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Showing NP-Card for 5-Hydroxykynurenine (NP0092157)

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Record Information
Version2.0
Created at2022-05-11 18:58:53 UTC
Updated at2022-05-11 18:58:53 UTC
NP-MRD IDNP0092157
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-Hydroxykynurenine
Description5-Hydroxykynurenine 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. A hydroxykynurenine that is kynurenine bearing a hydroxy group at the position 5. 5-Hydroxykynurenine is a very strong basic compound (based on its pKa). Within humans, 5-hydroxykynurenine participates in a number of enzymatic reactions. In particular, 5-hydroxykynurenine and formic acid can be biosynthesized from 5-hydroxy-N-formylkynurenine; which is mediated by the enzyme kynurenine formamidase. In addition, 5-hydroxykynurenine can be converted into 5-hydroxykynurenamine; which is mediated by the enzyme aromatic-L-amino-acid decarboxylase. In humans, 5-hydroxykynurenine is involved in tryptophan metabolism.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0092157 (5-Hydroxykynurenine)


  Mrv0541 02241204052D          

 16 16  0  0  0  0            999 V2000
   12.7992  -12.9185    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2116  -12.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7992  -11.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2116  -10.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0366  -10.7755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7992  -10.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2116   -9.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7992   -8.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2116   -7.9174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9743   -8.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5618   -9.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9743  -10.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5618  -10.7755    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0366  -12.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4491  -12.9185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4491  -11.4894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 14  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 12  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
M  END
Download

3D MOL for NP0092157 (5-Hydroxykynurenine)

     RDKit          3D

 28 28  0  0  0  0  0  0  0  0999 V2000
   -1.6102   -0.3450   -2.5619 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8989   -0.1165   -1.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1487    0.3245   -0.8044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4522    0.5523    0.5217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5017    0.3399    1.4974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7823    0.5624    2.8447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2384   -0.1051    1.1287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9515   -0.3278   -0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3718   -0.7911   -0.5989 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5739   -0.9657   -1.8446 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4800   -1.0692    0.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3881    0.1195    0.5391 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4337   -0.3046    1.4615 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0320    0.6126   -0.6823 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2832    0.6353   -0.8454 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2300    1.0771   -1.7092 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5300   -1.3331   -2.8762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4783    0.4027   -3.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8995    0.4913   -1.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4400    0.8987    0.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6038    1.4904    3.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4818   -0.2707    1.9178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0947   -1.9551   -0.0324 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0764   -1.3617    1.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7929    0.9002    1.0547 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0810   -0.4682    2.4126 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0329   -1.0459    1.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1467    2.0528   -1.9108 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 11  1  0
 11  9  1  0
  9 10  2  0
  9  8  1  0
  8  2  2  0
  2  1  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
 12 14  1  0
 14 16  1  0
 14 15  2  0
  7  8  1  0
 13 26  1  0
 13 27  1  0
 12 25  1  1
 11 23  1  0
 11 24  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  4 20  1  0
  6 21  1  0
  7 22  1  0
 16 28  1  0
M  END
Download

3D SDF for NP0092157 (5-Hydroxykynurenine)


  Mrv0541 02241204052D          

 16 16  0  0  0  0            999 V2000
   12.7992  -12.9185    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2116  -12.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7992  -11.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2116  -10.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0366  -10.7755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7992  -10.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2116   -9.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7992   -8.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2116   -7.9174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9743   -8.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5618   -9.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9743  -10.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5618  -10.7755    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0366  -12.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4491  -12.9185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4491  -11.4894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 14  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 12  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0092157

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(CC(=O)C1=C(N)C=CC(O)=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H12N2O4/c11-7-2-1-5(13)3-6(7)9(14)4-8(12)10(15)16/h1-3,8,13H,4,11-12H2,(H,15,16)

> <INCHI_KEY>
OTDQYOVYQQZAJL-UHFFFAOYSA-N

> <FORMULA>
C10H12N2O4

> <MOLECULAR_WEIGHT>
224.2133

> <EXACT_MASS>
224.079706882

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
21.525399736709765

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-4-(2-amino-5-hydroxyphenyl)-4-oxobutanoic acid

