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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2006-08-13 10:24:21 UTC

Update Date

2022-09-22 18:34:18 UTC

HMDB ID

HMDB0004078

Secondary Accession Numbers

HMDB04078

Metabolite Identification

Common Name

Cinnabarinic acid

Description

Cinnabarinic acid, also called Cinnabarinate or Cinnavalininate, belongs to the class of organic compounds known as phenoxazines. These are polycyclic aromatic compounds containing a phenoxazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a 1,4-oxazine ring. Cinnabarinic acid, is and endogenous metabolite arising from tryptophan metabolism. More specifically, it is a relatively obscure and unstable end-product of the tryptophan-kynurenine pathway. It results from the condensation of two molecules of 3-hydroxy-anthranilic acid via the action of catalase (PMID: 35469990 ). Cinnabarinic acid has been found to bind and to act as a partial agonist of type 4 metabotropic glutamate receptors (mGluR4) (PMID: 22311707 ). It also binds to the aryl hydrocarbon receptor (AhR) and can activate the NF-kappaB pathway (PMID: 35469990 ). Levels of Cinnabarinic acid have been found to increase substantially during inflammation induced by lipopolysaccharide (LPS). Cinnabarinic acid appears to have neuroprotective activity (PMID: 22311707 ). Cinnabarinic acid is present in trace amounts in human brain tissue. Interestingly, Cinnabarinic acid levels are reduced in the prefrontal cortex (PFC) of individuals affected by schizophrenia (PMID: 32506121 ). Cinnabarinic acid has been found to be a potent endogenous antipsychotic-like molecule and it has been suggested that reduced Cinnabarinic acid levels in the PFC might contribute to the pathophysiology of schizophrenia (PMID: 32506121 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0004078
     RDKit          3D
Cinnavalininate
 30 32  0  0  0  0  0  0  0  0999 V2000
    4.4601   -0.4469   -0.6114 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2185    0.1816   -0.3627 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0275   -0.5616   -0.3789 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1088   -1.9603   -0.6521 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0963   -2.6772   -0.6820 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3200   -2.5901   -0.8979 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8164    0.0353   -0.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3704   -0.5976   -0.1351 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5116    0.1022    0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7146   -0.5586    0.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8292   -1.9866   -0.1411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8625   -2.7164   -0.3802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1183   -2.5730   -0.1174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8675    0.1972    0.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8379    1.5424    0.6323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6235    2.1878    0.6275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4551    1.4796    0.3714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3089    2.0854    0.3663 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8278    1.4881    0.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9946    2.1976    0.1468 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1600    1.5237   -0.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2342    2.1963   -0.0875 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1625   -0.5585    0.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6683   -0.7996   -1.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3857   -3.1999   -1.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8370   -2.1948   -0.7273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7942   -0.3505    0.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7635    2.0549    0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5782    3.2497    0.8238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9920    3.2500    0.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  3  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21  2  1  0
 19  7  1  0
 17  9  1  0
  1 23  1  0
  1 24  1  0
  6 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 20 30  1  0
M  END

  Mrv0541 02231219522D          

 22 24  0  0  0  0            999 V2000
   13.8935   -2.5309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7609   -2.5309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8272   -5.3386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5217   -2.5468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1328   -2.5468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6234   -5.3577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6234   -3.7353    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8272   -3.7544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2121   -2.9348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4423   -2.9348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5133   -4.9425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5133   -4.1504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1412   -4.9425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9390   -4.9591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9390   -4.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1412   -4.1504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2213   -3.7269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4332   -3.7269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2213   -5.3660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4332   -5.3660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7155   -4.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7155   -4.9591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2 10  1  0  0  0  0
  3 11  1  0  0  0  0
  3 13  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  2  0  0  0  0
  6 14  2  0  0  0  0
  7 15  1  0  0  0  0
  8 12  2  0  0  0  0
  8 16  1  0  0  0  0
  9 17  1  0  0  0  0
 10 18  1  0  0  0  0
 11 12  1  0  0  0  0
 11 19  2  0  0  0  0
 12 17  1  0  0  0  0
 13 16  1  0  0  0  0
 13 20  2  0  0  0  0
 14 15  1  0  0  0  0
 14 19  1  0  0  0  0
 15 17  2  0  0  0  0
 16 18  2  0  0  0  0
 18 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 22  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004078

