MiMeDB: Showing metabocard for Cinnavalininate (MMDBc0030224)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:59:02 UTC

Update Date

2024-04-30 19:44:55 UTC

Metabolite ID

MMDBc0030224

Metabolite Identification

Common Name

Cinnavalininate

Description

Cinnavalininate is an intermediate in the tryptophan metabolic pathway [Kegg: C05640]. It is generated from 3-hydroxyanthranilate via the enzyme catalase (EC:1.11.1.6).

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>
MMDBc0030224

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₄H₈N₂O₆

Average Mass

300.2231

Monoisotopic Mass

300.038235998

IUPAC Name

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

Traditional Name

cinnabarinic acid

CAS Registry Number

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kal-1090000000-a9b3f04e0154e56a34ac	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-05fr-7019200000-9d027bf9474c784d794f	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0093000000-6eec5362c826437aa9f8	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a59-0090000000-ea4d6ec354a7ad615bcd	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a5i-2090000000-a1cd4541b5bfb101f231	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0090000000-7b8418c9fe543cb0ddfc	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bt9-0090000000-3aa6f5b7cbca4210c35f	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0bt9-0390000000-10af92579df64b8720cb	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0090000000-fb1be335f42676557e20	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bti-0090000000-54b079267e6329486c07	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03fr-0190000000-40328130c8a319d1d980	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0090000000-24fd7e79c1bc515afade	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0159-0090000000-dadf0f0bb8448267e058	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0090000000-362869951e6e3adac9c6	2021-09-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0193136	Catalase	Unknown	P04040	Homo sapiens
MMDBp0193303	Aryl hydrocarbon receptor	Unknown	P35869	Homo sapiens
MMDBp0196391	Metabotropic glutamate receptor 4	Unknown	Q14833	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0010276	3-Hydroxyanthranilic acid	Hydrogen peroxide	catalase		VMH; KEGG	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0004078

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

References

Synthesis Reference

Not Available

General References

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 ]
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 ]

Showing metabocard for Cinnavalininate (MMDBc0030224)

MOL for #<Metabolite:0x00007f46dc01a8e0>

3D MOL for #<Metabolite:0x00007f46dc01a8e0>

3D SDF for #<Metabolite:0x00007f46dc01a8e0>

3D-SDF for #<Metabolite:0x00007f46dc01a8e0>

PDB for #<Metabolite:0x00007f46dc01a8e0>

3D PDB for #<Metabolite:0x00007f46dc01a8e0>

SMILES for #<Metabolite:0x00007f46dc01a8e0>

INCHI for #<Metabolite:0x00007f46dc01a8e0>

Structure for #<Metabolite:0x00007f46dc01a8e0>

3D Structure for #<Metabolite:0x00007f46dc01a8e0>