Showing metabocard for Pyrroloquinoline quinone (HMDB0013636)

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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2010-07-16 13:49:07 UTC

Update Date

2022-09-22 18:34:21 UTC

HMDB ID

HMDB0013636

Secondary Accession Numbers

HMDB13636

Metabolite Identification

Common Name

Pyrroloquinoline quinone

Description

Pyrroloquinoline quinone, also known as coenzyme PQQ or methoxatin, 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. Pyrroloquinoline quinone exists in all living organisms, ranging from bacteria to humans. In humans, pyrroloquinoline quinone is involved in the disulfiram action pathway. Pyrroloquinoline quinone has been detected, but not quantified in, green vegetables. This could make pyrroloquinoline quinone a potential biomarker for the consumption of these foods. Pyrroloquinoline quinone is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Pyrroloquinoline quinone.

Structure

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

MOL for HMDB0013636 (Pyrroloquinoline quinone)

  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  0M  END

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3D MOL for HMDB0013636 (Pyrroloquinoline quinone)

HMDB0013636     RDKit          3DPyrroloquinoline 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  0M  END

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3D SDF for HMDB0013636 (Pyrroloquinoline quinone)

  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  0M  END> <DATABASE_ID>HMDB0013636> <DATABASE_NAME>hmdb> <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$$$$

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3D-SDF for HMDB0013636 (Pyrroloquinoline quinone)

HMDB0013636     RDKit          3DPyrroloquinoline 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  0M  END

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PDB for HMDB0013636 (Pyrroloquinoline quinone)

HEADER    PROTEIN                                 10-MAR-20   NONETITLE     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+0HETATM    2  C   UNK     0      -3.001  -4.234   0.000  0.00  0.00           C+0HETATM    3  O   UNK     0      -4.387  -3.616   0.000  0.00  0.00           O+0HETATM    4  O   UNK     0       1.462   5.772   0.000  0.00  0.00           O+0HETATM    5  C   UNK     0       2.232   4.387   0.000  0.00  0.00           C+0HETATM    6  O   UNK     0       3.926   4.541   0.000  0.00  0.00           O+0HETATM    7  O   UNK     0      -2.848   2.848   0.000  0.00  0.00           O+0HETATM    8  C   UNK     0      -2.077   1.462   0.000  0.00  0.00           C+0HETATM    9  O   UNK     0      -3.155   0.230   0.000  0.00  0.00           O+0HETATM   10  O   UNK     0       3.155  -3.616   0.000  0.00  0.00           O+0HETATM   11  C   UNK     0       2.232  -2.385   0.000  0.00  0.00           C+0HETATM   12  C   UNK     0       2.848  -0.999   0.000  0.00  0.00           C+0HETATM   13  O   UNK     0       4.387  -0.846   0.000  0.00  0.00           O+0HETATM   14  C   UNK     0       0.691  -2.540   0.000  0.00  0.00           C+0HETATM   15  C   UNK     0      -0.230  -1.307   0.000  0.00  0.00           C+0HETATM   16  N   UNK     0      -1.769  -1.769   0.000  0.00  0.00           N+0HETATM   17  C   UNK     0      -1.769  -3.308   0.000  0.00  0.00           C+0HETATM   18  C   UNK     0      -0.230  -3.771   0.000  0.00  0.00           C+0HETATM   19  C   UNK     0       0.384   0.076   0.000  0.00  0.00           C+0HETATM   20  C   UNK     0       1.924   0.384   0.000  0.00  0.00           C+0HETATM   21  N   UNK     0       2.540   1.769   0.000  0.00  0.00           N+0HETATM   22  C   UNK     0       1.616   3.001   0.000  0.00  0.00           C+0HETATM   23  C   UNK     0       0.077   2.848   0.000  0.00  0.00           C+0HETATM   24  C   UNK     0      -0.538   1.462   0.000  0.00  0.00           C+0CONECT    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    0END