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=C(C(O)=O)C2=NC3=C(C=CC=C3OC2=CC1=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H8N2O6/c15-10-6(17)4-8-12(9(10)14(20)21)16-11-5(13(18)19)2-1-3-7(11)22-8/h1-4H,15H2,(H,18,19)(H,20,21)

> <INCHI_KEY>
FSBKJYLVDRVPTK-UHFFFAOYSA-N

> <FORMULA>
C14H8N2O6

> <MOLECULAR_WEIGHT>
300.2231

> <EXACT_MASS>
300.038235998

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
27.383447390351158

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-amino-3-oxo-3H-phenoxazine-1,9-dicarboxylic acid

> <ALOGPS_LOGP>
0.70

> <JCHEM_LOGP>
0.4385754573333333

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.882453523470117

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.366796983750847

> <JCHEM_PKA_STRONGEST_BASIC>
-1.719341367235418

> <JCHEM_POLAR_SURFACE_AREA>
139.27999999999997

> <JCHEM_REFRACTIVITY>
76.89910000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.46e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cinnabarinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004078
     RDKit          3D
Cinnavalininate
 30 32  0  0  0  0  0  0  0  0999 V2000
    4.4601   -0.4469   -0.6114 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2185    0.1816   -0.3627 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0275   -0.5616   -0.3789 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1088   -1.9603   -0.6521 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0963   -2.6772   -0.6820 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3200   -2.5901   -0.8979 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8164    0.0353   -0.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3704   -0.5976   -0.1351 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5116    0.1022    0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7146   -0.5586    0.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8292   -1.9866   -0.1411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8625   -2.7164   -0.3802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1183   -2.5730   -0.1174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8675    0.1972    0.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8379    1.5424    0.6323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6235    2.1878    0.6275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4551    1.4796    0.3714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3089    2.0854    0.3663 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8278    1.4881    0.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9946    2.1976    0.1468 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1600    1.5237   -0.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2342    2.1963   -0.0875 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1625   -0.5585    0.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6683   -0.7996   -1.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3857   -3.1999   -1.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8370   -2.1948   -0.7273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7942   -0.3505    0.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7635    2.0549    0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5782    3.2497    0.8238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9920    3.2500    0.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  3  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21  2  1  0
 19  7  1  0
 17  9  1  0
  1 23  1  0
  1 24  1  0
  6 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 20 30  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      25.935  -4.724   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      18.220  -4.724   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      22.077  -9.965   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      23.374  -4.754   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      20.781  -4.754   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      27.297 -10.001   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0      27.297  -6.973   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      22.077  -7.008   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      24.663  -5.478   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.492  -5.478   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.358  -9.226   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.358  -7.747   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      20.797  -9.226   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      26.019  -9.257   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.019  -7.717   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.797  -7.747   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      24.680  -6.957   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      19.475  -6.957   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      24.680 -10.017   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      19.475 -10.017   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      18.136  -7.717   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      18.136  -9.257   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   11   13                                                       
CONECT    4    9                                                            
CONECT    5   10                                                            
CONECT    6   14                                                            
CONECT    7   15                                                            
CONECT    8   12   16                                                       
CONECT    9    1    4   17                                                  
CONECT   10    2    5   18                                                  
CONECT   11    3   12   19                                                  
CONECT   12    8   11   17                                                  
CONECT   13    3   16   20                                                  
CONECT   14    6   15   19                                                  
CONECT   15    7   14   17                                                  
CONECT   16    8   13   18                                                  
CONECT   17    9   12   15                                                  
CONECT   18   10   16   21                                                  
CONECT   19   11   14                                                       
CONECT   20   13   22                                                       
CONECT   21   18   22                                                       
CONECT   22   20   21                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0004078
HETATM    1  N1  UNL     1       4.460  -0.447  -0.611  1.00  0.00           N  
HETATM    2  C1  UNL     1       3.219   0.182  -0.363  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.027  -0.562  -0.379  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.109  -1.960  -0.652  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.096  -2.677  -0.682  1.00  0.00           O  
HETATM    6  O2  UNL     1       3.320  -2.590  -0.898  1.00  0.00           O  
HETATM    7  C4  UNL     1       0.816   0.035  -0.139  1.00  0.00           C  
HETATM    8  N2  UNL     1      -0.370  -0.598  -0.135  1.00  0.00           N  
HETATM    9  C5  UNL     1      -1.512   0.102   0.117  1.00  0.00           C  
HETATM   10  C6  UNL     1      -2.715  -0.559   0.117  1.00  0.00           C  
HETATM   11  C7  UNL     1      -2.829  -1.987  -0.141  1.00  0.00           C  
HETATM   12  O3  UNL     1      -1.863  -2.716  -0.380  1.00  0.00           O  
HETATM   13  O4  UNL     1      -4.118  -2.573  -0.117  1.00  0.00           O  
HETATM   14  C8  UNL     1      -3.868   0.197   0.381  1.00  0.00           C  
HETATM   15  C9  UNL     1      -3.838   1.542   0.632  1.00  0.00           C  
HETATM   16  C10 UNL     1      -2.623   2.188   0.628  1.00  0.00           C  
HETATM   17  C11 UNL     1      -1.455   1.480   0.371  1.00  0.00           C  
HETATM   18  O5  UNL     1      -0.309   2.085   0.366  1.00  0.00           O  
HETATM   19  C12 UNL     1       0.828   1.488   0.134  1.00  0.00           C  
HETATM   20  C13 UNL     1       1.995   2.198   0.147  1.00  0.00           C  
HETATM   21  C14 UNL     1       3.160   1.524  -0.103  1.00  0.00           C  
HETATM   22  O6  UNL     1       4.234   2.196  -0.088  1.00  0.00           O  
HETATM   23  H1  UNL     1       5.162  -0.558   0.143  1.00  0.00           H  
HETATM   24  H2  UNL     1       4.668  -0.800  -1.561  1.00  0.00           H  
HETATM   25  H3  UNL     1       3.386  -3.200  -1.702  1.00  0.00           H  
HETATM   26  H4  UNL     1      -4.837  -2.195  -0.727  1.00  0.00           H  
HETATM   27  H5  UNL     1      -4.794  -0.351   0.374  1.00  0.00           H  
HETATM   28  H6  UNL     1      -4.764   2.055   0.826  1.00  0.00           H  
HETATM   29  H7  UNL     1      -2.578   3.250   0.824  1.00  0.00           H  
HETATM   30  H8  UNL     1       1.992   3.250   0.346  1.00  0.00           H  
CONECT    1    2   23   24
CONECT    2    3    3   21
CONECT    3    4    7
CONECT    4    5    5    6
CONECT    6   25
CONECT    7    8    8   19
CONECT    8    9
CONECT    9   10   10   17
CONECT   10   11   14
CONECT   11   12   12   13
CONECT   13   26
CONECT   14   15   15   27
CONECT   15   16   28
CONECT   16   17   17   29
CONECT   17   18
CONECT   18   19
CONECT   19   20   20
CONECT   20   21   30
CONECT   21   22   22
END

