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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2010-07-16 13:49:07 UTC
Update Date2021-10-13 05:40:53 UTC
HMDB IDHMDB0013636
Secondary Accession Numbers
  • HMDB13636
Metabolite Identification
Common NamePyrroloquinoline quinone
DescriptionPyrroloquinoline 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
Data?1582753138
Synonyms
ValueSource
2,4,6-Tricarboxylic-pyrrolo[2,3-5,6]quinoline 8,9-quinoneChEBI
2,7,9-Tricarboxy-1H-pyrrolo(2,3-F)quinoline-4,5-dioneChEBI
4,5-Dihydro-4,5-dioxo-1H-pyrrolo[2,3-5,6]quinoline-2,7,9-tricarboxylic acidChEBI
4,5-Dioxo-4,5-dihydro-1H-pyrrolo[2,3-F]quinoline-2,7,9-tricarboxylateChEBI
Coenzyme PQQChEBI
MethoxatinChEBI
PQQChEBI
Pyrrolo-quinoline quinoneChEBI
Pyrroloquinoline-quinoneChEBI
4,5-Dihydro-4,5-dioxo-1H-pyrrolo[2,3-5,6]quinoline-2,7,9-tricarboxylateGenerator
4,5-Dioxo-4,5-dihydro-1H-pyrrolo[2,3-F]quinoline-2,7,9-tricarboxylic acidGenerator
2,7,9-Tricarboxy-1H-pyrrolo-(2,3-F)quinoline-4,5-dioneMeSH
2,7,9-Tricarboxypyrroloquinoline quinoneMeSH
4,5-Dihydro-4,5-dioxo-1-H-pyrrolo(2,3-F)quinoline-2,7,9-tricarboxylic acidMeSH
Coenzyme, PQQMeSH
Cofactor, PQQMeSH
PQQ CoenzymeMeSH
PQQ CofactorMeSH
PQQ, CoenzymeMeSH
Pyrrolo quinoline quinoneMeSH
Quinone, pyrrolo-quinolineMeSH
Quinone, pyrroloquinolineMeSH
Chemical FormulaC14H6N2O8
Average Molecular Weight330.206
Monoisotopic Molecular Weight330.012415178
IUPAC Name4,5-dioxo-1H,4H,5H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid
Traditional Namepyrroloquinoline quinone
CAS Registry Number72909-34-3
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 KeyMMXZSJMASHPLLR-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.
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
Ontology
Physiological effect

