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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:riboflavin
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Accession:CHEBI:17015 term browser browse the term
Definition:D-Ribitol in which the hydroxy group at position 5 is substituted by a 7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl moiety. It is a nutritional factor found in milk, eggs, malted barley, liver, kidney, heart, and leafy vegetables, but the richest natural source is yeast. The free form occurs only in the retina of the eye, in whey, and in urine; its principal forms in tissues and cells are as flavin mononucleotide and flavin-adenine dinucleotide.
Synonyms:exact_synonym: 1-deoxy-1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)-D-ribitol
 related_synonym: 1-deoxy-1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)pentitol;   5-deoxy-5-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)-D-ribitol;   6,7-dimethyl-9-D-ribitylisoalloxazine;   7,8-Dimethyl-10-ribitylisoalloxazine;   7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)benzo[g]pteridine-2,4(3H,10H)-dione;   7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)isoalloxazine;   7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]benzo[g]pteridine-2,4(3H,10H)-dione;   Aqua-Flave;   Beflavin;   Beflavine;   Bisulase;   Dermadram;   E101;   Fiboflavin;   Flavaxin;   Flavin Bb;   Flaxain;   Formula=C17H20N4O6;   Hyflavin;   InChI=1S/C17H20N4O6/c1-7-3-9-10(4-8(7)2)21(5-11(23)14(25)12(24)6-22)15-13(18-9)16(26)20-17(27)19-15/h3-4,11-12,14,22-25H,5-6H2,1-2H3,(H,20,26,27)/t11-,12+,14-/m0/s1;   InChIKey=AUNGANRZJHBGPY-SCRDCRAPSA-N;   Lactoflavin;   SMILES=CC1=C(C)C=C2N(C[C@H](O)[C@H](O)[C@H](O)CO)C3=NC(=O)NC(=O)C3=NC2=C1;   riboflavin (vit B2);   riboflavina;   riboflavine;   riboflavinum;   vitamin B2;   vitamin G;   vitasan B2
 alt_id: CHEBI:15044;   CHEBI:27299;   CHEBI:45214;   CHEBI:529204;   CHEBI:8843
 xref: Beilstein:97831;   CAS:83-88-5;   Chemspider:431981;   DrugBank:DB00140;   Drug_Central:2834;   FooDB:FDB012160;   HMDB:HMDB0000244;   KEGG:C00255;   KEGG:D00050;   KNApSAcK:C00001552;   LINCS:LSM-4084
 xref_mesh: MESH:D012256
 xref: MetaCyc:RIBOFLAVIN;   PDBeChem:RBF;   PMID:10566553;   PMID:11399071;   PMID:11606856;   PMID:12083520;   PMID:12354259;   PMID:12927541;   PMID:14963913;   PMID:16273338;   PMID:16460756;   PMID:16658098;   PMID:182198;   PMID:18832377;   PMID:19169240;   PMID:19212411;   PMID:19854891;   PMID:22770225;   PMID:2369885;   PMID:23818044;   PMID:24643482;   PMID:24816110;   PMID:25108762;   PMID:25468971;   PMID:25887755;   PMID:2631092;   PMID:29937405;   PMID:3142982;   PMID:33154451;   PMID:33304888;   PMID:33886098;   PMID:33892358;   PMID:34156642;   PMID:3592624;   PMID:3878498;   PMID:4019261;   PMID:6475825;   PMID:6546833;   PMID:6650303;   PMID:7101408;   PMID:7883462;   PMID:8487103;   PMID:8604671;   PMID:8678471;   PMID:8976642;   PMID:9184778;   PMID:9808225;   PMID:9874201;   Patent:US2807611;   Patent:US2876169;   Reaxys:97831;   Wikipedia:Riboflavin
 cyclic_relationship: is_conjugate_acid_of CHEBI:57986


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riboflavin term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Akt1 AKT serine/threonine kinase 1 increases phosphorylation ISO Riboflavin analog results in increased phosphorylation of AKT1 protein; Riboflavin results in increased phosphorylation of AKT1 protein CTD PMID:20688149 NCBI chr 6:131,713,716...131,735,319
Ensembl chr 6:131,713,720...131,733,921
JBrowse link
G Aspm assembly factor for spindle microtubules affects expression ISO Riboflavin affects the expression of ASPM CTD PMID:20848206 NCBI chr13:51,074,849...51,123,755
Ensembl chr13:51,074,849...51,123,755
JBrowse link
G Bax BCL2 associated X, apoptosis regulator increases expression ISO Riboflavin results in increased expression of BAX protein CTD PMID:12654180 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 decreases expression ISO Riboflavin results in decreased expression of BCL2 protein CTD PMID:12654180 NCBI chr13:22,689,783...22,853,920 JBrowse link
G Birc5 baculoviral IAP repeat-containing 5 affects expression ISO Riboflavin affects the expression of BIRC5 CTD PMID:20848206 NCBI chr10:103,072,530...103,081,382
Ensembl chr10:103,073,408...103,081,380
JBrowse link
G Casp3 caspase 3 increases activity ISO Riboflavin analog results in increased activity of CASP3 protein CTD PMID:20688149 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648
JBrowse link
G Casp8 caspase 8 increases activity ISO Riboflavin analog results in increased activity of CASP8 protein CTD PMID:20688149 NCBI chr 9:60,263,863...60,312,542
Ensembl chr 9:60,264,075...60,312,542
JBrowse link
G Casp9 caspase 9 increases activity ISO Riboflavin analog results in increased activity of CASP9 protein CTD PMID:20688149 NCBI chr 5:154,108,872...154,126,628
Ensembl chr 5:154,109,046...154,126,626
JBrowse link
G Ccnb1 cyclin B1 affects expression ISO Riboflavin affects the expression of CCNB1 CTD PMID:20848206 NCBI chr 2:31,912,190...31,921,163
Ensembl chr 2:31,912,193...31,921,172
JBrowse link
G Cebpb CCAAT/enhancer binding protein beta increases expression EXP Riboflavin deficiency results in increased expression of CEBPB mRNA; Riboflavin deficiency results in increased expression of CEBPB protein CTD PMID:16856317 NCBI chr 3:156,398,035...156,399,466
Ensembl chr 3:156,397,052...156,399,473
JBrowse link
G Crp C-reactive protein multiple interactions ISO [Folic Acid co-treated with Riboflavin co-treated with Vitamin B 6 co-treated with Vitamin B 12] results in decreased expression of CRP protein; [Vitamin E co-treated with Ascorbic Acid co-treated with Folic Acid co-treated with Riboflavin co-treated with Vitamin B 6 co-treated with Vitamin B 12] results in decreased expression of CRP protein CTD PMID:16517955 NCBI chr13:85,131,635...85,175,179
Ensembl chr13:85,124,977...85,175,178
JBrowse link
G Ctnnb1 catenin beta 1 increases expression ISO Riboflavin analog results in increased expression of CTNNB1 protein CTD PMID:20688149 NCBI chr 8:120,640,008...120,667,110
Ensembl chr 8:120,639,995...120,667,111
JBrowse link
G Ddit3 DNA-damage inducible transcript 3 affects expression ISO Riboflavin affects the expression of DDIT3 CTD PMID:16109485 NCBI chr 7:63,115,645...63,121,203
Ensembl chr 7:63,116,380...63,121,201
JBrowse link
G Gsk3b glycogen synthase kinase 3 beta increases phosphorylation ISO Riboflavin analog results in increased phosphorylation of GSK3B protein; Riboflavin results in increased phosphorylation of GSK3B protein CTD PMID:20688149 NCBI chr11:62,498,997...62,648,665
Ensembl chr11:62,504,316...62,648,646
JBrowse link
G Gsr glutathione-disulfide reductase affects expression ISO Riboflavin affects the expression of GSR CTD PMID:16109485 NCBI chr16:58,482,209...58,525,256
Ensembl chr16:58,482,505...58,525,661
JBrowse link
G Il1b interleukin 1 beta multiple interactions ISO [Ubiquinone co-treated with Niacin co-treated with Riboflavin] promotes the reaction [Tamoxifen results in decreased expression of IL1B protein] CTD PMID:17516992 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 ISO [Ubiquinone co-treated with Niacin co-treated with Riboflavin] promotes the reaction [Tamoxifen results in decreased expression of IL6 protein] CTD PMID:17516992 NCBI chr 4:5,214,602...5,219,178
Ensembl chr 4:5,213,394...5,219,178
JBrowse link
G Iyd iodotyrosine deiodinase multiple interactions ISO Riboflavin inhibits the reaction [IYD protein results in increased metabolism of Monoiodotyrosine] CTD PMID:33352258 NCBI chr 1:40,003,999...40,019,323
Ensembl chr 1:40,004,041...40,019,319
JBrowse link
G Kif23 kinesin family member 23 affects expression ISO Riboflavin affects the expression of KIF23 CTD PMID:20848206 NCBI chr 8:62,397,908...62,425,162
Ensembl chr 8:62,397,948...62,425,072
JBrowse link
G Mmp9 matrix metallopeptidase 9 increases activity ISO Riboflavin analog results in increased activity of MMP9 protein; Riboflavin results in increased activity of MMP9 protein CTD PMID:20688149 NCBI chr 3:153,684,158...153,692,118
Ensembl chr 3:153,683,858...153,692,120
JBrowse link
G Mthfr methylenetetrahydrofolate reductase affects response to substance ISO MTHFR gene polymorphism affects the susceptibility to Riboflavin CTD PMID:17303386 NCBI chr 5:158,465,248...158,484,999
Ensembl chr 5:158,465,296...158,483,797
JBrowse link
G Myc MYC proto-oncogene, bHLH transcription factor increases expression ISO Riboflavin results in increased expression of MYC protein CTD PMID:12654180 NCBI chr 7:93,593,705...93,598,633
Ensembl chr 7:93,593,705...93,598,630
JBrowse link
G Nos2 nitric oxide synthase 2 multiple interactions ISO Lipopolysaccharides inhibits the reaction [Riboflavin results in increased expression of NOS2] CTD PMID:21356098 NCBI chr10:63,815,308...63,851,208
Ensembl chr10:63,815,308...63,851,210
JBrowse link
G Parp1 poly (ADP-ribose) polymerase 1 multiple interactions
increases cleavage
ISO [Niacin co-treated with Ubiquinone co-treated with Riboflavin] results in increased expression of PARP1 protein
Riboflavin analog results in increased cleavage of PARP1 protein
CTD PMID:18377693 PMID:20688149 NCBI chr13:92,307,593...92,339,406
Ensembl chr13:92,307,586...92,339,404
JBrowse link
G Plagl1 PLAG1 like zinc finger 1 affects expression ISO Riboflavin affects the expression of PLAGL1 CTD PMID:16109485 NCBI chr 1:7,477,295...7,517,229
Ensembl chr 1:7,477,177...7,517,228
JBrowse link
G Ppargc1a PPARG coactivator 1 alpha increases expression ISO Riboflavin results in increased expression of PPARGC1A mRNA CTD PMID:23056435 NCBI chr14:58,860,752...59,516,525
Ensembl chr14:58,861,144...59,512,656
JBrowse link
G Runx2 RUNX family transcription factor 2 increases expression ISO Riboflavin analog results in increased expression of RUNX2 protein CTD PMID:20688149 NCBI chr 9:16,167,504...16,492,826
Ensembl chr 9:16,167,482...16,492,167
JBrowse link
G Slc52a3 solute carrier family 52 member 3 multiple interactions
increases transport
EXP Acids promotes the reaction [SLC52A3 protein results in increased transport of Riboflavin]; Amiloride inhibits the reaction [SLC52A3 protein results in increased transport of Riboflavin]; Flavin Mononucleotide inhibits the reaction [SLC52A3 protein results in increased transport of Riboflavin]; Flavin-Adenine Dinucleotide inhibits the reaction [SLC52A3 protein results in increased transport of Riboflavin]; lumiflavin inhibits the reaction [SLC52A3 protein results in increased transport of Riboflavin] CTD PMID:19122205 NCBI chr 3:140,498,924...140,515,845
Ensembl chr 3:140,509,473...140,514,096
JBrowse link
G Tnf tumor necrosis factor multiple interactions ISO [Ubiquinone co-treated with Niacin co-treated with Riboflavin] promotes the reaction [Tamoxifen results in decreased expression of TNF protein]
Lipopolysaccharides inhibits the reaction [Riboflavin results in increased expression of TNF]
CTD PMID:17516992 PMID:21356098 NCBI chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629
JBrowse link
G Tnfsf11 TNF superfamily member 11 affects expression ISO Riboflavin analog affects the expression of TNFSF11 protein CTD PMID:20688149 NCBI chr15:53,674,990...53,705,171
Ensembl chr15:53,673,877...53,705,445
JBrowse link
G Tp53 tumor protein p53 increases expression ISO Riboflavin results in increased expression of TP53 protein CTD PMID:12654180 NCBI chr10:54,300,070...54,311,525
Ensembl chr10:54,300,048...54,311,524
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19821
    role 19769
      chemical role 19345
        antioxidant 14443
          riboflavin 31
            7,8-didemethyl-8-hydroxy-5-deazariboflavin + 0
            8-amino-8-demethylriboflavin + 0
            8-demethyl-8-(methylamino)riboflavin 0
            dihydroriboflavins + 0
            riboflavin cyclic 4',5'-phosphate 0
            riboflavin sodium phosphate 0
            roseoflavin 0
            vitamin B complex 0
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
                                      benzopteridine 35
                                        benzo[g]pteridine-2,4-dione 35
                                          isoalloxazine 34
                                            7,8-dimethylisoalloxazine 34
                                              flavin 34
                                                riboflavin 31
                                                  7,8-didemethyl-8-hydroxy-5-deazariboflavin + 0
                                                  8-amino-8-demethylriboflavin + 0
                                                  8-demethyl-8-(methylamino)riboflavin 0
                                                  dihydroriboflavins + 0
                                                  riboflavin cyclic 4',5'-phosphate 0
                                                  riboflavin sodium phosphate 0
                                                  roseoflavin 0
                                                  vitamin B complex 0
paths to the root