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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:amodiaquine
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Accession:CHEBI:2674 term browser browse the term
Definition:A quinoline having a chloro group at the 7-position and an aryl amino group at the 4-position.
Synonyms:exact_synonym: 4-[(7-chloroquinolin-4-yl)amino]-2-[(diethylamino)methyl]phenol
 related_synonym: Formula=C20H22ClN3O;   InChI=1S/C20H22ClN3O/c1-3-24(4-2)13-14-11-16(6-8-20(14)25)23-18-9-10-22-19-12-15(21)5-7-17(18)19/h5-12,25H,3-4,13H2,1-2H3,(H,22,23);   InChIKey=OVCDSSHSILBFBN-UHFFFAOYSA-N;   SMILES=CCN(CC)Cc1cc(Nc2ccnc3cc(Cl)ccc23)ccc1O;   amodiaquina;   amodiaquinum
 xref: Beilstein:300962;   CAS:86-42-0;   DrugBank:DB00613;   Drug_Central:186;   KEGG:C07626;   KEGG:D02922;   LINCS:LSM-4042
 xref_mesh: MESH:D000655
 xref: PDBeChem:CQA;   PMID:11044276;   PMID:11971651;   PMID:17046445;   PMID:17222819;   PMID:18419816;   PMID:18855526;   PMID:19024339;   PMID:19245687;   PMID:26206402;   PMID:26597254;   PMID:26647924;   PMID:26735991;   PMID:26851641;   PMID:26900802;   PMID:26930583;   PMID:27031231;   PMID:8885219;   Patent:US2474821;   Reaxys:300962;   Wikipedia:Amodiaquine
 cyclic_relationship: is_conjugate_base_of CHEBI:131327


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amodiaquine term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Ache acetylcholinesterase multiple interactions ISO Amodiaquine analog inhibits the reaction [Paraoxon results in decreased activity of ACHE protein]; Amodiaquine inhibits the reaction [Paraoxon results in decreased activity of ACHE protein] CTD PMID:29614332 NCBI chr12:19,407,359...19,413,713 JBrowse link
G Bax BCL2 associated X, apoptosis regulator multiple interactions
increases expression
ISO [Ketoconazole inhibits the reaction [CYP3A4 protein results in increased susceptibility to Amodiaquine]] which results in increased expression of BAX protein; [Rifampin inhibits the reaction [CYP2C8 protein results in increased susceptibility to Amodiaquine]] which results in increased expression of BAX protein
Amodiaquine results in increased expression of BAX protein
CTD PMID:31629065 NCBI chr 1:95,940,001...95,945,407 JBrowse link
G Bche butyrylcholinesterase multiple interactions ISO Amodiaquine inhibits the reaction [Paraoxon results in decreased activity of BCHE protein] CTD PMID:29614332 NCBI chr 2:158,308,674...158,401,148 JBrowse link
G Bcl2 BCL2, apoptosis regulator decreases expression
multiple interactions
ISO Amodiaquine results in decreased expression of BCL2 protein
[Ketoconazole inhibits the reaction [CYP3A4 protein results in increased susceptibility to Amodiaquine]] which results in decreased expression of BCL2 protein; [Rifampin inhibits the reaction [CYP2C8 protein results in increased susceptibility to Amodiaquine]] which results in decreased expression of BCL2 protein
CTD PMID:31629065 NCBI chr13:22,689,783...22,853,920 JBrowse link
G Bmp6 bone morphogenetic protein 6 increases expression ISO Amodiaquine results in increased expression of BMP6 mRNA CTD PMID:32816093 NCBI chr17:26,318,121...26,469,034 JBrowse link
G Casp3 caspase 3 increases cleavage ISO Amodiaquine results in increased cleavage of CASP3 protein CTD PMID:31629065 NCBI chr16:45,662,910...45,681,171 JBrowse link
G Ccnd1 cyclin D1 affects expression ISO Amodiaquine affects the expression of CCND1 protein CTD PMID:24113242 NCBI chr 1:200,089,002...200,098,524 JBrowse link
G Cdkn1a cyclin-dependent kinase inhibitor 1A affects expression ISO Amodiaquine affects the expression of CDKN1A mRNA; Amodiaquine affects the expression of CDKN1A protein CTD PMID:24113242 NCBI chr20:7,149,177...7,159,727 JBrowse link
G Ctla4 cytotoxic T-lymphocyte-associated protein 4 multiple interactions ISO CTLA4 protein affects the reaction [[PDCD1 protein co-treated with TGFB1 protein] affects the reaction [Amodiaquine results in increased expression of GPT protein]]; CTLA4 protein affects the reaction [PDCD1 protein affects the reaction [[LY6C1 protein co-treated with LY6G protein] affects the reaction [Amodiaquine results in increased expression of GPT protein]]] CTD PMID:29938495 NCBI chr 9:62,318,874...62,325,978 JBrowse link
