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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 2:213,032,135...213,052,192
Ensembl chr 2:213,031,838...213,055,003
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 chr16:65,185,574...65,228,742
Ensembl chr16:65,185,574...65,228,394
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 chr19:13,452,365...13,479,823
Ensembl chr19:13,472,884...13,479,818
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 3:137,030,200...137,036,581
Ensembl chr 3:137,030,205...137,036,601
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 chr10:89,638,618...89,736,108
Ensembl chr10:89,638,599...89,736,108
JBrowse link
G Nfe2l2 NFE2 like bZIP transcription factor 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 3:81,001,529...81,031,165
Ensembl chr 3:81,001,529...81,029,090
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 chr10:64,313,335...64,349,221
Ensembl chr10:64,313,335...64,401,880
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 chr19:52,205,374...52,220,267
Ensembl chr19:52,205,314...52,220,260
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 chr14:63,073,505...63,729,215
Ensembl chr14:63,273,189...63,729,213
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 chr13:64,714,063...64,722,320
Ensembl chr13:64,713,619...64,722,320
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 1:212,354,336...212,364,815
Ensembl chr 1:212,333,035...212,364,817
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 chr11:42,942,742...42,948,399
Ensembl chr11:42,942,678...42,948,399
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 chr16:5,729,381...5,755,170
Ensembl chr16:5,729,991...5,756,431
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 chr20:3,626,685...3,629,303
Ensembl chr20:3,626,532...3,629,303
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 5:77,507,455...77,519,685
Ensembl chr 5:77,507,321...77,520,307
JBrowse link

Term paths to the root
Path 1
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  CHEBI ontology 20862
    role 20820
      chemical role 20396
        antioxidant 16464
          benfotiamine 15
Path 2
Term Annotations click to browse term
  CHEBI ontology 20862
    subatomic particle 20860
      composite particle 20860
        hadron 20860
          baryon 20860
            nucleon 20860
              atomic nucleus 20860
                atom 20860
                  main group element atom 20781
                    p-block element atom 20781
                      carbon group element atom 20715
                        carbon atom 20710
                          organic molecular entity 20710
                            organic molecule 20654
                              organic cyclic compound 20404
                                organic heterocyclic compound 19388
                                  heteroarene 17448
                                    monocyclic heteroarene 15186
                                      azole 14620
                                        thiazoles 1816
                                          1,3-thiazoles 1249
                                            1,3-thiazolium cation 38
                                              vitamin B1 38
                                                thiamine(1+) 38
                                                  benfotiamine 15
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