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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 2:210,347,482...210,367,537
Ensembl chr 2:210,347,482...210,367,535
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 chr16:58,482,209...58,525,256
Ensembl chr16:58,482,505...58,525,661
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 chr19:13,466,287...13,474,082
Ensembl chr19:13,467,244...13,474,079
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 3:116,577,005...116,583,386
Ensembl chr 3:116,577,010...116,583,415
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 chr10:89,138,644...89,236,137
Ensembl chr10:89,138,627...89,236,129
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 3:60,594,239...60,621,785
Ensembl chr 3:60,594,242...60,621,737
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 chr10:63,815,308...63,851,208
Ensembl chr10:63,815,308...63,851,210
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 chr19:35,295,633...35,310,528
Ensembl chr19:35,295,573...35,310,557
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 chr14:58,860,752...59,516,525
Ensembl chr14:58,861,144...59,512,656
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 chr13:62,164,080...62,169,770
Ensembl chr13:62,163,932...62,172,188
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 1:202,925,001...202,935,484
Ensembl chr 1:202,924,945...202,935,484
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 chr11:29,456,673...29,462,249
Ensembl chr11:29,456,558...29,462,249
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 chr16:5,723,764...5,748,702
Ensembl chr16:5,723,762...5,748,698
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 chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629
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 5:72,712,334...72,724,564
Ensembl chr 5:72,711,933...72,724,629
JBrowse link

Term paths to the root
Path 1
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  CHEBI ontology 19800
    role 19751
      chemical role 19320
        antioxidant 14438
          benfotiamine 15
Path 2
Term Annotations click to browse term
  CHEBI ontology 19800
    subatomic particle 19799
      composite particle 19799
        hadron 19799
          baryon 19799
            nucleon 19799
              atomic nucleus 19799
                atom 19799
                  main group element atom 19698
                    p-block element atom 19698
                      carbon group element atom 19619
                        carbon atom 19609
                          organic molecular entity 19609
                            organic molecule 19549
                              organic cyclic compound 19343
                                organic heterocyclic compound 18584
                                  heteroarene 16542
                                    monocyclic heteroarene 13505
                                      azole 12710
                                        thiazoles 1722
                                          1,3-thiazoles 1164
                                            1,3-thiazolium cation 31
                                              vitamin B1 31
                                                thiamine(1+) 31
                                                  benfotiamine 15
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