(2S)-4-(2-aminophenyl)-2-azaniumyl-4-oxobutanoate
Basic information
- CAS
2922-83-0- Standard SMILES
Nc1ccccc1C(=O)C[C@H]([NH3+])C(=O)[O-]- InChIKey
YGPSJZOEDVAXAB-QMMMGPOBSA-N- Molecular formula
- C10H12N2O3
- Average molar mass
- 208.21 g/mol
- Monoisotopic mass
- 208.08479225
Overview
L-kynurenine zwitterion is zwitterionic form of L-kynurenine arising from transfer of a proton from the carboxy to the amino group; major species at pH 7.3. It is a tautomer of a L-kynurenine.
Names & identifiers
- Preferred name
- (2S)-4-(2-aminophenyl)-2-azaniumyl-4-oxobutanoate
- IUPAC
- (2S)-4-(2-aminophenyl)-2-azaniumyl-4-oxobutanoate
- English name
- L-KYNURENINE
- Molecular formula
- C10H12N2O3
- Molecular weight
- 208.21
Names & synonyms
L-2-Amino-3-(2-aminobenzoyl)propionic acid(2S)-4-(2-aminophenyl)-2-azaniumyl-4-oxobutanoateL-kynurenine zwitterionCHEBI:57959(2S)-4-(2-aminophenyl)-2-ammonio-4-oxobutanoate(S)-2-AMino-4-(2-aMinophenyl)-4-oxobutanoic acidCCRIS 4425L-KYNURENINEJACS-2922-83-0(S)-KynurenineKynurenine (L)L-Kynurenine L-Kynurenine Hydrate
Show more names
L-Kynurenine13C4,15N-L-kynurenine
Database identifiers
- CAS
2922-83-0- PubChem CID
- 6971029
- ChEBI
CHEBI:57959
Properties
Computed structural properties
- XLogP
- -1.4
- Topological polar surface area
- 111 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 3
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 250
Experimental & physicochemical properties
Melting Point191 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 219 °C · 219 °C
- Boiling point
- 466.6 · 466.6±45.0 °C(Predicted)
- Density
- 1.343 · 1.343±0.06 g/cm3(Predicted)
- refractive index
- -33 ° · -33 ° (C=0.4, H2O)
- storage temp.
- 2 · under inert gas (nitrogen or Argon) at 2–8 °C
- solubility
- Soluble in DMSO (up to 2 mg/ml) or in Water (up to 2 mg/ml).
- pka
- 2.21 · 2.21±0.23(Predicted)
- form
- crystalline
- color
- light yellow
- optical activity
- -30.525 · -30.525 (H2O)
- Merck
- 14 · 14,5328
- Stability
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- rtecs
- CY9049700
- hs_code
- 2922500090
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P280-P301+P312-P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
Tissue LocationsBrain
Cellular LocationsCytoplasm
Metabolite PathwaysTryptophan metabolism
Applications
DescriptionKynurenine (2922-83-0) is a tryptophan catabolite.1Endogenous tumor-promoting ligand of the human aryl hydrocarbon receptor (AhR). Constitutively generated by human tumor cells via the action of the tryptophan degrading enzyme, tryptophan-2,3-dioxygenase (TDO). Kynurenine suppresses antitumor immune responses and promotes tumor cell survival and motility.2
UsesL-Kynurenine has been used as a standard for indoleamine-2,3-dioxygenase (IDO) assay. It has also been used as a standard to extract and quantify kynurenine from cultured cells and media.
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