Adverse health effect

Disposition

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility211.8 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.097 g/LALOGPS
logP10(0.46) g/LALOGPS
logP10(0.37) g/LChemAxon
logS10(-3.5) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+176.64831661259
DarkChem[M-H]-175.81931661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Pyrroloquinoline quinoneOC(=O)C1=CC2=C(N1)C1=C(N=C(C=C1C(O)=O)C(O)=O)C(=O)C2=O3924.2Standard polar33892256
Pyrroloquinoline quinoneOC(=O)C1=CC2=C(N1)C1=C(N=C(C=C1C(O)=O)C(O)=O)C(=O)C2=O2242.9Standard non polar33892256
Pyrroloquinoline quinoneOC(=O)C1=CC2=C(N1)C1=C(N=C(C=C1C(O)=O)C(O)=O)C(=O)C2=O3434.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Pyrroloquinoline quinone,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC2=C([NH]1)C1=C(C(=O)O)C=C(C(=O)O)N=C1C(=O)C2=O3229.9Semi standard non polar33892256
Pyrroloquinoline quinone,1TMS,isomer #2C[Si](C)(C)OC(=O)C1=CC(C(=O)O)=NC2=C1C1=C(C=C(C(=O)O)[NH]1)C(=O)C2=O3268.0Semi standard non polar33892256
Pyrroloquinoline quinone,1TMS,isomer #3C[Si](C)(C)OC(=O)C1=CC(C(=O)O)=C2C(=N1)C(=O)C(=O)C1=C2[NH]C(C(=O)O)=C13229.6Semi standard non polar33892256
Pyrroloquinoline quinone,1TMS,isomer #4C[Si](C)(C)N1C(C(=O)O)=CC2=C1C1=C(C(=O)O)C=C(C(=O)O)N=C1C(=O)C2=O3223.5Semi standard non polar33892256
Pyrroloquinoline quinone,2TMS,isomer #1C[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=O3189.9Semi standard non polar33892256
Pyrroloquinoline quinone,2TMS,isomer #2C[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)=C13154.2Semi standard non polar33892256
Pyrroloquinoline quinone,2TMS,isomer #3C[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)C3175.3Semi standard non polar33892256
Pyrroloquinoline quinone,2TMS,isomer #4C[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)=C13190.4Semi standard non polar33892256
Pyrroloquinoline quinone,2TMS,isomer #5C[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=O3239.1Semi standard non polar33892256
Pyrroloquinoline quinone,2TMS,isomer #6C[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)=C13153.9Semi standard non polar33892256
Pyrroloquinoline quinone,3TMS,isomer #1C[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)=C13167.6Semi standard non polar33892256
Pyrroloquinoline quinone,3TMS,isomer #2C[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=O3142.6Semi standard non polar33892256
Pyrroloquinoline quinone,3TMS,isomer #3C[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)=C13107.3Semi standard non polar33892256
Pyrroloquinoline quinone,3TMS,isomer #4C[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)=C13149.6Semi standard non polar33892256
Pyrroloquinoline quinone,4TMS,isomer #1C[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)=C13112.8Semi standard non polar33892256
Pyrroloquinoline quinone,4TMS,isomer #1C[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)=C13271.3Standard non polar33892256
Pyrroloquinoline quinone,4TMS,isomer #1C[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)=C13666.3Standard polar33892256
Pyrroloquinoline quinone,1TBDMS,isomer #1CC(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=O3459.1Semi standard non polar33892256
Pyrroloquinoline quinone,1TBDMS,isomer #2CC(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=O3500.2Semi standard non polar33892256
Pyrroloquinoline quinone,1TBDMS,isomer #3CC(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)=C13464.3Semi standard non polar33892256
Pyrroloquinoline quinone,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)N1C(C(=O)O)=CC2=C1C1=C(C(=O)O)C=C(C(=O)O)N=C1C(=O)C2=O3482.8Semi standard non polar33892256
Pyrroloquinoline quinone,2TBDMS,isomer #1CC(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=O3595.2Semi standard non polar33892256
Pyrroloquinoline quinone,2TBDMS,isomer #2CC(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)=C13550.2Semi standard non polar33892256
Pyrroloquinoline quinone,2TBDMS,isomer #3CC(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)C3609.8Semi standard non polar33892256
Pyrroloquinoline quinone,2TBDMS,isomer #4CC(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)=C13614.1Semi standard non polar33892256
Pyrroloquinoline quinone,2TBDMS,isomer #5CC(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=O3706.9Semi standard non polar33892256
Pyrroloquinoline quinone,2TBDMS,isomer #6CC(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)=C13643.3Semi standard non polar33892256
Pyrroloquinoline quinone,3TBDMS,isomer #1CC(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)=C13677.4Semi standard non polar33892256
Pyrroloquinoline quinone,3TBDMS,isomer #2CC(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=O3720.2Semi standard non polar33892256
Pyrroloquinoline quinone,3TBDMS,isomer #3CC(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)=C13691.8Semi standard non polar33892256
Pyrroloquinoline quinone,3TBDMS,isomer #4CC(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)=C13795.8Semi standard non polar33892256
Pyrroloquinoline quinone,4TBDMS,isomer #1CC(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)=C13791.3Semi standard non polar33892256
Pyrroloquinoline quinone,4TBDMS,isomer #1CC(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)=C14003.4Standard non polar33892256
Pyrroloquinoline quinone,4TBDMS,isomer #1CC(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)=C13962.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Pyrroloquinoline quinone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0rkl-1293000000-f89d3e9669ea624200012017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pyrroloquinoline quinone GC-MS (3 TMS) - 70eV, Positivesplash10-00di-5001920000-ffb897aa3432011415542017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pyrroloquinoline quinone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrroloquinoline quinone 10V, Positive-QTOFsplash10-03dr-0059000000-fe32e3dcdbb122899a9b2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrroloquinoline quinone 20V, Positive-QTOFsplash10-01p9-0093000000-0057ba82bb1928e2b7292015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrroloquinoline quinone 40V, Positive-QTOFsplash10-00kf-0090000000-7a80db950a195ffc246a2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrroloquinoline quinone 10V, Negative-QTOFsplash10-01ti-0089000000-3940ecb0162179ef62fc2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrroloquinoline quinone 20V, Negative-QTOFsplash10-00kr-0092000000-47c12a164c99ff5da5732015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrroloquinoline quinone 40V, Negative-QTOFsplash10-00ku-0090000000-968a80882216e4efda232015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrroloquinoline quinone 10V, Positive-QTOFsplash10-03di-0009000000-84aa1fbc000600884df52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrroloquinoline quinone 20V, Positive-QTOFsplash10-02ai-0059000000-1b2548c8675bc744991a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrroloquinoline quinone 40V, Positive-QTOFsplash10-014l-0094000000-fd415930659367c11a262021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrroloquinoline quinone 10V, Negative-QTOFsplash10-0006-0090000000-984e546238980fbb8d352021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrroloquinoline quinone 20V, Negative-QTOFsplash10-0006-0090000000-899cb3d0e242698d7cf32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrroloquinoline quinone 40V, Negative-QTOFsplash10-0006-0090000000-899cb3d0e242698d7cf32021-09-22Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB03205
Phenol Explorer Compound IDNot Available
FooDB IDFDB012848
KNApSAcK IDC00053736
Chemspider ID997
KEGG Compound IDC00113
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPyrroloquinoline_quinone
METLIN IDNot Available
PubChem Compound1024
PDB IDNot Available
ChEBI ID18315
Food Biomarker OntologyNot Available
VMH IDPQQ
MarkerDB IDNot Available
Good Scents IDrw1842891
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. Kasahara T, Kato T: Nutritional biochemistry: A new redox-cofactor vitamin for mammals. Nature. 2003 Apr 24;422(6934):832. [PubMed:12712191 ]