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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:N-methylnicotinate
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Accession:CHEBI:18123 term browser browse the term
Definition:An iminium betaine that is the conjugate base of N-methylnicotinic acid, arising from deprotonation of the carboxy group.
Synonyms:exact_synonym: 1-methylpyridinium-3-carboxylate
 related_synonym: 1-Methyl-3-pyridiniumcarboxylate;   1-Methylpyridinio-3-carboxylate;   1-methylnicotinate;   3-Carboxy-1-methylpyridinium hydroxide inner salt;   Betain nicotinate;   Betaine nicotinate;   Caffearin;   Caffearine;   Coffearin;   Formula=C7H7NO2;   Gynesine;   InChI=1S/C7H7NO2/c1-8-4-2-3-6(5-8)7(9)10/h2-5H,1H3;   InChIKey=WWNNZCOKKKDOPX-UHFFFAOYSA-N;   N-methyl-nicotinate;   Nicotinic acid N-methylbetaine;   SMILES=C[n+]1cccc(c1)C([O-])=O;   Trigenelline;   Trigonellin;   Trigonelline
 alt_id: CHEBI:12522;   CHEBI:19067;   CHEBI:7320
 xref: Beilstein:3905114;   CAS:535-83-1;   HMDB:HMDB0000875;   KEGG:C01004;   KNApSAcK:C00001555
 xref_mesh: MESH:C009560
 xref: MetaCyc:METHYLNICOTINATE;   PMID:13128691;   PMID:17190852;   PMID:185134;   PMID:22242555;   PMID:22312719;   PMID:22393699;   PMID:22559314;   PMID:24047691;   Reaxys:3905114
 cyclic_relationship: is_conjugate_base_of CHEBI:50521



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N-methylnicotinate term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Ace angiotensin I converting enzyme multiple interactions ISO
EXP
oltipraz affects the reaction [trigonelline affects the reaction [INS2 protein affects the expression of ACE mRNA]]; oltipraz affects the reaction [trigonelline affects the reaction [INS2 protein affects the expression of ACE protein]]; trigonelline affects the reaction [INS2 protein affects the expression of ACE mRNA]; trigonelline affects the reaction [INS2 protein affects the expression of ACE protein]
oltipraz inhibits the reaction [trigonelline inhibits the reaction [Glucose results in increased expression of ACE mRNA]]; trigonelline inhibits the reaction [Glucose results in increased expression of ACE mRNA]
CTD PMID:29211853 NCBI chr10:90,910,316...90,930,437
Ensembl chr10:90,910,316...90,931,131
JBrowse link
G Ace2 angiotensin I converting enzyme 2 multiple interactions ISO
EXP
oltipraz affects the reaction [trigonelline affects the reaction [INS2 protein affects the expression of ACE2 mRNA]]; oltipraz affects the reaction [trigonelline affects the reaction [INS2 protein affects the expression of ACE2 protein]]; trigonelline affects the reaction [INS2 protein affects the expression of ACE2 mRNA]; trigonelline affects the reaction [INS2 protein affects the expression of ACE2 protein]
oltipraz inhibits the reaction [trigonelline inhibits the reaction [Glucose results in decreased expression of ACE2 mRNA]]; trigonelline inhibits the reaction [Glucose results in decreased expression of ACE2 mRNA]
CTD PMID:29211853 NCBI chr  X:30,293,597...30,340,961
Ensembl chr  X:30,293,589...30,340,977
JBrowse link
G Agt angiotensinogen multiple interactions ISO
EXP
oltipraz affects the reaction [trigonelline affects the reaction [INS2 protein affects the expression of AGT mRNA]]; oltipraz affects the reaction [trigonelline affects the reaction [INS2 protein affects the expression of AGT protein]]; trigonelline affects the reaction [INS2 protein affects the expression of AGT mRNA]; trigonelline affects the reaction [INS2 protein affects the expression of AGT protein]
oltipraz inhibits the reaction [trigonelline inhibits the reaction [Glucose results in increased expression of AGT mRNA]]; trigonelline inhibits the reaction [Glucose results in increased expression of AGT mRNA]
CTD PMID:29211853 NCBI chr19:52,529,139...52,549,618
Ensembl chr19:52,529,185...52,540,977
JBrowse link
G Atg7 autophagy related 7 multiple interactions ISO trigonelline inhibits the reaction [Palmitic Acid results in decreased expression of ATG7 protein]
ATG7 protein affects the reaction [trigonelline inhibits the reaction [Palmitic Acid results in increased expression of PPARG protein]]; ATG7 protein affects the reaction [trigonelline inhibits the reaction [Palmitic Acid results in increased expression of SREBF1 protein]]; trigonelline inhibits the reaction [Palmitic Acid results in decreased expression of ATG7 protein]
