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Human Metabolome Database Version 3.5

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Showing metabocard for Pyrroloquinoline quinone (HMDB13636)

Record Information
Version 3.5
Creation Date 2010-07-16 07:49:07 -0600
Update Date 2013-05-29 13:48:57 -0600
HMDB ID HMDB13636
Secondary Accession Numbers None
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 Link_out]. 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 Link_out].
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Methoxatin
  2. PQQ
  3. Pyrrolo-quinoline quinone
  4. Pyrroloquinoline-quinone
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 IUPAC 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
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Alpha Amino Acids and Derivatives
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Prosthetic group [Fig](KEGG)
  • pyrroloquinoline cofactor(ChEBI)
  • quinone(ChEBI)
  • tricarboxylic acid(ChEBI)
Substituents
  • Benzoquinone
  • Carboxylic Acid
  • Ketone
  • Pyridine
  • Pyridine Carboxylic Acid
  • Pyrrole
  • Pyrroloquinoline
  • Tricarboxylic Acid Derivative
Direct Parent Alpha Amino Acids and Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.097 g/L ALOGPS
LogP 0.46 ALOGPS
LogP 0.37 ChemAxon
LogS -3.53 ALOGPS
pKa (strongest acidic) 3.05 ChemAxon
pKa (strongest basic) -3.3 ChemAxon
Hydrogen Acceptor Count 9 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 174.72 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 74.53 ChemAxon
Polarizability 29.04 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -3 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB03205 Link_out
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB012848
KNApSAcK ID Not Available
Chemspider ID 997 Link_out
KEGG Compound ID C00113 Link_out
BioCyc ID PQQ Link_out
BiGG ID Not Available
Wikipedia Link Pyrroloquinoline_quinone Link_out
NuGOwiki Link HMDB13636 Link_out
Metagene Link HMDB13636 Link_out
METLIN ID Not Available
PubChem Compound 1024 Link_out
PDB ID PQQ Link_out
ChEBI ID 18315 Link_out
References
Synthesis Reference Not 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 Link_out
  2. Kasahara T, Kato T: Nutritional biochemistry: A new redox-cofactor vitamin for mammals. Nature. 2003 Apr 24;422(6934):832. Pubmed: 12712191 Link_out