MiMeDB: Showing metabocard for Pyrroloquinoline quinone (MMDBc0030383)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 00:06:08 UTC

Update Date

2024-04-30 19:46:24 UTC

Metabolite ID

MMDBc0030383

Metabolite Identification

Common Name

Pyrroloquinoline quinone

Description

Enzymes containing PQQ are called quinoproteins. PQQ and quinoproteins play a role in the redox metabolism and structural integrity of cells and tissues [PMID:2558842 ]. It was reported that aminoadipate semialdehyde dehydrogenase (AASDH) might also use PQQ as a cofactor, suggesting a possibility that PQQ is a vitamin in mammals. [PMID:12712191 ]

Structure

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

HMDB0013636
     RDKit          3D
Pyrroloquinoline quinone
 30 32  0  0  0  0  0  0  0  0999 V2000
    5.1896   -1.2544    1.4257 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6756   -0.6262    0.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4988   -0.0839   -0.5284 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2269   -0.4387    0.3491 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6722    0.2485   -0.7017 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2671    0.3988   -0.7639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7479    1.0957   -1.9176 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6970    2.3485   -1.8981 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3057    0.4450   -3.0574 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5266   -0.1518    0.2358 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0865   -0.8443    1.2936 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4474   -0.9609    1.3047 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3460   -1.4493    2.3900 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8934   -2.0641    3.3197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0905   -1.3079    2.3623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8600   -1.7763    3.2380 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6891   -0.5825    1.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0099   -0.2661    0.9495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0561    0.4539   -0.2104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2641    0.9556   -0.8381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1606    1.6024   -1.9024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5316    0.7597   -0.3259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7620    0.5914   -0.6318 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9363   -0.0215    0.2331 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5235    0.9324   -0.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3140    0.6608   -1.4596 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2290    0.9286   -3.9417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8513   -0.5665    1.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8348   -0.1528   -0.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6009    1.1261   -1.5073 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
  7  8  2  0
  7  9  1  0
  6 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 19 23  1  0
 23 24  1  0
 12  4  1  0
 24 17  2  0
 24 10  1  0
  3 25  1  0
  5 26  1  0
  9 27  1  0
 18 28  1  0
 22 29  1  0
 23 30  1  0
M  END


  Mrv1652303102016522D          

 24 26  0  0  0  0            999 V2000
   -1.5255   -3.0924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6075   -2.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3500   -1.9373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7831    3.0924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1957    2.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1030    2.4328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5255    1.5255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1128    0.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6904    0.1234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6904   -1.9373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1957   -1.2778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5255   -0.5353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3500   -0.4533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3704   -1.3606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1234   -0.7002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9479   -0.9479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9479   -1.7724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1234   -2.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2055    0.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0308    0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3606    0.9479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8659    1.6075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0414    1.5255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2884    0.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2 17  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5 22  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 24  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 14  1  0  0  0  0
 12 13  2  0  0  0  0
 12 20  1  0  0  0  0
 14 15  2  0  0  0  0
 14 18  1  0  0  0  0
 15 16  1  0  0  0  0
 15 19  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 19 20  2  0  0  0  0
 19 24  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0030383

> <DATABASE_NAME>
MIME

> <SMILES>
OC(=O)C1=CC2=C(N1)C1=C(N=C(C=C1C(O)=O)C(O)=O)C(=O)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H6N2O8/c17-10-4-2-6(14(23)24)15-8(4)7-3(12(19)20)1-5(13(21)22)16-9(7)11(10)18/h1-2,15H,(H,19,20)(H,21,22)(H,23,24)

> <INCHI_KEY>
MMXZSJMASHPLLR-UHFFFAOYSA-N

> <FORMULA>
C14H6N2O8

> <MOLECULAR_WEIGHT>
330.206

> <EXACT_MASS>
330.012415178

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
28.908528171020595

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,5-dioxo-1H,4H,5H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid

> <ALOGPS_LOGP>
0.46

> <JCHEM_LOGP>
0.365369383

> <ALOGPS_LOGS>
-3.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
2.929788089193029

