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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 chr12:19,406,133...19,413,713
Ensembl chr12:19,407,360...19,413,651 		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
Ensembl chr 1:95,938,808...95,945,368 		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
Ensembl chr 2:158,307,584...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
Ensembl chr13:22,684,989...22,853,743
Ensembl chr13:22,684,989...22,853,743 		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...26,469,691
Ensembl chr17:26,318,569...26,470,365 		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
Ensembl chr16:45,662,910...45,684,648 		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
Ensembl chr 1:200,089,002...200,098,602 		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
Ensembl chr20:7,149,217...7,159,585 		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
Ensembl chr 9:62,319,312...62,324,963 		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
Ensembl chr15:37,389,629...37,410,500 		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
Ensembl chr 1:197,527,467...197,539,488 		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
Ensembl chr17:764,309...770,548 		JBrowse link
G Cyp1a1 cytochrome P450, family 1, subfamily a, polypeptide 1 increases activity
increases metabolic processing
decreases response to substance
multiple interactions		 ISO Amodiaquine results in increased activity of CYP1A1 protein
CYP1A1 protein results in increased metabolism of Amodiaquine
CYP1A1 protein results in decreased susceptibility to Amodiaquine
[CYP1A1 protein results in increased metabolism of Amodiaquine] which results in increased abundance of desethylamodiaquine		 CTD PMID:12451431 PMID:31629065 NCBI chr 8:58,096,021...58,102,130
Ensembl chr 8:58,096,077...58,102,125 		JBrowse link
G Cyp1a2 cytochrome P450, family 1, subfamily a, polypeptide 2 decreases activity
multiple interactions
increases metabolic processing		 ISO Amodiaquine results in decreased activity of CYP1A2 protein
[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
Ensembl chr 8:58,075,367...58,082,312 		JBrowse link
G Cyp1b1 cytochrome P450, family 1, subfamily b, polypeptide 1 decreases response to substance
multiple interactions
increases metabolic processing		 ISO CYP1B1 protein results in decreased susceptibility to 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
Ensembl chr 6:15,342,344...15,350,917 		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
Ensembl 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
Ensembl chr 1:81,652,787...81,732,143 		JBrowse link
G Cyp2c11 cytochrome P450, subfamily 2, polypeptide 11 multiple interactions
increases metabolic processing		 ISO [CYP2C18 protein results in increased metabolism of Amodiaquine] which results in increased abundance of desethylamodiaquine CTD PMID:31629065 NCBI chr 1:236,762,719...236,799,069
Ensembl chr 1:236,762,842...236,799,066 		JBrowse link
G Cyp2c6 cytochrome P450, family 2, subfamily C, polypeptide 6 decreases activity
multiple interactions
increases metabolic processing		 ISO Amodiaquine results in decreased activity of CYP2C19 protein
[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
Ensembl chr 1:237,693,094...238,057,596 		JBrowse link
G Cyp2c79 cytochrome P450, family 2, subfamily c, polypeptide 79 multiple interactions
affects metabolic processing
increases metabolic processing
increases response to substance		 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 More...
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
Ensembl chr 7:113,881,618...113,891,759 		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
Ensembl chr 1:195,840,058...195,864,023 		JBrowse link
G Cyp3a2 cytochrome P450, family 3, subfamily a, polypeptide 2 multiple interactions
increases response to substance
increases metabolic processing		 ISO [CYP3A4 protein results in increased metabolism of Amodiaquine] which results in increased abundance of and results in increased secretion of desethylamodiaquine; [CYP3A4 protein results in increased metabolism of Amodiaquine] which results in increased chemical synthesis of amodiaquine quinoneimine; [CYP3A4 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 MAPK3 protein; [CYP3A4 protein results in increased susceptibility to Amodiaquine] which results in increased phosphorylation of MAPK8 protein; [Ketoconazole inhibits the reaction [CYP3A4 protein results in increased susceptibility to Amodiaquine]] which 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 MCL1 protein; [Ketoconazole inhibits the reaction [CYP3A4 protein results in increased susceptibility to Amodiaquine]] which results in increased expression of BAX protein; Ketoconazole inhibits the reaction [CYP3A4 protein results in increased susceptibility to Amodiaquine] CTD PMID:28478157 PMID:31629065 NCBI chr12:9,207,978...9,230,064
Ensembl chr12:9,015,383...9,285,008 		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
Ensembl chr12:16,806,207...16,846,422 		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
Ensembl chr 3:143,049,478...143,075,361 		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
Ensembl 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
Ensembl chr 7:108,416,642...108,419,494 		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
Ensembl chr 3:116,526,604...116,536,822 		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
Ensembl chr 4:157,712,667...157,720,404 		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
Ensembl chr11:83,957,813...84,023,616 		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
Ensembl chr 1:181,366,637...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
Ensembl chr16:8,638,924...8,721,981 		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
Ensembl chr 2:183,219,220...183,222,303 		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
Ensembl chr 4:45,790,791...45,897,876 		JBrowse link
G Mpo myeloperoxidase affects response to substance ISO MPO protein affects the susceptibility to Amodiaquine CTD PMID:24588327 NCBI chr10:72,594,883...72,608,862
Ensembl chr10:72,594,661...72,604,819 		JBrowse link
G Nqo2 N-ribosyldihydronicotinamide:quinone dehydrogenase 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
Ensembl chr17:30,909,187...30,938,320 		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
Ensembl chr 3:41,689,851...41,697,877 		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
Ensembl chr 9:94,418,791...94,431,937 		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
Ensembl chr 9:85,284,335...85,503,044 		JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 decreases expression ISO Amodiaquine results in decreased expression of PTGS2 mRNA CTD PMID:32816093 NCBI chr13:62,163,936...62,172,193
Ensembl chr13:62,163,932...62,172,188 		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
Ensembl chr15:48,371,296...48,502,302 		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
Ensembl chr 1:81,196,532...81,212,847 		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
Ensembl chr 3:36,502,188...36,521,649 		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
Ensembl chr10:54,300,048...54,311,524 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19911
    role 19854
      application 19722
        pro-agent 11554
          prodrug 11316
            amodiaquine 44
              amodiaquine hydrochloride 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19911
    subatomic particle 19909
      composite particle 19909
        hadron 19880
          baryon 19880
            nucleon 19909
              atomic nucleus 19880
                atom 19909
                  main group element atom 19849
                    main group molecular entity 19849
                      s-block molecular entity 19681
                        hydrogen molecular entity 19662
                          hydrides 19167
                            inorganic hydride 18182
                              pnictogen hydride 18172
                                nitrogen hydride 18085
                                  azane 17866
                                    ammonia 17865
                                      organic amino compound 17888
                                        aromatic amine 15504
                                          aminoquinoline 1741
                                            amodiaquine 44
                                              amodiaquine hydrochloride 0
paths to the root