G Ctsb cathepsin B decreases activity ISO Amodiaquine results in decreased activity of CTSB protein CTD PMID:24113242 NCBI chr15:37,389,636...37,410,508 JBrowse link
G Ctsd cathepsin D decreases activity ISO Amodiaquine results in decreased activity of CTSD protein CTD PMID:24113242 NCBI chr 1:197,527,467...197,539,343 JBrowse link
G Ctsl cathepsin L decreases activity ISO Amodiaquine results in decreased activity of CTSL protein CTD PMID:24113242 NCBI chr17:764,370...770,533 JBrowse link
G Cyp1a1 cytochrome P450, family 1, subfamily a, polypeptide 1 increases activity
multiple interactions
decreases response to substance
increases metabolic processing
ISO Amodiaquine results in increased activity of CYP1A1 protein
[CYP1A1 protein results in increased metabolism of Amodiaquine] which results in increased abundance of desethylamodiaquine
CYP1A1 protein results in decreased susceptibility to Amodiaquine
CTD PMID:12451431 PMID:31629065 NCBI chr 8:58,096,021...58,102,130 JBrowse link
G Cyp1a2 cytochrome P450, family 1, subfamily a, polypeptide 2 decreases activity
increases metabolic processing
multiple interactions
ISO Amodiaquine results in decreased activity of CYP1A2 protein
CYP1A2 protein results in increased metabolism of Amodiaquine
[CYP1A2 protein results in increased metabolism of Amodiaquine] which results in increased abundance of desethylamodiaquine; [Gemfibrozil results in decreased activity of CYP1A2 protein] which results in decreased metabolism of Amodiaquine; [Trimethoprim results in decreased activity of CYP1A2 protein] which results in decreased metabolism of Amodiaquine
CTD PMID:11124226 PMID:26599973 PMID:31629065 NCBI chr 8:58,075,367...58,082,255 JBrowse link
G Cyp1b1 cytochrome P450, family 1, subfamily b, polypeptide 1 decreases response to substance
increases metabolic processing
multiple interactions
ISO CYP1B1 protein results in decreased susceptibility to Amodiaquine
CYP1B1 protein results in increased metabolism of Amodiaquine
[CYP1B1 protein results in increased metabolism of Amodiaquine] which results in increased abundance of desethylamodiaquine
CTD PMID:31629065 NCBI chr 6:15,342,312...15,350,886 JBrowse link
G Cyp2a1 cytochrome P450, family 2, subfamily a, polypeptide 1 increases metabolic processing
multiple interactions
ISO CYP2A13 protein results in increased metabolism of Amodiaquine
[CYP2A13 protein results in increased metabolism of Amodiaquine] which results in increased abundance of desethylamodiaquine
CTD PMID:31629065 NCBI chr 1:82,231,611...82,244,887 JBrowse link
G Cyp2b3 cytochrome P450, family 2, subfamily b, polypeptide 3 multiple interactions
increases metabolic processing
ISO [CYP2B6 protein results in increased metabolism of Amodiaquine] which results in increased abundance of desethylamodiaquine CTD PMID:31629065 NCBI chr 1:81,652,762...81,732,153 JBrowse link
G Cyp2c24 cytochrome P450, family 2, subfamily c, polypeptide 24 increases metabolic processing
multiple interactions
ISO CYP2C18 protein results in increased metabolism of Amodiaquine
[CYP2C18 protein results in increased metabolism of Amodiaquine] which results in increased abundance of desethylamodiaquine
CTD PMID:31629065 NCBI chr 1:236,873,967...236,936,238 JBrowse link
G Cyp2c6v1 cytochrome P450, family 2, subfamily C, polypeptide 6, variant 1 decreases activity
increases metabolic processing
multiple interactions
ISO Amodiaquine results in decreased activity of CYP2C19 protein
CYP2C19 protein results in increased metabolism of Amodiaquine
[CYP2C19 protein results in increased metabolism of Amodiaquine] which results in increased abundance of desethylamodiaquine
CTD PMID:11124226 PMID:31629065 NCBI chr 1:237,938,521...237,976,238 JBrowse link
G Cyp2c79 cytochrome P450, family 2, subfamily c, polypeptide 79 multiple interactions
increases response to substance
affects metabolic processing
increases metabolic processing
ISO [5-bromotryptamine analog results in decreased activity of CYP2C8 protein] which results in decreased metabolism of Amodiaquine; [5-chlorotryptamine analog results in decreased activity of CYP2C8 protein] which results in decreased metabolism of Amodiaquine; [5-fluorotryptamine analog results in decreased activity of CYP2C8 protein] which results in decreased metabolism of Amodiaquine; [CYP2C8 protein results in increased metabolism of Amodiaquine] which results in increased abundance of and results in increased secretion of desethylamodiaquine; [CYP2C8 protein results in increased metabolism of Amodiaquine] which results in increased abundance of desethylamodiaquine; [CYP2C8 protein results in increased metabolism of Amodiaquine] which results in increased chemical synthesis of amodiaquine quinoneimine; [CYP2C8 protein results in increased metabolism of Amodiaquine] which results in increased chemical synthesis of desethylamodiaquine; [CYP2C8 protein results in increased susceptibility to Amodiaquine] which results in increased phosphorylation of MAPK1 protein; [CYP2C8 protein results in increased susceptibility to Amodiaquine] which results in increased phosphorylation of MAPK3 protein; [CYP2C8 protein results in increased susceptibility to Amodiaquine] which results in increased phosphorylation of MAPK8 protein; [Gemfibrozil co-treated with Amodiaquine] results in decreased activity of CYP2C8 protein; [Rifampin inhibits the reaction [CYP2C8 protein results in increased susceptibility to Amodiaquine]] which results in decreased expression of BCL2 protein; [Rifampin inhibits the reaction [CYP2C8 protein results in increased susceptibility to Amodiaquine]] which results in decreased expression of MCL1 protein; [Rifampin inhibits the reaction [CYP2C8 protein results in increased susceptibility to Amodiaquine]] which results in increased expression of BAX protein; [Tryptamines analog results in decreased activity of CYP2C8 protein] which results in decreased metabolism of Amodiaquine; Felodipine inhibits the reaction [CYP2C8 protein results in increased metabolism of Amodiaquine]; Rifampin inhibits the reaction [CYP2C8 protein results in increased susceptibility to Amodiaquine]
CYP2C8 protein affects the metabolism of Amodiaquine
CTD PMID:12920490 PMID:15155557 PMID:15601807 PMID:15626586 PMID:15771232 PMID:17286541 PMID:17565714 PMID:22634058 PMID:26599973 PMID:28119166 PMID:28478157 PMID:31629065
G Cyp2d4 cytochrome P450, family 2, subfamily d, polypeptide 4 increases metabolic processing
multiple interactions
ISO CYP2D6 protein results in increased metabolism of Amodiaquine
[CYP2D6 protein results in increased metabolism of Amodiaquine] which results in increased abundance of desethylamodiaquine; [CYP2D6 protein results in increased metabolism of Amodiaquine] which results in increased chemical synthesis of amodiaquine quinoneimine
CTD PMID:28478157 PMID:31629065 PMID:33259822 NCBI chr 7:113,882,584...113,891,754 JBrowse link
G Cyp2e1 cytochrome P450, family 2, subfamily e, polypeptide 1 multiple interactions
increases metabolic processing
ISO [CYP2E1 protein results in increased metabolism of Amodiaquine] which results in increased abundance of desethylamodiaquine CTD PMID:31629065 NCBI chr 1:195,840,330...195,850,728 JBrowse link
G Cyp3a9 cytochrome P450, family 3, subfamily a, polypeptide 9 increases metabolic processing
multiple interactions
ISO CYP3A5 protein results in increased metabolism of Amodiaquine
[CYP3A5 protein results in increased metabolism of Amodiaquine] which results in increased abundance of desethylamodiaquine
CTD PMID:31629065 NCBI chr12:16,806,222...16,846,428 JBrowse link
G E2f1 E2F transcription factor 1 affects expression ISO Amodiaquine affects the expression of E2F1 mRNA; Amodiaquine affects the expression of E2F1 protein CTD PMID:24113242 NCBI chr 3:143,064,535...143,075,362 JBrowse link
