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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:harmine
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Accession:CHEBI:28121 term browser browse the term
Definition:A harmala alkaloid in which the harman skeleton is methoxy-substituted at C-7.
Synonyms:exact_synonym: 7-methoxy-1-methyl-9H-pyrido[3,4-b]indole
 related_synonym: 6-Methoxyharman;   7-methoxy-1-methyl-9H-beta-carboline;   Banisterine;   Formula=C13H12N2O;   InChI=1S/C13H12N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-7,15H,1-2H3;   InChIKey=BXNJHAXVSOCGBA-UHFFFAOYSA-N;   Leucoharmine;   SMILES=COc1ccc2c(c1)[nH]c1c(C)nccc21;   Telepathine;   Yageine;   Yajeine
 alt_id: CHEBI:24477;   CHEBI:5624
 xref: Beilstein:178813;   CAS:442-51-3;   DrugBank:DB07919;   KEGG:C06538;   KNApSAcK:C00001737;   LINCS:LSM-5451
 xref_mesh: MESH:D006247
 xref: PDBeChem:HRM;   PMID:11473435;   PMID:22877698;   Reaxys:178813;   Wikipedia:Harmine


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harmine term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Ache acetylcholinesterase decreases activity ISO Harmine results in decreased activity of ACHE protein CTD PMID:34078836 NCBI chr12:19,406,133...19,413,713
Ensembl chr12:19,407,360...19,413,651 		JBrowse link
G Ahr aryl hydrocarbon receptor multiple interactions ISO Harmine inhibits the reaction [Tetrachlorodibenzodioxin binds to AHR protein] CTD PMID:22001777 NCBI chr 6:52,234,089...52,271,568
Ensembl chr 6:52,234,089...52,271,568 		JBrowse link
G Axin2 axin 2 multiple interactions ISO Harmine inhibits the reaction [WNT3A protein results in increased expression of AXIN2 mRNA] CTD PMID:20519739 NCBI chr10:93,893,830...93,927,042
Ensembl chr10:93,899,245...93,926,231 		JBrowse link
G Bcl2l11 Bcl2-like 11 multiple interactions ISO Harmine promotes the reaction [Erlotinib Hydrochloride results in increased expression of BCL2L11 protein] CTD PMID:30171258 NCBI chr 3:115,366,783...115,404,068
Ensembl chr 3:115,366,646...115,404,068 		JBrowse link
G Camk2d calcium/calmodulin-dependent protein kinase II delta decreases expression EXP harmine decreases expression of camk2d protein after myocardial infarction in rat heart left ventricle RGD PMID:26067684 RGD:11097969 NCBI chr 2:215,023,785...215,287,351
Ensembl chr 2:215,024,004...215,286,178 		JBrowse link
G Ccna1 cyclin A1 increases expression ISO Harmine results in increased expression of CCNA1 mRNA; Harmine results in increased expression of CCNA1 protein CTD PMID:25751815 NCBI chr 2:139,231,738...139,278,066
Ensembl chr 2:139,201,074...139,243,157 		JBrowse link
G Ccne2 cyclin E2 increases expression ISO Harmine results in increased expression of CCNE2 mRNA; Harmine results in increased expression of CCNE2 protein CTD PMID:25751815 NCBI chr 5:24,285,078...24,298,258
Ensembl chr 5:24,284,922...24,297,632 		JBrowse link
G Cdc25a cell division cycle 25A increases expression ISO Harmine results in increased expression of CDC25A mRNA CTD PMID:25751815 NCBI chr 8:109,864,356...109,882,734
Ensembl chr 8:109,864,478...109,882,701 		JBrowse link
G Cdc25c cell division cycle 25C increases expression ISO Harmine results in increased expression of CDC25C mRNA CTD PMID:25751815 NCBI chr18:26,335,156...26,356,199
Ensembl chr18:26,335,834...26,356,185 		JBrowse link
G Cdk1 cyclin-dependent kinase 1 increases expression ISO Harmine results in increased expression of CDK1 mRNA; Harmine results in increased expression of CDK1 protein CTD PMID:25751815 NCBI chr20:19,266,226...19,281,417
Ensembl chr20:19,266,248...19,281,408 		JBrowse link
G Cdkn1b cyclin-dependent kinase inhibitor 1B decreases phosphorylation EXP Harmine results in decreased phosphorylation of CDKN1B protein CTD PMID:26953159 NCBI chr 4:167,760,067...167,765,177
Ensembl chr 4:167,760,181...167,764,982 		JBrowse link
G Cdkn1c cyclin-dependent kinase inhibitor 1C decreases expression ISO Harmine results in decreased expression of CDKN1C mRNA; Harmine results in decreased expression of CDKN1C protein CTD PMID:25751815 NCBI chr 1:198,655,394...198,658,097
