Identification
- Generic Name
- Pyrroloquinoline Quinone
- DrugBank Accession Number
- DB03205
- Background
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]
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Pyrroloquinoline Quinone (DB03205)
- Weight
- Average: 330.206
Monoisotopic: 330.012415178 - Chemical Formula
- C14H6N2O8
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UQuinohemoprotein ethanol dehydrogenase type-1 Not Available Comamonas testosteroni UQuinoprotein glucose dehydrogenase B Not Available Acinetobacter calcoaceticus UPyrroloquinoline-quinone synthase Not Available Klebsiella pneumoniae UQuinoprotein ethanol dehydrogenase Not Available Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228) UQuinohemoprotein alcohol dehydrogenase ADH IIB Not Available Pseudomonas 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
Pathway Category Aromatic L-Aminoacid Decarboxylase Deficiency Disease Tyrosine Metabolism Metabolic Catecholamine Biosynthesis Metabolic Tyrosinemia Type I Disease Disulfiram Action Pathway Drug action Alkaptonuria Disease Hawkinsinuria Disease Tyrosinemia, Transient, of the Newborn Disease Tyrosine Hydroxylase Deficiency Disease Dopamine beta-Hydroxylase Deficiency Disease Monoamine Oxidase-A Deficiency (MAO-A) Disease - Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Nmnpqq Pyrroloquinoline Quinone (10 mg/100mg) + Nicotinamide Mononucleotide (45 mg/100mg) Powder Topical Golden Life Health Products Limited 2020-12-23 Not applicable US 
- Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Nmnpqq Pyrroloquinoline Quinone (10 mg/100mg) + Nicotinamide Mononucleotide (45 mg/100mg) Powder Topical Golden Life Health Products Limited 2020-12-23 Not applicable US
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- Aromatic heteropolycyclic compound / Aryl ketone / Azacycle / Carboxylic acid / Carboxylic acid derivative / Heteroaromatic compound / Hydrocarbon derivative / Indole or derivatives / Ketone / O-quinone show 19 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- quinone, pyrroloquinoline cofactor, tricarboxylic acid (CHEBI:18315) / Prosthetic group [Fig] (C00113)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 47819QGH5L
- CAS number
- 72909-34-3
- 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
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
- HMDB0013636
- KEGG Compound
- C00113
- PubChem Compound
- 1024
- PubChem Substance
- 46505152
- ChemSpider
- 997
- ChEBI
- 18315
- ChEMBL
- CHEMBL1235421
- ZINC
- ZINC000001532545
- PDBe Ligand
- PQQ
- PDB Entries
- 1c9u / 1cq1 / 1cru / 1flg / 1g72 / 1h4i / 1h4j / 1kb0 / 1kv9 / 1lrw … show 32 more
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Powder Topical - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0966 mg/mL ALOGPS logP 0.46 ALOGPS logP -1 Chemaxon logS -3.5 ALOGPS pKa (Strongest Acidic) 0.83 Chemaxon pKa (Strongest Basic) 5.52 Chemaxon Physiological Charge -3 Chemaxon Hydrogen Acceptor Count 9 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 174.72 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 74.53 m3·mol-1 Chemaxon Polarizability 28.91 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.917 Blood Brain Barrier - 0.5523 Caco-2 permeable - 0.7899 P-glycoprotein substrate Non-substrate 0.6068 P-glycoprotein inhibitor I Non-inhibitor 0.9449 P-glycoprotein inhibitor II Non-inhibitor 0.9416 Renal organic cation transporter Non-inhibitor 0.9159 CYP450 2C9 substrate Non-substrate 0.7947 CYP450 2D6 substrate Non-substrate 0.815 CYP450 3A4 substrate Non-substrate 0.7006 CYP450 1A2 substrate Inhibitor 0.786 CYP450 2C9 inhibitor Non-inhibitor 0.7198 CYP450 2D6 inhibitor Non-inhibitor 0.82 CYP450 2C19 inhibitor Non-inhibitor 0.7513 CYP450 3A4 inhibitor Non-inhibitor 0.9038 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8592 Ames test Non AMES toxic 0.7699 Carcinogenicity Non-carcinogens 0.9621 Biodegradation Not ready biodegradable 0.9412 Rat acute toxicity 2.4887 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9921 hERG inhibition (predictor II) Non-inhibitor 0.8806
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0rkl-1293000000-f89d3e9669ea62420001 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-03di-0009000000-dad334ceaaa97c0330b9 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-03di-0039000000-0e8ee2b066fca751484f Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-0090000000-0dc59a98817f619ab7b7 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-015c-0096000000-8d17b75736cd0d73f3ce Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-0090000000-05bebea77271a532f20e Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-0090000000-f38e0166e5ed3b576233 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 186.8633403 predictedDarkChem Lite v0.1.0 [M-H]- 186.7595403 predictedDarkChem Lite v0.1.0 [M-H]- 187.0132403 predictedDarkChem Lite v0.1.0 [M-H]- 169.01259 predictedDeepCCS 1.0 (2019) [M+H]+ 188.1766403 predictedDarkChem Lite v0.1.0 [M+H]+ 188.2875403 predictedDarkChem Lite v0.1.0 [M+H]+ 188.7660403 predictedDarkChem Lite v0.1.0 [M+H]+ 171.37059 predictedDeepCCS 1.0 (2019) [M+Na]+ 188.2913403 predictedDarkChem Lite v0.1.0 [M+Na]+ 188.2265403 predictedDarkChem Lite v0.1.0 [M+Na]+ 187.7338403 predictedDarkChem Lite v0.1.0 [M+Na]+ 178.33739 predictedDeepCCS 1.0 (2019)
Targets
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- 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
- 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
- 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 at June 13, 2005 13:24 / Updated at June 12, 2020 16:52