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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:quinacrine
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Accession:CHEBI:8711 term browser browse the term
Definition:A member of the class of acridines that is acridine substituted by a chloro group at position 6, a methoxy group at position 2 and a [5-(diethylamino)pentan-2-yl]nitrilo group at position 9.
Synonyms:exact_synonym: 4-N-(6-chloro-2-methoxyacridin-9-yl)-1-N,1-N-diethylpentane-1,4-diamine
 related_synonym: 2-methoxy-6-chloro-9-diethylaminopentylaminoacridine;   3-chloro-7-methoxy-9-(1-methyl-4-diethylaminobutylamino)acridine;   6-chloro-9-((4-(diethylamino)-1-methylbutyl)amino)-2-methoxyacridine;   Formula=C23H30ClN3O;   InChI=1S/C23H30ClN3O/c1-5-27(6-2)13-7-8-16(3)25-23-19-11-9-17(24)14-22(19)26-21-12-10-18(28-4)15-20(21)23/h9-12,14-16H,5-8,13H2,1-4H3,(H,25,26);   InChIKey=GPKJTRJOBQGKQK-UHFFFAOYSA-N;   N(4)-(6-chloro-2-methoxy-9-acridinyl)-N(1),N(1)-diethyl-1,4-pentanediamine;   SMILES=CCN(CC)CCCC(C)Nc1c2ccc(Cl)cc2nc2ccc(OC)cc12;   mepacrine
 xref: Beilstein:497807;   Beilstein:95500;   CAS:83-89-6;   DrugBank:DB01103;   Drug_Central:2338;   HMDB:HMDB0015235;   KEGG:C07339;   KEGG:D08179;   LINCS:LSM-1577
 xref_mesh: MESH:D011796
 xref: MetaCyc:ATABRINE;   PMID:11339632;   PMID:11908878;   PMID:19747949;   Reaxys:95500;   Wikipedia:Quinacrine


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quinacrine term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Abcb1a ATP binding cassette subfamily B member 1A increases transport
multiple interactions
ISO ABCB1 protein results in increased transport of Quinacrine
Elacridar inhibits the reaction [ABCB1 protein results in increased transport of Quinacrine]
CTD PMID:16581945 NCBI chr 4:22,339,829...22,517,642
Ensembl chr 4:22,133,521...22,425,515
JBrowse link
G Agt angiotensinogen multiple interactions ISO Quinacrine inhibits the reaction [AGT protein results in increased metabolism of and results in increased abundance of Arachidonic Acid] CTD PMID:16257180 NCBI chr19:57,321,594...57,333,460
Ensembl chr19:57,321,640...57,333,433
JBrowse link
G Bax BCL2 associated X, apoptosis regulator increases response to substance
increases expression
multiple interactions
ISO BAX protein results in increased susceptibility to Quinacrine
Quinacrine results in increased expression of BAX mRNA
4-(4-fluorophenyl)-2-(4-hydroxyphenyl)-5-(4-pyridyl)imidazole inhibits the reaction [Quinacrine results in increased expression of BAX mRNA]; 4-(4-fluorophenyl)-2-(4-hydroxyphenyl)-5-(4-pyridyl)imidazole inhibits the reaction [Quinacrine results in increased expression of BAX protein]; BTRC protein inhibits the reaction [Quinacrine results in increased expression of BAX protein]; mithramycin A inhibits the reaction [Quinacrine results in increased expression of BAX mRNA]; mithramycin A inhibits the reaction [Quinacrine results in increased expression of BAX protein]; Quinacrine promotes the reaction [SP1 protein binds to BAX promoter]; Quinacrine results in increased expression of and affects the localization of BAX protein
CTD PMID:16177561, PMID:28867437 NCBI chr 1:101,451,801...101,457,207
Ensembl chr 1:101,451,802...101,457,207
JBrowse link
G Btrc beta-transducin repeat containing E3 ubiquitin protein ligase decreases expression
multiple interactions
ISO Quinacrine results in decreased expression of BTRC protein
4-(4-fluorophenyl)-2-(4-hydroxyphenyl)-5-(4-pyridyl)imidazole inhibits the reaction [Quinacrine results in decreased expression of BTRC protein]; BTRC protein inhibits the reaction [Quinacrine results in increased expression of BAX protein]; BTRC protein inhibits the reaction [Quinacrine results in increased expression of SP1 protein]; FOXP3 protein affects the reaction [Quinacrine results in decreased expression of BTRC protein]; MIR183 mRNA affects the reaction [Quinacrine results in decreased expression of BTRC protein]; Quinacrine results in decreased expression of and results in decreased stability of BTRC mRNA
CTD PMID:28867437 NCBI chr 1:265,100,094...265,270,263
Ensembl chr 1:265,157,379...265,269,837
JBrowse link
G Casp3 caspase 3 increases cleavage
multiple interactions
increases activity
ISO Quinacrine results in increased cleavage of CASP3 protein
GSK3B protein affects the reaction [Quinacrine results in increased activity of CASP3 protein]
CTD PMID:28720477, PMID:28867437 NCBI chr16:48,845,011...48,863,249
Ensembl chr16:48,845,012...48,863,204
JBrowse link
G Casp9 caspase 9 increases cleavage ISO Quinacrine results in increased cleavage of CASP9 protein CTD PMID:28867437 NCBI chr 5:160,356,211...160,373,774
Ensembl chr 5:160,355,833...160,373,778
JBrowse link
G Ccnd1 cyclin D1 decreases expression
multiple interactions
ISO Quinacrine results in decreased expression of CCND1 protein
GSK3B protein affects the reaction [Quinacrine results in decreased expression of CCND1 protein]
CTD PMID:28720477 NCBI chr 1:218,090,750...218,100,447
Ensembl chr 1:218,090,750...218,100,325
JBrowse link
G Csnk1a1 casein kinase 1, alpha 1 increases expression
multiple interactions
ISO Quinacrine results in increased expression of CSNK1A1 protein
GSK3B protein affects the reaction [Quinacrine results in increased expression of CSNK1A1 protein]
CTD PMID:28720477 NCBI chr18:56,887,722...56,910,610
Ensembl chr18:56,887,354...56,918,345
JBrowse link
G Ctnnb1 catenin beta 1 multiple interactions
decreases expression
ISO GSK3B protein affects the reaction [Quinacrine results in decreased expression of CTNNB1 protein] CTD PMID:28720477 NCBI chr 8:129,601,511...129,628,378
Ensembl chr 8:129,617,812...129,627,372
JBrowse link
G Cyp1a1 cytochrome P450, family 1, subfamily a, polypeptide 1 increases metabolic processing ISO CYP1A1 protein results in increased metabolism of Quinacrine CTD PMID:16581945 NCBI chr 8:62,472,087...62,478,122
Ensembl chr 8:62,472,095...62,478,147
JBrowse link
G Cyp2e1 cytochrome P450, family 2, subfamily e, polypeptide 1 multiple interactions
decreases expression
EXP Quinacrine binds to and results in decreased activity of CYP2E1 protein
Quinacrine results in decreased expression of CYP2E1 protein
CTD PMID:18754103 NCBI chr 1:213,511,892...213,522,195
Ensembl chr 1:213,511,874...213,535,542
JBrowse link
G Cyp3a9 cytochrome P450, family 3, subfamily a, polypeptide 9 increases metabolic processing ISO CYP3A5 protein results in increased metabolism of Quinacrine CTD PMID:16581945 NCBI chr12:19,074,288...19,114,491
Ensembl chr12:19,074,583...19,114,399
JBrowse link
G Foxp3 forkhead box P3 increases expression
multiple interactions
ISO Quinacrine results in increased expression of FOXP3 mRNA; Quinacrine results in increased expression of FOXP3 protein
4-(4-fluorophenyl)-2-(4-hydroxyphenyl)-5-(4-pyridyl)imidazole inhibits the reaction [Quinacrine results in increased expression of FOXP3 mRNA]; 4-(4-fluorophenyl)-2-(4-hydroxyphenyl)-5-(4-pyridyl)imidazole inhibits the reaction [Quinacrine results in increased expression of FOXP3 protein]; FOXP3 protein affects the reaction [Quinacrine results in decreased expression of BTRC protein]; FOXP3 protein affects the reaction [Quinacrine results in increased expression of MIR183 mRNA]; FOXP3 protein affects the reaction [Quinacrine results in increased expression of SP1 protein]
CTD PMID:28867437 NCBI chr  X:15,753,175...15,768,648
Ensembl chr  X:15,753,175...15,768,522
JBrowse link
G Gli1 GLI family zinc finger 1 decreases expression
multiple interactions
ISO Quinacrine results in decreased expression of GLI1 protein
GSK3B protein affects the reaction [Quinacrine results in decreased expression of GLI1 protein]
CTD PMID:28720477 NCBI chr 7:70,620,794...70,633,171
Ensembl chr 7:70,620,766...70,630,338
JBrowse link
G Gsk3b glycogen synthase kinase 3 beta increases expression
multiple interactions
ISO Quinacrine results in increased expression of GSK3B mRNA
GSK3B protein affects the reaction [Quinacrine results in decreased expression of CCND1 protein]; GSK3B protein affects the reaction [Quinacrine results in decreased expression of CTNNB1 protein]; GSK3B protein affects the reaction [Quinacrine results in decreased expression of GLI1 protein]; GSK3B protein affects the reaction [Quinacrine results in decreased expression of MYC protein]; GSK3B protein affects the reaction [Quinacrine results in increased activity of CASP3 protein]; GSK3B protein affects the reaction [Quinacrine results in increased expression of CSNK1A1 protein]; Quinacrine results in increased expression of and results in decreased phosphorylation of GSK3B protein
CTD PMID:28720477 NCBI chr11:65,060,884...65,208,842
Ensembl chr11:65,066,235...65,209,268
JBrowse link
G Il1a interleukin 1 alpha multiple interactions ISO Quinacrine inhibits the reaction [Tetradecanoylphorbol Acetate results in increased expression of IL1A mRNA] CTD PMID:8435107 NCBI chr 3:121,824,712...121,836,122
Ensembl chr 3:121,825,412...121,836,086
JBrowse link
G Kcnh2 potassium voltage-gated channel subfamily H member 2 decreases activity ISO Quinacrine results in decreased activity of KCNH2 protein CTD PMID:28551711 NCBI chr 4:7,355,066...7,387,282
Ensembl chr 4:7,355,574...7,387,253
JBrowse link
G Mapk1 mitogen activated protein kinase 1 decreases phosphorylation
multiple interactions
ISO Quinacrine results in decreased phosphorylation of MAPK1 protein
4-(4-fluorophenyl)-2-(4-hydroxyphenyl)-5-(4-pyridyl)imidazole inhibits the reaction [Quinacrine results in decreased phosphorylation of MAPK1 protein]; Acetylcysteine inhibits the reaction [Quinacrine results in decreased phosphorylation of MAPK1 protein]
CTD PMID:28867437 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 decreases phosphorylation
multiple interactions
ISO Quinacrine results in decreased phosphorylation of MAPK3 protein
4-(4-fluorophenyl)-2-(4-hydroxyphenyl)-5-(4-pyridyl)imidazole inhibits the reaction [Quinacrine results in decreased phosphorylation of MAPK3 protein]; Acetylcysteine inhibits the reaction [Quinacrine results in decreased phosphorylation of MAPK3 protein]
CTD PMID:28867437 NCBI chr 1:198,192,773...198,198,975
Ensembl chr 1:198,192,773...198,198,975
JBrowse link
G Mir183 microRNA 183 multiple interactions
increases expression
ISO FOXP3 protein affects the reaction [Quinacrine results in increased expression of MIR183 mRNA]; MIR183 mRNA affects the reaction [Quinacrine results in decreased expression of BTRC protein]; MIR183 mRNA affects the reaction [Quinacrine results in increased expression of SP1 protein] CTD PMID:28867437 NCBI chr 4:57,463,569...57,463,678
Ensembl chr 4:57,463,569...57,463,678
JBrowse link
G Myc MYC proto-oncogene, bHLH transcription factor decreases expression
multiple interactions
ISO Quinacrine results in decreased expression of MYC protein
GSK3B protein affects the reaction [Quinacrine results in decreased expression of MYC protein]
CTD PMID:28720477 NCBI chr 7:102,586,313...102,591,240
Ensembl chr 7:102,586,313...102,591,240
JBrowse link
G Nqo2 N-ribosyldihydronicotinamide:quinone reductase 2 multiple interactions ISO Quinacrine binds to and results in decreased activity of NQO2 protein CTD PMID:15078100 NCBI chr17:32,131,847...32,158,559
Ensembl chr17:32,132,347...32,158,538
JBrowse link