Ensembl chr 1:198,655,407...198,658,048 		JBrowse link
G Cdkn2a cyclin-dependent kinase inhibitor 2A decreases expression ISO Harmine results in decreased expression of CDKN2A mRNA; Harmine results in decreased expression of CDKN2A protein CTD PMID:25751815 NCBI chr 5:103,984,949...103,992,143
Ensembl chr 5:103,984,949...104,003,149 		JBrowse link
G Cdkn2b cyclin-dependent kinase inhibitor 2B decreases expression ISO Harmine results in decreased expression of CDKN2B mRNA CTD PMID:25751815 NCBI chr 5:104,009,839...104,019,082
Ensembl chr 5:104,010,680...104,019,050 		JBrowse link
G Chd4 chromodomain helicase DNA binding protein 4 multiple interactions
increases phosphorylation		 ISO AZD 6244 inhibits the reaction [Harmine results in increased phosphorylation of CHD4 protein]; Harmine inhibits the reaction [CHD4 protein affects the expression of UCP1 mRNA]; Harmine inhibits the reaction [CHD4 protein binds to UCP1 promoter] CTD PMID:27805061 NCBI chr 4:157,898,503...157,931,632
Ensembl chr 4:157,899,391...157,931,541 		JBrowse link
G Cidea cell death-inducing DFFA-like effector a multiple interactions
increases expression		 ISO Harmine affects the reaction [Dietary Fats affects the expression of CIDEA mRNA]
Harmine results in increased expression of CIDEA protein		 CTD PMID:27805061 NCBI chr18:60,894,917...60,920,485
Ensembl chr18:60,894,874...60,920,481 		JBrowse link
G Cyp1a1 cytochrome P450, family 1, subfamily a, polypeptide 1 multiple interactions
decreases stability
decreases activity		 ISO benzyloxycarbonylleucyl-leucyl-leucine aldehyde inhibits the reaction [Harmine results in decreased stability of CYP1A1 protein]; Harmine inhibits the reaction [Tetrachlorodibenzodioxin results in increased expression of CYP1A1 mRNA]; Harmine inhibits the reaction [Tetrachlorodibenzodioxin results in increased expression of CYP1A1 protein]
Harmine results in decreased activity of CYP1A1 protein		 CTD PMID:22001777 NCBI chr 8:58,096,021...58,102,130
Ensembl chr 8:58,096,077...58,102,125 		JBrowse link
G Dio2 iodothyronine deiodinase 2 increases expression ISO Harmine results in increased expression of DIO2 protein CTD PMID:27805061 NCBI chr 6:109,665,523...109,679,809
Ensembl chr 6:109,665,523...109,679,809 		JBrowse link
G Dyrk1a dual specificity tyrosine phosphorylation regulated kinase 1A multiple interactions
decreases activity
affects binding
decreases expression 		ISO
EXP		 Harmine inhibits the reaction [DYRK1A protein results in increased phosphorylation of MAPT protein]
Harmine results in decreased activity of DYRK1A protein
Harmine binds to DYRK1A protein
harmine decreases expression of dyrk1a protein after myocardial infarction in rat heart left ventricle		 CTD
RGD		 PMID:21573099 PMID:25751815 PMID:26067684 RGD:11097969 NCBI chr11:33,890,706...34,009,420
Ensembl chr11:33,890,490...34,009,420 		JBrowse link
G E2f1 E2F transcription factor 1 increases expression ISO Harmine results in increased expression of E2F1 mRNA; Harmine results in increased expression of E2F1 protein CTD PMID:25751815 NCBI chr 3:143,064,535...143,075,362
Ensembl chr 3:143,049,478...143,075,361 		JBrowse link
G E2f2 E2F transcription factor 2 increases expression ISO Harmine results in increased expression of E2F2 mRNA; Harmine results in increased expression of E2F2 protein CTD PMID:25751815 NCBI chr 5:148,399,193...148,422,595
Ensembl chr 5:148,399,642...148,421,217 		JBrowse link
G E2f7 E2F transcription factor 7 increases expression ISO Harmine results in increased expression of E2F7 mRNA CTD PMID:25751815 NCBI chr 7:46,150,533...46,192,739
Ensembl chr 7:46,151,293...46,192,734 		JBrowse link
G E2f8 E2F transcription factor 8 increases expression ISO Harmine results in increased expression of E2F8 mRNA CTD PMID:25751815 NCBI chr 1:98,565,717...98,584,265
Ensembl chr 1:98,565,717...98,584,098 		JBrowse link
G Fabp4 fatty acid binding protein 4 multiple interactions ISO [phenylamil co-treated with Harmine] results in increased expression of FABP4 mRNA CTD PMID:20519739 NCBI chr 2:91,580,879...91,585,567
