NO5/c1-22-7-6-14-9-19-20(27-12-26-19)10-15(14)17(23)8-13-4-5-18(24-2)21(25-3)16(13)11-22/h4-5,9-10H,6-8,11-12H2,1-3H3

InChI Key

HYBRYAPKQCZIAE-UHFFFAOYSA-N

Isomeric SMILES

COC1=C(OC)C2=C(CC(=O)C3=C(CCN(C)C2)C=C2OCOC2=C3)C=C1

Average Molecular Weight

369.411

Monoisotopic Molecular Weight

369.157622851

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
Anisole
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Aralkylamine
Benzenoid
Ketone
Tertiary amine
Tertiary aliphatic amine
Acetal
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Organooxygen compound
Hydrocarbon derivative
Amine
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dibenzazecine alkaloid (CHEBI:17390 )
Isoquinoline alkaloids (C02134 )
a small molecule (ALLOCRYPTOPINE )

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	160.5 oC
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

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0009000000-ce0c9de9daa7ecc957fe	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dj-0609000000-3e7b629c694247ab37fe	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002f-1900000000-02589253879ac7231767	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-c7ed985cf580bb10595d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0gb9-0009000000-2562c02bc56526e790dd	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-006x-6269000000-7d9c64483d5fb3c07467	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0009000000-ad1696003a3beba4181b	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0009000000-d594dd1aaea05b7b05f3	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00e9-0079000000-c98f187cb22bdb279ca1	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-c0b0af865b3879fc49f6	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0009000000-7072102416df1e826f05	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-0049000000-df41ddb5e7027542be33	2021-10-21	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

C02134

Pubchem Compound ID

98570

Pubchem Substance ID

Not Available

ChEBI ID

17390

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

ALPHA-ALLOCRYPTOPINE

BIGG ID

Not Available

KNApSAcK ID

C00001799

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

Descriptor	ID	Definition	Reference
anti arrhythmic	38070	A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.	DUKE
cardioactive	38070	A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.	DUKE
oxytocic	36063	A drug that stimulates contraction of the myometrium. Oxytocics are used to induce labour, obstetric at term, to prevent or control postpartum or postabortion haemorrhage, and to assess foetal status in high risk pregnancies. They may also be used alone or with other drugs to induce abortions (abortifacients).	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

alpha-Allocryptopine (FDB005759)

Structure for FDB005759 (alpha-Allocryptopine)