HMDB0004078
     RDKit          3D
Cinnavalininate
 30 32  0  0  0  0  0  0  0  0999 V2000
    4.4601   -0.4469   -0.6114 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2185    0.1816   -0.3627 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0275   -0.5616   -0.3789 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1088   -1.9603   -0.6521 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0963   -2.6772   -0.6820 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3200   -2.5901   -0.8979 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8164    0.0353   -0.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3704   -0.5976   -0.1351 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5116    0.1022    0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7146   -0.5586    0.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8292   -1.9866   -0.1411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8625   -2.7164   -0.3802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1183   -2.5730   -0.1174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8675    0.1972    0.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8379    1.5424    0.6323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6235    2.1878    0.6275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4551    1.4796    0.3714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3089    2.0854    0.3663 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8278    1.4881    0.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9946    2.1976    0.1468 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1600    1.5237   -0.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2342    2.1963   -0.0875 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1625   -0.5585    0.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6683   -0.7996   -1.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3857   -3.1999   -1.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8370   -2.1948   -0.7273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7942   -0.3505    0.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7635    2.0549    0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5782    3.2497    0.8238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9920    3.2500    0.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  3  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21  2  1  0
 19  7  1  0
 17  9  1  0
  1 23  1  0
  1 24  1  0
  6 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 20 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Cinnabarinic acid	Kegg
Cinnabarinate	Generator
Cinnavalininic acid	Generator
2-amino-3-oxo-3H-Phenoxazin-1,9-dicarboxylic acid	HMDB
2-amino-3H-Phenoxazin-one-1,9-dicarboxylic acid	HMDB
2-amino-3-oxo-3H-Phenoxazin-1,9-dicarboxylate	HMDB
2-amino-3H-Phenoxazin-one-1,9-dicarboxylate	HMDB

