ChemFOnt: Showing chemical card for alpha-Allocryptopine (CFc000282199)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:34:20 UTC

Chemfont ID

CFc000282199

Molecule Identification

Common Name

alpha-Allocryptopine

Definition

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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5,7,8,15-Tetrahydro-3,4-dimethoxy-6-methyl(1,3)benzodioxolo(5,6-e)(2)benzazecin-14(6H)-one	ChEBI
alpha-Fagarine	ChEBI
beta-Homochelidonine	ChEBI
Thalictrimine	ChEBI
a-Fagarine	Generator
Α-fagarine	Generator
b-Homochelidonine	Generator
Β-homochelidonine	Generator
a-Allocryptopine	Generator
Α-allocryptopine	Generator
Allo-cryptopine	MeSH
alpha-Allocryptopine	ChEBI

Chemical Formula

C₂₁H₂₃NO₅

Average Molecular Weight

369.411

Monoisotopic Molecular Weight

369.157622851

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

Traditional Name

β-allocryptopine

CAS Registry Number

485-91-6

SMILES

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

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

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.

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 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302683)

Food

Cereal and cereal product

Cereal

Barley (FooDB: FOOD00088)

Process

Not Available

Role

Biological role

Anti arrhythmic (HMDB: HMDB0302683)
Cardioactive (HMDB: HMDB0302683)

Industrial application

Oxytocic (HMDB: HMDB0302683)

Physical Properties

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