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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 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 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 activity
decreases stability
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
affects binding
decreases activity
ISO Harmine inhibits the reaction [DYRK1A protein results in increased phosphorylation of MAPT protein]
Harmine binds to DYRK1A protein
Harmine results in decreased activity of DYRK1A protein
CTD PMID:21573099 PMID:25751815 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 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 2:91,580,858...91,585,578
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 4:161,639,561...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 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...107,435,061
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 chr18:74,046,421...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 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...44,078,463
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 19823
    role 19773
      biological role 19773
        biochemical role 19390
          metabolite 19367
            harmine 43
              6-bromoharmine 0
              N(2)-methylharmine 0
              N-butylharmine 0
              N-ethylharmine 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19823
    subatomic particle 19821
      composite particle 19821
        hadron 19821
          baryon 19821
            nucleon 19821
              atomic nucleus 19821
                atom 19821
                  main group element atom 19720
                    p-block element atom 19720
                      carbon group element atom 19643
                        carbon atom 19633
                          organic molecular entity 19633
                            organic molecule 19572
                              organic cyclic compound 19366
                                organic heterocyclic compound 18604
                                  organic heteropolycyclic compound 18067
                                    organic heterotricyclic compound 14649
                                      pyridoindole 114
                                        beta-carbolines 97
                                          harmala alkaloid 52
                                            harman 52
                                              harmine 43
                                                6-bromoharmine 0
                                                N(2)-methylharmine 0
                                                N-butylharmine 0
                                                N-ethylharmine 0
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