Chemical Formula

C₁₄H₈N₂O₆

Average Molecular Weight

300.2231

Monoisotopic Molecular Weight

300.038235998

IUPAC Name

2-amino-3-oxo-3H-phenoxazine-1,9-dicarboxylic acid

Traditional Name

cinnabarinic acid

CAS Registry Number

606-59-7

SMILES

NC1=C(C(O)=O)C2=NC3=C(C=CC=C3OC2=CC1=O)C(O)=O

InChI Identifier

InChI=1S/C14H8N2O6/c15-10-6(17)4-8-12(9(10)14(20)21)16-11-5(13(18)19)2-1-3-7(11)22-8/h1-4H,15H2,(H,18,19)(H,20,21)

InChI Key

FSBKJYLVDRVPTK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenoxazines. These are polycyclic aromatic compounds containing a phenoxazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a 1,4-oxazine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzoxazines

Sub Class

Phenoxazines

Direct Parent

Phenoxazines

Alternative Parents

Substituents

Phenoxazine
Dicarboxylic acid or derivatives
Benzenoid
Heteroaromatic compound
Vinylogous amide
Cyclic ketone
Amino acid
Amino acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Azacycle
Primary amine
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Amine
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenoxazine (CHEBI:3715 )

Ontology

Not Available

Endogenous (HMDB: HMDB0004078)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tryptophan Metabolism (PathBank: SMP0063693)
Tryptophan Metabolism (HMDB: HMDB0004078)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	0.604	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.15 g/L	ALOGPS
logP	0.7	ALOGPS
logP	0.44	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	2.37	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	139.28 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	76.9 m³·mol⁻¹	ChemAxon
Polarizability	27.38 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	167.821	31661259
DarkChem	[M-H]-	164.081	31661259
DeepCCS	[M+H]+	173.238	30932474
DeepCCS	[M-H]-	170.88	30932474
DeepCCS	[M-2H]-	203.766	30932474
DeepCCS	[M+Na]+	179.331	30932474
AllCCS	[M+H]+	165.0	32859911
AllCCS	[M+H-H2O]+	161.6	32859911
AllCCS	[M+NH4]+	168.1	32859911
AllCCS	[M+Na]+	169.0	32859911
AllCCS	[M-H]-	164.1	32859911
AllCCS	[M+Na-2H]-	163.3	32859911
AllCCS	[M+HCOO]-	162.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cinnavalininate	NC1=C(C(O)=O)C2=NC3=C(C=CC=C3OC2=CC1=O)C(O)=O	4102.7	Standard polar	33892256
Cinnavalininate	NC1=C(C(O)=O)C2=NC3=C(C=CC=C3OC2=CC1=O)C(O)=O	2149.3	Standard non polar	33892256
Cinnavalininate	NC1=C(C(O)=O)C2=NC3=C(C=CC=C3OC2=CC1=O)C(O)=O	3126.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cinnavalininate,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1=C(N)C(=O)C=C2OC3=CC=CC(C(=O)O)=C3N=C21	3150.4	Semi standard non polar	33892256
Cinnavalininate,1TMS,isomer #2	C[Si](C)(C)OC(=O)C1=CC=CC2=C1N=C1C(=CC(=O)C(N)=C1C(=O)O)O2	3141.2	Semi standard non polar	33892256
Cinnavalininate,1TMS,isomer #3	C[Si](C)(C)NC1=C(C(=O)O)C2=NC3=C(C(=O)O)C=CC=C3OC2=CC1=O	3168.4	Semi standard non polar	33892256
Cinnavalininate,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=C(N)C(=O)C=C2OC3=CC=CC(C(=O)O[Si](C)(C)C)=C3N=C21	3117.0	Semi standard non polar	33892256
Cinnavalininate,2TMS,isomer #2	C[Si](C)(C)NC1=C(C(=O)O[Si](C)(C)C)C2=NC3=C(C(=O)O)C=CC=C3OC2=CC1=O	3178.0	Semi standard non polar	33892256
Cinnavalininate,2TMS,isomer #3	C[Si](C)(C)NC1=C(C(=O)O)C2=NC3=C(C(=O)O[Si](C)(C)C)C=CC=C3OC2=CC1=O	3126.0	Semi standard non polar	33892256
Cinnavalininate,2TMS,isomer #4	C[Si](C)(C)N(C1=C(C(=O)O)C2=NC3=C(C(=O)O)C=CC=C3OC2=CC1=O)[Si](C)(C)C	3067.6	Semi standard non polar	33892256