Ensembl chr 2:91,580,885...91,585,578 		JBrowse link
G Foxm1 forkhead box M1 increases expression ISO Harmine results in increased expression of FOXM1 mRNA; Harmine results in increased expression of FOXM1 protein CTD PMID:25751815 NCBI chr 4:161,639,538...161,652,012
Ensembl chr 4:161,638,816...161,650,684 		JBrowse link
G Id2 inhibitor of DNA binding 2 multiple interactions ISO Harmine inhibits the reaction [WNT3A protein results in decreased expression of ID2 mRNA] CTD PMID:20519739 NCBI chr 6:41,740,556...41,742,393
Ensembl chr 6:41,728,946...41,744,400 		JBrowse link
G Ins1 insulin 1 multiple interactions ISO Harmine affects the reaction [LEPR protein affects the susceptibility to INS1 protein] CTD PMID:27805061 NCBI chr 1:251,244,973...251,245,540
Ensembl chr 1:251,244,973...251,245,536 		JBrowse link
G Ins2 insulin 2 increases expression ISO Harmine results in increased expression of INS mRNA CTD PMID:25751815 NCBI chr 1:197,843,277...197,992,522
Ensembl chr 1:197,843,281...197,864,775 		JBrowse link
G Lepr leptin receptor multiple interactions ISO Harmine affects the reaction [LEPR protein affects the susceptibility to INS1 protein] CTD PMID:27805061 NCBI chr 5:116,294,409...116,477,904
Ensembl chr 5:116,289,823...116,475,908 		JBrowse link
G Mafa MAF bZIP transcription factor A increases expression ISO Harmine results in increased expression of MAFA mRNA; Harmine results in increased expression of MAFA protein CTD PMID:25751815 NCBI chr 7:107,432,292...107,435,084
Ensembl chr 7:107,433,605...107,434,690 		JBrowse link
G Maoa monoamine oxidase A decreases activity EXP
ISO		 Harmine results in decreased activity of MAOA protein CTD PMID:24373881 PMID:28302559 NCBI chr  X:6,032,172...6,098,308
Ensembl chr  X:6,030,795...6,099,593 		JBrowse link
G Mapk1 mitogen activated protein kinase 1 increases phosphorylation ISO Harmine results in increased phosphorylation of MAPK1 protein CTD PMID:27805061 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 increases phosphorylation ISO Harmine results in increased phosphorylation of MAPK3 protein CTD PMID:27805061 NCBI chr 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863 		JBrowse link
G Mapt microtubule-associated protein tau multiple interactions ISO Harmine inhibits the reaction [DYRK1A protein results in increased phosphorylation of MAPT protein] CTD PMID:21573099 NCBI chr10:89,138,644...89,236,137
Ensembl chr10:89,138,627...89,236,129 		JBrowse link
G Myc MYC proto-oncogene, bHLH transcription factor increases expression ISO Harmine results in increased expression of MYC protein CTD PMID:25751815 NCBI chr 7:93,593,705...93,598,633
Ensembl chr 7:93,593,705...93,598,630 		JBrowse link
G Nfatc1 nuclear factor of activated T-cells 1 affects localization ISO Harmine affects the localization of NFATC1 protein CTD PMID:25751815 NCBI chr18:74,046,422...74,156,041
Ensembl chr18:74,046,904...74,156,028 		JBrowse link
G Nfatc2 nuclear factor of activated T-cells 2 affects localization ISO Harmine affects the localization of NFATC2 protein CTD PMID:25751815 NCBI chr 3:157,195,970...157,328,640
Ensembl chr 3:157,198,872...157,328,325 		JBrowse link
G Nfatc3 nuclear factor of activated T-cells 3 affects localization ISO Harmine affects the localization of NFATC3 protein CTD PMID:25751815 NCBI chr19:33,960,643...34,035,150
Ensembl chr19:33,960,852...34,035,150 		JBrowse link
G Nfatc4 nuclear factor of activated T-cells 4 affects localization ISO Harmine affects the localization of NFATC4 protein CTD PMID:25751815 NCBI chr15:29,286,998...29,314,610
Ensembl chr15:29,305,535...29,314,610 		JBrowse link
G Parp1 poly (ADP-ribose) polymerase 1 multiple interactions ISO Harmine promotes the reaction [Erlotinib Hydrochloride results in increased cleavage of PARP1 protein] CTD PMID:30171258 NCBI chr13:92,307,593...92,339,406
Ensembl chr13:92,307,586...92,339,404 		JBrowse link
G Pdx1 pancreatic and duodenal homeobox 1 increases expression ISO Harmine results in increased expression of PDX1 mRNA; Harmine results in increased expression of PDX1 protein CTD PMID:25751815 NCBI chr12:7,757,865...7,763,064
