ChemFOnt: Showing chemical card for Hygrine (CFc000282418)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:34:45 UTC

Chemfont ID

CFc000282418

Molecule Identification

Common Name

Hygrine

Definition

Hygrine, also known as (+)-hygrine or (+)-N-methyl-2-acetonylpyrrolidine, belongs to alkaloids and derivatives class of compounds. Those are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic propertiesand is also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. Hygrine is soluble (in water) and an extremely weak acidic compound (based on its pKa). Hygrine can be found in pomegranate, which makes hygrine a potential biomarker for the consumption of this food product. Hygrine is a pyrrolidine alkaloid, found mainly in coca leaves (0.2%). It was first isolated by Carl Liebermann in 1889 (along with a related compound cuscohygrine) as an alkaloid accompanying cocaine in coca. Hygrine is extracted as a thick yellow oil, having a pungent taste and odor .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+)-Hygrine	ChEBI
(+)-N-Methyl-2-acetonylpyrrolidine	ChEBI
(R)-(+)-Hygrine	ChEBI
(R)-1-(1-Methyl-2-pyrrolidinyl)-2-propanone	ChEBI
(R)-Hygrine	ChEBI
1-[(2R)-1-Methylpyrrolidin-2-yl]acetone	ChEBI
Hygrine, 2-(14)C-labeled, (+-)-isomer	MeSH
1-[(2R)-1-Methyl-2-pyrrolidinyl]-2-propanone	PhytoBank
D-(+)-Hygrine	PhytoBank

Chemical Formula

C₈H₁₅NO

Average Molecular Weight

141.2108

Monoisotopic Molecular Weight

141.115364107

IUPAC Name

1-[(2R)-1-methylpyrrolidin-2-yl]propan-2-one

Traditional Name

(+)-hygrine

CAS Registry Number

496-49-1

SMILES

CN1CCC[C@@H]1CC(C)=O

InChI Identifier

InChI=1S/C8H15NO/c1-7(10)6-8-4-3-5-9(8)2/h8H,3-6H2,1-2H3/t8-/m1/s1

InChI Key

ADKXZIOQKHHDNQ-MRVPVSSYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Not Available

Sub Class

Not Available

Direct Parent

Alkaloids and derivatives

Alternative Parents

Substituents

Alkaloid or derivatives
Beta-aminoketone
N-alkylpyrrolidine
Pyrrolidine
Ketone
Tertiary amine
Tertiary aliphatic amine
Organoheterocyclic compound
Azacycle
Organopnictogen compound
Organic nitrogen compound
Amine
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

pyrrolidine alkaloid (CHEBI:46750 )
1-(1-methylpyrrolidin-2-yl)acetone (CHEBI:46750 )
Pyrrolidine alkaloids (C06179 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302902)

Food

Fruit

Tropical fruit

Pomegranate (FooDB: FOOD00151)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	279 g/L	ALOGPS
logP	0.71	ALOGPS
logP	0.7	ChemAxon
logS	0.3	ALOGPS
pKa (Strongest Acidic)	18.54	ChemAxon
pKa (Strongest Basic)	9.27	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	20.31 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	41.53 m³·mol⁻¹	ChemAxon
Polarizability	16.35 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