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Showing NP-Card for (+-)-kynurenine (NP0210579)

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Record Information
Version2.0
Created at2022-09-05 08:27:48 UTC
Updated at2022-09-05 08:27:48 UTC
NP-MRD IDNP0210579
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+-)-kynurenine
DescriptionKynurenine 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. Kynurenine is a very strong basic compound (based on its pKa). In humans, kynurenine is involved in tryptophan metabolism. Outside of the human body, Kynurenine is found, on average, in the highest concentration within a few different foods, such as sunburst squash (pattypan squash), yellow zucchinis, and spinachs. Kynurenine has also been detected, but not quantified in, a few different foods, such as barley, broccoli, and carrots. This could make kynurenine a potential biomarker for the consumption of these foods. (+-)-kynurenine is found in Bombyx mori and Streptomyces albidoflavus. (+-)-kynurenine was first documented in 2003 (PMID: 14651996). A ketone that is alanine in which one of the methyl hydrogens is substituted by a 2-aminobenzoyl group (PMID: 16139256) (PMID: 17386621) (PMID: 19027117).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0210579 ((+-)-kynurenine)


  Mrv0541 09041212592D          

 15 15  0  0  0  0            999 V2000
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  3  2  0  0  0  0
  7  4  2  0  0  0  0
  7  6  1  0  0  0  0
  8  5  1  0  0  0  0
  9  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  2  0  0  0  0
 14 10  2  0  0  0  0
 15 10  1  0  0  0  0
M  END
Download

3D MOL for NP0210579 ((+-)-kynurenine)

     RDKit          3D

 27 27  0  0  0  0  0  0  0  0999 V2000
   -1.5357   -2.4701    0.3310 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9066   -1.1486   -0.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1181   -0.9636   -0.7417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5124    0.2546   -1.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6776    1.3337   -1.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4447    1.1545   -0.3915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0647   -0.0787    0.0517 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2037   -0.2669    0.7031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5219   -1.4299    1.0975 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1271    0.8427    0.9214 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2813    0.8985   -0.0601 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8806    1.0318   -1.4239 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1776   -0.2590    0.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5989   -0.5661    1.2139 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5473   -0.9986   -1.0193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8979   -2.8059    1.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9195   -3.0142   -0.3000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7842   -1.8158   -0.8786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4754    0.4118   -1.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9795    2.2929   -1.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8354    2.0590   -0.2948 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6699    1.8440    0.9750 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5543    0.6884    1.9614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9127    1.8023    0.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1695    1.9248   -1.8691 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0556    0.1876   -1.9985 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4514   -0.9094   -1.4917 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11 10  1  0
 10  8  1  0
  8  9  2  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
 11 13  1  0
 13 15  1  0
 13 14  2  0
  2  7  1  0
 12 25  1  0
 12 26  1  0
 11 24  1  1
 10 22  1  0
 10 23  1  0
  6 21  1  0
  5 20  1  0
  4 19  1  0
  3 18  1  0
  1 16  1  0
  1 17  1  0
 15 27  1  0
M  END
Download

3D SDF for NP0210579 ((+-)-kynurenine)


  Mrv0541 09041212592D          

 15 15  0  0  0  0            999 V2000
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  3  2  0  0  0  0
  7  4  2  0  0  0  0
  7  6  1  0  0  0  0
  8  5  1  0  0  0  0
  9  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  2  0  0  0  0
 14 10  2  0  0  0  0
 15 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0210579

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C10H12N2O3

> <MOLECULAR_WEIGHT>
208.2139

> <EXACT_MASS>
208.08479226

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
20.591144970696817

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-4-(2-aminophenyl)-4-oxobutanoic acid

> <ALOGPS_LOGP>
-1.93

> <JCHEM_LOGP>
-1.9081918809836254

> <ALOGPS_LOGS>
-2.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.06926978291992

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.193089749657625

> <JCHEM_PKA_STRONGEST_BASIC>
8.96449885088756

> <JCHEM_POLAR_SURFACE_AREA>
106.41000000000001

> <JCHEM_REFRACTIVITY>
55.050200000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.67e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+-)-kynurenine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0210579 ((+-)-kynurenine)

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PDB for NP0210579 ((+-)-kynurenine)
HEADER    PROTEIN                                 04-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    6                                                       
CONECT    4    2    7                                                       
CONECT    5    8    9                                                       
CONECT    6    3    7    9                                                  
CONECT    7    4    6   11                                                  
CONECT    8    5   10   12                                                  
CONECT    9    5    6   13                                                  
CONECT   10    8   14   15                                                  
CONECT   11    7                                                            
CONECT   12    8                                                            
CONECT   13    9                                                            
CONECT   14   10                                                            
CONECT   15   10                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

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3D PDB for NP0210579 ((+-)-kynurenine)
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SMILES for NP0210579 ((+-)-kynurenine)
NC(CC(=O)C1=CC=CC=C1N)C(O)=O
Download
INCHI for NP0210579 ((+-)-kynurenine)
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)
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View in JSmol
Synonyms
ValueSource
3-AnthraniloylalanineKegg
Chemical FormulaC10H12N2O3
Average Mass208.2139 Da
Monoisotopic Mass208.08479 Da
IUPAC Name2-amino-4-(2-aminophenyl)-4-oxobutanoic acid
Traditional Name(+-)-kynurenine
CAS Registry NumberNot Available
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 KeyYGPSJZOEDVAXAB-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Bombyx moriLOTUS Database
Streptomyces albidoflavusLOTUS Database
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.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentAlkyl-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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.9ALOGPS
logP-1.9ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.19ChemAxon
pKa (Strongest Basic)8.96ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area106.41 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity55.05 m³·mol⁻¹ChemAxon
Polarizability20.59 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030010  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC01718  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkKynurenine  
METLIN IDNot Available
PubChem Compound846  
PDB IDNot Available
ChEBI ID28683  
Good Scents IDNot Available
References
General References
  1. Cerstiaens A, Huybrechts J, Kotanen S, Lebeau I, Meylaers K, De Loof A, Schoofs L: Neurotoxic and neurobehavioral effects of kynurenines in adult insects. Biochem Biophys Res Commun. 2003 Dec 26;312(4):1171-7. doi:  10.1016/j.bbrc.2003.11.051. [PubMed:14651996  ] 
  2. Schrocksnadel K, Wirleitner B, Winkler C, Fuchs D: Monitoring tryptophan metabolism in chronic immune activation. Clin Chim Acta. 2006 Feb;364(1-2):82-90. doi: 10.1016/j.cca.2005.06.013. Epub  2005 Sep 1. [PubMed:16139256  ] 
  3. Mitsuhashi S, Fukushima T, Tomiya M, Santa T, Imai K, Toyo'oka T: Determination of kynurenine levels in rat plasma by high-performance liquid chromatography with pre-column fluorescence derivatization. Anal Chim Acta. 2007 Feb 19;584(2):315-21. doi: 10.1016/j.aca.2006.11.040. Epub  2006 Nov 19. [PubMed:17386621  ] 
  4. Pawlak K, Brzosko S, Mysliwiec M, Pawlak D: Kynurenine, quinolinic acid--the new factors linked to carotid atherosclerosis in patients with end-stage renal disease. Atherosclerosis. 2009 Jun;204(2):561-6. doi:  10.1016/j.atherosclerosis.2008.10.002. Epub 2008 Oct 14. [PubMed:19027117  ] 
  5. LOTUS database [Link]