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.6824176863730189

> <JCHEM_PKA_STRONGEST_BASIC>
4.4608840963532455

> <JCHEM_POLAR_SURFACE_AREA>
174.71999999999997

> <JCHEM_REFRACTIVITY>
74.5325

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.66e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pyrroloquinoline quinone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013636
     RDKit          3D
Pyrroloquinoline quinone
 30 32  0  0  0  0  0  0  0  0999 V2000
    5.1896   -1.2544    1.4257 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6756   -0.6262    0.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4988   -0.0839   -0.5284 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2269   -0.4387    0.3491 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6722    0.2485   -0.7017 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2671    0.3988   -0.7639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7479    1.0957   -1.9176 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6970    2.3485   -1.8981 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3057    0.4450   -3.0574 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5266   -0.1518    0.2358 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0865   -0.8443    1.2936 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4474   -0.9609    1.3047 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3460   -1.4493    2.3900 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8934   -2.0641    3.3197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0905   -1.3079    2.3623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8600   -1.7763    3.2380 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6891   -0.5825    1.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0099   -0.2661    0.9495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0561    0.4539   -0.2104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2641    0.9556   -0.8381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1606    1.6024   -1.9024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5316    0.7597   -0.3259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7620    0.5914   -0.6318 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9363   -0.0215    0.2331 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5235    0.9324   -0.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3140    0.6608   -1.4596 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2290    0.9286   -3.9417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8513   -0.5665    1.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8348   -0.1528   -0.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6009    1.1261   -1.5073 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
  7  8  2  0
  7  9  1  0
  6 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 19 23  1  0
 23 24  1  0
 12  4  1  0
 24 17  2  0
 24 10  1  0
  3 25  1  0
  5 26  1  0
  9 27  1  0
 18 28  1  0
 22 29  1  0
 23 30  1  0
M  END

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  O   UNK     0      -2.848  -5.772   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -3.001  -4.234   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -4.387  -3.616   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.462   5.772   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.232   4.387   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.926   4.541   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -2.848   2.848   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.077   1.462   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.155   0.230   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       3.155  -3.616   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.232  -2.385   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.848  -0.999   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.387  -0.846   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.691  -2.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.230  -1.307   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      -1.769  -1.769   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      -1.769  -3.308   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.230  -3.771   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.384   0.076   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.924   0.384   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       2.540   1.769   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       1.616   3.001   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.077   2.848   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.538   1.462   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2                                                            
CONECT    4    5                                                            
CONECT    5    4    6   22                                                  
CONECT    6    5                                                            
CONECT    7    8                                                            
CONECT    8    7    9   24                                                  
CONECT    9    8                                                            
CONECT   10   11                                                            
CONECT   11   10   12   14                                                  
CONECT   12   11   13   20                                                  
CONECT   13   12                                                            
CONECT   14   11   15   18                                                  
CONECT   15   14   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17    2   16   18                                                  
CONECT   18   14   17                                                       
CONECT   19   15   20   24                                                  
CONECT   20   12   19   21                                                  
CONECT   21   20   22                                                       
CONECT   22    5   21   23                                                  
CONECT   23   22   24                                                       
CONECT   24    8   19   23                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0013636
HETATM    1  O1  UNL     1       5.190  -1.254   1.426  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.676  -0.626   0.466  1.00  0.00           C  
HETATM    3  O2  UNL     1       5.499  -0.084  -0.528  1.00  0.00           O  
HETATM    4  C2  UNL     1       3.227  -0.439   0.349  1.00  0.00           C  
HETATM    5  C3  UNL     1       2.672   0.248  -0.702  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.267   0.399  -0.764  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.748   1.096  -1.918  1.00  0.00           C  
HETATM    8  O3  UNL     1       0.697   2.348  -1.898  1.00  0.00           O  
HETATM    9  O4  UNL     1       0.306   0.445  -3.057  1.00  0.00           O  
HETATM   10  C6  UNL     1       0.527  -0.152   0.236  1.00  0.00           C  
HETATM   11  C7  UNL     1       1.086  -0.844   1.294  1.00  0.00           C  
HETATM   12  N1  UNL     1       2.447  -0.961   1.305  1.00  0.00           N  
HETATM   13  C8  UNL     1       0.346  -1.449   2.390  1.00  0.00           C  
HETATM   14  O5  UNL     1       0.893  -2.064   3.320  1.00  0.00           O  
HETATM   15  C9  UNL     1      -1.091  -1.308   2.362  1.00  0.00           C  
HETATM   16  O6  UNL     1      -1.860  -1.776   3.238  1.00  0.00           O  
HETATM   17  C10 UNL     1      -1.689  -0.582   1.260  1.00  0.00           C  
HETATM   18  C11 UNL     1      -3.010  -0.266   0.950  1.00  0.00           C  
HETATM   19  C12 UNL     1      -3.056   0.454  -0.210  1.00  0.00           C  
HETATM   20  C13 UNL     1      -4.264   0.956  -0.838  1.00  0.00           C  
HETATM   21  O7  UNL     1      -4.161   1.602  -1.902  1.00  0.00           O  
HETATM   22  O8  UNL     1      -5.532   0.760  -0.326  1.00  0.00           O  
HETATM   23  N2  UNL     1      -1.762   0.591  -0.632  1.00  0.00           N  
HETATM   24  C14 UNL     1      -0.936  -0.022   0.233  1.00  0.00           C  
HETATM   25  H1  UNL     1       5.524   0.932  -0.670  1.00  0.00           H  
HETATM   26  H2  UNL     1       3.314   0.661  -1.460  1.00  0.00           H  
HETATM   27  H3  UNL     1       0.229   0.929  -3.942  1.00  0.00           H  
HETATM   28  H4  UNL     1      -3.851  -0.567   1.565  1.00  0.00           H  
HETATM   29  H5  UNL     1      -5.835  -0.153  -0.039  1.00  0.00           H  
HETATM   30  H6  UNL     1      -1.601   1.126  -1.507  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   25
CONECT    4    5    5   12
CONECT    5    6   26
CONECT    6    7   10   10
CONECT    7    8    8    9
CONECT    9   27
CONECT   10   11   24
CONECT   11   12   12   13
CONECT   13   14   14   15
CONECT   15   16   16   17
CONECT   17   18   24   24
CONECT   18   19   19   28
CONECT   19   20   23
CONECT   20   21   21   22
CONECT   22   29
CONECT   23   24   30
END

HMDB0013636
     RDKit          3D
Pyrroloquinoline quinone
 30 32  0  0  0  0  0  0  0  0999 V2000
    5.1896   -1.2544    1.4257 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6756   -0.6262    0.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4988   -0.0839   -0.5284 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2269   -0.4387    0.3491 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6722    0.2485   -0.7017 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2671    0.3988   -0.7639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7479    1.0957   -1.9176 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6970    2.3485   -1.8981 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3057    0.4450   -3.0574 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5266   -0.1518    0.2358 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0865   -0.8443    1.2936 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4474   -0.9609    1.3047 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3460   -1.4493    2.3900 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8934   -2.0641    3.3197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0905   -1.3079    2.3623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8600   -1.7763    3.2380 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6891   -0.5825    1.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0099   -0.2661    0.9495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0561    0.4539   -0.2104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2641    0.9556   -0.8381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1606    1.6024   -1.9024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5316    0.7597   -0.3259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7620    0.5914   -0.6318 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9363   -0.0215    0.2331 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5235    0.9324   -0.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3140    0.6608   -1.4596 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2290    0.9286   -3.9417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8513   -0.5665    1.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8348   -0.1528   -0.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6009    1.1261   -1.5073 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
  7  8  2  0
  7  9  1  0
  6 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 19 23  1  0
 23 24  1  0
 12  4  1  0
 24 17  2  0
 24 10  1  0
  3 25  1  0
  5 26  1  0
  9 27  1  0
 18 28  1  0
 22 29  1  0
 23 30  1  0
M  END

Synonyms

Value	Source
2,4,6-Tricarboxylic-pyrrolo[2,3-5,6]quinoline 8,9-quinone	ChEBI
2,7,9-Tricarboxy-1H-pyrrolo(2,3-F)quinoline-4,5-dione	ChEBI
4,5-Dihydro-4,5-dioxo-1H-pyrrolo[2,3-5,6]quinoline-2,7,9-tricarboxylic acid	ChEBI
4,5-Dioxo-4,5-dihydro-1H-pyrrolo[2,3-F]quinoline-2,7,9-tricarboxylate	ChEBI
Coenzyme PQQ	ChEBI
Methoxatin	ChEBI
PQQ	ChEBI
Pyrrolo-quinoline quinone	ChEBI
Pyrroloquinoline-quinone	ChEBI
4,5-Dihydro-4,5-dioxo-1H-pyrrolo[2,3-5,6]quinoline-2,7,9-tricarboxylate	Generator
4,5-Dioxo-4,5-dihydro-1H-pyrrolo[2,3-F]quinoline-2,7,9-tricarboxylic acid	Generator
2,7,9-Tricarboxy-1H-pyrrolo-(2,3-F)quinoline-4,5-dione	MeSH
2,7,9-Tricarboxypyrroloquinoline quinone	MeSH
4,5-Dihydro-4,5-dioxo-1-H-pyrrolo(2,3-F)quinoline-2,7,9-tricarboxylic acid	MeSH
Coenzyme, PQQ	MeSH
Cofactor, PQQ	MeSH
PQQ Coenzyme	MeSH
PQQ Cofactor	MeSH
PQQ, Coenzyme	MeSH
Pyrrolo quinoline quinone	MeSH
Quinone, pyrrolo-quinoline	MeSH
Quinone, pyrroloquinoline	MeSH

Molecular Formula

C₁₄H₆N₂O₈

Average Mass

330.206

Monoisotopic Mass

330.012415178

IUPAC Name

4,5-dioxo-1H,4H,5H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid

Traditional Name

pyrroloquinoline quinone

CAS Registry Number

72909-34-3

SMILES

OC(=O)C1=CC2=C(N1)C1=C(N=C(C=C1C(O)=O)C(O)=O)C(=O)C2=O

InChI Identifier

InChI=1S/C14H6N2O8/c17-10-4-2-6(14(23)24)15-8(4)7-3(12(19)20)1-5(13(21)22)16-9(7)11(10)18/h1-2,15H,(H,19,20)(H,21,22)(H,23,24)

InChI Key

MMXZSJMASHPLLR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrroloquinoline quinones. Pyrroloquinoline quinones are compounds with a structure based on the 2,7,-tricarboxy-1H-pyrrolo[2,3-f ]quinoline-4,5-dione. Pyrroloquinoline Quinones usually bear a carboxylic acid group at the C-2, C-7 and C-9 positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Pyrroloquinolines

Direct Parent

Pyrroloquinoline quinones

Alternative Parents

Substituents

Pyrroloquinoline quinone
Quinoline-4-carboxylic acid
Quinoline-2-carboxylic acid
Indole or derivatives
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Tricarboxylic acid or derivatives
O-quinone
Pyrrole-2-carboxylic acid
Pyrrole-2-carboxylic acid or derivatives
Aryl ketone
Quinone
Pyridine
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Vinylogous amide
Ketone
Azacycle
Carboxylic acid derivative
Carboxylic acid
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

quinone (CHEBI:18315 )
pyrroloquinoline cofactor (CHEBI:18315 )
tricarboxylic acid (CHEBI:18315 )
Prosthetic group [Fig] (C00113 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.097 g/L	ALOGPS
logP	0.46	ALOGPS
logP	0.37	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	0.68	ChemAxon
pKa (Strongest Basic)	4.46	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	174.72 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	74.53 m³·mol⁻¹	ChemAxon
Polarizability	28.91 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	splash10-0rkl-1293000000-f89d3e9669ea62420001	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-00di-5001920000-ffb897aa343201141554	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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dr-0059000000-fe32e3dcdbb122899a9b	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01p9-0093000000-0057ba82bb1928e2b729	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-0090000000-7a80db950a195ffc246a	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01ti-0089000000-3940ecb0162179ef62fc	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kr-0092000000-47c12a164c99ff5da573	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00ku-0090000000-968a80882216e4efda23	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0009000000-84aa1fbc000600884df5	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02ai-0059000000-1b2548c8675bc744991a	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014l-0094000000-fd415930659367c11a26	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0090000000-984e546238980fbb8d35	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0090000000-899cb3d0e242698d7cf3	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-0090000000-899cb3d0e242698d7cf3	2021-09-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-21	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

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

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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	51	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool; Human subgingival plaque; Human sputum	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

External Links

HMDB ID

HMDB0013636

DrugBank ID

DB03205

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pyrroloquinoline_quinone

METLIN ID

Not Available

PubChem Compound

1024

PDB ID

Not Available

ChEBI ID

18315

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Paz MA, Fluckiger R, Torrelio BM, Gallop PM: Methoxatin (PQQ), coenzyme for copper-dependent amine and mixed-function oxidation in mammalian tissues. Connect Tissue Res. 1989;20(1-4):251-7. doi: 10.3109/03008208909023895. [PubMed:2558842 ]
Kasahara T, Kato T: Nutritional biochemistry: A new redox-cofactor vitamin for mammals. Nature. 2003 Apr 24;422(6934):832. doi: 10.1038/422832a. [PubMed:12712191 ]

Showing metabocard for Pyrroloquinoline quinone (MMDBc0030383)

MOL for #<Metabolite:0x00007f46d9eb5ba0>

3D MOL for #<Metabolite:0x00007f46d9eb5ba0>

3D SDF for #<Metabolite:0x00007f46d9eb5ba0>

3D-SDF for #<Metabolite:0x00007f46d9eb5ba0>

PDB for #<Metabolite:0x00007f46d9eb5ba0>

3D PDB for #<Metabolite:0x00007f46d9eb5ba0>

SMILES for #<Metabolite:0x00007f46d9eb5ba0>

INCHI for #<Metabolite:0x00007f46d9eb5ba0>

Structure for #<Metabolite:0x00007f46d9eb5ba0>

3D Structure for #<Metabolite:0x00007f46d9eb5ba0>