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CHEBI ONTOLOGY - ANNOTATIONS

The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at http://www.ebi.ac.uk/chebi/. The data is made available under the Creative Commons License (CC BY 3.0, http://creativecommons.org/licenses/by/3.0/). For more information see: Degtyarenko et al. (2008) ChEBI: a database and ontology for chemical entities of biological interest. Nucleic Acids Res. 36, D344–D350.
Term:pyrroloquinoline quinone
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Accession:CHEBI:18315 term browser browse the term
Definition:A pyrroloquinoline having oxo groups at the 4- and 5-positions and carboxy groups at the 2-, 7- and 9-positions.
Synonyms:exact_synonym: 4,5-dioxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid
 related_synonym: 2,4,6-tricarboxylic-pyrrolo[2,3-5,6]quinoline 8,9-quinone;   2,7,9-tricarboxy-1H-pyrrolo(2,3-f)quinoline-4,5-dione;   4,5-Dioxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate;   4,5-dihydro-4,5-dioxo-1H-pyrrolo[2,3-5,6]quinoline-2,7,9-tricarboxylic acid;   Formula=C14H6N2O8;   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;   PQQ;   Pyrrolo-quinoline quinone;   SMILES=OC(=O)c1cc(C(O)=O)c-2c(n1)C(=O)C(=O)c1cc([nH]c-21)C(O)=O;   coenzyme PQQ;   methoxatin
 alt_id: CHEBI:14986;   CHEBI:26460;   CHEBI:45251;   CHEBI:49082;   CHEBI:7881
 xref: Beilstein:3596812;   CAS:72909-34-3;   COMe:MOL000073;   Chemspider:997;   DrugBank:DB03205;   FooDB:FDB012848;   Gmelin:56633;   HMDB:HMDB0013636;   KEGG:C00113;   KNApSAcK:C00053736
 xref_mesh: MESH:D045542
 xref: PDBeChem:PQQ;   PMID:32695625;   PMID:34140030;   PMID:34227919;   RESID:AA0283;   Wikipedia:Pyrroloquinoline_quinone
 cyclic_relationship: is_conjugate_acid_of CHEBI:58442


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pyrroloquinoline quinone term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Acox1 acyl-CoA oxidase 1 increases expression EXP PQQ Cofactor results in increased expression of ACOX1 mRNA CTD PMID:25843018 NCBI chr10:101,406,197...101,431,252
Ensembl chr10:101,406,197...101,431,232 		JBrowse link
G Atg12 autophagy related 12 multiple interactions ISO PQQ Cofactor inhibits the reaction [Doxorubicin results in increased expression of ATG12 protein] CTD PMID:31226464 NCBI chr18:39,452,247...39,462,424
Ensembl chr18:39,452,191...39,462,418 		JBrowse link
G Atg16l1 autophagy related 16-like 1 multiple interactions ISO PQQ Cofactor inhibits the reaction [Doxorubicin results in increased expression of ATG16L1 protein] CTD PMID:31226464 NCBI chr 9:88,420,737...88,457,530
Ensembl chr 9:88,422,038...88,457,529 		JBrowse link
G Atg5 autophagy related 5 multiple interactions ISO PQQ Cofactor inhibits the reaction [Doxorubicin results in increased expression of ATG5 protein] CTD PMID:31226464 NCBI chr20:47,798,217...47,889,216
Ensembl chr20:47,798,290...47,889,209 		JBrowse link
G Atg7 autophagy related 7 multiple interactions ISO PQQ Cofactor inhibits the reaction [Doxorubicin results in increased expression of ATG7 protein] CTD PMID:31226464 NCBI chr 4:147,718,663...147,925,656
Ensembl chr 4:147,718,752...147,925,593 		JBrowse link
G Atm ATM serine/threonine kinase multiple interactions EXP PQQ Cofactor inhibits the reaction [Diethylhexyl Phthalate results in increased expression of ATM mRNA] CTD PMID:28115068 NCBI chr 8:53,828,741...53,932,773
Ensembl chr 8:53,831,093...53,932,437 		JBrowse link
G Bax BCL2 associated X, apoptosis regulator multiple interactions
increases expression		 ISO PQQ Cofactor inhibits the reaction [Rotenone affects the expression of BAX protein]; PQQ Cofactor inhibits the reaction [Rotenone results in increased expression of BAX protein]
PQQ Cofactor analog results in increased expression of BAX mRNA; PQQ Cofactor results in increased expression of BAX mRNA		 CTD PMID:24755484 PMID:26276080 PMID:32068067 NCBI chr 1:95,940,001...95,945,407
