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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:benfotiamine
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Accession:CHEBI:41039 term browser browse the term
Definition:A thioester that is a synthetic analogue of thiamine obtained by acylative cleavage of the thiazole ring and O-phospohorylation.
Synonyms:exact_synonym: S-[2-{[(4-amino-2-methylpyrimidin-5-yl)methyl](formyl)amino}-5-(phosphonooxy)pent-2-en-3-yl] benzenecarbothioate
 related_synonym: Benphothiamine;   Benzoylthiamine O-monophosphate;   Benzoylthiamine monophosphate;   Formula=C19H23N4O6PS;   InChI=1S/C19H23N4O6PS/c1-13(23(12-24)11-16-10-21-14(2)22-18(16)20)17(8-9-29-30(26,27)28)31-19(25)15-6-4-3-5-7-15/h3-7,10,12H,8-9,11H2,1-2H3,(H2,20,21,22)(H2,26,27,28);   InChIKey=BTNNPSLJPBRMLZ-UHFFFAOYSA-N;   N-((4-Amino-2-methyl-5-pyrimidinyl)methyl)-N-(4-hydroxy-2-mercapto-1-methyl-1-butenyl)formamide S-benzoate O-phosphate;   S-Benzoylthiamine O-monophosphate;   S-Benzoylthiamine monophosphate;   SMILES=[H]C(=O)N(Cc1cnc(C)nc1N)C(C)=C(CCOP(O)(O)=O)SC(=O)c1ccccc1;   benfotiamina;   benfotiaminum
 alt_id: CHEBI:31259
 xref: CAS:22457-89-2;   KEGG:D01255;   LINCS:LSM-5213
 xref_mesh: MESH:C013835
 xref: PDBeChem:BFT;   PMID:21288652;   PMID:21511829;   PMID:21984258;   PMID:22067901;   PMID:22271422;   PMID:22402947;   PMID:22446172;   PMID:22527094;   PMID:22792314;   PMID:22961478;   PMID:22982063;   PMID:22997160;   PMID:23066179;   PMID:23091724;   PMID:23119057;   PMID:23278494;   PMID:23279611;   PMID:23292796;   PMID:23369791;   Patent:US2006045896;   Reaxys:771326;   Wikipedia:Benfotiamine


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benfotiamine term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Gclm glutamate cysteine ligase, modifier subunit multiple interactions
increases expression
ISO NFE2L2 protein affects the reaction [benphothiamine metabolite results in increased expression of GCLM mRNA]; NFE2L2 protein affects the reaction [benphothiamine results in increased expression of GCLM mRNA]
benphothiamine metabolite results in increased expression of GCLM mRNA; benphothiamine results in increased expression of GCLM mRNA
CTD PMID:29860433 NCBI chr 2:225,827,504...225,847,876
Ensembl chr 2:225,827,504...225,847,874
JBrowse link
G Gsr glutathione-disulfide reductase multiple interactions
increases expression
ISO NFE2L2 protein affects the reaction [benphothiamine results in increased expression of GSR mRNA] CTD PMID:29860433 NCBI chr16:62,197,617...62,239,987
Ensembl chr16:62,197,617...62,241,361
JBrowse link
G Hmox1 heme oxygenase 1 increases expression
multiple interactions
ISO benphothiamine metabolite results in increased expression of HMOX1 mRNA; benphothiamine results in increased expression of HMOX1 mRNA
benphothiamine inhibits the reaction [MAPT protein results in increased expression of HMOX1 mRNA]; NFE2L2 protein affects the reaction [benphothiamine metabolite results in increased expression of HMOX1 mRNA]; NFE2L2 protein affects the reaction [benphothiamine results in increased expression of HMOX1 mRNA]
CTD PMID:29860433 NCBI chr19:14,508,634...14,515,455
Ensembl chr19:14,508,616...14,515,456
JBrowse link
G Il1b interleukin 1 beta multiple interactions ISO [benphothiamine co-treated with MAPT protein] results in decreased expression of IL1B protein CTD PMID:29860433 NCBI chr 3:121,876,256...121,882,637
Ensembl chr 3:121,876,263...121,882,726
JBrowse link
G Mapt microtubule-associated protein tau decreases phosphorylation
multiple interactions
ISO benphothiamine results in decreased phosphorylation of MAPT protein
[benphothiamine co-treated with MAPT protein] results in decreased expression of IL1B protein; [benphothiamine co-treated with MAPT protein] results in decreased expression of NOS2 protein; [benphothiamine co-treated with MAPT protein] results in decreased expression of PTGS2 protein; [benphothiamine co-treated with MAPT protein] results in decreased expression of RELA protein; [benphothiamine co-treated with MAPT protein] results in decreased expression of TNF protein; [benphothiamine co-treated with MAPT protein] results in increased expression of NQO1 mRNA; [benphothiamine co-treated with MAPT protein] results in increased expression of TXN mRNA; benphothiamine inhibits the reaction [MAPT protein results in decreased activity of TKT protein]; benphothiamine inhibits the reaction [MAPT protein results in decreased expression of NOS2 mRNA]; benphothiamine inhibits the reaction [MAPT protein results in decreased expression of PPARGC1A protein]; benphothiamine inhibits the reaction [MAPT protein results in decreased expression of SOD1 protein]; benphothiamine inhibits the reaction [MAPT protein results in increased expression of HMOX1 mRNA]
CTD PMID:29860433 NCBI chr10:92,289,002...92,386,517
Ensembl chr10:92,288,910...92,386,517
JBrowse link
G Nfe2l2 nuclear factor, erythroid 2-like 2 multiple interactions ISO NFE2L2 protein affects the reaction [benphothiamine metabolite results in increased expression of GCLM mRNA]; NFE2L2 protein affects the reaction [benphothiamine metabolite results in increased expression of HMOX1 mRNA]; NFE2L2 protein affects the reaction [benphothiamine metabolite results in increased expression of NQO1 mRNA]; NFE2L2 protein affects the reaction [benphothiamine results in increased expression of GCLM mRNA]; NFE2L2 protein affects the reaction [benphothiamine results in increased expression of GSR mRNA]; NFE2L2 protein affects the reaction [benphothiamine results in increased expression of HMOX1 mRNA]; NFE2L2 protein affects the reaction [benphothiamine results in increased expression of NQO1 mRNA] CTD PMID:29860433 NCBI chr 3:62,497,568...62,525,146
Ensembl chr 3:62,497,571...62,524,996
JBrowse link
G Nos2 nitric oxide synthase 2 multiple interactions ISO [benphothiamine co-treated with MAPT protein] results in decreased expression of NOS2 protein; benphothiamine inhibits the reaction [MAPT protein results in decreased expression of NOS2 mRNA] CTD PMID:29860433 NCBI chr10:66,188,290...66,221,621
Ensembl chr10:66,189,786...66,313,190
JBrowse link
G Nqo1 NAD(P)H quinone dehydrogenase 1 increases expression
multiple interactions
ISO benphothiamine metabolite results in increased expression of NQO1 mRNA; benphothiamine results in increased expression of NQO1 mRNA
[benphothiamine co-treated with MAPT protein] results in increased expression of NQO1 mRNA; NFE2L2 protein affects the reaction [benphothiamine metabolite results in increased expression of NQO1 mRNA]; NFE2L2 protein affects the reaction [benphothiamine results in increased expression of NQO1 mRNA]
CTD PMID:29860433 NCBI chr19:38,422,210...38,437,103
Ensembl chr19:38,422,164...38,437,180
JBrowse link
G Ppargc1a PPARG coactivator 1 alpha multiple interactions ISO benphothiamine inhibits the reaction [MAPT protein results in decreased expression of PPARGC1A protein] CTD PMID:29860433 NCBI chr14:63,095,291...63,190,688
Ensembl chr14:63,095,720...63,187,009
JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 multiple interactions ISO [benphothiamine co-treated with MAPT protein] results in decreased expression of PTGS2 protein CTD PMID:29860433 NCBI chr13:67,351,230...67,356,920
Ensembl chr13:67,351,087...67,359,335
JBrowse link
G Rela RELA proto-oncogene, NF-kB subunit multiple interactions ISO [benphothiamine co-treated with MAPT protein] results in decreased expression of RELA protein CTD PMID:29860433 NCBI chr 1:220,992,770...221,003,249
Ensembl chr 1:220,992,770...221,003,249
JBrowse link
G Sod1 superoxide dismutase 1 multiple interactions ISO benphothiamine inhibits the reaction [MAPT protein results in decreased expression of SOD1 protein] CTD PMID:29860433 NCBI chr11:30,363,282...30,368,858
Ensembl chr11:30,363,280...30,368,862
JBrowse link
G Tkt transketolase multiple interactions EXP
ISO
[benphothiamine co-treated with Streptozocin] results in increased activity of TKT protein
benphothiamine inhibits the reaction [MAPT protein results in decreased activity of TKT protein]
CTD PMID:12592403 PMID:29860433 NCBI chr16:6,609,670...6,634,608
Ensembl chr16:6,609,668...6,634,595
JBrowse link
G Tnf tumor necrosis factor multiple interactions ISO [benphothiamine co-treated with MAPT protein] results in decreased expression of TNF protein CTD PMID:29860433 NCBI chr20:5,189,382...5,192,000
Ensembl chr20:5,189,390...5,192,000
JBrowse link
G Txn1 thioredoxin 1 multiple interactions ISO [benphothiamine co-treated with MAPT protein] results in increased expression of TXN mRNA CTD PMID:29860433 NCBI chr 5:75,049,735...75,057,731
Ensembl chr 5:75,049,747...75,057,752
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19883
    role 19833
      chemical role 19351
        antioxidant 14255
          benfotiamine 15
Path 2
Term Annotations click to browse term
  CHEBI ontology 19883
    subatomic particle 19881
      composite particle 19881
        hadron 19881
          baryon 19881
            nucleon 19881
              atomic nucleus 19881
                atom 19881
                  main group element atom 19771
                    p-block element atom 19771
                      carbon group element atom 19679
                        carbon atom 19668
                          organic molecular entity 19668
                            organic group 18580
                              organic divalent group 18571
                                organodiyl group 18571
                                  carbonyl group 18479
                                    carbonyl compound 18479
                                      carboxylic acid 18153
                                        carboacyl group 17410
                                          univalent carboacyl group 17410
                                            carbamoyl group 17192
                                              carboxamide 17192
                                                formamides 1352
                                                  benfotiamine 15
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