Drug Details

General Information of the Drug (ID: DR5963)
Name
Pyrroloquinoline quinone
Synonyms
methoxatin; pyrroloquinoline quinone; 72909-34-3; 4,5-dioxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid; Coenzyme pqq; Pyrrolo-quinoline quinone; UNII-47819QGH5L; Pyrroloquinoline-quinone; PQQ;Methoxatin; 4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid; PQQ; CHEBI:18315; 47819QGH5L; pyrroloquinolinedione tricarboxylic acid; 2,7,9-Tricarboxy-1H-pyrrolo(2,3-f)quinoline-4,5-dione; Pqq coenzyme; Pqq cofactor; 4,5-dioxo-1H,4H,5H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid; 4,5-Dihydro-4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid; 4,5-Dihydro-4,5-dioxo-1H-pyrrolo(2,3-f)quinoline-2,7,9-tricarboxylic acid; 1H-Pyrrolo(2,3-f)quinoline-2,7,9-tricarboxylic acid, 4,5-dihydro-4,5-dioxo-; Pyrroloquinolinequinone; 4,5-Dioxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate; Methoxantin; Methoxatine; 2,7,9-Tricarboxypyrroloquinoline quinone; 1H-Pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid, 4,5-dihydro-4,5-dioxo-; 2,4,6-tricarboxylic-pyrrolo[2,3-5,6]quinoline 8,9-quinone; Pyrroloquinoline dione; 4,5-dihydro-4,5-dioxo-1H-pyrrolo[2,3-5,6]quinoline-2,7,9-tricarboxylic acid; Pyrroloquinoline quinone/PQQ; SCHEMBL37975; Pyrroloquinoline quinone(PQQ); Pyrroloquinoline Quinone (PQQ); CHEMBL1235421; DTXSID3041162; SCHEMBL21049248; BCP06301; ZINC1532545; ANW-49082; MFCD00043125; AKOS015920260; CS-W009276; DB03205; GS-6613; QC-4272; VA11282; Pyrroloquinoline dione tricarboxylic acid; AK-76674; AB0026456; DB-055694; HY-100196; A9450; FT-0617182; Pyrroloquinoline quinone, >=95.0% (HPLC); Pyrroloquinoline quinone, >=97.0% (HPLC); W8127; C00113; S-7393; 909M343; Q414583; C(=O)(O)C1=CC=2C(C=3C(=CC(=NC=3C(C=2O)=O)C(=O)O)C(=O)O)=N1; 4,5-Dioxo-4,5-dihydro-1H-pyrrolo-[2,3-f]quinoline-2,7,9-tricarboxylic acid
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Molecular Type
Small molecule
Disease Osteoporosis [ICD-11: FB83] Investigative [1]
Structure
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2D MOL

