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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 chr14:104,769,349...104,795,748
Ensembl chr14:104,769,349...104,795,751 		JBrowse link
G ASPM assembly factor for spindle microtubules affects expression EXP Riboflavin affects the expression of ASPM CTD PMID:20848206 NCBI chr 1:197,084,127...197,146,669
Ensembl chr 1:197,084,121...197,146,694 		JBrowse link
G BAX BCL2 associated X, apoptosis regulator increases expression EXP Riboflavin results in increased expression of BAX protein CTD PMID:12654180 NCBI chr19:48,954,875...48,961,798
Ensembl chr19:48,954,815...48,961,798 		JBrowse link
G BCL2 BCL2 apoptosis regulator decreases expression EXP Riboflavin results in decreased expression of BCL2 protein CTD PMID:12654180 NCBI chr18:63,123,346...63,320,090
Ensembl chr18:63,123,346...63,320,128 		JBrowse link
G BIRC5 baculoviral IAP repeat containing 5 affects expression EXP Riboflavin affects the expression of BIRC5 CTD PMID:20848206 NCBI chr17:78,214,253...78,225,635
Ensembl chr17:78,214,186...78,225,636 		JBrowse link
G CASP3 caspase 3 increases activity ISO Riboflavin analog results in increased activity of CASP3 protein CTD PMID:20688149 NCBI chr 4:184,627,696...184,649,447
Ensembl chr 4:184,627,696...184,650,062 		JBrowse link
G CASP8 caspase 8 increases activity ISO Riboflavin analog results in increased activity of CASP8 protein CTD PMID:20688149 NCBI chr 2:201,233,463...201,287,711
Ensembl chr 2:201,233,443...201,361,836 		JBrowse link
G CASP9 caspase 9 increases activity ISO Riboflavin analog results in increased activity of CASP9 protein CTD PMID:20688149 NCBI chr 1:15,491,401...15,524,912
Ensembl chr 1:15,490,832...15,526,534 		JBrowse link
G CAT catalase multiple interactions ISO Riboflavin inhibits the reaction [Lipopolysaccharides results in decreased expression of CAT protein] CTD PMID:26360969 NCBI chr11:34,438,934...34,472,060
Ensembl chr11:34,438,934...34,472,060 		JBrowse link
G CCNB1 cyclin B1 affects expression EXP Riboflavin affects the expression of CCNB1 CTD PMID:20848206 NCBI chr 5:69,167,150...69,178,245
Ensembl chr 5:69,167,135...69,178,245 		JBrowse link
G CEBPB CCAAT enhancer binding protein beta increases expression ISO Riboflavin deficiency results in increased expression of CEBPB mRNA; Riboflavin deficiency results in increased expression of CEBPB protein CTD PMID:16856317 NCBI chr20:50,190,583...50,192,690
Ensembl chr20:50,190,830...50,192,668 		JBrowse link
G CRP C-reactive protein multiple interactions EXP [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 chr 1:159,712,289...159,714,589
Ensembl chr 1:159,712,289...159,714,589 		JBrowse link
G CTNNB1 catenin beta 1 increases expression ISO Riboflavin analog results in increased expression of CTNNB1 protein CTD PMID:20688149 NCBI chr 3:41,199,505...41,240,443
Ensembl chr 3:41,194,741...41,260,096 		JBrowse link
G CXCL8 C-X-C motif chemokine ligand 8 multiple interactions EXP [Ubiquinone co-treated with Niacin co-treated with Riboflavin] promotes the reaction [Tamoxifen results in decreased expression of CXCL8 protein] CTD PMID:17516992 NCBI chr 4:73,740,569...73,743,716
Ensembl chr 4:73,740,519...73,743,716 		JBrowse link
G DDIT3 DNA damage inducible transcript 3 affects expression EXP Riboflavin affects the expression of DDIT3 CTD PMID:16109485 NCBI chr12:57,516,588...57,520,517
Ensembl chr12:57,516,588...57,521,737 		JBrowse link
G GPX1 glutathione peroxidase 1 multiple interactions ISO Riboflavin inhibits the reaction [Lipopolysaccharides results in decreased activity of GPX1 protein] CTD PMID:26360969 NCBI chr 3:49,357,176...49,358,353
Ensembl chr 3:49,357,174...49,358,605 		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 chr 3:119,821,321...120,094,447
Ensembl chr 3:119,821,321...120,094,994 		JBrowse link
G GSR glutathione-disulfide reductase affects expression
multiple interactions		 EXP
ISO		 Riboflavin affects the expression of GSR
Riboflavin inhibits the reaction [Lipopolysaccharides results in decreased activity of GSR protein]		 CTD PMID:16109485 PMID:26360969 NCBI chr 8:30,678,066...30,727,846
Ensembl chr 8:30,678,066...30,727,846 		JBrowse link
G IL1B interleukin 1 beta multiple interactions EXP [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 2:112,829,751...112,836,779
Ensembl chr 2:112,829,751...112,836,816 		JBrowse link
G IL6 interleukin 6 multiple interactions EXP [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 7:22,727,200...22,731,998
Ensembl chr 7:22,725,884...22,732,002 		JBrowse link
G IYD iodotyrosine deiodinase multiple interactions EXP Riboflavin inhibits the reaction [IYD protein results in increased metabolism of Monoiodotyrosine] CTD PMID:33352258 NCBI chr 6:150,369,012...150,405,969
Ensembl chr 6:150,368,892...150,405,969 		JBrowse link
G KIF23 kinesin family member 23 affects expression EXP Riboflavin affects the expression of KIF23 CTD PMID:20848206 NCBI chr15:69,414,349...69,448,427
Ensembl chr15:69,414,246...69,448,427 		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 chr20:46,008,908...46,016,561
Ensembl chr20:46,008,908...46,016,561 		JBrowse link
G MPO myeloperoxidase multiple interactions ISO Riboflavin inhibits the reaction [Lipopolysaccharides results in increased activity of MPO protein] CTD PMID:26360969 NCBI chr17:58,269,855...58,280,935
Ensembl chr17:58,269,855...58,280,935 		JBrowse link
G MTHFR methylenetetrahydrofolate reductase affects response to substance EXP MTHFR gene polymorphism affects the susceptibility to Riboflavin CTD PMID:17303386 NCBI chr 1:11,785,723...11,805,964
Ensembl chr 1:11,785,723...11,806,455 		JBrowse link
G MYC MYC proto-oncogene, bHLH transcription factor increases expression EXP Riboflavin results in increased expression of MYC protein CTD PMID:12654180 NCBI chr 8:127,735,434...127,742,951
Ensembl chr 8:127,735,434...127,742,951 		JBrowse link
G NOS2 nitric oxide synthase 2 multiple interactions ISO Lipopolysaccharides inhibits the reaction [Riboflavin results in increased expression of NOS2]
Riboflavin inhibits the reaction [Lipopolysaccharides results in increased expression of NOS2 mRNA]		 CTD PMID:21356098 PMID:26360969 NCBI chr17:27,756,766...27,800,529
Ensembl chr17:27,756,766...27,800,529 		JBrowse link
G PARP1 poly(ADP-ribose) polymerase 1 multiple interactions
increases cleavage		 EXP
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 chr 1:226,360,691...226,408,093
Ensembl chr 1:226,360,210...226,408,154 		JBrowse link
G PLAGL1 PLAG1 like zinc finger 1 affects expression EXP Riboflavin affects the expression of PLAGL1 CTD PMID:16109485 NCBI chr 6:143,940,300...144,064,599
Ensembl chr 6:143,940,300...144,064,599 		JBrowse link
G PPARGC1A PPARG coactivator 1 alpha increases expression EXP Riboflavin results in increased expression of PPARGC1A mRNA CTD PMID:23056435 NCBI chr 4:23,792,021...24,472,905
Ensembl chr 4:23,755,041...23,904,089 		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 6:45,328,330...45,551,082
Ensembl chr 6:45,328,157...45,664,349 		JBrowse link
G SLC52A3 solute carrier family 52 member 3 multiple interactions
increases transport		 ISO 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 chr20:760,080...780,033
Ensembl chr20:760,080...776,015 		JBrowse link
G TNF tumor necrosis factor multiple interactions EXP
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 chr 6:31,575,565...31,578,336
Ensembl chr 6:31,575,565...31,578,336 		JBrowse link
G TNFSF11 TNF superfamily member 11 affects expression ISO Riboflavin analog affects the expression of TNFSF11 protein CTD PMID:20688149 NCBI chr13:42,562,736...42,608,013
Ensembl chr13:42,562,736...42,608,013 		JBrowse link
G TP53 tumor protein p53 increases expression EXP Riboflavin results in increased expression of TP53 protein CTD PMID:12654180 NCBI chr17:7,668,421...7,687,490
Ensembl chr17:7,661,779...7,687,538 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 26034
    role 25961
      chemical role 24242
        antioxidant 17487
          riboflavin 35
            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 26034
    subatomic particle 26009
      composite particle 26009
        hadron 26020
          baryon 26009
            nucleon 26009
              atomic nucleus 26009
                atom 26009
                  main group element atom 25834
                    p-block element atom 25834
                      carbon group element atom 25434
                        carbon atom 25403
                          organic molecular entity 25392
                            organic molecule 25222
                              organic cyclic compound 24274
                                organic heterocyclic compound 22328
                                  organic heteropolycyclic compound 21329
                                    organic heterotricyclic compound 15986
                                      benzopteridine 39
                                        benzo[g]pteridine-2,4-dione 39
                                          isoalloxazine 38
                                            7,8-dimethylisoalloxazine 38
                                              flavin 38
                                                riboflavin 35
                                                  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