| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:34:52 UTC |
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| Update Date | 2020-06-04 20:08:18 UTC |
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| BMDB ID | BMDB0000684 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | L-Kynurenine |
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| Description | L-Kynurenine, also known as quinurenine, 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. L-Kynurenine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Kynurenine exists in all eukaryotes, ranging from yeast to humans. L-Kynurenine participates in a number of enzymatic reactions, within cattle. In particular, L-Kynurenine and formic acid can be biosynthesized from n'-formylkynurenine; which is mediated by the enzyme kynurenine formamidase. In addition, L-Kynurenine can be converted into 2-aminobenzoic acid and L-alanine through the action of the enzyme kynureninase. In cattle, L-kynurenine is involved in the metabolic pathway called the tryptophan metabolism pathway. |
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| Structure | |
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| Synonyms | | Value | Source |
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| (2S)-2-Amino-4-(2-aminophenyl)-4-oxobutanoic acid | ChEBI | | 3-Anthraniloyl-L-alanine | ChEBI | | KYNURENINE | ChEBI | | (2S)-2-Amino-4-(2-aminophenyl)-4-oxobutanoate | Generator | | (S)-alpha,2-Diamino-3-hydroxy-gamma-oxo-benzenebutanoate | HMDB | | (S)-alpha,2-Diamino-3-hydroxy-gamma-oxo-benzenebutanoic acid | HMDB | | 3-Anthraniloyl-alanine | HMDB | | 3-Anthraniloylalanine | HMDB | | alpha,2-Diamino-gamma-oxo-benzenebutanoate | HMDB | | alpha,2-Diamino-gamma-oxo-benzenebutanoic acid | HMDB | | DL-Kynurenine | HMDB | | Kynurenin | HMDB | | Quinurenine | HMDB | | L-Kynurenine | HMDB | | 3-(2-aminobenzoyl)-L-alanine | HMDB | | KYNA | HMDB |
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| Chemical Formula | C10H12N2O3 |
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| Average Molecular Weight | 208.2139 |
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| Monoisotopic Molecular Weight | 208.08479226 |
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| IUPAC Name | (2S)-2-amino-4-(2-aminophenyl)-4-oxobutanoic acid |
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| Traditional Name | L-kynurenine |
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| CAS Registry Number | 2922-83-0 |
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| SMILES | N[C@@H](CC(=O)C1=CC=CC=C1N)C(O)=O |
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| 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)/t8-/m0/s1 |
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| InChI Key | YGPSJZOEDVAXAB-QMMMGPOBSA-N |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Organic oxygen compounds |
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| Class | Organooxygen compounds |
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| Sub Class | Carbonyl compounds |
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| Direct Parent | Alkyl-phenylketones |
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| Alternative Parents | |
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| Substituents | - Alkyl-phenylketone
- Butyrophenone
- Alpha-amino acid
- Alpha-amino acid or derivatives
- L-alpha-amino acid
- Benzoyl
- Gamma-keto acid
- Aniline or substituted anilines
- Aryl alkyl ketone
- Monocyclic benzene moiety
- Beta-aminoketone
- Keto acid
- Benzenoid
- Vinylogous amide
- Amino acid
- Amino acid or derivatives
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Primary aliphatic amine
- Amine
- Hydrocarbon derivative
- Organopnictogen compound
- Organic oxide
- Organic nitrogen compound
- Organonitrogen compound
- Primary amine
- Aromatic homomonocyclic compound
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| Molecular Framework | Aromatic homomonocyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Status | Detected and Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 191 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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| Biological Properties |
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| Cellular Locations | |
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| Biospecimen Locations | - Blood
- Brain
- Epidermis
- Fibroblasts
- Intestine
- Liver
- Longissimus Thoracis Muscle
- Milk
- Neuron
- Placenta
- Ruminal Fluid
- Semimembranosus Muscle
- Spleen
- Testis
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| Pathways | |
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| Normal Concentrations |
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| Blood | Detected and Quantified | 0.5-2 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 7 +/- 2 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 3.9-7 uM | Not Specified | Not Specified | Normal | | details | | Brain | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Epidermis | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Fibroblasts | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Intestine | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected and Quantified | 3 +/- 2 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Longissimus Thoracis Muscle | Detected and Quantified | 0.6 +/- 0.2 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Neuron | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 20.2 +/- 0.03 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 20.23 +/- 0.03 uM | Not Specified | Not Specified | Normal | | details | | Semimembranosus Muscle | Detected and Quantified | 0.5 +/- 0.2 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Spleen | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Testis | Detected and Quantified | 0.9 +/- 0.4 nmol/g of tissue | Not Specified | Not Specified | Normal | | details |
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| Abnormal Concentrations |
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| Not Available |
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| External Links |
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| HMDB ID | HMDB0000684 |
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| DrugBank ID | DB02070 |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB022181 |
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| KNApSAcK ID | C00007604 |
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| Chemspider ID | 141580 |
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| KEGG Compound ID | C00328 |
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| BioCyc ID | CPD-14736 |
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| BiGG ID | 1445574 |
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| Wikipedia Link | Kynurenine |
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| METLIN ID | 72 |
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| PubChem Compound | 161166 |
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| PDB ID | Not Available |
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| ChEBI ID | 16946 |
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| References |
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| Synthesis Reference | Hayaishi, Osamu. L-Kynurenine sulfate monohydrate. Biochemical Preparations (1953), 3 108-11. |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| General References | - Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
- Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
- Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]
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