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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;   DrugBank:DB03205;   Gmelin:56633;   KEGG:C00113
 xref_mesh: MESH:D045542
 xref: PDBeChem:PQQ;   RESID:AA0283
 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 chr10:104,724,534...104,748,003
Ensembl chr10:104,722,958...104,748,050
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 chr18:40,721,799...40,732,143
Ensembl chr18:40,721,800...40,732,126
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 9:94,879,876...94,915,231
Ensembl chr 9:94,879,745...94,915,228
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 chr20:49,301,783...49,393,147
Ensembl chr20:49,318,308...49,393,140
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 4:146,570,113...146,777,093
Ensembl chr 4:146,598,413...146,777,124
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 8:58,015,938...58,119,973
Ensembl chr 8:58,015,940...58,120,045
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 1:101,451,801...101,457,207
Ensembl chr 1:101,451,802...101,457,207
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 chr13:26,605,426...26,769,374
Ensembl chr13:26,605,426...26,769,374
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 chr16:48,845,011...48,863,249
Ensembl chr16:48,845,012...48,863,204
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 5:160,356,211...160,373,774
Ensembl chr 5:160,355,833...160,373,778
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 3:93,379,872...93,412,058
Ensembl chr 3:93,379,874...93,412,058
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 chr12:38,490,230...38,503,344
Ensembl chr12:38,490,230...38,503,330
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 chr11:88,830,968...88,882,271
Ensembl chr11:88,830,957...88,880,198
JBrowse link
G Fasn fatty acid synthase decreases expression EXP PQQ Cofactor results in decreased expression of FASN mRNA CTD PMID:25843018 NCBI chr10:109,987,735...110,005,901
Ensembl chr10:109,987,735...110,005,901
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 8:85,059,051...85,097,471
Ensembl chr 8:85,059,051...85,097,468
JBrowse link
G Gfap glial fibrillary acidic protein increases expression ISO PQQ Cofactor results in increased expression of GFAP mRNA CTD PMID:28578007 NCBI chr10:90,990,762...90,999,435
Ensembl chr10:90,990,762...90,999,506
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 chr19:14,508,634...14,515,455
Ensembl chr19:14,508,616...14,515,456
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 chr16:81,689,576...81,714,341
Ensembl chr16:81,689,335...81,714,419
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:124,722,628...124,766,079
Ensembl chr  X:124,722,628...124,766,044
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 9:73,204,753...73,462,965
Ensembl chr 9:73,319,710...73,462,972
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 chr11:88,203,863...88,273,301
Ensembl chr11:88,211,599...88,273,254
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 1:198,192,773...198,198,975
Ensembl chr 1:198,192,773...198,198,975
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 5:164,684,244...164,715,414
Ensembl chr 5:164,684,509...164,714,145
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 9:69,919,863...69,953,182
Ensembl chr 9:69,919,867...69,953,182
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 chr13:89,606,848...89,623,506
Ensembl chr13:89,606,840...89,619,398
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 3:79,721,686...79,728,863
Ensembl chr 3:79,721,694...79,728,879
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 2:46,372,488...46,476,162
Ensembl chr 2:46,372,518...46,476,203
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 4:57,335,732...57,445,317
Ensembl chr 4:57,378,069...57,445,341
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 chr13:98,857,255...98,889,444
Ensembl chr13:98,857,177...98,889,716
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 chr14:63,095,291...63,190,688
Ensembl chr14:63,095,720...63,187,009
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 1:31,545,631...31,570,601
Ensembl chr 1:31,545,631...31,570,601
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 1:280,397,831...280,457,968
Ensembl chr 1:280,423,079...280,457,148
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 1:47,914,757...47,921,587
Ensembl chr 1:47,914,759...47,921,587
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 chr20:18,594,057...18,606,106
Ensembl chr20:18,594,037...18,606,151
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 1:216,073,034...216,080,287
Ensembl chr 1:216,073,031...216,080,287
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 chr19:59,863,421...59,873,411
Ensembl chr19:59,863,421...59,873,411
JBrowse link

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Term Annotations click to browse term
  CHEBI ontology 19816
    role 19764
      biological role 19764
        biochemical role 19313
          cofactor 15548
            pyrroloquinoline quinone 37
Path 2
Term Annotations click to browse term
  CHEBI ontology 19816
    subatomic particle 19814
      composite particle 19814
        hadron 19814
          baryon 19814
            nucleon 19814
              atomic nucleus 19814
                atom 19814
                  main group element atom 19702
                    p-block element atom 19702
                      carbon group element atom 19608
                        carbon atom 19597
                          organic molecular entity 19597
                            organic group 18537
                              organic divalent group 18530
                                organodiyl group 18530
                                  carbonyl group 18436
                                    carbonyl compound 18436
                                      ketone 16173
                                        cyclic ketone 13877
                                          quinone 8342
                                            orthoquinones 86
                                              pyrroloquinoline quinone 37
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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.