Send us a Message
Submit Data |  Help |  Video Tutorials |  News |  Publications |  Download |  REST API |  Citing RGD |  Contact   
Search RGD Grant Resources Citing RGD About Us Contact Us
Genes Variants Community Projects QTLs Strains Markers Genome Information Ontologies Cell Lines References Download Submit Data
OntoMate (Literature Search) JBrowse (Genome Browser) Synteny Browser (VCMap) Variant Visualizer Multi-Ontology Enrichment (MOET) Gene-Ortholog Location Finder (GOLF) InterViewer (Protein-Protein Interactions) PhenoMiner (Quatitative Phenotypes) Gene Annotator OLGA (Gene List Generator) AllianceMine GViewer (Genome Viewer)
Aging & Age-Related Disease Cancer & Neoplastic Disease Cardiovascular Disease Coronavirus Disease Developmental Disease Diabetes Hematologic Disease Immune & Inflammatory Disease Infectious Disease Liver Disease Neurological Disease Obesity & Metabolic Syndrome Renal Disease Respiratory Disease Sensory Organ Disease
Find Models   new Genetic Models Autism Models Rat PhenoMiner (Quantitative Phenotypes) Chinchilla PhenoMiner Expected Ranges (Quantitative Phenotype) PhenoMiner Term Comparison Hybrid Rat Diversity Panel Phenotypes Phenotypes in Other Animal Models Animal Husbandry Strain Medical Records Phylogenetics Strain Availability Calendar Rats 101 Submissions Photo Archive
Pathways
Rat Community Forum Directory of Rat Laboratories Video Tutorials News RGD Publications RGD Presentations Archive Nomenclature Guidelines Resource Links Laboratory Resources Employment Resources

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:harmaline
go back to main search page
Accession:CHEBI:28172 term browser browse the term
Definition:A harmala alkaloid in which the harman skeleton is methoxy-substituted at C-7 and has been reduced across the 3,4 bond.
Synonyms:exact_synonym: 7-methoxy-1-methyl-4,9-dihydro-3H-pyrido[3,4-b]indole
 related_synonym: 3,4-Dihydroharmine;   7-methoxy-1-methyl-4,9-dihydro-3H-beta-carboline;   Armalin;   Dihydroharmine;   Formula=C13H14N2O;   Harmalol methyl ether;   Harmidine;   InChI=1S/C13H14N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-4,7,15H,5-6H2,1-2H3;   InChIKey=RERZNCLIYCABFS-UHFFFAOYSA-N;   O-Methylharmalol;   SMILES=COc1ccc2c3CCN=C(C)c3[nH]c2c1;   harmalin
 alt_id: CHEBI:24475;   CHEBI:5621
 xref: Beilstein:207310;   CAS:304-21-2;   KEGG:C06536;   KNApSAcK:C00001735
 xref_mesh: MESH:D006246
 xref: Reaxys:207310


show annotations for term's descendants           Sort by:
harmaline term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Ccl2 C-C motif chemokine ligand 2 multiple interactions ISO Harmaline inhibits the reaction [lipopolysaccharide, E coli O55-B5 results in increased expression of CCL2 protein] CTD PMID:12107048 NCBI chr10:67,005,424...67,007,222
Ensembl chr10:67,005,424...67,007,226 		JBrowse link
G Cdh1 cadherin 1 increases expression ISO Harmaline results in increased expression of CDH1 protein CTD PMID:35963316 NCBI chr19:34,492,371...34,561,775
Ensembl chr19:34,492,371...34,561,775 		JBrowse link
G Cyp1a1 cytochrome P450, family 1, subfamily a, polypeptide 1 multiple interactions
decreases stability
decreases activity		 ISO [Cycloheximide co-treated with Harmaline] results in decreased expression of CYP1A1 protein; benzyloxycarbonylleucyl-leucyl-leucine aldehyde inhibits the reaction [[Cycloheximide co-treated with Harmaline] results in decreased expression of CYP1A1 protein]; Harmaline inhibits the reaction [Benzo(a)pyrene results in increased activity of CYP1A1 protein]; Harmaline inhibits the reaction [Tetrachlorodibenzodioxin results in increased expression of and results in increased activity of CYP1A1 protein]; Harmaline inhibits the reaction [Tetrachlorodibenzodioxin results in increased expression of CYP1A1 mRNA]
Harmaline results in decreased stability of CYP1A1 protein
Harmaline results in decreased activity of CYP1A1 protein		 CTD PMID:22037238 NCBI chr 8:58,096,021...58,102,130
Ensembl chr 8:58,096,077...58,102,125 		JBrowse link
G Eng endoglin decreases expression
multiple interactions		 ISO Harmaline results in decreased expression of ENG mRNA
Doxorubicin promotes the reaction [Harmaline results in decreased expression of ENG mRNA]		 CTD PMID:35963316 NCBI chr 3:15,934,566...15,972,618
Ensembl chr 3:15,934,518...15,973,230 		JBrowse link
G Ifng interferon gamma increases secretion ISO Harmaline results in increased secretion of IFNG protein CTD PMID:35963316 NCBI chr 7:53,903,339...53,907,375
Ensembl chr 7:53,903,337...53,907,375 		JBrowse link