G Ereg epiregulin increases expression ISO Amodiaquine results in increased expression of EREG mRNA CTD PMID:32816093 NCBI chr14:17,027,287...17,041,062 JBrowse link
G Gpt glutamic--pyruvic transaminase multiple interactions ISO [LY6C1 protein co-treated with LY6G protein] affects the reaction [Amodiaquine results in increased expression of GPT protein]; [PDCD1 protein co-treated with LAG3 protein] affects the reaction [Amodiaquine results in increased expression of GPT protein]; [PDCD1 protein co-treated with TGFB1 protein] affects the reaction [Amodiaquine results in increased expression of GPT protein]; CTLA4 protein affects the reaction [[PDCD1 protein co-treated with TGFB1 protein] affects the reaction [Amodiaquine results in increased expression of GPT protein]]; CTLA4 protein affects the reaction [PDCD1 protein affects the reaction [[LY6C1 protein co-treated with LY6G protein] affects the reaction [Amodiaquine results in increased expression of GPT protein]]]; PDCD1 protein affects the reaction [[LY6C1 protein co-treated with LY6G protein] affects the reaction [Amodiaquine results in increased expression of GPT protein]] CTD PMID:29938495 NCBI chr 7:108,416,646...108,419,495 JBrowse link
G Il1a interleukin 1 alpha decreases expression ISO Amodiaquine results in decreased expression of IL1A mRNA CTD PMID:32816093 NCBI chr 3:116,526,601...116,537,055 JBrowse link
G Lag3 lymphocyte activating 3 multiple interactions ISO [PDCD1 protein co-treated with LAG3 protein] affects the reaction [Amodiaquine results in increased expression of GPT protein] CTD PMID:29938495 NCBI chr 4:157,712,665...157,722,229 JBrowse link
G Mapk1 mitogen activated protein kinase 1 multiple interactions ISO [CYP2C8 protein results in increased susceptibility to Amodiaquine] which results in increased phosphorylation of MAPK1 protein; [CYP3A4 protein results in increased susceptibility to Amodiaquine] which results in increased phosphorylation of MAPK1 protein CTD PMID:31629065 NCBI chr11:83,957,813...84,023,629 JBrowse link
G Mapk3 mitogen activated protein kinase 3 multiple interactions ISO [CYP2C8 protein results in increased susceptibility to Amodiaquine] which results in increased phosphorylation of MAPK3 protein; [CYP3A4 protein results in increased susceptibility to Amodiaquine] which results in increased phosphorylation of MAPK3 protein CTD PMID:31629065 NCBI chr 1:181,366,646...181,372,863 JBrowse link
G Mapk8 mitogen-activated protein kinase 8 multiple interactions ISO [CYP2C8 protein results in increased susceptibility to Amodiaquine] which results in increased phosphorylation of MAPK8 protein; [CYP3A4 protein results in increased susceptibility to Amodiaquine] which results in increased phosphorylation of MAPK8 protein CTD PMID:31629065 NCBI chr16:8,638,897...8,721,960 JBrowse link
G Mcl1 MCL1 apoptosis regulator, BCL2 family member decreases expression
multiple interactions
ISO Amodiaquine results in decreased expression of MCL1 protein
[Ketoconazole inhibits the reaction [CYP3A4 protein results in increased susceptibility to Amodiaquine]] which results in decreased expression of MCL1 protein; [Rifampin inhibits the reaction [CYP2C8 protein results in increased susceptibility to Amodiaquine]] which results in decreased expression of MCL1 protein
CTD PMID:31629065 NCBI chr 2:183,219,137...183,235,676 JBrowse link
G Met MET proto-oncogene, receptor tyrosine kinase increases expression ISO Amodiaquine results in increased expression of MET mRNA CTD PMID:32816093 NCBI chr 4:45,790,456...45,898,139 JBrowse link
G Mpo myeloperoxidase affects response to substance ISO MPO protein affects the susceptibility to Amodiaquine CTD PMID:24588327 NCBI chr10:72,594,458...72,608,862 JBrowse link
G Nqo2 N-ribosyldihydronicotinamide:quinone reductase 2 multiple interactions ISO Amodiaquine inhibits the reaction [NQO2 protein results in increased reduction of Vitamin K 3] CTD PMID:29281794 NCBI chr17:30,909,482...30,938,725 JBrowse link