Ensembl chr 1:95,938,808...95,945,368 		JBrowse link
G Bcl2 BCL2, apoptosis regulator multiple interactions
decreases expression		 ISO PQQ Cofactor inhibits the reaction [Rotenone affects the expression of BCL2 protein]; PQQ Cofactor inhibits the reaction [Rotenone results in decreased expression of BCL2 protein]
PQQ Cofactor analog results in decreased expression of BCL2 mRNA; PQQ Cofactor results in decreased expression of BCL2 mRNA		 CTD PMID:24755484 PMID:26276080 PMID:32068067 NCBI chr13:22,689,783...22,853,920
Ensembl chr13:22,684,989...22,853,743
Ensembl chr13:22,684,989...22,853,743 		JBrowse link
G Casp3 caspase 3 multiple interactions
increases cleavage		 EXP
ISO		 PQQ Cofactor inhibits the reaction [Rotenone results in increased activity of CASP3 protein]
PQQ Cofactor analog results in increased cleavage of CASP3 protein; PQQ Cofactor results in increased cleavage of CASP3 protein
PQQ Cofactor inhibits the reaction [Doxorubicin results in increased expression of CASP3 protein modified form]		 CTD PMID:27108097 PMID:31226464 PMID:32068067 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648 		JBrowse link
G Casp9 caspase 9 multiple interactions ISO PQQ Cofactor inhibits the reaction [Doxorubicin results in increased expression of CASP9 protein modified form] CTD PMID:31226464 NCBI chr 5:154,108,872...154,126,628
Ensembl chr 5:154,109,046...154,126,626 		JBrowse link
G Cat catalase multiple interactions
increases activity		 EXP PQQ Cofactor inhibits the reaction [Rotenone results in decreased activity of CAT protein]
PQQ Cofactor results in increased activity of CAT protein		 CTD PMID:25843018 NCBI chr 3:89,842,393...89,874,577
Ensembl chr 3:89,842,399...89,874,478 		JBrowse link
G Diablo diablo, IAP-binding mitochondrial protein multiple interactions ISO PQQ Cofactor inhibits the reaction [Rotenone results in increased expression of DIABLO protein] CTD PMID:26276080 NCBI chr12:33,055,784...33,070,401
Ensembl chr12:33,055,263...33,070,387 		JBrowse link
G Dnm1l dynamin 1-like multiple interactions ISO
EXP		 PQQ Cofactor inhibits the reaction [Rotenone affects the localization of DNM1L protein]; PQQ Cofactor inhibits the reaction [Rotenone results in decreased expression of DNM1L mRNA] CTD PMID:30240821 NCBI chr11:84,581,216...84,632,382
Ensembl chr11:84,581,216...84,631,482 		JBrowse link
G Fasn fatty acid synthase decreases expression EXP PQQ Cofactor results in decreased expression of FASN mRNA CTD PMID:25843018 NCBI chr10:106,072,093...106,090,259
Ensembl chr10:106,072,091...106,090,261 		JBrowse link
G Gclc glutamate-cysteine ligase, catalytic subunit multiple interactions EXP PQQ Cofactor inhibits the reaction [Rotenone results in decreased expression of GCLC mRNA] CTD PMID:26276080 NCBI chr 8:78,629,899...78,668,547
Ensembl chr 8:78,630,127...78,668,544 		JBrowse link
G Gfap glial fibrillary acidic protein increases expression ISO PQQ Cofactor results in increased expression of GFAP mRNA CTD PMID:28578007 NCBI chr10:87,852,891...87,861,631
Ensembl chr10:87,852,890...87,861,589 		JBrowse link
G Hmox1 heme oxygenase 1 multiple interactions EXP PQQ Cofactor inhibits the reaction [Rotenone results in decreased expression of HMOX1 mRNA] CTD PMID:26276080 NCBI chr19:13,466,287...13,474,082
Ensembl chr19:13,467,244...13,474,079 		JBrowse link
G Ins1 insulin 1 multiple interactions ISO PQQ Cofactor inhibits the reaction [Streptozocin results in decreased expression of INS1 protein] CTD PMID:26343954 NCBI chr 1:251,244,973...251,245,540
Ensembl chr 1:251,244,973...251,245,536 		JBrowse link
G Lamp1 lysosomal-associated membrane protein 1 multiple interactions ISO PQQ Cofactor inhibits the reaction [Doxorubicin results in decreased expression of LAMP1 protein] CTD PMID:31226464 NCBI chr16:76,355,982...76,380,700
Ensembl chr16:76,355,984...76,381,883 		JBrowse link
