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Showing NP-Card for Xanthurenic acid (NP0001425)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:59:07 UTC
NP-MRD IDNP0001425
Secondary Accession NumbersNone
Natural Product Identification
Common NameXanthurenic acid
DescriptionXanthurenic acid, also known as xanthurenate or 8-hydroxykynurenic acid, is a member of the class of compounds known as quinoline carboxylic acids. Quinoline carboxylic acids are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions. Xanthurenic acid is slightly soluble (in water). Xanthurenic acid can be found primarily in blood, feces, and urine, as well as in human epidermis tissue. Within the cell, xanthurenic acid is primarily located in the membrane. Xanthurenic acid exists in all eukaryotes, ranging from yeast to humans. In humans, xanthurenic acid is involved in the tryptophan metabolism. Moreover, xanthurenic acid is found to be associated with citrullinemia type I, which is an inborn error of metabolism. Xanthurenic acid is a metabolite from tryptophan catabolism. It is a substrate of the enzyme methyltransferases (EC 2.1.1.-) In pathway tryptophan metabolism (KEGG).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001425 (Xanthurenic acid)

Xylulose-5-phosphate.mol
  Mrv1652305271900322D          

 15 16  0  0  0  0            999 V2000
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
  2 13  2  0  0  0  0
  1 14  2  0  0  0  0
  1 15  1  0  0  0  0
M  END
Download

3D MOL for NP0001425 (Xanthurenic acid)

HMDB0000881
     RDKit          3D
Xanthurenic acid
 22 23  0  0  0  0  0  0  0  0999 V2000
   -4.1210    0.5738   -0.1209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2339   -0.3160   -0.1763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5932   -1.6496   -0.3166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8428    0.1010   -0.0889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5080    1.4208    0.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1762    1.7380    0.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2033    3.0574    0.2648 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7738    0.7458    0.0620 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1297    1.0231    0.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0660    0.0129    0.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6919   -1.3113   -0.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3485   -1.6125   -0.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9666   -2.9463   -0.2862 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4148   -0.5987   -0.0794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8975   -0.8536   -0.1485 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4348   -2.3423    0.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2964    2.1761    0.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4415    3.8163    0.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4118    2.0638    0.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1292    0.2275    0.1263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4199   -2.1240   -0.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0101   -3.2022   -0.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15  4  1  0
 14  8  1  0
  3 16  1  0
  5 17  1  0
  7 18  1  0
  9 19  1  0
 10 20  1  0
 11 21  1  0
 13 22  1  0
M  END
Download

3D SDF for NP0001425 (Xanthurenic acid)

Xylulose-5-phosphate.mol
  Mrv1652305271900322D          

 15 16  0  0  0  0            999 V2000
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
  2 13  2  0  0  0  0
  1 14  2  0  0  0  0
  1 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001425

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=NC2=C(O)C=CC=C2C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H7NO4/c12-7-3-1-2-5-8(13)4-6(10(14)15)11-9(5)7/h1-4,12H,(H,11,13)(H,14,15)

> <INCHI_KEY>
FBZONXHGGPHHIY-UHFFFAOYSA-N

> <FORMULA>
C10H7NO4

> <MOLECULAR_WEIGHT>
205.1669

> <EXACT_MASS>
205.037507717

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
19.064003634931545

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,8-dihydroxyquinoline-2-carboxylic acid

> <ALOGPS_LOGP>
2.01

> <JCHEM_LOGP>
-0.16662861726590097

> <ALOGPS_LOGS>
-2.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.066086911279461

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.1352227807412834

> <JCHEM_PKA_STRONGEST_BASIC>
5.753313640791366

> <JCHEM_POLAR_SURFACE_AREA>
90.65

> <JCHEM_REFRACTIVITY>
50.8253

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.63e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
xanthurenic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0001425 (Xanthurenic acid)

HMDB0000881
     RDKit          3D
Xanthurenic acid
 22 23  0  0  0  0  0  0  0  0999 V2000
   -4.1210    0.5738   -0.1209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2339   -0.3160   -0.1763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5932   -1.6496   -0.3166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8428    0.1010   -0.0889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5080    1.4208    0.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1762    1.7380    0.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2033    3.0574    0.2648 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7738    0.7458    0.0620 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1297    1.0231    0.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0660    0.0129    0.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6919   -1.3113   -0.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3485   -1.6125   -0.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9666   -2.9463   -0.2862 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4148   -0.5987   -0.0794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8975   -0.8536   -0.1485 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4348   -2.3423    0.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2964    2.1761    0.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4415    3.8163    0.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4118    2.0638    0.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1292    0.2275    0.1263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4199   -2.1240   -0.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0101   -3.2022   -0.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15  4  1  0
 14  8  1  0
  3 16  1  0
  5 17  1  0
  7 18  1  0
  9 19  1  0
 10 20  1  0
 11 21  1  0
 13 22  1  0
M  END
Download

