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
Accession: CHEBI:18315
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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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
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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
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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
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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
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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
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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
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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
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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
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Casp3
caspase 3
multiple interactions increases cleavage
EXP ISO
PQQ Cofactor inhibits the reaction [Rotenone results in increased activity of CASP3 protein] PQQ Cofactor inhibits the reaction [Doxorubicin results in increased expression of CASP3 protein modified form] PQQ Cofactor analog results in increased cleavage of CASP3 protein; PQQ Cofactor results in increased cleavage of CASP3 protein
CTD
PMID:27108097 PMID:31226464 PMID:32068067
NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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 NCBI chr MT:5,323...6,867 NCBI chr MT:5,323...6,867
Ensembl chr MT:5,323...6,867
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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Tfam
transcription factor A, mitochondrial
increases expression decreases expression multiple interactions
EXP ISO
PQQ Cofactor results in increased expression of TFAM mRNA PQQ Cofactor results in decreased 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]
CTD
PMID:25843018 PMID:28578007 PMID:30240821
NCBI chr20:17,356,243...17,368,293
Ensembl chr20:17,356,197...17,368,292
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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
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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
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