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3D PDB for HMDB0013636 (Pyrroloquinoline quinone)

COMPND    HMDB0013636HETATM    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    2CONECT    2    3    4CONECT    3   25CONECT    4    5    5   12CONECT    5    6   26CONECT    6    7   10   10CONECT    7    8    8    9CONECT    9   27CONECT   10   11   24CONECT   11   12   12   13CONECT   13   14   14   15CONECT   15   16   16   17CONECT   17   18   24   24CONECT   18   19   19   28CONECT   19   20   23CONECT   20   21   21   22CONECT   22   29CONECT   23   24   30END

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SMILES for HMDB0013636 (Pyrroloquinoline quinone)

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

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INCHI for HMDB0013636 (Pyrroloquinoline quinone)

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)

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Structure for HMDB0013636 (Pyrroloquinoline quinone)

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3D Structure for HMDB0013636 (Pyrroloquinoline quinone)

HMDB0013636     RDKit          3DPyrroloquinoline 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  0M  END

View in JSmol View Stereo Labels

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

Chemical Formula

C₁₄H₆N₂O₈

Average Molecular Weight

330.206

Monoisotopic Molecular Weight

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)

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB:HMDB0013636)

Organelle

Mitochondrion (HMDB:HMDB0013636)

Route of exposure

Enteral

Ingestion (HMDB:HMDB0013636)

Source

Exogenous

Exogenous (HMDB:HMDB0013636)

Food

Food (HMDB:HMDB0013636)

Vegetable

Leaf vegetable

Green vegetables (FooDB:FOOD00872)

Endogenous

Endogenous (HMDB:HMDB0013636)

Plant

Plant (HMDB:HMDB0013636)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tyrosine Metabolism (PathBank:SMP0087328)
Catecholamine Biosynthesis (HMDB:HMDB0013636)
Catecholamine Biosynthesis (PathBank:SMP0063606)

Disease pathway

Tyrosinemia, Transient, of the Newborn (PathBank:SMP0120779)
Aromatic L-Aminoacid Decarboxylase Deficiency (PathBank:SMP0120457)
Tyrosine Hydroxylase Deficiency (PathBank:SMP0120562)
Hawkinsinuria (PathBank:SMP0120711)
Tyrosinemia Type I (PathBank:SMP0120729)
Alkaptonuria (PathBank:SMP0120453)
Dopamine beta-Hydroxylase Deficiency (PathBank:SMP0120563)
Monoamine Oxidase-A Deficiency (MAO-A) (PathBank:SMP0120817)