PDB for NP0001425 (Xanthurenic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Xylulose-5-phosphate.mol                          
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000   3.080   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       0.000  -1.540   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2   14   15                                                  
CONECT    2    1    3   13                                                  
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                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    6   13                                                  
CONECT   13   12    2                                                       
CONECT   14    1                                                            
CONECT   15    1                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END
Download

3D PDB for NP0001425 (Xanthurenic acid)

COMPND    HMDB0000881
HETATM    1  O1  UNL     1      -4.121   0.574  -0.121  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.234  -0.316  -0.176  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.593  -1.650  -0.317  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.843   0.101  -0.089  1.00  0.00           C  
HETATM    5  C3  UNL     1      -1.508   1.421   0.049  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.176   1.738   0.125  1.00  0.00           C  
HETATM    7  O3  UNL     1       0.203   3.057   0.265  1.00  0.00           O  
HETATM    8  C5  UNL     1       0.774   0.746   0.062  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.130   1.023   0.135  1.00  0.00           C  
HETATM   10  C7  UNL     1       3.066   0.013   0.070  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.692  -1.311  -0.070  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.348  -1.612  -0.145  1.00  0.00           C  
HETATM   13  O4  UNL     1       0.967  -2.946  -0.286  1.00  0.00           O  
HETATM   14  C10 UNL     1       0.415  -0.599  -0.079  1.00  0.00           C  
HETATM   15  N1  UNL     1      -0.898  -0.854  -0.148  1.00  0.00           N  
HETATM   16  H1  UNL     1      -3.435  -2.342   0.413  1.00  0.00           H  
HETATM   17  H2  UNL     1      -2.296   2.176   0.095  1.00  0.00           H  
HETATM   18  H3  UNL     1      -0.442   3.816   0.316  1.00  0.00           H  
HETATM   19  H4  UNL     1       2.412   2.064   0.244  1.00  0.00           H  
HETATM   20  H5  UNL     1       4.129   0.227   0.126  1.00  0.00           H  
HETATM   21  H6  UNL     1       3.420  -2.124  -0.124  1.00  0.00           H  
HETATM   22  H7  UNL     1      -0.010  -3.202  -0.344  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   16
CONECT    4    5    5   15
CONECT    5    6   17
CONECT    6    7    8    8
CONECT    7   18
CONECT    8    9   14
CONECT    9   10   10   19
CONECT   10   11   20
CONECT   11   12   12   21
CONECT   12   13   14
CONECT   13   22
CONECT   14   15   15
END
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SMILES for NP0001425 (Xanthurenic acid)

OC(=O)C1=NC2=C(O)C=CC=C2C(O)=C1
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INCHI for NP0001425 (Xanthurenic acid)