G Lamp2 lysosomal-associated membrane protein 2 multiple interactions ISO PQQ Cofactor inhibits the reaction [Doxorubicin results in decreased expression of LAMP2 protein] CTD PMID:31226464 NCBI chr  X:117,173,097...117,222,090
Ensembl chr  X:117,057,606...117,260,522 		JBrowse link
G Map2 microtubule-associated protein 2 decreases expression ISO PQQ Cofactor results in decreased expression of MAP2 mRNA CTD PMID:28578007 NCBI chr 9:67,723,422...67,981,886
Ensembl chr 9:67,723,371...67,979,809 		JBrowse link
G Mapk1 mitogen activated protein kinase 1 multiple interactions ISO [Rotenone co-treated with PQQ Cofactor] results in increased phosphorylation of MAPK1 protein CTD PMID:24755484 NCBI chr11:83,957,813...84,023,629
Ensembl chr11:83,957,813...84,023,616 		JBrowse link
G Mapk3 mitogen activated protein kinase 3 multiple interactions ISO [Rotenone co-treated with PQQ Cofactor] results in increased phosphorylation of MAPK3 protein CTD PMID:24755484 NCBI chr 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863 		JBrowse link
G Mfn2 mitofusin 2 multiple interactions EXP
ISO		 PQQ Cofactor inhibits the reaction [Rotenone results in decreased expression of MFN2 mRNA]
PQQ Cofactor inhibits the reaction [Rotenone affects the localization of MFN2 protein]; PQQ Cofactor inhibits the reaction [Rotenone results in decreased expression of MFN2 mRNA]		 CTD PMID:30240821 NCBI chr 5:158,304,285...158,335,502
Ensembl chr 5:158,304,287...158,335,342 		JBrowse link
G Mt-co1 mitochondrially encoded cytochrome c oxidase I affects expression ISO PQQ Cofactor affects the expression of COX1 protein CTD PMID:28578007 NCBI chr MT:5,323...6,867
Ensembl chr MT:5,323...6,867 		JBrowse link
G Ndufs1 NADH:ubiquinone oxidoreductase core subunit S1 multiple interactions
increases response to substance		 ISO
EXP		 2-(2-amino-3-methoxyphenyl)-4H-1-benzopyran-4-one inhibits the reaction [PQQ Cofactor inhibits the reaction [Rotenone results in decreased expression of NDUFS1 mRNA]]; PQQ Cofactor inhibits the reaction [Rotenone results in decreased expression of NDUFS1 mRNA]
NDUFS1 mRNA results in increased susceptibility to PQQ Cofactor		 CTD PMID:24755484 PMID:26276080 PMID:27108097 NCBI chr 9:64,546,430...64,579,751
Ensembl chr 9:64,546,225...64,579,893 		JBrowse link
G Ndufs2 NADH:ubiquinone oxidoreductase core subunit S2 multiple interactions EXP PQQ Cofactor inhibits the reaction [Rotenone results in decreased expression of NDUFS2 mRNA] CTD PMID:26276080 NCBI chr13:83,654,402...83,671,474
Ensembl chr13:83,654,406...83,671,420 		JBrowse link
G Ndufs3 NADH:ubiquinone oxidoreductase core subunit S3 multiple interactions EXP PQQ Cofactor inhibits the reaction [Rotenone results in decreased expression of NDUFS3 mRNA] CTD PMID:26276080 NCBI chr 3:76,876,646...76,883,824
Ensembl chr 3:76,876,646...76,883,824 		JBrowse link
G Ndufs4 NADH:ubiquinone oxidoreductase subunit S4 multiple interactions
increases response to substance		 ISO
EXP		 2-(2-amino-3-methoxyphenyl)-4H-1-benzopyran-4-one inhibits the reaction [PQQ Cofactor inhibits the reaction [Rotenone results in decreased expression of NDUFS4 mRNA]]; PQQ Cofactor inhibits the reaction [Rotenone results in decreased expression of NDUFS4 mRNA]
NDUFS4 mRNA results in increased susceptibility to PQQ Cofactor		 CTD PMID:24755484 PMID:26276080 PMID:27108097 NCBI chr 2:45,951,327...46,061,829
Ensembl chr 2:45,951,313...46,061,846 		JBrowse link
G Nrf1 nuclear respiratory factor 1 increases expression ISO PQQ Cofactor results in increased expression of NRF1 mRNA CTD PMID:28578007 NCBI chr 4:58,664,932...58,772,328
Ensembl chr 4:58,664,957...58,825,328 		JBrowse link
G Parp1 poly (ADP-ribose) polymerase 1 multiple interactions ISO PQQ Cofactor analog results in decreased expression of and results in increased cleavage of PARP1 protein; PQQ Cofactor results in decreased expression of and results in increased cleavage of PARP1 protein CTD PMID:32068067 NCBI chr13:92,307,593...92,339,406
Ensembl chr13:92,307,586...92,339,404 		JBrowse link