Ensembl chr12:7,757,865...7,763,064 		JBrowse link
G Pln phospholamban increases expression EXP harmine increases expression of Pln protein after myocardial infarction in rat heart left ventricle RGD PMID:26067684 RGD:11097969 NCBI chr20:32,629,537...32,639,559 JBrowse link
G Pparg peroxisome proliferator-activated receptor gamma multiple interactions
increases expression		 ISO [phenylamil co-treated with Harmine] results in increased expression of PPARG mRNA
Harmine results in increased expression of PPARG protein		 CTD PMID:20519739 PMID:27805061 NCBI chr 4:148,423,102...148,548,471
Ensembl chr 4:148,423,194...148,548,468 		JBrowse link
G Ppargc1a PPARG coactivator 1 alpha increases expression
multiple interactions		 ISO Harmine results in increased expression of PPARGC1A protein
Harmine affects the reaction [Dietary Fats affects the expression of PPARGC1A mRNA]		 CTD PMID:27805061 NCBI chr14:58,860,752...59,516,525
Ensembl chr14:58,861,144...59,512,656 		JBrowse link
G Prdm16 PR/SET domain 16 increases expression
multiple interactions		 ISO Harmine results in increased expression of PRDM16 protein
Harmine affects the reaction [Dietary Fats affects the expression of PRDM16 mRNA]		 CTD PMID:27805061 NCBI chr 5:164,879,864...165,203,986
Ensembl chr 5:164,880,587...165,203,601 		JBrowse link
G Ucp1 uncoupling protein 1 increases expression
multiple interactions		 ISO Harmine results in increased expression of UCP1 mRNA; Harmine results in increased expression of UCP1 protein
2-chloro-5-nitrobenzanilide inhibits the reaction [Harmine results in increased expression of UCP1 mRNA]; AZD 6244 inhibits the reaction [Harmine results in increased expression of UCP1 mRNA]; Harmine affects the reaction [Dietary Fats affects the expression of UCP1 mRNA]; Harmine inhibits the reaction [CHD4 protein affects the expression of UCP1 mRNA]; Harmine inhibits the reaction [CHD4 protein binds to UCP1 promoter]; N4-(9-ethyl-9H-carbazol-3-yl)-N2-(3-morpholin-4-ylpropyl)-pyrimidine-2,4-diamine inhibits the reaction [Harmine results in increased expression of UCP1 mRNA]		 CTD PMID:27805061 NCBI chr19:24,808,782...24,816,853
Ensembl chr19:24,808,783...24,816,852 		JBrowse link
G Wnt3a Wnt family member 3A multiple interactions ISO Harmine inhibits the reaction [WNT3A protein results in decreased expression of ID2 mRNA]; Harmine inhibits the reaction [WNT3A protein results in increased expression of AXIN2 mRNA] CTD PMID:20519739 NCBI chr10:44,034,174...44,078,366
Ensembl chr10:44,034,194...44,078,324 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19911
    role 19854
      biological role 19852
        biochemical role 19582
          metabolite 19562
            harmine 47
              6-bromoharmine 0
              N(2)-methylharmine 0
              N-butylharmine 0
              N-ethylharmine 0
              harmine-d3 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
                    p-block element atom 19849
                      carbon group element atom 19766
                        carbon atom 19785
                          organic molecular entity 19785
                            organic molecule 19737
                              organic cyclic compound 19526
                                organic heterocyclic compound 18870
                                  organic heteropolycyclic compound 18315
                                    organic heterotricyclic compound 15868
                                      pyridoindole 136
                                        beta-carbolines 117
                                          harmala alkaloid 72
                                            harman 71
                                              harmine 47
                                                6-bromoharmine 0
                                                N(2)-methylharmine 0
                                                N-butylharmine 0
                                                N-ethylharmine 0
                                                harmine-d3 0
paths to the root