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Record Information
Version2.0
Creation Date2012-08-09 09:16:19 -0600
Update Date2015-06-03 17:21:33 -0600
Secondary Accession Numbers
  • ECMDB21461
Identification
Name:Pyrroloquinoline quinone
DescriptionEnzymes 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
Thumb
Synonyms:
  • 2,7,9-Tricarboxy-1H-pyrrolo[2,3-f]quinoline-4,5-dione
  • Methoxatin
  • PQQ
  • Pyrrolo-quinoline quinone
  • Pyrroloquinoline-quinone
Chemical Formula:C14H6N2O8
Weight:Average: 330.206
Monoisotopic: 330.012415178
InChI Key:MMXZSJMASHPLLR-UHFFFAOYSA-N
InChI: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)
CAS number:72909-34-3
IUPAC Name:4,5-dioxo-1H,4H,5H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid
Traditional IUPAC Name:pyrroloquinoline quinone
SMILES:OC(=O)C1=CC2=C(N1)C1=C(N=C(C=C1C(O)=O)C(O)=O)C(=O)C2=O
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassPyrroloquinolines
Direct ParentPyrroloquinoline 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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.097 g/LALOGPS
logP0.46ALOGPS
logP0.37ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)0.68ChemAxon
pKa (Strongest Basic)4.46ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area174.72 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity74.53 m³·mol⁻¹ChemAxon
Polarizability28.91 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0rkl-1293000000-f89d3e9669ea62420001View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00di-5001920000-ffb897aa343201141554View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dr-0059000000-fe32e3dcdbb122899a9bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-0093000000-0057ba82bb1928e2b729View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-0090000000-7a80db950a195ffc246aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01ti-0089000000-3940ecb0162179ef62fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-0092000000-47c12a164c99ff5da573View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ku-0090000000-968a80882216e4efda23View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0009000000-84aa1fbc000600884df5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02ai-0059000000-1b2548c8675bc744991aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-0094000000-fd415930659367c11a26View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-984e546238980fbb8d35View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0090000000-899cb3d0e242698d7cf3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0090000000-899cb3d0e242698d7cf3View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Kasahara, T., Kato, T. (2003). "Nutritional biochemistry: A new redox-cofactor vitamin for mammals." Nature 422:832. Pubmed: 12712191
  • Paz, M. A., Fluckiger, R., Torrelio, B. M., Gallop, P. M. (1989). "Methoxatin (PQQ), coenzyme for copper-dependent amine and mixed-function oxidation in mammalian tissues." Connect Tissue Res 20:251-257. Pubmed: 2558842
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID18315
HMDB IDHMDB13636
Pubchem Compound ID0
Kegg IDC00113
ChemSpider ID997
WikipediaPyrroloquinoline_quinone
BioCyc IDNot Available
Ligand ExpoPQQ

Enzymes

General function:
Involved in oxidoreductase activity, acting on CH-OH group of donors
Specific function:
GDH is probably involved in energy conservation rather than in sugar metabolism
Gene Name:
gcd
Uniprot ID:
P15877
Molecular weight:
86747
Reactions
D-glucose + ubiquinone = D-glucono-1,5-lactone + ubiquinol.