Drug action pathway

Disulfiram Action Pathway (HMDB:HMDB0013636)
Disulfiram Action Pathway (PathBank:SMP0000429)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB:HMDB0013636)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	211.8 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	176.648	31661259
DarkChem	[M-H]-	175.819	31661259
DeepCCS	[M+H]+	171.371	30932474
DeepCCS	[M-H]-	169.013	30932474
DeepCCS	[M-2H]-	203.06	30932474
DeepCCS	[M+Na]+	178.337	30932474
AllCCS	[M+H]+	171.2	32859911
AllCCS	[M+H-H2O]+	167.9	32859911
AllCCS	[M+NH4]+	174.3	32859911
AllCCS	[M+Na]+	175.1	32859911
AllCCS	[M-H]-	169.0	32859911
AllCCS	[M+Na-2H]-	168.3	32859911
AllCCS	[M+HCOO]-	167.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.02 minutes	32390414
Predicted by Siyang on May 30, 2022	12.3612 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.74 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	115.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1504.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	318.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	63.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	178.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	75.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	353.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	481.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	163.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	762.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	333.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1441.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	280.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	316.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	873.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	191.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	471.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pyrroloquinoline quinone	OC(=O)C1=CC2=C(N1)C1=C(N=C(C=C1C(O)=O)C(O)=O)C(=O)C2=O	3924.2	Standard polar	33892256
Pyrroloquinoline quinone	OC(=O)C1=CC2=C(N1)C1=C(N=C(C=C1C(O)=O)C(O)=O)C(=O)C2=O	2242.9	Standard non polar	33892256
Pyrroloquinoline quinone	OC(=O)C1=CC2=C(N1)C1=C(N=C(C=C1C(O)=O)C(O)=O)C(=O)C2=O	3434.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Pyrroloquinoline quinone,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC2=C([NH]1)C1=C(C(=O)O)C=C(C(=O)O)N=C1C(=O)C2=O	3229.9	Semi standard non polar	33892256
Pyrroloquinoline quinone,1TMS,isomer #2	C[Si](C)(C)OC(=O)C1=CC(C(=O)O)=NC2=C1C1=C(C=C(C(=O)O)[NH]1)C(=O)C2=O	3268.0	Semi standard non polar	33892256
Pyrroloquinoline quinone,1TMS,isomer #3	C[Si](C)(C)OC(=O)C1=CC(C(=O)O)=C2C(=N1)C(=O)C(=O)C1=C2[NH]C(C(=O)O)=C1	3229.6	Semi standard non polar	33892256
Pyrroloquinoline quinone,1TMS,isomer #4	C[Si](C)(C)N1C(C(=O)O)=CC2=C1C1=C(C(=O)O)C=C(C(=O)O)N=C1C(=O)C2=O	3223.5	Semi standard non polar	33892256
Pyrroloquinoline quinone,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC2=C([NH]1)C1=C(C(=O)O[Si](C)(C)C)C=C(C(=O)O)N=C1C(=O)C2=O	3189.9	Semi standard non polar	33892256
Pyrroloquinoline quinone,2TMS,isomer #2	C[Si](C)(C)OC(=O)C1=CC(C(=O)O)=C2C(=N1)C(=O)C(=O)C1=C2[NH]C(C(=O)O[Si](C)(C)C)=C1	3154.2	Semi standard non polar	33892256
Pyrroloquinoline quinone,2TMS,isomer #3	C[Si](C)(C)OC(=O)C1=CC2=C(C3=C(C(=O)O)C=C(C(=O)O)N=C3C(=O)C2=O)N1[Si](C)(C)C	3175.3	Semi standard non polar	33892256
Pyrroloquinoline quinone,2TMS,isomer #4	C[Si](C)(C)OC(=O)C1=CC(C(=O)O[Si](C)(C)C)=C2C(=N1)C(=O)C(=O)C1=C2[NH]C(C(=O)O)=C1	3190.4	Semi standard non polar	33892256
Pyrroloquinoline quinone,2TMS,isomer #5	C[Si](C)(C)OC(=O)C1=CC(C(=O)O)=NC2=C1C1=C(C=C(C(=O)O)N1[Si](C)(C)C)C(=O)C2=O	3239.1	Semi standard non polar	33892256
Pyrroloquinoline quinone,2TMS,isomer #6	C[Si](C)(C)OC(=O)C1=CC(C(=O)O)=C2C(=N1)C(=O)C(=O)C1=C2N([Si](C)(C)C)C(C(=O)O)=C1	3153.9	Semi standard non polar	33892256