G Ppargc1a PPARG coactivator 1 alpha multiple interactions
increases expression		 EXP
ISO		 PQQ Cofactor inhibits the reaction [Rotenone results in decreased expression of PPARGC1A mRNA]; PQQ Cofactor inhibits the reaction [Rotenone results in decreased expression of PPARGC1A protein]; PQQ Cofactor promotes the reaction [Rotenone results in increased expression of PPARGC1A mRNA]
PQQ Cofactor results in increased expression of PPARGC1A mRNA		 CTD PMID:25843018 PMID:28578007 PMID:30240821 NCBI chr14:58,860,752...59,516,525
Ensembl chr14:58,861,144...59,512,656 		JBrowse link
G Sdha succinate dehydrogenase complex flavoprotein subunit A increases expression ISO PQQ Cofactor results in increased expression of SDHA protein CTD PMID:28578007 NCBI chr 1:28,935,965...28,960,936
Ensembl chr 1:28,940,164...28,961,535 		JBrowse link
G Slc18a2 solute carrier family 18 member A2 multiple interactions EXP PQQ Cofactor inhibits the reaction [Rotenone results in decreased expression of SLC18A2 protein] CTD PMID:26276080 NCBI chr 1:258,413,748...258,449,143
Ensembl chr 1:258,413,959...258,448,325 		JBrowse link
G Sod2 superoxide dismutase 2 increases activity
multiple interactions		 EXP PQQ Cofactor results in increased activity of SOD2 protein
PQQ Cofactor inhibits the reaction [Rotenone results in decreased activity of SOD2 protein]		 CTD PMID:25843018 NCBI chr 1:47,638,318...47,645,163
Ensembl chr 1:47,636,528...47,645,189 		JBrowse link
G Tfam transcription factor A, mitochondrial increases expression
multiple interactions
decreases expression		 EXP
ISO		 PQQ Cofactor results in increased expression of TFAM mRNA
PQQ Cofactor inhibits the reaction [Rotenone results in decreased expression of TFAM mRNA]; PQQ Cofactor inhibits the reaction [Rotenone results in decreased expression of TFAM protein]
PQQ Cofactor results in decreased expression of TFAM mRNA		 CTD PMID:25843018 PMID:28578007 PMID:30240821 NCBI chr20:17,356,243...17,368,293
Ensembl chr20:17,356,197...17,368,292 		JBrowse link
G Th tyrosine hydroxylase multiple interactions EXP PQQ Cofactor inhibits the reaction [Rotenone results in decreased expression of TH protein] CTD PMID:26276080 PMID:27108097 NCBI chr 1:198,071,500...198,078,832
Ensembl chr 1:198,071,503...198,109,767 		JBrowse link
G Tomm20 translocase of outer mitochondrial membrane 20 multiple interactions ISO PQQ Cofactor inhibits the reaction [Doxorubicin results in decreased expression of TOMM20 protein] CTD PMID:31226464 NCBI chr19:54,925,197...54,935,188
Ensembl chr19:54,923,402...54,935,198 		JBrowse link
Term paths to the root
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Term Annotations click to browse term
  CHEBI ontology 19876
    role 19851
      chemical role 19472
        antioxidant 16032
          pyrroloquinoline quinone 38
Path 2
Term Annotations click to browse term
  CHEBI ontology 19876
    subatomic particle 19874
      composite particle 19874
        hadron 19874
          baryon 19874
            nucleon 19874
              atomic nucleus 19905
                atom 19905
                  main group element atom 19821
                    p-block element atom 19821
                      carbon group element atom 19768
                        carbon atom 19764
                          organic molecular entity 19764
                            organic group 18962
                              organic divalent group 18943
                                organodiyl group 18915
                                  carbonyl group 18869
                                    carbonyl compound 18869
                                      ketone 17170
                                        cyclic ketone 15686
                                          quinone 8575
                                            orthoquinones 88
                                              pyrroloquinoline quinone 38
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