InChI=1S/C10H7NO4/c12-7-3-1-2-5-8(13)4-6(10(14)15)11-9(5)7/h1-4,12H,(H,11,13)(H,14,15)
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View in JSmol
Synonyms
ValueSource
XanthurenateKegg
8-Hydroxykynurenic acidHMDB
Gametocyte activating factor (gaf)HMDB
4,8-Dihydroxy-2-quinolinecarboxylateHMDB
4,8-Dihydroxy-2-quinolinecarboxylic acidHMDB
4,8-Dihydroxy-quinaldateHMDB
4,8-Dihydroxy-quinaldic acidHMDB
4,8-DihydroxyquinaldateHMDB
4,8-Dihydroxyquinaldic acidHMDB
4,8-DihydroxyquinaldinateHMDB
4,8-Dihydroxyquinaldinic acidHMDB
4,8-Dihydroxyquinoline-2-carboxylateHMDB
4,8-Dihydroxyquinoline-2-carboxylic acidHMDB
4-Oxoxanthurenic acidHMDB
8-HydroxykynurenateHMDB
OxoxanthurenateHMDB
XanthurateHMDB
Xanthuric acidHMDB
Chemical FormulaC10H7NO4
Average Mass205.1669 Da
Monoisotopic Mass205.03751 Da
IUPAC Name4,8-dihydroxyquinoline-2-carboxylic acid
Traditional Namexanthurenic acid
CAS Registry Number59-00-7
SMILES
OC(=O)C1=NC2=C(O)C=CC=C2C(O)=C1
InChI Identifier
InChI=1S/C10H7NO4/c12-7-3-1-2-5-8(13)4-6(10(14)15)11-9(5)7/h1-4,12H,(H,11,13)(H,14,15)
InChI KeyFBZONXHGGPHHIY-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aedes aegyptiLOTUS Database
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Apis ceranaLOTUS Database
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
Procambarus clarkiiLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassQuinoline carboxylic acids
Direct ParentQuinoline carboxylic acids
Alternative Parents
Substituents
  • Quinoline-2-carboxylic acid
  • Dihydroquinolone
  • Hydroxyquinoline
  • 8-hydroxyquinoline
  • Dihydroquinoline
  • Pyridine carboxylic acid
  • Pyridine carboxylic acid or derivatives
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous amide
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point289 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility112800 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.63 g/LALOGPS
logP2.01ALOGPS
logP-0.17ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.14ChemAxon
pKa (Strongest Basic)5.75ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area90.65 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity50.83 m³·mol⁻¹ChemAxon
Polarizability19.06 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000881
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022297
KNApSAcK IDNot Available
Chemspider ID5497
KEGG Compound IDC02470
BioCyc IDXANTHURENATE
BiGG IDNot Available
Wikipedia LinkXanthurenic_acid
METLIN ID5841
PubChem Compound5699
PDB IDNot Available
ChEBI ID10072
Good Scents IDrw1710051
References
General References
  1. Igari T, Tsuchizawa M, Shimamura T: Alteration of tryptophan metabolism in the synovial fluid of patients with rheumatoid arthritis and osteoarthritis. Tohoku J Exp Med. 1987 Oct;153(2):79-86. [PubMed:3500530 ]
  2. Calandra P: Research on tryptophan metabolites "via kynurenine" in epidermis of man and mouse. Acta Vitaminol Enzymol. 1975;29(1-6):158-60. [PubMed:1244085 ]
  3. Bapurao S, Krishnaswamy K: Vitamin B6 nutritional status of pellagrins and their leucine tolerance. Am J Clin Nutr. 1978 May;31(5):819-24. [PubMed:206127 ]
  4. Shibata K, Fukuwatari T, Murakami M, Sasaki R: Increase in conversion of tryptophan to niacin in pregnant rats. Adv Exp Med Biol. 2003;527:435-41. [PubMed:15206761 ]
  5. Forrest CM, Gould SR, Darlington LG, Stone TW: Levels of purine, kynurenine and lipid peroxidation products in patients with inflammatory bowel disease. Adv Exp Med Biol. 2003;527:395-400. [PubMed:15206756 ]
  6. Hoes MJ, Loeffen T, Vree TB: Kinetics of L-tryptophan in depressive patients: a possible correlation between the plasma concentrations of L-tryptophan and some psychiatric rating scales. Psychopharmacology (Berl). 1981;75(4):350-3. [PubMed:6803278 ]
  7. Malina HZ, Hess OM: Xanthurenic acid translocates proapoptotic Bcl-2 family proteins into mitochondria and impairs mitochondrial function. BMC Cell Biol. 2004 Apr 6;5:14. [PubMed:15068490 ]
  8. Bapurao S, Raman L, Tulpule PG: Biochemical assessment of vitamin B6 nutritional status in pregnant women with orolingual manifestations. Am J Clin Nutr. 1982 Oct;36(4):581-6. [PubMed:7124659 ]
  9. Malina HZ: Comment on 'The photosensitiser xanthurenic acid is not present in normal human lenses' by P.G. Hains et al. [Exp. Eye Res. 77 (2003) 547-553]. Exp Eye Res. 2004 Sep;79(3):443-5; author reply 447-8. [PubMed:15336509 ]
  10. Forrest CM, Kennedy A, Stone TW, Stoy N, Darlington LG: Kynurenine and neopterin levels in patients with rheumatoid arthritis and osteoporosis during drug treatment. Adv Exp Med Biol. 2003;527:287-95. [PubMed:15206742 ]