Cinnavalininate,3TMS,isomer #1	C[Si](C)(C)NC1=C(C(=O)O[Si](C)(C)C)C2=NC3=C(C(=O)O[Si](C)(C)C)C=CC=C3OC2=CC1=O	3134.8	Semi standard non polar	33892256
Cinnavalininate,3TMS,isomer #1	C[Si](C)(C)NC1=C(C(=O)O[Si](C)(C)C)C2=NC3=C(C(=O)O[Si](C)(C)C)C=CC=C3OC2=CC1=O	3077.0	Standard non polar	33892256
Cinnavalininate,3TMS,isomer #1	C[Si](C)(C)NC1=C(C(=O)O[Si](C)(C)C)C2=NC3=C(C(=O)O[Si](C)(C)C)C=CC=C3OC2=CC1=O	3882.5	Standard polar	33892256
Cinnavalininate,3TMS,isomer #2	C[Si](C)(C)OC(=O)C1=C(N([Si](C)(C)C)[Si](C)(C)C)C(=O)C=C2OC3=CC=CC(C(=O)O)=C3N=C21	3047.8	Semi standard non polar	33892256
Cinnavalininate,3TMS,isomer #2	C[Si](C)(C)OC(=O)C1=C(N([Si](C)(C)C)[Si](C)(C)C)C(=O)C=C2OC3=CC=CC(C(=O)O)=C3N=C21	3211.2	Standard non polar	33892256
Cinnavalininate,3TMS,isomer #2	C[Si](C)(C)OC(=O)C1=C(N([Si](C)(C)C)[Si](C)(C)C)C(=O)C=C2OC3=CC=CC(C(=O)O)=C3N=C21	3642.4	Standard polar	33892256
Cinnavalininate,3TMS,isomer #3	C[Si](C)(C)OC(=O)C1=CC=CC2=C1N=C1C(=CC(=O)C(N([Si](C)(C)C)[Si](C)(C)C)=C1C(=O)O)O2	3009.0	Semi standard non polar	33892256
Cinnavalininate,3TMS,isomer #3	C[Si](C)(C)OC(=O)C1=CC=CC2=C1N=C1C(=CC(=O)C(N([Si](C)(C)C)[Si](C)(C)C)=C1C(=O)O)O2	3147.6	Standard non polar	33892256
Cinnavalininate,3TMS,isomer #3	C[Si](C)(C)OC(=O)C1=CC=CC2=C1N=C1C(=CC(=O)C(N([Si](C)(C)C)[Si](C)(C)C)=C1C(=O)O)O2	3611.4	Standard polar	33892256
Cinnavalininate,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1=C(N([Si](C)(C)C)[Si](C)(C)C)C(=O)C=C2OC3=CC=CC(C(=O)O[Si](C)(C)C)=C3N=C21	3084.8	Semi standard non polar	33892256
Cinnavalininate,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1=C(N([Si](C)(C)C)[Si](C)(C)C)C(=O)C=C2OC3=CC=CC(C(=O)O[Si](C)(C)C)=C3N=C21	3149.4	Standard non polar	33892256
Cinnavalininate,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1=C(N([Si](C)(C)C)[Si](C)(C)C)C(=O)C=C2OC3=CC=CC(C(=O)O[Si](C)(C)C)=C3N=C21	3423.7	Standard polar	33892256
Cinnavalininate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=C(N)C(=O)C=C2OC3=CC=CC(C(=O)O)=C3N=C21	3396.8	Semi standard non polar	33892256
Cinnavalininate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC2=C1N=C1C(=CC(=O)C(N)=C1C(=O)O)O2	3390.2	Semi standard non polar	33892256
Cinnavalininate,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=C(C(=O)O)C2=NC3=C(C(=O)O)C=CC=C3OC2=CC1=O	3436.4	Semi standard non polar	33892256
Cinnavalininate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=C(N)C(=O)C=C2OC3=CC=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C3N=C21	3554.4	Semi standard non polar	33892256
Cinnavalininate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=C(C(=O)O[Si](C)(C)C(C)(C)C)C2=NC3=C(C(=O)O)C=CC=C3OC2=CC1=O	3615.4	Semi standard non polar	33892256
Cinnavalininate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=C(C(=O)O)C2=NC3=C(C(=O)O[Si](C)(C)C(C)(C)C)C=CC=C3OC2=CC1=O	3590.0	Semi standard non polar	33892256
Cinnavalininate,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C1=C(C(=O)O)C2=NC3=C(C(=O)O)C=CC=C3OC2=CC1=O)[Si](C)(C)C(C)(C)C	3533.9	Semi standard non polar	33892256
Cinnavalininate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=C(C(=O)O[Si](C)(C)C(C)(C)C)C2=NC3=C(C(=O)O[Si](C)(C)C(C)(C)C)C=CC=C3OC2=CC1=O	3712.8	Semi standard non polar	33892256
Cinnavalininate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=C(C(=O)O[Si](C)(C)C(C)(C)C)C2=NC3=C(C(=O)O[Si](C)(C)C(C)(C)C)C=CC=C3OC2=CC1=O	3580.0	Standard non polar	33892256
Cinnavalininate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=C(C(=O)O[Si](C)(C)C(C)(C)C)C2=NC3=C(C(=O)O[Si](C)(C)C(C)(C)C)C=CC=C3OC2=CC1=O	4003.6	Standard polar	33892256