G Il1b interleukin 1 beta multiple interactions ISO Harmaline inhibits the reaction [IL1B protein results in increased activity of [RELA protein binds to NFKB1 protein]]; Harmaline inhibits the reaction [IL1B protein results in increased secretion of CXCL8 protein] CTD PMID:12065299 NCBI chr 3:116,577,005...116,583,386
Ensembl chr 3:116,577,010...116,583,415 		JBrowse link
G Il4 interleukin 4 affects secretion
multiple interactions		 ISO Harmaline affects the secretion of IL4 protein
Doxorubicin affects the reaction [Harmaline results in decreased secretion of IL4 protein]		 CTD PMID:35963316 NCBI chr10:37,771,203...37,776,750
Ensembl chr10:37,771,203...37,776,750 		JBrowse link
G Kdr kinase insert domain receptor multiple interactions
decreases expression		 ISO Doxorubicin promotes the reaction [Harmaline results in decreased expression of KDR mRNA] CTD PMID:35963316 NCBI chr14:32,217,871...32,261,018
Ensembl chr14:32,217,871...32,261,018 		JBrowse link
G Maoa monoamine oxidase A decreases activity EXP
ISO		 Harmaline results in decreased activity of MAOA protein CTD PMID:15178694 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 Mki67 marker of proliferation Ki-67 decreases expression ISO Harmaline results in decreased expression of MKI67 protein CTD PMID:35963316 NCBI chr 1:190,496,319...190,522,983
Ensembl chr 1:190,496,319...190,522,762 		JBrowse link
G Mmp2 matrix metallopeptidase 2 decreases expression ISO Harmaline results in decreased expression of MMP2 protein CTD PMID:35963316 NCBI chr19:14,154,657...14,182,870
Ensembl chr19:14,154,657...14,182,870 		JBrowse link
G Nfkb1 nuclear factor kappa B subunit 1 multiple interactions ISO Harmaline inhibits the reaction [IL1B protein results in increased activity of [RELA protein binds to NFKB1 protein]]; Harmaline inhibits the reaction [lipopolysaccharide, E coli O55-B5 affects the localization of and results in increased activity of NFKB1 protein] CTD PMID:12065299 PMID:12107048 NCBI chr 2:224,016,214...224,132,135
Ensembl chr 2:224,016,214...224,110,404 		JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 multiple interactions
decreases expression		 ISO Doxorubicin promotes the reaction [Harmaline results in decreased expression of PTGS2 mRNA] CTD PMID:35963316 NCBI chr13:62,163,936...62,172,193
Ensembl chr13:62,163,932...62,172,188 		JBrowse link
G Rela RELA proto-oncogene, NF-kB subunit multiple interactions ISO Harmaline inhibits the reaction [IL1B protein results in increased activity of [RELA protein binds to NFKB1 protein]]; Harmaline inhibits the reaction [lipopolysaccharide, E coli O55-B5 affects the localization of and results in increased activity of RELA protein] CTD PMID:12065299 PMID:12107048 NCBI chr 1:202,925,001...202,935,484
Ensembl chr 1:202,924,945...202,935,484 		JBrowse link
G Vegfa vascular endothelial growth factor A multiple interactions
decreases expression		 ISO Doxorubicin promotes the reaction [Harmaline results in decreased expression of VEGFA mRNA]
Harmaline results in decreased expression of VEGFA mRNA; Harmaline results in decreased expression of VEGFA protein		 CTD PMID:35963316 NCBI chr 9:14,955,300...14,970,641
Ensembl chr 9:14,955,300...14,970,641 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19811
    role 19818
      biological role 19785
        antimicrobial agent 18104
          antiviral agent 11061
            anti-HIV agent 2718
              harman 71
                harmaline 15
Path 2
Term Annotations click to browse term
  CHEBI ontology 19811
    subatomic particle 19809
      composite particle 19809
        hadron 19840
          baryon 19809
            nucleon 19809
              atomic nucleus 19809
                atom 19809
                  main group element atom 19759
                    p-block element atom 19759
                      carbon group element atom 19708
                        carbon atom 19734
                          organic molecular entity 19705
                            organic molecule 19658
                              organic cyclic compound 19471
                                organic heterocyclic compound 18862
                                  organic heteropolycyclic compound 18301
                                    organic heterotricyclic compound 15641
                                      pyridoindole 136
                                        beta-carbolines 117
                                          harmala alkaloid 72
                                            harman 71
                                              harmaline 15
paths to the root