CTD PMID:30208301 NCBI chr 4:147,718,663...147,925,656
Ensembl chr 4:147,718,752...147,925,593
JBrowse link
G Bax BCL2 associated X, apoptosis regulator multiple interactions EXP
ISO
trigonelline inhibits the reaction [[Oxygen deficiency co-treated with Glucose deficiency] results in increased expression of BAX protein]
[trigonelline co-treated with Cisplatin] results in increased expression of BAX protein; [trigonelline co-treated with Etoposide] results in increased expression of BAX protein
CTD PMID:31935362 PMID:33148531 NCBI chr 1:95,940,001...95,945,407
Ensembl chr 1:95,938,808...95,945,368
JBrowse link
G Bcl2 BCL2, apoptosis regulator multiple interactions EXP
ISO
trigonelline inhibits the reaction [[Oxygen deficiency co-treated with Glucose deficiency] results in decreased expression of BCL2 protein]
[trigonelline co-treated with Cisplatin] results in decreased expression of BCL2 protein; [trigonelline co-treated with Etoposide] results in decreased expression of BCL2 protein
CTD PMID:31935362 PMID:33148531 NCBI chr13:22,689,783...22,853,920
Ensembl chr13:22,684,989...22,853,743
Ensembl chr13:22,684,989...22,853,743
JBrowse link
G Becn1 beclin 1 multiple interactions ISO trigonelline inhibits the reaction [Palmitic Acid results in decreased expression of BECN1 protein]
trigonelline inhibits the reaction [[Cholesterol, Dietary co-treated with Dietary Fats] results in decreased expression of BECN1 protein]; trigonelline inhibits the reaction [Palmitic Acid results in decreased expression of BECN1 protein]
CTD PMID:30208301 NCBI chr10:86,231,387...86,246,742
Ensembl chr10:86,231,388...86,246,742
JBrowse link
G Casp3 caspase 3 increases activity
multiple interactions
ISO
EXP
trigonelline results in increased activity of CASP3 protein
2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one inhibits the reaction [trigonelline inhibits the reaction [[Oxygen deficiency co-treated with Glucose deficiency] results in increased activity of CASP3 protein]]; trigonelline inhibits the reaction [[Oxygen deficiency co-treated with Glucose deficiency] results in increased activity of CASP3 protein]
[trigonelline co-treated with Cisplatin] results in increased cleavage of CASP3 protein; [trigonelline co-treated with Etoposide] results in increased cleavage of CASP3 protein
CTD PMID:26593444 PMID:31935362 PMID:33148531 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648
JBrowse link
G Cd36 CD36 molecule multiple interactions ISO trigonelline inhibits the reaction [[Cholesterol, Dietary co-treated with Dietary Fats] results in increased expression of CD36 protein]; trigonelline inhibits the reaction [Palmitic Acid results in increased expression of CD36 protein] CTD PMID:30208301 NCBI chr 4:17,317,343...17,410,084
Ensembl chr 4:17,354,466...17,513,903
JBrowse link
G Ddit3 DNA-damage inducible transcript 3 multiple interactions ISO [trigonelline co-treated with ferric citrate] results in increased expression of DDIT3 mRNA CTD PMID:29959986 NCBI chr 7:63,115,645...63,121,203
Ensembl chr 7:63,116,380...63,121,201
JBrowse link
G Egf epidermal growth factor multiple interactions ISO trigonelline inhibits the reaction [EGF protein results in increased phosphorylation of EGFR protein]; trigonelline inhibits the reaction [EGF protein results in increased phosphorylation of MAPK1 protein]; trigonelline inhibits the reaction [EGF protein results in increased phosphorylation of MAPK3 protein]; trigonelline inhibits the reaction [EGF protein results in increased phosphorylation of NFE2L2 protein] CTD PMID:33148531 NCBI chr 2:218,219,408...218,302,370
Ensembl chr 2:218,219,415...218,302,064
JBrowse link
G Egfr epidermal growth factor receptor multiple interactions
decreases phosphorylation
ISO trigonelline inhibits the reaction [EGF protein results in increased phosphorylation of EGFR protein]
trigonelline results in decreased phosphorylation of EGFR protein
CTD PMID:33148531 NCBI chr14:91,176,931...91,349,722
Ensembl chr14:91,177,067...91,344,382
JBrowse link
G Eif2s1 eukaryotic translation initiation factor 2 subunit alpha multiple interactions ISO trigonelline inhibits the reaction [Palmitic Acid results in increased phosphorylation of EIF2S1 protein] CTD PMID:30208301 NCBI chr 6:97,672,829...97,697,499
Ensembl chr 6:97,672,766...97,706,225
JBrowse link
G Fth1 ferritin heavy chain 1 multiple interactions ISO [trigonelline co-treated with ferric citrate] results in increased expression of FTH1 mRNA CTD PMID:29959986 NCBI chr 1:206,627,142...206,629,430
Ensembl chr 1:206,627,103...206,725,424
JBrowse link
G Ftl1 ferritin light chain 1 multiple interactions ISO [trigonelline co-treated with ferric citrate] results in increased expression of FTL mRNA CTD PMID:29959986 NCBI chr 1:95,936,390...95,938,234
Ensembl chr 1:95,936,387...95,939,725
Ensembl chr10:95,936,387...95,939,725
JBrowse link
G Gclc glutamate-cysteine ligase, catalytic subunit multiple interactions ISO trigonelline inhibits the reaction [Pyocyanine results in increased expression of GCLC mRNA] CTD PMID:24015256 NCBI chr 8:78,629,899...78,668,547
Ensembl chr 8:78,630,127...78,668,544
JBrowse link
G Hmox1 heme oxygenase 1 decreases expression ISO trigonelline results in decreased expression of HMOX1 mRNA; trigonelline results in decreased expression of HMOX1 protein CTD PMID:33148531 NCBI chr19:13,466,287...13,474,082
Ensembl chr19:13,467,244...13,474,079
JBrowse link
G Hspa5 heat shock protein family A (Hsp70) member 5 multiple interactions ISO trigonelline inhibits the reaction [Palmitic Acid results in increased expression of HSPA5 protein] CTD PMID:30208301 NCBI chr 3:18,055,507...18,059,969
Ensembl chr 3:18,055,405...18,059,891
JBrowse link
G Il1b interleukin 1 beta multiple interactions EXP trigonelline inhibits the reaction [[Oxygen deficiency co-treated with Glucose deficiency] results in increased expression of IL1B protein] CTD PMID:31935362 NCBI chr 3:116,577,005...116,583,386
Ensembl chr 3:116,577,010...116,583,415
JBrowse link
G Il6 interleukin 6 multiple interactions EXP trigonelline inhibits the reaction [[Oxygen deficiency co-treated with Glucose deficiency] results in increased expression of IL6 protein] CTD PMID:31935362 NCBI chr 4:5,214,602...5,219,178
Ensembl chr 4:5,213,394...5,219,178
JBrowse link
G Ins2 insulin 2 multiple interactions ISO oltipraz affects the reaction [trigonelline affects the reaction [INS2 protein affects the expression of ACE mRNA]]; oltipraz affects the reaction [trigonelline affects the reaction [INS2 protein affects the expression of ACE protein]]; oltipraz affects the reaction [trigonelline affects the reaction [INS2 protein affects the expression of ACE2 mRNA]]; oltipraz affects the reaction [trigonelline affects the reaction [INS2 protein affects the expression of ACE2 protein]]; oltipraz affects the reaction [trigonelline affects the reaction [INS2 protein affects the expression of AGT mRNA]]; oltipraz affects the reaction [trigonelline affects the reaction [INS2 protein affects the expression of AGT protein]]; oltipraz affects the reaction [trigonelline affects the reaction [INS2 protein affects the expression of MAS1 mRNA]]; oltipraz affects the reaction [trigonelline affects the reaction [INS2 protein affects the expression of MAS1 protein]]; oltipraz affects the reaction [trigonelline affects the reaction [INS2 protein affects the expression of NFE2L2 protein]]; oltipraz inhibits the reaction [trigonelline affects the reaction [INS2 protein affects the expression of NFE2L2 mRNA]]; trigonelline affects the reaction [INS2 protein affects the expression of ACE mRNA]; trigonelline affects the reaction [INS2 protein affects the expression of ACE protein]; trigonelline affects the reaction [INS2 protein affects the expression of ACE2 mRNA]; trigonelline affects the reaction [INS2 protein affects the expression of ACE2 protein]; trigonelline affects the reaction [INS2 protein affects the expression of AGT mRNA]; trigonelline affects the reaction [INS2 protein affects the expression of AGT protein]; trigonelline affects the reaction [INS2 protein affects the expression of MAS1 mRNA]; trigonelline affects the reaction [INS2 protein affects the expression of MAS1 protein]; trigonelline affects the reaction [INS2 protein affects the expression of NFE2L2 mRNA]; trigonelline affects the reaction [INS2 protein affects the expression of NFE2L2 protein]; trigonelline inhibits the reaction [INS2 protein affects the abundance of angiotensin I (1-7)] CTD PMID:29211853 NCBI chr 1:197,843,277...197,992,522
Ensembl chr 1:197,843,281...197,864,775
JBrowse link
G Keap1 Kelch-like ECH-associated protein 1 multiple interactions ISO [trigonelline co-treated with ferric citrate] results in decreased expression of KEAP1 mRNA CTD PMID:29959986 NCBI chr 8:19,768,375...19,777,862
Ensembl chr 8:19,768,375...19,777,862
JBrowse link
G Lepr leptin receptor affects abundance ISO LEPR affects the abundance of trigonelline CTD PMID:20567778 NCBI chr 5:116,294,409...116,477,904
Ensembl chr 5:116,289,823...116,475,908
JBrowse link
G Mapk1 mitogen activated protein kinase 1 multiple interactions
decreases phosphorylation
ISO trigonelline inhibits the reaction [EGF protein results in increased phosphorylation of MAPK1 protein]
trigonelline results in decreased phosphorylation of MAPK1 protein
CTD PMID:33148531 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 multiple interactions
decreases phosphorylation
ISO trigonelline inhibits the reaction [EGF protein results in increased phosphorylation of MAPK3 protein]
trigonelline results in decreased phosphorylation of MAPK3 protein
CTD PMID:33148531 NCBI chr 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863
JBrowse link
G Mas1 MAS1 proto-oncogene, G protein-coupled receptor multiple interactions EXP
ISO
oltipraz inhibits the reaction [trigonelline inhibits the reaction [Glucose results in decreased expression of MAS1 mRNA]]; trigonelline inhibits the reaction [Glucose results in decreased expression of MAS1 mRNA]
oltipraz affects the reaction [trigonelline affects the reaction [INS2 protein affects the expression of MAS1 mRNA]]; oltipraz affects the reaction [trigonelline affects the reaction [INS2 protein affects the expression of MAS1 protein]]; trigonelline affects the reaction [INS2 protein affects the expression of MAS1 mRNA]; trigonelline affects the reaction [INS2 protein affects the expression of MAS1 protein]
CTD PMID:29211853 NCBI chr 1:47,879,956...47,911,500
Ensembl chr 1:47,880,309...47,911,709
JBrowse link
G Mtor mechanistic target of rapamycin kinase multiple interactions ISO trigonelline inhibits the reaction [Palmitic Acid results in increased phosphorylation of MTOR protein] CTD PMID:30208301 NCBI chr 5:158,884,856...158,994,311
Ensembl chr 5:158,884,804...158,994,311
JBrowse link
G Myc MYC proto-oncogene, bHLH transcription factor decreases expression ISO trigonelline results in decreased expression of MYC mRNA CTD PMID:26593444 NCBI chr 7:93,593,705...93,598,633
Ensembl chr 7:93,593,705...93,598,630
JBrowse link
G Nfe2l2 NFE2 like bZIP transcription factor 2 multiple interactions
decreases phosphorylation
ISO
EXP
trigonelline inhibits the reaction [EGF protein results in increased phosphorylation of NFE2L2 protein]; trigonelline inhibits the reaction [ferric citrate affects the localization of NFE2L2 protein]; trigonelline inhibits the reaction [NFE2L2 protein results in decreased susceptibility to Cisplatin]; trigonelline inhibits the reaction [NFE2L2 protein results in decreased susceptibility to Etoposide]; trigonelline inhibits the reaction [Pyocyanine results in increased expression of and affects the localization of NFE2L2 protein]
trigonelline results in decreased phosphorylation of NFE2L2 protein
oltipraz inhibits the reaction [trigonelline inhibits the reaction [Glucose results in increased expression of NFE2L2 protein]]; trigonelline inhibits the reaction [Glucose results in increased expression of NFE2L2 protein]
oltipraz affects the reaction [trigonelline affects the reaction [INS2 protein affects the expression of NFE2L2 protein]]; oltipraz inhibits the reaction [trigonelline affects the reaction [INS2 protein affects the expression of NFE2L2 mRNA]]; trigonelline affects the reaction [INS2 protein affects the expression of NFE2L2 mRNA]; trigonelline affects the reaction [INS2 protein affects the expression of NFE2L2 protein]
CTD PMID:24015256 PMID:29211853 PMID:29959986 PMID:33148531 NCBI chr 3:60,594,239...60,621,785
Ensembl chr 3:60,594,242...60,621,737
JBrowse link
G Nqo1 NAD(P)H quinone dehydrogenase 1 multiple interactions
decreases expression
ISO trigonelline inhibits the reaction [ferric citrate results in increased expression of NQO1 protein]; trigonelline inhibits the reaction [Pyocyanine results in increased expression of NQO1 mRNA]
trigonelline results in decreased expression of NQO1 mRNA; trigonelline results in decreased expression of NQO1 protein
CTD PMID:24015256 PMID:29959986 PMID:33148531 NCBI chr19:35,295,633...35,310,528
Ensembl chr19:35,295,573...35,310,557
JBrowse link
G Parp1 poly (ADP-ribose) polymerase 1 multiple interactions ISO trigonelline inhibits the reaction [Palmitic Acid results in increased cleavage of PARP1 protein]
[trigonelline co-treated with Cisplatin] results in increased cleavage of PARP1 protein; [trigonelline co-treated with Etoposide] results in increased cleavage of PARP1 protein
CTD PMID:30208301 PMID:33148531 NCBI chr13:92,307,593...92,339,406
Ensembl chr13:92,307,586...92,339,404
JBrowse link
G Plin1 perilipin 1 multiple interactions ISO trigonelline inhibits the reaction [Palmitic Acid results in increased expression of PLIN1 protein] CTD PMID:30208301 NCBI chr 1:133,664,294...133,676,854
Ensembl chr 1:133,664,892...133,676,828
JBrowse link
G Pparg peroxisome proliferator-activated receptor gamma multiple interactions ISO ATG7 protein affects the reaction [trigonelline inhibits the reaction [Palmitic Acid results in increased expression of PPARG protein]]; trigonelline inhibits the reaction [Palmitic Acid results in increased expression of PPARG protein]
trigonelline inhibits the reaction [[Cholesterol, Dietary co-treated with Dietary Fats] results in increased expression of PPARG protein]; trigonelline inhibits the reaction [Palmitic Acid results in increased expression of PPARG protein]
CTD PMID:30208301 NCBI chr 4:148,423,102...148,548,471
Ensembl chr 4:148,423,194...148,548,468
JBrowse link
G Sqstm1 sequestosome 1 multiple interactions ISO trigonelline inhibits the reaction [[Cholesterol, Dietary co-treated with Dietary Fats] results in increased expression of SQSTM1 protein]; trigonelline inhibits the reaction [Palmitic Acid results in increased expression of SQSTM1 protein] CTD PMID:30208301 NCBI chr10:34,525,517...34,536,685
Ensembl chr10:34,525,519...34,536,673
JBrowse link
G Srebf1 sterol regulatory element binding transcription factor 1 multiple interactions ISO trigonelline inhibits the reaction [[Cholesterol, Dietary co-treated with Dietary Fats] results in increased expression of SREBF1 protein]; trigonelline inhibits the reaction [Palmitic Acid results in increased expression of SREBF1 protein]
ATG7 protein affects the reaction [trigonelline inhibits the reaction [Palmitic Acid results in increased expression of SREBF1 protein]]; trigonelline inhibits the reaction [Palmitic Acid results in increased expression of SREBF1 protein]
CTD PMID:30208301 NCBI chr10:45,007,637...45,029,650
Ensembl chr10:45,007,637...45,029,650
JBrowse link
G Tnf tumor necrosis factor multiple interactions EXP 2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one inhibits the reaction [trigonelline inhibits the reaction [[Oxygen deficiency co-treated with Glucose deficiency] results in increased expression of TNF protein]]; trigonelline inhibits the reaction [[Oxygen deficiency co-treated with Glucose deficiency] results in increased expression of TNF protein] CTD PMID:31935362 NCBI chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 20057
    role 20023
      biological role 20010
        physiological role 20008
          food component 20008
            N-methylnicotinate 36
Path 2
Term Annotations click to browse term
  CHEBI ontology 20057
    subatomic particle 20056
      composite particle 20068
        hadron 20056
          baryon 20056
            nucleon 20056
              atomic nucleus 20056
                atom 20056
                  main group element atom 19971
                    main group molecular entity 19959
                      s-block molecular entity 19758
                        hydrogen molecular entity 19764
                          hydrides 19134
                            inorganic hydride 17935
                              pnictogen hydride 17901
                                nitrogen hydride 17789
                                  ammonium 8314
                                    ammonium ion derivative 8310
                                      quaternary ammonium ion 5215
                                        quaternary nitrogen compound 760
                                          iminium betaine 50
                                            N-methylnicotinate 36
paths to the root