Submit Data |  Help |  Video Tutorials |  News |  Publications |  FTP Download |  REST API |  Citing RGD |  Contact   

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
go back to main search page
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


show annotations for term's descendants           Sort by:
 
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 6:54,963,990...55,001,806
Ensembl chr 6:54,963,990...55,001,464
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 chr10:97,212,483...97,238,824
Ensembl chr10:97,212,432...97,239,642
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 3:120,726,906...120,764,192
Ensembl chr 3:120,726,906...120,764,192
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 2:144,456,689...144,503,570
Ensembl chr 2:144,458,153...144,467,912
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 5:24,434,077...24,446,406
Ensembl chr 5:24,434,872...24,446,406
JBrowse link
G Cdc25a cell division cycle 25A increases expression ISO Harmine results in increased expression of CDC25A mRNA CTD PMID:25751815 NCBI chr 8:117,953,223...117,971,552
Ensembl chr 8:117,953,444...117,971,519
JBrowse link
G Cdc25c cell division cycle 25C increases expression ISO Harmine results in increased expression of CDC25C mRNA CTD PMID:25751815 NCBI chr18:27,528,768...27,550,316
Ensembl chr18:27,528,354...27,550,224
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 chr20:20,576,341...20,591,510
Ensembl chr20:20,576,377...20,591,549
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 4:168,689,043...168,694,159
Ensembl chr 4:168,689,163...168,693,964
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 1:216,661,067...216,663,791
Ensembl chr 1:216,661,080...216,663,721
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 5:107,823,323...107,832,405
Ensembl chr 5:107,823,330...107,841,175
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 5:107,834,353...107,857,428
Ensembl chr 5:107,845,951...107,858,104
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 4:157,612,531...157,645,660
Ensembl chr 4:157,612,536...157,645,659
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 chr18:63,082,861...63,108,450
Ensembl chr18:63,098,144...63,108,051
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 8:62,472,087...62,478,122
Ensembl chr 8:62,472,095...62,478,147
JBrowse link
G Dio2 iodothyronine deiodinase 2 increases expression ISO Harmine results in increased expression of DIO2 protein CTD PMID:27805061 NCBI chr 6:114,475,156...114,489,443
Ensembl chr 6:114,476,142...114,476,723
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 chr11:34,858,339...34,958,733
Ensembl chr11:34,865,532...34,956,536
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 3:150,062,895...150,073,721
Ensembl chr 3:150,047,826...150,073,721
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 5:154,516,611...154,540,228
Ensembl chr 5:154,522,119...154,540,265
JBrowse link
G E2f7 E2F transcription factor 7 increases expression ISO Harmine results in increased expression of E2F7 mRNA CTD PMID:25751815 NCBI chr 7:53,275,659...53,318,261
Ensembl chr 7:53,275,676...53,316,481
JBrowse link
G E2f8 E2F transcription factor 8 increases expression ISO Harmine results in increased expression of E2F8 mRNA CTD PMID:25751815 NCBI chr 1:104,185,436...104,203,683
Ensembl chr 1:104,187,100...104,202,591
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 2:93,792,666...93,797,267
Ensembl chr 2:93,792,601...93,797,305
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 4:161,685,236...161,697,633
Ensembl chr 4:161,685,258...161,696,305
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 6:44,360,077...44,361,908
Ensembl chr 6:44,348,501...44,363,915
JBrowse link
G Ins2 insulin 2 increases expression ISO Harmine results in increased expression of INS mRNA CTD PMID:25751815 NCBI chr 1:215,856,967...215,858,034
Ensembl chr 1:215,856,971...215,858,034
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 5:120,503,475...120,682,281
Ensembl chr 5:120,564,645...120,682,221
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 7:116,779,368...116,781,815
Ensembl chr 7:116,780,681...116,781,766
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:6,554,698...6,620,722
Ensembl chr  X:6,554,698...6,620,722
JBrowse link
G Mapk1 mitogen activated protein kinase 1 increases phosphorylation ISO Harmine results in increased phosphorylation of MAPK1 protein CTD PMID:27805061 NCBI chr11:88,203,863...88,273,301
Ensembl chr11:88,211,599...88,273,254
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 1:198,192,773...198,198,975
Ensembl chr 1:198,192,773...198,198,975
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 chr10:92,289,002...92,386,517
Ensembl chr10:92,288,910...92,386,517
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 7:102,586,313...102,591,240
Ensembl chr 7:102,586,313...102,591,240
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 chr18:77,203,517...77,322,690
Ensembl chr18:77,203,525...77,322,690
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 3:165,241,750...165,374,644
Ensembl chr 3:165,245,238...165,360,292
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 chr19:38,039,542...38,114,003
Ensembl chr19:38,039,564...38,114,003
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 chr15:34,493,163...34,502,238
Ensembl chr15:34,493,138...34,504,326
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 chr13:98,857,255...98,889,444
Ensembl chr13:98,857,177...98,889,716
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 chr12:9,496,044...9,501,211
Ensembl chr12:9,496,044...9,501,213
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 4:147,274,055...147,399,383
Ensembl chr 4:147,274,107...147,399,380
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 chr14:63,095,291...63,190,688
Ensembl chr14:63,095,720...63,187,009
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 5:171,662,277...171,711,561
Ensembl chr 5:171,662,277...171,710,316
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 chr19:24,456,976...24,464,808
Ensembl chr19:24,456,976...24,464,807
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 chr10:45,598,898...45,643,151
Ensembl chr10:45,598,912...45,638,035
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19785
    role 19732
      biological role 19732
        biochemical role 19281
          metabolite 19262
            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 19785
    subatomic particle 19782
      composite particle 19782
        hadron 19782
          baryon 19782
            nucleon 19782
              atomic nucleus 19782
                atom 19782
                  main group element atom 19670
                    p-block element atom 19670
                      carbon group element atom 19572
                        carbon atom 19561
                          organic molecular entity 19561
                            organic molecule 19486
                              organic cyclic compound 19282
                                organic heterocyclic compound 18407
                                  organic heteropolycyclic compound 17820
                                    organic heterotricyclic compound 14571
                                      pyridoindole 113
                                        beta-carbolines 96
                                          harmala alkaloid 52
                                            harman 52
                                              harmine 43
                                                6-bromoharmine 0
                                                N(2)-methylharmine 0
                                                N-butylharmine 0
                                                N-ethylharmine 0
paths to the root

NHLBI Logo

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