Cinnavalininate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)C=C2OC3=CC=CC(C(=O)O)=C3N=C21	3683.6	Semi standard non polar	33892256
Cinnavalininate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)C=C2OC3=CC=CC(C(=O)O)=C3N=C21	3748.2	Standard non polar	33892256
Cinnavalininate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)C=C2OC3=CC=CC(C(=O)O)=C3N=C21	3834.3	Standard polar	33892256
Cinnavalininate,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC2=C1N=C1C(=CC(=O)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1C(=O)O)O2	3646.3	Semi standard non polar	33892256
Cinnavalininate,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC2=C1N=C1C(=CC(=O)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1C(=O)O)O2	3689.6	Standard non polar	33892256
Cinnavalininate,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC2=C1N=C1C(=CC(=O)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1C(=O)O)O2	3816.6	Standard polar	33892256
Cinnavalininate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)C=C2OC3=CC=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C3N=C21	3799.9	Semi standard non polar	33892256
Cinnavalininate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)C=C2OC3=CC=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C3N=C21	3837.0	Standard non polar	33892256
Cinnavalininate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)C=C2OC3=CC=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C3N=C21	3753.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cinnabarinic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kal-1090000000-a9b3f04e0154e56a34ac	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cinnabarinic acid GC-MS (2 TMS) - 70eV, Positive	splash10-05fr-7019200000-9d027bf9474c784d794f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cinnabarinic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cinnabarinic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnabarinic acid 10V, Positive-QTOF	splash10-001i-0093000000-6eec5362c826437aa9f8	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnabarinic acid 20V, Positive-QTOF	splash10-0a59-0090000000-ea4d6ec354a7ad615bcd	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnabarinic acid 40V, Positive-QTOF	splash10-0a5i-2090000000-a1cd4541b5bfb101f231	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnabarinic acid 10V, Negative-QTOF	splash10-0a4i-0090000000-7b8418c9fe543cb0ddfc	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnabarinic acid 20V, Negative-QTOF	splash10-0bt9-0090000000-3aa6f5b7cbca4210c35f	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnabarinic acid 40V, Negative-QTOF	splash10-0bt9-0390000000-10af92579df64b8720cb	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnabarinic acid 10V, Negative-QTOF	splash10-03di-0090000000-fb1be335f42676557e20	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnabarinic acid 20V, Negative-QTOF	splash10-0bti-0090000000-54b079267e6329486c07	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnabarinic acid 40V, Negative-QTOF	splash10-03fr-0190000000-40328130c8a319d1d980	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnabarinic acid 10V, Positive-QTOF	splash10-001i-0090000000-24fd7e79c1bc515afade	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnabarinic acid 20V, Positive-QTOF	splash10-0159-0090000000-dadf0f0bb8448267e058	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnabarinic acid 40V, Positive-QTOF	splash10-000i-0090000000-362869951e6e3adac9c6	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Tryptophan metabolism	Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023302