> <ALOGPS_LOGP>
-2.17

> <JCHEM_LOGP>
-2.2166730141507074

> <ALOGPS_LOGS>
-1.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.89292664584021

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.9781795743085331

> <JCHEM_PKA_STRONGEST_BASIC>
8.908716626078787

> <JCHEM_POLAR_SURFACE_AREA>
126.64000000000001

> <JCHEM_REFRACTIVITY>
57.03110000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.12e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxykynurenine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0092157 (5-Hydroxykynurenine)

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PDB for NP0092157 (5-Hydroxykynurenine)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  N   UNK     0      23.892 -24.115   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      24.662 -22.781   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.892 -21.447   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      24.662 -20.114   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      26.202 -20.114   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      23.892 -18.781   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.662 -17.447   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      23.892 -16.113   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      24.662 -14.779   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      22.352 -16.113   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.582 -17.447   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.352 -18.781   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      21.582 -20.114   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      26.202 -22.781   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      26.972 -24.115   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      26.972 -21.447   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12    6   11   13                                                  
CONECT   13   12                                                            
CONECT   14    2   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

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3D PDB for NP0092157 (5-Hydroxykynurenine)
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SMILES for NP0092157 (5-Hydroxykynurenine)
NC(CC(=O)C1=C(N)C=CC(O)=C1)C(O)=O
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INCHI for NP0092157 (5-Hydroxykynurenine)
InChI=1S/C10H12N2O4/c11-7-2-1-5(13)3-6(7)9(14)4-8(12)10(15)16/h1-3,8,13H,4,11-12H2,(H,15,16)
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View in JSmol
Synonyms
ValueSource
2-Amino-4-(2-amino-5-hydroxyphenyl)-4-oxobutanoic acidChEBI
2-Amino-4-(2-amino-5-hydroxyphenyl)-4-oxobutanoateGenerator
5-Hydroxy-L-kynurenineHMDB
5-Hydroxykynurenine, (L)-isomerHMDB
Chemical FormulaC10H12N2O4
Average Mass224.2133 Da
Monoisotopic Mass224.07971 Da
IUPAC Name2-amino-4-(2-amino-5-hydroxyphenyl)-4-oxobutanoic acid
Traditional Name5-hydroxykynurenine
CAS Registry NumberNot Available
SMILES
NC(CC(=O)C1=C(N)C=CC(O)=C1)C(O)=O
InChI Identifier
InChI=1S/C10H12N2O4/c11-7-2-1-5(13)3-6(7)9(14)4-8(12)10(15)16/h1-3,8,13H,4,11-12H2,(H,15,16)
InChI KeyOTDQYOVYQQZAJL-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
    • 

  • P-aminophenol
    • 

  • Aminophenol
    • 

  • Benzoyl
    • 

  • Gamma-keto acid
    • 

  • Aryl alkyl ketone
    • 

  • Aniline or substituted anilines
    • 

  • Phenol
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • Beta-aminoketone
    • 

  • Keto acid
    • 

  • Vinylogous amide
    • 

  • Amino acid
    • 

  • Amino acid or derivatives
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Organic oxide
    • 

  • Amine
    • 

  • Organonitrogen compound
    • 

  • Primary amine
    • 

  • Hydrocarbon derivative
    • 

  • Primary aliphatic amine
    • 

  • Organopnictogen compound
    • 

  • Organic nitrogen 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-2.2ALOGPS
logP-2.2ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)0.98ChemAxon
pKa (Strongest Basic)8.91ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area126.64 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity57.03 m³·mol⁻¹ChemAxon
Polarizability21.53 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0012819  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029180  
KNApSAcK IDNot Available
Chemspider ID389616  
KEGG Compound IDC05651  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link3-Hydroxykynurenine  
METLIN IDNot Available
PubChem Compound440745  
PDB IDNot Available
ChEBI ID2076  
Good Scents IDNot Available
References
General ReferencesNot Available