3D MOL

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Formula
C14H6N2O8
PubChem CID
1024
Canonical SMILES
C1=C(C2=C(C(=O)C(=O)C3=C2NC(=C3)C(=O)O)N=C1C(=O)O)C(=O)O
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)
InChIKey
MMXZSJMASHPLLR-UHFFFAOYSA-N
CAS Number
CAS 72909-34-3
ChEBI ID
CHEBI:18315
DrugBank ID
DB03205
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Lithium      Spodumene     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression p38 beta  Molecule Info 
Pathway MAP
                    In-vivo Model Male APP/PS1 transgenic mice and littermate wild type control were used in this study.
                    Experimental
                    Result(s)		 This study demonstrated the efficacy of a novel AD therapeutic strategy targeting at multiple disease-causing mechanisms through the synergistic effects of microdose lithium and pyrroloquinoline quinone.
Target and Pathway
Target(s) DNA-binding factor KBF1 (p105)  Molecule Info  [3]
KEGG Pathway MAPK signaling pathway Click to Show/Hide
2 Ras signaling pathway
3 cAMP signaling pathway
4 Chemokine signaling pathway
5 NF-kappa B signaling pathway
6 HIF-1 signaling pathway
7 Sphingolipid signaling pathway
8 PI3K-Akt signaling pathway
9 Apoptosis
10 Osteoclast differentiation
11 Toll-like receptor signaling pathway
12 NOD-like receptor signaling pathway
13 RIG-I-like receptor signaling pathway
14 Cytosolic DNA-sensing pathway
15 T cell receptor signaling pathway
16 B cell receptor signaling pathway
17 TNF signaling pathway
18 Neurotrophin signaling pathway
19 Prolactin signaling pathway
20 Adipocytokine signaling pathway
21 Non-alcoholic fatty liver disease (NAFLD)
22 Cocaine addiction
23 Epithelial cell signaling in Helicobacter pylori infection
24 Shigellosis
25 Salmonella infection
26 Pertussis
27 Legionellosis
28 Leishmaniasis
29 Chagas disease (American trypanosomiasis)
30 Toxoplasmosis
31 Amoebiasis
32 Tuberculosis
33 Hepatitis C
34 Hepatitis B
35 Measles
36 Influenza A
37 HTLV-I infection
38 Herpes simplex infection
39 Epstein-Barr virus infection
40 Pathways in cancer
41 Transcriptional misregulation in cancer
42 Viral carcinogenesis
43 MicroRNAs in cancer
44 Pancreatic cancer
45 Prostate cancer
46 Chronic myeloid leukemia
47 Acute myeloid leukemia
48 Small cell lung cancer
49 Inflammatory bowel disease (IBD)
NetPath Pathway IL5 Signaling Pathway Click to Show/Hide
2 IL1 Signaling Pathway
3 TCR Signaling Pathway
4 IL2 Signaling Pathway
5 TNFalpha Signaling Pathway
6 Leptin Signaling Pathway
Panther Pathway Apoptosis signaling pathway Click to Show/Hide
2 T cell activation
Pathwhiz Pathway Intracellular Signalling Through Adenosine Receptor A2a and Adenosine Click to Show/Hide
2 Intracellular Signalling Through Adenosine Receptor A2b and Adenosine
Pathway Interaction Database Fc-epsilon receptor I signaling in mast cells Click to Show/Hide
2 BCR signaling pathway
3 LPA receptor mediated events
4 Atypical NF-kappaB pathway
5 Canonical NF-kappaB pathway
6 CD40/CD40L signaling
7 IL12-mediated signaling events
8 Alternative NF-kappaB pathway
9 Osteopontin-mediated events
10 Angiopoietin receptor Tie2-mediated signaling
11 Signaling events mediated by HDAC Class I
12 Regulation of Telomerase
13 IL1-mediated signaling events
14 Glucocorticoid receptor regulatory network
15 TNF receptor signaling pathway
16 IL2 signaling events mediated by PI3K
17 Ceramide signaling pathway
18 amb2 Integrin signaling
19 IL23-mediated signaling events
20 HIV-1 Nef: Negative effector of Fas and TNF-alpha
21 EPO signaling pathway
Reactome Activation of NF-kappaB in B cells Click to Show/Hide
2 RIP-mediated NFkB activation via ZBP1
3 Regulated proteolysis of p75NTR
4 NF-kB is activated and signals survival
5 Senescence-Associated Secretory Phenotype (SASP)
6 FCERI mediated NF-kB activation
7 DEx/H-box helicases activate type I IFN and inflammatory cytokines production
8 Transcriptional regulation of white adipocyte differentiation
9 TAK1 activates NFkB by phosphorylation and activation of IKKs complex
10 Interleukin-1 processing
11 IKBKG deficiency causes anhidrotic ectodermal dysplasia with immunodeficiency (EDA-ID) (via TLR)
12 IkBA variant leads to EDA-ID
13 CLEC7A (Dectin-1) signaling
14 CD209 (DC-SIGN) signaling
15 CLEC7A/inflammasome pathway
16 MAP3K8 (TPL2)-dependent MAPK1/3 activation
17 TRAF6 mediated NF-kB activation
WikiPathways Toll-like receptor signaling pathway Click to Show/Hide
2 DNA Damage Response (only ATM dependent)
3 SIDS Susceptibility Pathways
4 TCR Signaling Pathway
5 Notch Signaling Pathway
6 TGF Beta Signaling Pathway
7 Oxidative Stress
8 IL-4 Signaling Pathway
9 Apoptosis Modulation by HSP70
10 MAPK Signaling Pathway
11 Myometrial Relaxation and Contraction Pathways
12 IL1 and megakaryotyces in obesity
13 Apoptosis-related network due to altered Notch3 in ovarian cancer
14 Hair Follicle Development: Cytodifferentiation (Part 3 of 3)
15 Hair Follicle Development: Organogenesis (Part 2 of 3)
16 Hair Follicle Development: Induction (Part 1 of 3)
17 Selenium Metabolism and Selenoproteins
18 Cardiac Hypertrophic Response
19 Cytosolic sensors of pathogen-associated DNA
20 Fc epsilon receptor (FCERI) signaling
21 Transcriptional Regulation of White Adipocyte Differentiation
22 Signaling by the B Cell Receptor (BCR)
23 TAK1 activates NFkB by phosphorylation and activation of IKKs complex
24 Structural Pathway of Interleukin 1 (IL-1)
25 EBV LMP1 signaling
26 Aryl Hydrocarbon Receptor
27 T-Cell Receptor and Co-stimulatory Signaling
28 Apoptosis
29 Quercetin and Nf-kB/ AP-1 Induced Cell Apoptosis
30 BDNF signaling pathway
31 Integrated Pancreatic Cancer Pathway
32 Oncostatin M Signaling Pathway
33 Corticotropin-releasing hormone
34 AGE/RAGE pathway
35 TNF alpha Signaling Pathway
36 B Cell Receptor Signaling Pathway
37 TSLP Signaling Pathway
38 IL17 signaling pathway
39 Neural Crest Differentiation
40 TWEAK Signaling Pathway
41 Leptin signaling pathway
42 RANKL/RANK Signaling Pathway
43 Integrated Breast Cancer Pathway
44 Signalling by NGF
45 IL-1 signaling pathway
46 TCR signaling
47 RIG-I/MDA5 mediated induction of IFN-alpha/beta pathways
48 Interleukin-1 signaling
49 Interleukin-1 processing
50 Apoptosis Modulation and Signaling
51 Folate Metabolism
52 TFs Regulate miRNAs related to cardiac hypertrophy
53 MicroRNAs in cardiomyocyte hypertrophy
54 Vitamin B12 Metabolism
55 Selenium Micronutrient Network
56 Regulation of toll-like receptor signaling pathway
57 Osteopontin Signaling
References
Reference 1 Pyrroloquinoline Quinone Prevents Estrogen Deficiency-Induced Osteoporosis by Inhibiting Oxidative Stress and Osteocyte Senescence. Int J Biol Sci. 2019 Jan 1;15(1):58-68.
Reference 2 Beneficial synergistic effects of microdose lithium with pyrroloquinoline quinone in an Alzheimer's disease mouse model. Neurobiol Aging. 2014 Dec;35(12):2736-2745.
Reference 3 IKKbeta-mediated nuclear factor-kappaB activation attenuates smac mimetic-induced apoptosis in cancer cells. Mol Cancer Ther. 2009 Jun;8(6):1636-45.
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