G Otc ornithine carbamoyltransferase multiple interactions EXP Quinacrine inhibits the reaction [PRL protein results in increased activity of OTC protein]; Quinacrine inhibits the reaction [Tetradecanoylphorbol Acetate results in increased activity of OTC protein] CTD PMID:3097147 NCBI chr  X:13,524,804...13,601,074
Ensembl chr  X:13,524,607...13,601,069
JBrowse link
G Parp1 poly (ADP-ribose) polymerase 1 increases cleavage ISO Quinacrine results in increased cleavage of PARP1 protein CTD PMID:28867437 NCBI chr13:98,857,255...98,889,444
Ensembl chr13:98,857,177...98,889,716
JBrowse link
G Prl prolactin multiple interactions EXP Quinacrine inhibits the reaction [PRL protein results in increased activity of OTC protein] CTD PMID:3097147 NCBI chr17:39,814,236...39,824,299
Ensembl chr17:39,814,244...39,824,299
JBrowse link
G Sp1 Sp1 transcription factor multiple interactions ISO 4-(4-fluorophenyl)-2-(4-hydroxyphenyl)-5-(4-pyridyl)imidazole inhibits the reaction [Quinacrine results in increased expression of SP1 protein]; BTRC protein inhibits the reaction [Quinacrine results in increased expression of SP1 protein]; FOXP3 protein affects the reaction [Quinacrine results in increased expression of SP1 protein]; MIR183 mRNA affects the reaction [Quinacrine results in increased expression of SP1 protein]; Quinacrine promotes the reaction [SP1 protein binds to BAX promoter]; Quinacrine results in increased expression of and results in increased stability of SP1 protein CTD PMID:28867437 NCBI chr 7:144,014,173...144,044,635
Ensembl chr 7:144,014,173...144,044,629
JBrowse link
G Tlr3 toll-like receptor 3 multiple interactions ISO Quinacrine inhibits the reaction [Poly I-C results in increased activity of TLR3 protein] CTD PMID:21398612 NCBI chr16:50,016,466...50,031,011
Ensembl chr16:50,016,857...50,031,214
JBrowse link
G Tp53 tumor protein p53 increases activity
multiple interactions
ISO Quinacrine results in increased activity of TP53 protein
Quinacrine results in increased stability of and results in increased activity of TP53 protein
CTD PMID:12082016, PMID:16177561 NCBI chr10:56,186,299...56,198,449
Ensembl chr10:56,187,020...56,198,449
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19792
    role 19738
      biological role 19737
        aetiopathogenetic role 18869
          genotoxin 16985
            acridine 28
              quinacrine 28
                (R)-quinacrine 0
                (S)-quinacrine 0
                quinacrine mustard + 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19792
    subatomic particle 19788
      composite particle 19788
        hadron 19788
          baryon 19788
            nucleon 19788
              atomic nucleus 19788
                atom 19788
                  main group element atom 19675
                    p-block element atom 19675
                      carbon group element atom 19571
                        carbon atom 19560
                          organic molecular entity 19560
                            organic molecule 19483
                              organic cyclic compound 19252
                                organic heterocyclic compound 18422
                                  organic heteropolycyclic compound 17835
                                    organic heterotricyclic compound 14591
                                      dibenzopyridine 154
                                        acridines 121
                                          acridine 28
                                            quinacrine 28
                                              (R)-quinacrine 0
                                              (S)-quinacrine 0
                                              quinacrine mustard + 0
paths to the root

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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.