ChemFOnt: Showing chemical card for Kynurenine (CFc000337404)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:31:08 UTC

Chemfont ID

CFc000337404

Molecule Identification

Common Name

Kynurenine

Definition

Kynurenine, also known as 3-anthraniloylalanine, is a member of the class of compounds known as alkyl-phenylketones. Alkyl-phenylketones are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Kynurenine is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Kynurenine can be found in a number of food items such as yellow zucchini, carrot, spinach, and broccoli, which makes kynurenine a potential biomarker for the consumption of these food products. Kynurenine is synthesized by the enzyme tryptophan dioxygenase, which is made primarily but not exclusively in the liver, and indoleamine 2,3-dioxygenase, which is made in many tissues in response to immune activation. Kynurenine and its further breakdown products carry out diverse biological functions, including dilating blood vessels during inflammation and regulating the immune response. Some cancers increase kynurenine production, which increases tumor growth .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
D-Kynurenine	HMDB
3-(2-aminobenzoyl)-D-alanine	HMDB
DL-Kynurenine	HMDB
D-Kynurenin	HMDB
D-Quinurenine	HMDB
3-Anthraniloyl-D-alanine	HMDB
(2R)-2-Amino-4-(2-aminophenyl)-4-oxobutanoic acid	HMDB
(2R)-2-Amino-4-(2-aminophenyl)-4-oxobutanoate	HMDB

Chemical Formula

C₁₀H₁₂N₂O₃

Average Molecular Weight

208.2139

Monoisotopic Molecular Weight

208.08479226

IUPAC Name

2-amino-4-(2-aminophenyl)-4-oxobutanoic acid

Traditional Name

(+-)-kynurenine

CAS Registry Number

343-65-7

SMILES

NC(CC(=O)C1=CC=CC=C1N)C(O)=O

InChI Identifier

InChI=1S/C10H12N2O3/c11-7-4-2-1-3-6(7)9(13)5-8(12)10(14)15/h1-4,8H,5,11-12H2,(H,14,15)

InChI Key

YGPSJZOEDVAXAB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Butyrophenone
Alpha-amino acid
Alpha-amino acid or derivatives
Benzoyl
Aniline or substituted anilines
Aryl alkyl ketone
Gamma-keto acid
Monocyclic benzene moiety
Beta-aminoketone
Benzenoid
Keto acid
Vinylogous amide
Amino acid
Amino acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Primary aliphatic amine
Organonitrogen compound
Primary amine
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Amine
Organopnictogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

substituted aniline (CHEBI:28683 )
non-proteinogenic alpha-amino acid (CHEBI:28683 )
aromatic ketone (CHEBI:28683 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0000684)

Food

Cereal and cereal product

Cereal

Barley (FooDB: FOOD00088)

Vegetable

Cabbage

Broccoli (FooDB: FOOD00034)

Root vegetable

Carrot (FooDB: FOOD00245)

Leaf vegetable

Spinach (FooDB: FOOD00178)

Gourd

Yellow zucchini (FooDB: FOOD00876)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.67 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-1.9	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	1.19	ChemAxon
pKa (Strongest Basic)	8.96	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	106.41 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	55.05 m³·mol⁻¹	ChemAxon
Polarizability	20.59 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon