Pyrroloquinoline Quinone

Identification

Name
Pyrroloquinoline Quinone
Accession Number
DB03205  (EXPT02652)
Type
Small Molecule
Groups
Experimental
Description

A pyrrolo-quinoline having two adjacent keto-groups at the 4 and 5 positions and three acidic carboxyl groups. It is a coenzyme of some DEHYDROGENASES. [PubChem]

Structure
Thumb
Synonyms
Not Available
Categories
UNII
47819QGH5L
CAS number
72909-34-3
Weight
Average: 330.206
Monoisotopic: 330.012415178
Chemical Formula
C14H6N2O8
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)
IUPAC Name
4,5-dioxo-1H,4H,5H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid
SMILES
OC(=O)C1=CC2=C(N1)C1=C(N=C(C=C1C(O)=O)C(O)=O)C(=O)C2=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UQuinohemoprotein ethanol dehydrogenase type-1Not AvailableComamonas testosteroni
UQuinoprotein glucose dehydrogenase BNot AvailableAcinetobacter calcoaceticus
UPyrroloquinoline-quinone synthaseNot AvailableKlebsiella pneumoniae
UQuinoprotein ethanol dehydrogenaseNot AvailablePseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
UQuinohemoprotein alcohol dehydrogenase ADH IIBNot AvailablePseudomonas putida
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Aromatic L-Aminoacid Decarboxylase DeficiencyDisease
Catecholamine BiosynthesisMetabolic
Tyrosine MetabolismMetabolic
Tyrosinemia, transient, of the newbornDisease
Tyrosinemia Type IDisease
Disulfiram Action PathwayDrug action
Tyrosine hydroxylase deficiencyDisease
AlkaptonuriaDisease
HawkinsinuriaDisease
Dopamine beta-hydroxylase deficiencyDisease
Monoamine oxidase-a deficiency (MAO-A)Disease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

J. Kempf, Damodara Gopal, Walter Stalzer, "Synthesis of pyrroloquinoline quinone (PQQ)." U.S. Patent US20070072894, issued March 29, 2007.

US20070072894
General References
Not Available
External Links
Human Metabolome Database
HMDB13636
KEGG Compound
C00113
PubChem Compound
1024
PubChem Substance
46505152
ChemSpider
997
ChEBI
18315
ChEMBL
CHEMBL1235421
HET
PQQ
PDB Entries
1c9u / 1cq1 / 1cru / 1flg / 1g72 / 1h4i / 1h4j / 1kb0 / 1kv9 / 1lrw
show 18 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0966 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity74.53 m3·mol-1ChemAxon
Polarizability28.91 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.917
Blood Brain Barrier-0.5523
Caco-2 permeable-0.7899
P-glycoprotein substrateNon-substrate0.6068
P-glycoprotein inhibitor INon-inhibitor0.9449
P-glycoprotein inhibitor IINon-inhibitor0.9416
Renal organic cation transporterNon-inhibitor0.9159
CYP450 2C9 substrateNon-substrate0.7947
CYP450 2D6 substrateNon-substrate0.815
CYP450 3A4 substrateNon-substrate0.7006
CYP450 1A2 substrateInhibitor0.786
CYP450 2C9 inhibitorNon-inhibitor0.7198
CYP450 2D6 inhibitorNon-inhibitor0.82
CYP450 2C19 inhibitorNon-inhibitor0.7513
CYP450 3A4 inhibitorNon-inhibitor0.9038
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8592
Ames testNon AMES toxic0.7699
CarcinogenicityNon-carcinogens0.9621
BiodegradationNot ready biodegradable0.9412
Rat acute toxicity2.4887 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9921
hERG inhibition (predictor II)Non-inhibitor0.8806
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03dr-0059000000-fe32e3dcdbb122899a9b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01p9-0093000000-0057ba82bb1928e2b729
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kf-0090000000-7a80db950a195ffc246a
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-01ti-0089000000-3940ecb0162179ef62fc
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kr-0092000000-47c12a164c99ff5da573
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00ku-0090000000-968a80882216e4efda23

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Pyrroloquinolines
Direct Parent
Pyrroloquinoline quinones
Alternative Parents
Quinoline carboxylic acids / Tricarboxylic acids and derivatives / Pyridinecarboxylic acids / Indoles and derivatives / Pyrrole 2-carboxylic acids / Aryl ketones / O-quinones / Substituted pyrroles / Vinylogous amides / Heteroaromatic compounds
show 6 more
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
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
quinone, pyrroloquinoline cofactor, tricarboxylic acid (CHEBI:18315) / Prosthetic group [Fig] (C00113)

Targets

Kind
Protein
Organism
Comamonas testosteroni
Pharmacological action
Unknown
General Function
Oxidoreductase activity, acting on ch-oh group of donors
Specific Function
Catalyzes the dye-linked oxidation of primary alcohols to the corresponding aldehydes and the (subsequent) oxidation of the aldehydes to carboxylic acids.
Gene Name
qheDH
Uniprot ID
Q46444
Uniprot Name
Quinohemoprotein ethanol dehydrogenase type-1
Molecular Weight
76822.435 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Acinetobacter calcoaceticus
Pharmacological action
Unknown
General Function
Quinoprotein glucose dehydrogenase activity
Specific Function
Oxidizes glucose to gluconolactone.
Gene Name
gdhB
Uniprot ID
P13650
Uniprot Name
Quinoprotein glucose dehydrogenase B
Molecular Weight
52772.255 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Klebsiella pneumoniae
Pharmacological action
Unknown
General Function
Pyrroloquinoline-quinone synthase activity
Specific Function
Ring cyclization and eight-electron oxidation of 3a-(2-amino-2-carboxyethyl)-4,5-dioxo-4,5,6,7,8,9-hexahydroquinoline-7,9-dicarboxylic-acid to PQQ.
Gene Name
pqqC
Uniprot ID
P27505
Uniprot Name
Pyrroloquinoline-quinone synthase
Molecular Weight
28985.66 Da
Kind
Protein
Organism
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Pharmacological action
Unknown
General Function
Ethanol:cytochrome c oxidoreductase activity
Specific Function
Catalyzes the oxidation of primary alcohols except for methanol that is a very poor substrate.
Gene Name
exaA
Uniprot ID
Q9Z4J7
Uniprot Name
Quinoprotein ethanol dehydrogenase
Molecular Weight
68122.88 Da
Kind
Protein
Organism
Pseudomonas putida
Pharmacological action
Unknown
General Function
Pyrroloquinoline quinone binding
Specific Function
Catalyzes the dye-linked oxidation of primary alcohols to the corresponding aldehydes and the (subsequent) oxidation of the aldehydes to carboxylic acids. Exhibits activity with longer mono-alcohol...
Gene Name
qbdA
Uniprot ID
Q8GR64
Uniprot Name
Quinohemoprotein alcohol dehydrogenase ADH IIB
Molecular Weight
74968.745 Da

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:24