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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2010-07-16 13:49:07 UTC
Update Date2017-12-20 20:29:34 UTC
HMDB IDHMDB0013636
Secondary Accession Numbers
  • HMDB13636
Metabolite Identification
Common NamePyrroloquinoline 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
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
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
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
DescriptionThis compound belongs to the class of organic compounds known as pyrroloquinoline quinones. These 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
  • Tricarboxylic acid or derivatives
  • Pyridine carboxylic acid or derivatives
  • Pyridine carboxylic acid
  • Indole or derivatives
  • Aryl ketone
  • Quinone
  • Pyrrole-2-carboxylic acid or derivatives
  • Pyrrole-2-carboxylic acid
  • O-quinone
  • Substituted pyrrole
  • Pyridine
  • Heteroaromatic compound
  • Vinylogous amide
  • Pyrrole
  • Ketone
  • Azacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Route of exposure:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.097 g/LALOGPS
logP0.46ALOGPS
logP0.37ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)3.05ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
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
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 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
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
FoodDB IDFDB012848
KNApSAcK IDNot Available
Chemspider ID997
KEGG Compound IDC00113
BioCyc IDPQQ
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1024
PDB IDPQQ
ChEBI ID18315
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 ]