Pyrroloquinoline quinone,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(C(=O)O[Si](C)(C)C)=C2C(=N1)C(=O)C(=O)C1=C2[NH]C(C(=O)O[Si](C)(C)C)=C1	3167.6	Semi standard non polar	33892256
Pyrroloquinoline quinone,3TMS,isomer #2	C[Si](C)(C)OC(=O)C1=CC(C(=O)O)=NC2=C1C1=C(C=C(C(=O)O[Si](C)(C)C)N1[Si](C)(C)C)C(=O)C2=O	3142.6	Semi standard non polar	33892256
Pyrroloquinoline quinone,3TMS,isomer #3	C[Si](C)(C)OC(=O)C1=CC(C(=O)O)=C2C(=N1)C(=O)C(=O)C1=C2N([Si](C)(C)C)C(C(=O)O[Si](C)(C)C)=C1	3107.3	Semi standard non polar	33892256
Pyrroloquinoline quinone,3TMS,isomer #4	C[Si](C)(C)OC(=O)C1=CC(C(=O)O[Si](C)(C)C)=C2C(=N1)C(=O)C(=O)C1=C2N([Si](C)(C)C)C(C(=O)O)=C1	3149.6	Semi standard non polar	33892256
Pyrroloquinoline quinone,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(C(=O)O[Si](C)(C)C)=C2C(=N1)C(=O)C(=O)C1=C2N([Si](C)(C)C)C(C(=O)O[Si](C)(C)C)=C1	3112.8	Semi standard non polar	33892256
Pyrroloquinoline quinone,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(C(=O)O[Si](C)(C)C)=C2C(=N1)C(=O)C(=O)C1=C2N([Si](C)(C)C)C(C(=O)O[Si](C)(C)C)=C1	3271.3	Standard non polar	33892256
Pyrroloquinoline quinone,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(C(=O)O[Si](C)(C)C)=C2C(=N1)C(=O)C(=O)C1=C2N([Si](C)(C)C)C(C(=O)O[Si](C)(C)C)=C1	3666.3	Standard polar	33892256
Pyrroloquinoline quinone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=C([NH]1)C1=C(C(=O)O)C=C(C(=O)O)N=C1C(=O)C2=O	3459.1	Semi standard non polar	33892256
Pyrroloquinoline quinone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(C(=O)O)=NC2=C1C1=C(C=C(C(=O)O)[NH]1)C(=O)C2=O	3500.2	Semi standard non polar	33892256
Pyrroloquinoline quinone,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(C(=O)O)=C2C(=N1)C(=O)C(=O)C1=C2[NH]C(C(=O)O)=C1	3464.3	Semi standard non polar	33892256
Pyrroloquinoline quinone,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N1C(C(=O)O)=CC2=C1C1=C(C(=O)O)C=C(C(=O)O)N=C1C(=O)C2=O	3482.8	Semi standard non polar	33892256
Pyrroloquinoline quinone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=C([NH]1)C1=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C(C(=O)O)N=C1C(=O)C2=O	3595.2	Semi standard non polar	33892256
Pyrroloquinoline quinone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(C(=O)O)=C2C(=N1)C(=O)C(=O)C1=C2[NH]C(C(=O)O[Si](C)(C)C(C)(C)C)=C1	3550.2	Semi standard non polar	33892256
Pyrroloquinoline quinone,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=C(C3=C(C(=O)O)C=C(C(=O)O)N=C3C(=O)C2=O)N1[Si](C)(C)C(C)(C)C	3609.8	Semi standard non polar	33892256
Pyrroloquinoline quinone,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C2C(=N1)C(=O)C(=O)C1=C2[NH]C(C(=O)O)=C1	3614.1	Semi standard non polar	33892256
Pyrroloquinoline quinone,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(C(=O)O)=NC2=C1C1=C(C=C(C(=O)O)N1[Si](C)(C)C(C)(C)C)C(=O)C2=O	3706.9	Semi standard non polar	33892256
Pyrroloquinoline quinone,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(C(=O)O)=C2C(=N1)C(=O)C(=O)C1=C2N([Si](C)(C)C(C)(C)C)C(C(=O)O)=C1	3643.3	Semi standard non polar	33892256
Pyrroloquinoline quinone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C2C(=N1)C(=O)C(=O)C1=C2[NH]C(C(=O)O[Si](C)(C)C(C)(C)C)=C1	3677.4	Semi standard non polar	33892256
Pyrroloquinoline quinone,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(C(=O)O)=NC2=C1C1=C(C=C(C(=O)O[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C)C(=O)C2=O	3720.2	Semi standard non polar	33892256
Pyrroloquinoline quinone,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(C(=O)O)=C2C(=N1)C(=O)C(=O)C1=C2N([Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)=C1	3691.8	Semi standard non polar	33892256
Pyrroloquinoline quinone,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C2C(=N1)C(=O)C(=O)C1=C2N([Si](C)(C)C(C)(C)C)C(C(=O)O)=C1	3795.8	Semi standard non polar	33892256
Pyrroloquinoline quinone,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C2C(=N1)C(=O)C(=O)C1=C2N([Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)=C1	3791.3	Semi standard non polar	33892256