KNApSAcK ID

Not Available

Chemspider ID

102864

KEGG Compound ID

C05640

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

114918

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

M01572

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Gomez-Pineiro RJ, Dali M, Mansuy D, Boucher JL: Unstability of cinnabarinic acid, an endogenous metabolite of tryptophan, under situations mimicking physiological conditions. Biochimie. 2022 Aug;199:150-157. doi: 10.1016/j.biochi.2022.04.009. Epub 2022 Apr 22. [PubMed:35469990 ]
Fazio F, Lionetto L, Molinaro G, Bertrand HO, Acher F, Ngomba RT, Notartomaso S, Curini M, Rosati O, Scarselli P, Di Marco R, Battaglia G, Bruno V, Simmaco M, Pin JP, Nicoletti F, Goudet C: Cinnabarinic acid, an endogenous metabolite of the kynurenine pathway, activates type 4 metabotropic glutamate receptors. Mol Pharmacol. 2012 May;81(5):643-56. doi: 10.1124/mol.111.074765. Epub 2012 Feb 6. [PubMed:22311707 ]
Ulivieri M, Wieronska JM, Lionetto L, Martinello K, Cieslik P, Chocyk A, Curto M, Di Menna L, Iacovelli L, Traficante A, Liberatore F, Mascio G, Antenucci N, Giannino G, Vergassola M, Pittaluga A, Bruno V, Battaglia G, Fucile S, Simmaco M, Nicoletti F, Pilc A, Fazio F: The Trace Kynurenine, Cinnabarinic Acid, Displays Potent Antipsychotic-Like Activity in Mice and Its Levels Are Reduced in the Prefrontal Cortex of Individuals Affected by Schizophrenia. Schizophr Bull. 2020 Dec 1;46(6):1471-1481. doi: 10.1093/schbul/sbaa074. [PubMed:32506121 ]

Enzymes

Enzyme Details

1. Catalase

General function:: Involved in catalase activity
Specific function:: Occurs in almost all aerobically respiring organisms and serves to protect cells from the toxic effects of hydrogen peroxide. Promotes growth of cells including T-cells, B-cells, myeloid leukemia cells, melanoma cells, mastocytoma cells and normal and transformed fibroblast cells.
Gene Name:: CAT
Uniprot ID:: P04040
Molecular weight:: 59755.82

Reactions

3-Hydroxyanthranilic acid + Oxygen → Cinnabarinic acid + Superoxide + Hydrogen peroxide + Hydrogen Ion	details

Enzyme Details

2. Aryl hydrocarbon receptor

General function:: Involved in transcription regulator activity
Specific function:: Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues
Gene Name:: AHR
Uniprot ID:: P35869
Molecular weight:: 96146.7

Enzyme Details

3. Metabotropic glutamate receptor 4

General function:: Involved in G-protein coupled receptor activity
Specific function:: Receptor for glutamate. The activity of this receptor is mediated by a G-protein that inhibits adenylate cyclase activity
Gene Name:: GRM4
Uniprot ID:: Q14833
Molecular weight:: 101866.8

Showing metabocard for Cinnabarinic acid (HMDB0004078)

MOL for HMDB0004078 (Cinnabarinic acid)

3D MOL for HMDB0004078 (Cinnabarinic acid)

3D SDF for HMDB0004078 (Cinnabarinic acid)

3D-SDF for HMDB0004078 (Cinnabarinic acid)

PDB for HMDB0004078 (Cinnabarinic acid)

3D PDB for HMDB0004078 (Cinnabarinic acid)

SMILES for HMDB0004078 (Cinnabarinic acid)

INCHI for HMDB0004078 (Cinnabarinic acid)

Structure for HMDB0004078 (Cinnabarinic acid)

3D Structure for HMDB0004078 (Cinnabarinic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions