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Bovine Rumen Metabolome Database



Showing metabocard for L-Kynurenine (RMDB00684)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-06-15 11:23:33
Accession Number RMDB00684
Common Name L-Kynurenine
Description Kynurenine is a metabolite of the amino acid tryptophan used in the production of niacin. L-kynurenine is a central compound of the pathway of tryptophan metabolism pathway since it can change to the neuroprotective agent kynurenic acid or to the neurotoxic agent quinolinic acid. The break-up of these endogenous compounds' balance can be observable in many disorders. It can occur in neurodegenerative disorders, such as Parkinson's disease, Huntington's and Alzheimer's disease, in stroke, in epilepsy, in multiple sclerosis, in amyotrophic lateral sclerosis, and in mental failures, such as schizophrenia and depression.
Synonyms
  1. (S)-alpha,2-diamino-3-hydroxy-gamma-oxo-Benzenebutanoate
  2. (S)-alpha,2-diamino-3-hydroxy-gamma-oxo-Benzenebutanoic acid
  3. (alphaS)-alpha,2-diamino-3-hydroxy-gamma-oxo-Benzenebutanoate
  4. (alphaS)-alpha,2-diamino-3-hydroxy-gamma-oxo-Benzenebutanoic acid
  5. 3-(3-Hydroxyanthraniloyl)-L-alanine
  6. 3-Anthraniloylalanine
  7. 3-Hydroxy-L-kynurenine
  8. 3-anthraniloyl-Alanine
  9. 3-anthraniloyl-L-alanine
  10. DL-Kynureninefree base
  11. Kynurenin
  12. Quinurenine
  13. alpha,2-diamino-gamma-oxo-Benzenebutanoate
  14. alpha,2-diamino-gamma-oxo-Benzenebutanoic acid
  15. dl-Kynurenine
Chemical IUPAC Name 2-amino-4-(2-aminophenyl)-4-oxo-butanoic acid
Chemical Formula C10H12N2O3
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Amino acids and Amino Acid conjugates
Class
  • Amino Acids
Sub Class
  • NA
Family
  • Mammalian_Metabolite
Species
  • ketone; primary amine; primary aliphatic amine (alkylamine); primary aromatic amine; carboxylic acid; aromatic compound; alpha-aminoacid
Biofunction
  • Component of Tryptophan metabolism
Application
Source
  • Endogenous
Average Molecular Weight 208.214
Monoisotopic Molecular Weight 208.084793
Isomeric SMILES N[C@@H](CC(=O)C1=CC=CC=C1N)C(O)=O
Canonical SMILES NC(CC(=O)C1=CC=CC=C1N)C(O)=O
KEGG Compound ID C01718 Link Image
BioCyc ID L-KYNURENINE Link Image
BiGG ID 1445574 Link Image
Wikipedia Link Kynurenine Link Image
METLIN ID 72 Link Image
PubChem Compound 846 Link Image
PubChem Substance 11375672 Link Image
ChEBI ID Not Available
CAS Registry Number 343-65-7
InChI Identifier InChI=1/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
Synthesis Reference Hayaishi, Osamu. L-Kynurenine sulfate monohydrate. Biochemical Preparations (1953), 3 108-11.
Melting Point (Experimental) 191 oC
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 986.0 mg/mL [MEYLAN,WM et al. (1996)]; 1.67 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -1.93 [Predicted by ALOGPS]; -2.2 [Predicted by PubChem via XLOGP]; -2.25 [MEYLAN,WM & HOWARD,PH (1995)] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID 1T5M Link Image
Experimental PDB File Show
Experimental PDB Structure
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
Download File
Show Experimental Conditions Link Image
Medium Energy
Download File
Show Experimental Conditions Link Image
High Energy
Download File
Show Experimental Conditions Link Image
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm (Predicted from LogP)
Biofluid Location
  • Rumen
Tissue Location
Concentrations (Normal)
Biofluid Rumen
Value 20.2 +/- 0.03 uM
Age N/A
Sex N/A
Condition Normal
Breed Not Available
Experimental Condition Not Available
Comments Not Available
References
  • The rumen metabolome (in preparation)
Concentrations (Abnormal) Not Available
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References
  1. Wikipedia Link Image
Metabolic Enzymes
  1. Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial
  2. Kynurenine--oxoglutarate transaminase 3
Enzyme 1 [top]
Enzyme 1 ID 239
Enzyme 1 Name Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial
Enzyme 1 Synonyms
  1. KAT/AadAT
  2. Kynurenine aminotransferase II
  3. Kynurenine--oxoglutarate aminotransferase II
  4. Kynurenine--oxoglutarate transaminase II
  5. 2-aminoadipate transaminase
  6. 2-aminoadipate aminotransferase
  7. Alpha-aminoadipate aminotransferase
  8. AadAT
Enzyme 1 Gene Name AADAT
Enzyme 1 Protein Sequence >Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial
MNYARFITATSAARKPSTIRVMTEILSKAPKSVISLATGAPNPNTFPFKTAVITIENGKP
IQFNEQMMKRALQYSQSAGIPELLSWLKQLQVKLHNPPTIHYAPTQGQMDLCVTCGSQEG
LCKVFEMIVNPGDNILVNEPIYSGTIHALQPLGCNMINVSSDEHGIIPDSLREILSKWKP
EDSKNPKKNSPKFLYTVPNGNNPSGNSLTAERKREIYELARKYDFLIIEDDPYYFMQFNK
PWAPTFLSMDEDGRVIRADSFSKVLSSGLRIGFITGPKPLIERIVLHIQVSTMHPSTFAQ
LLVSQLLYQWGEEGFLGHVDRVIDFYRKQRDALMAAADKWLSGLAEWHVPTAGMFLWVKI
KGIHDVRKLIEEKAFKKEIFMLPGCGFYTDSSAPCPYFRASFSSASPEQMDLAFQRLAQL
IKESL
Enzyme 1 Number of Residues 425
Enzyme 1 Molecular Weight 47900.9
Enzyme 1 Theoretical pI 8.72
Enzyme 1 GO Classification
Function
Process
Component
Enzyme 1 General Function Transcription
Enzyme 1 Specific Function Shows activity also towards tryptophan, aspartate and hydroxykinurenine
Enzyme 1 Pathways
  • Amino-acid degradation
  • L-lysine degradation via saccharopine pathway
  • glutaryl-CoA from L-lysine:step 4/6
Enzyme 1 Reactions Not Available
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • None
Enzyme 1 Transmembrane Regions
  • None
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 59858053 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID Q5E9N4 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name AADAT_BOVIN Link Image
Enzyme 1 PDB ID Not Available
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence >1278 bp
ATGAATTACGCTCGGTTCATTACCGCCACGAGCGCGGCCAGAAAGCCTTCTACCATCCGA
GTCATGACTGAAATATTGAGCAAGGCACCGAAATCTGTCATCTCCTTGGCAACTGGGGCA
CCAAACCCCAACACGTTCCCTTTCAAGACTGCGGTCATCACCATAGAAAACGGAAAACCC
ATCCAATTTAATGAACAGATGATGAAGAGAGCACTGCAGTATTCTCAGAGTGCTGGAATC
CCAGAGCTGTTATCCTGGCTAAAACAGTTACAAGTAAAATTGCATAATCCGCCCACCATC
CATTATGCACCCACCCAAGGACAGATGGACTTATGTGTCACATGTGGCAGCCAAGAAGGT
CTCTGTAAGGTATTTGAAATGATCGTTAATCCTGGAGATAATATCCTTGTAAATGAACCT
ATTTATTCAGGAACAATTCATGCTCTGCAACCCCTGGGCTGCAACATGATTAATGTTTCC
AGTGATGAGCACGGGATTATTCCAGACTCCCTCAGAGAAATACTTTCCAAATGGAAACCA
GAAGATTCAAAGAACCCCAAGAAAAACAGCCCCAAATTTCTTTACACTGTCCCAAATGGC
AACAACCCCTCTGGGAACTCATTAACAGCTGAGCGCAAAAGGGAAATCTATGAGCTCGCA
AGAAAATATGACTTCCTCATCATAGAAGATGATCCTTACTATTTTATGCAGTTCAACAAG
CCCTGGGCACCGACATTTCTCTCCATGGACGAGGATGGGCGCGTCATCCGAGCTGACTCT
TTTTCCAAAGTCCTGTCCTCAGGGTTGAGAATAGGGTTTATAACTGGTCCAAAGCCCTTG
ATTGAGAGAATTGTTTTACACATACAAGTTTCAACAATGCACCCCAGCACTTTTGCTCAG
CTCCTGGTATCACAGCTTCTATACCAATGGGGAGAAGAGGGCTTCCTGGGTCACGTAGAC
AGGGTTATTGATTTCTACAGGAAGCAGAGGGATGCATTAATGGCAGCAGCAGACAAGTGG
TTAAGTGGTTTGGCAGAATGGCATGTTCCTACTGCAGGAATGTTTCTATGGGTTAAAATT
AAGGGCATTCATGATGTAAGAAAACTGATCGAAGAAAAAGCCTTTAAGAAAGAGATATTC
ATGCTTCCGGGATGTGGTTTCTACACTGACAGTTCAGCTCCTTGCCCGTACTTCAGAGCA
TCCTTCTCTTCAGCTTCTCCAGAACAGATGGACTTGGCCTTTCAGAGACTGGCCCAACTT
ATAAAAGAATCTTTATGA
Enzyme 1 GenBank Gene ID BT020844 Link Image
Enzyme 1 GeneCard ID AADAT Link Image
Enzyme 1 GenAtlas ID Not Available
Enzyme 1 HGNC ID Not Available
Enzyme 1 Chromosome Location Chromosome:4
Enzyme 1 Locus 4q33
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References
  1. [PubMed Link Image]
Enzyme 1 Metabolite References Not Available
Enzyme 2 [top]
Enzyme 2 ID 861
Enzyme 2 Name Kynurenine--oxoglutarate transaminase 3
Enzyme 2 Synonyms
  1. Kynurenine--oxoglutarate transaminase III
  2. Kynurenine aminotransferase III
  3. KATIII
  4. Cysteine-S-conjugate beta-lyase 2
Enzyme 2 Gene Name CCBL2
Enzyme 2 Protein Sequence >Kynurenine--oxoglutarate transaminase 3
MFLAWERLCTLSCRPKFLKTVWASKILGLSTSAKMSLRFKNAKRIEGLDSNIWIEFTKLA
ADPSVVNLGQGLPDISPPVYVKEELSKIAAIDNLNQYTRGFGHPSLVKALSCLYEKFYHN
KINPNEEILVTVGAYGSLFNAIQGLIDEGDEVIVIVPFFDCYESMVRMAGATPVFVPLRC
KPVDGKKCSSSDWTLDPQELASKFNSKTKAIILNTPHNPLGKVYTKEELQVIADLCIKYD
TLCISDEVYEWLVYTGNKHFKIATFPGMWERTITIGSAGKTFSVTGWKLGWSIGPKHLIK
HLQTVQQNTVYTCATPLQEALAQAFWIDIKRMDDPECYFNSLPKELEVKRDRMVHLLESV
GLKSIVPDGGYFIIADVSLLDVDLLDMKDSNEPYDYKFVKWMIKNKKLSAIPVSAFCNAE
TKSQFEKFVRFCFIKKDSTLDAAEEIIKAWSRQNS
Enzyme 2 Number of Residues 455
Enzyme 2 Molecular Weight 51471.2
Enzyme 2 Theoretical pI 7.82
Enzyme 2 GO Classification
Function
Process
Component
Enzyme 2 General Function Amino acid transport and metabolism
Enzyme 2 Specific Function Catalyzes the irreversible transamination of the L- tryptophan metabolite L-kynurenine to form kynurenic acid (KA). May catalyze the beta-elimination of S-conjugates and Se- conjugates of L-(seleno)cysteine, resulting in the cleavage of the C-S or C-Se bond
Enzyme 2 Pathways Not Available
Enzyme 2 Reactions Not Available
Enzyme 2 Pfam Domain Function
Enzyme 2 Signals
  • None
Enzyme 2 Transmembrane Regions
  • None
Enzyme 2 Essentiality Not Available
Enzyme 2 GenBank ID Protein 112362049 Link Image
Enzyme 2 UniProtKB/Swiss-Prot ID Q0P5G4 Link Image
Enzyme 2 UniProtKB/Swiss-Prot Entry Name KAT3_BOVIN Link Image
Enzyme 2 PDB ID Not Available
Enzyme 2 Cellular Location Not Available
Enzyme 2 Gene Sequence >1368 bp
ATGTTTTTGGCCTGGGAGAGACTCTGCACCCTTAGCTGTAGACCTAAATTCCTGAAGACA
GTTTGGGCTTCAAAAATCCTTGGACTCTCTACTTCTGCTAAAATGTCTTTGAGATTCAAA
AATGCAAAACGAATTGAAGGCCTTGATAGCAATATATGGATTGAATTTACCAAACTGGCT
GCAGACCCTTCTGTTGTGAATCTTGGCCAAGGCCTTCCAGATATATCCCCTCCTGTATAT
GTAAAGGAAGAATTATCCAAGATTGCAGCAATTGATAATCTGAATCAGTACACACGGGGC
TTTGGTCATCCATCACTTGTGAAAGCTCTGTCCTGCCTATATGAAAAGTTTTATCACAAT
AAAATCAATCCAAATGAAGAAATCCTTGTGACAGTAGGAGCATATGGATCTCTTTTTAAT
GCCATTCAAGGATTGATTGATGAGGGGGATGAAGTCATAGTGATAGTGCCTTTCTTTGAC
TGCTATGAGTCCATGGTGAGAATGGCTGGAGCAACACCTGTTTTTGTTCCCCTGAGATGT
AAACCTGTTGATGGGAAAAAATGCTCTAGTTCTGACTGGACCTTAGATCCTCAAGAACTG
GCAAGCAAATTTAATTCCAAAACCAAAGCTATAATACTAAATACTCCACATAACCCCCTT
GGCAAGGTGTATACCAAAGAGGAACTCCAAGTAATTGCCGACCTTTGCATCAAATATGAC
ACACTCTGCATCAGTGATGAGGTTTATGAATGGCTTGTATATACTGGAAATAAGCATTTT
AAAATAGCCACTTTTCCAGGTATGTGGGAGAGAACAATAACCATAGGAAGTGCTGGAAAG
ACTTTCAGTGTAACTGGCTGGAAGCTTGGCTGGTCCATTGGTCCTAAACATTTGATAAAA
CATTTACAGACAGTTCAGCAAAACACCGTTTATACTTGTGCAACCCCTTTACAGGAAGCC
TTGGCTCAAGCTTTCTGGATTGACATCAAGCGCATGGATGACCCAGAATGTTACTTCAAT
TCTTTGCCAAAAGAGTTAGAAGTAAAAAGAGATCGGATGGTACATTTACTTGAAAGTGTT
GGCCTAAAATCCATAGTTCCTGATGGGGGATACTTCATCATTGCTGACGTGTCTTTGCTA
GATGTAGACCTCTTGGATATGAAGGACAGCAATGAACCTTATGACTATAAATTCGTGAAA
TGGATGATTAAAAATAAGAAACTGTCAGCCATCCCAGTTTCAGCATTCTGTAATGCAGAA
ACCAAATCACAGTTTGAGAAATTTGTGCGATTTTGCTTCATTAAAAAAGACAGTACACTG
GATGCCGCTGAAGAAATCATCAAGGCATGGAGTAGACAGAACTCTTGA
Enzyme 2 GenBank Gene ID BC120067 Link Image
Enzyme 2 GeneCard ID CCBL2 Link Image
Enzyme 2 GenAtlas ID Not Available
Enzyme 2 HGNC ID Not Available
Enzyme 2 Chromosome Location Chromosome:1
Enzyme 2 Locus 1p22.2
Enzyme 2 SNPs SNPJam Report Link Image
Enzyme 2 General References Not Available
Enzyme 2 Metabolite References Not Available