Pyrroloquinoline quinone,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C2C(=N1)C(=O)C(=O)C1=C2N([Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)=C1	4003.4	Standard non polar	33892256
Pyrroloquinoline quinone,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C2C(=N1)C(=O)C(=O)C1=C2N([Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)=C1	3962.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Pyrroloquinoline quinone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0rkl-1293000000-f89d3e9669ea62420001	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyrroloquinoline quinone GC-MS (3 TMS) - 70eV, Positive	splash10-00di-5001920000-ffb897aa343201141554	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyrroloquinoline quinone 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 - Pyrroloquinoline quinone 10V, Positive-QTOF	splash10-03dr-0059000000-fe32e3dcdbb122899a9b	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrroloquinoline quinone 20V, Positive-QTOF	splash10-01p9-0093000000-0057ba82bb1928e2b729	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrroloquinoline quinone 40V, Positive-QTOF	splash10-00kf-0090000000-7a80db950a195ffc246a	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrroloquinoline quinone 10V, Negative-QTOF	splash10-01ti-0089000000-3940ecb0162179ef62fc	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrroloquinoline quinone 20V, Negative-QTOF	splash10-00kr-0092000000-47c12a164c99ff5da573	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrroloquinoline quinone 40V, Negative-QTOF	splash10-00ku-0090000000-968a80882216e4efda23	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrroloquinoline quinone 10V, Positive-QTOF	splash10-03di-0009000000-84aa1fbc000600884df5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrroloquinoline quinone 20V, Positive-QTOF	splash10-02ai-0059000000-1b2548c8675bc744991a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrroloquinoline quinone 40V, Positive-QTOF	splash10-014l-0094000000-fd415930659367c11a26	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrroloquinoline quinone 10V, Negative-QTOF	splash10-0006-0090000000-984e546238980fbb8d35	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrroloquinoline quinone 20V, Negative-QTOF	splash10-0006-0090000000-899cb3d0e242698d7cf3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrroloquinoline quinone 40V, Negative-QTOF	splash10-0006-0090000000-899cb3d0e242698d7cf3	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Tyrosine metabolism	Not Available
Aromatic L-Aminoacid Decarboxylase Deficiency		Not Available
Tyrosine hydroxylase deficiency		Not Available
Tyrosine metabolism	Not Available
Alkaptonuria		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

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

VMH ID

PQQ

MarkerDB ID

Not Available

Good Scents ID

rw1842891

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

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. [PubMed:2558842]
Kasahara T, Kato T: Nutritional biochemistry: A new redox-cofactor vitamin for mammals. Nature. 2003 Apr 24;422(6934):832. [PubMed:12712191]

Movatterモバイル変換

Showing metabocard for Pyrroloquinoline quinone (HMDB0013636)

MOL for HMDB0013636 (Pyrroloquinoline quinone)

3D MOL for HMDB0013636 (Pyrroloquinoline quinone)

3D SDF for HMDB0013636 (Pyrroloquinoline quinone)

3D-SDF for HMDB0013636 (Pyrroloquinoline quinone)

PDB for HMDB0013636 (Pyrroloquinoline quinone)

3D PDB for HMDB0013636 (Pyrroloquinoline quinone)

SMILES for HMDB0013636 (Pyrroloquinoline quinone)

INCHI for HMDB0013636 (Pyrroloquinoline quinone)

Structure for HMDB0013636 (Pyrroloquinoline quinone)

3D Structure for HMDB0013636 (Pyrroloquinoline quinone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra