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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:harmaline
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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


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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 Cyp1a1 cytochrome P450, family 1, subfamily a, polypeptide 1 multiple interactions
decreases activity
decreases stability
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 activity of CYP1A1 protein
Harmaline results in decreased stability 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 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 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 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 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

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19821
    role 19769
      biological role 19769
        antimicrobial agent 17408
          antiviral agent 10293
            anti-HIV agent 1225
              harman 52
                harmaline 6
Path 2
Term Annotations click to browse term
  CHEBI ontology 19821
    subatomic particle 19819
      composite particle 19819
        hadron 19819
          baryon 19819
            nucleon 19819
              atomic nucleus 19819
                atom 19819
                  main group element atom 19716
                    p-block element atom 19716
                      carbon group element atom 19640
                        carbon atom 19630
                          organic molecular entity 19630
                            organic molecule 19569
                              organic cyclic compound 19360
                                organic heterocyclic compound 18591
                                  organic heteropolycyclic compound 18064
                                    organic heterotricyclic compound 14645
                                      pyridoindole 114
                                        beta-carbolines 97
                                          harmala alkaloid 52
                                            harman 52
                                              harmaline 6
paths to the root