G Nr4a2 nuclear receptor subfamily 4, group A, member 2 multiple interactions ISO Amodiaquine binds to and results in increased activity of NR4A2 protein CTD PMID:31175960 NCBI chr 3:41,689,847...41,707,036 JBrowse link
G Pdcd1 programmed cell death 1 multiple interactions ISO [PDCD1 protein co-treated with LAG3 protein] affects the reaction [Amodiaquine results in increased expression of GPT protein]; [PDCD1 protein co-treated with TGFB1 protein] affects the reaction [Amodiaquine results in increased expression of GPT protein]; CTLA4 protein affects the reaction [[PDCD1 protein co-treated with TGFB1 protein] affects the reaction [Amodiaquine results in increased expression of GPT protein]]; CTLA4 protein affects the reaction [PDCD1 protein affects the reaction [[LY6C1 protein co-treated with LY6G protein] affects the reaction [Amodiaquine results in increased expression of GPT protein]]]; PDCD1 protein affects the reaction [[LY6C1 protein co-treated with LY6G protein] affects the reaction [Amodiaquine results in increased expression of GPT protein]] CTD PMID:29938495 NCBI chr 9:94,418,786...94,431,945 JBrowse link
G Pid1 phosphotyrosine interaction domain containing 1 increases expression ISO Amodiaquine results in increased expression of PID1 mRNA CTD PMID:32816093 NCBI chr 9:85,284,335...85,503,035 JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 decreases expression ISO Amodiaquine results in decreased expression of PTGS2 mRNA CTD PMID:32816093 NCBI chr13:62,164,080...62,169,770 JBrowse link
G Rb1 RB transcriptional corepressor 1 affects phosphorylation ISO Amodiaquine affects the phosphorylation of RB1 protein CTD PMID:24113242 NCBI chr15:48,371,295...48,502,473 JBrowse link
G Tgfb1 transforming growth factor, beta 1 multiple interactions ISO [PDCD1 protein co-treated with TGFB1 protein] affects the reaction [Amodiaquine results in increased expression of GPT protein]; CTLA4 protein affects the reaction [[PDCD1 protein co-treated with TGFB1 protein] affects the reaction [Amodiaquine results in increased expression of GPT protein]] CTD PMID:29938495 NCBI chr 1:81,196,532...81,212,848 JBrowse link
G Tnfaip6 TNF alpha induced protein 6 decreases expression ISO Amodiaquine results in decreased expression of TNFAIP6 mRNA CTD PMID:32816093 NCBI chr 3:36,502,250...36,521,652 JBrowse link
G Tp53 tumor protein p53 increases activity
affects expression
ISO Amodiaquine results in increased activity of TP53 protein
Amodiaquine affects the expression of TP53 protein
CTD PMID:12082016 PMID:24113242 NCBI chr10:54,300,070...54,311,525 JBrowse link

Term paths to the root
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Term Annotations click to browse term
  CHEBI ontology 19762
    role 19708
      application 19396
        pro-agent 10089
          prodrug 9894
            amodiaquine 43
              amodiaquine hydrochloride 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19762
    subatomic particle 19760
      composite particle 19760
        hadron 19760
          baryon 19760
            nucleon 19760
              atomic nucleus 19760
                atom 19760
                  main group element atom 19651
                    main group molecular entity 19651
                      s-block molecular entity 19418
                        hydrogen molecular entity 19413
                          hydrides 18746
                            inorganic hydride 17471
                              pnictogen hydride 17448
                                nitrogen hydride 17302
                                  azane 17009
                                    ammonia 17008
                                      organic amino compound 17007
                                        aromatic amine 13671
                                          aminoquinoline 1696
                                            amodiaquine 43
                                              amodiaquine hydrochloride 0
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