ChemFOnt: Showing chemical card for Candicine (CFc000282904)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:35:41 UTC

Chemfont ID

CFc000282904

Molecule Identification

Common Name

Candicine

Definition

Candicine is a member of the class of compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine. Candicine is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Candicine can be found in barley, which makes candicine a potential biomarker for the consumption of this food product. Candicine is a naturally occurring organic compound that is a quaternary ammonium salt with a phenethylamine skeleton. It is the N,N,N-trimethyl derivative of the well-known biogenic amine tyramine, and, being a natural product with a positively charged nitrogen atom in its molecular structure, it is classed as an alkaloid. Although it is found in a variety of plants, including barley, its properties have not been extensively studied with modern techniques. Candicine is toxic after parenteral administration, producing symptoms of neuromuscular blockade; further details are given in the "Pharmacology" section below.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₁₁H₁₈NO

Average Molecular Weight

180.2667

Monoisotopic Molecular Weight

180.138839203

IUPAC Name

[2-(4-hydroxyphenyl)ethyl]trimethylazanium

Traditional Name

candicine

CAS Registry Number

6656-13-9

SMILES

C[N+](C)(C)CCC1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C11H17NO/c1-12(2,3)9-8-10-4-6-11(13)7-5-10/h4-7H,8-9H2,1-3H3/p+1

InChI Key

PTOJXIKSKSASRB-UHFFFAOYSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenethylamines

Direct Parent

Phenethylamines

Alternative Parents

Substituents

Phenethylamine
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Quaternary ammonium salt
Tetraalkylammonium salt
Amine
Organonitrogen compound
Hydrocarbon derivative
Organic salt
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organic cation
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

primary amine (CHEBI:3350 )
Tyramine derivatives (C10575 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0303388)

Food

Cereal and cereal product

Cereal

Barley (FooDB: FOOD00088)

Process

Not Available

Role

Biological role

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.012 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-2.3	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	10.09	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	67.25 m³·mol⁻¹	ChemAxon
Polarizability	21.45 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon