CHEBI:17015 - riboflavin

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ChEBI Name riboflavin
ChEBI ID CHEBI:17015
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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:45214, CHEBI:15044, CHEBI:27299, CHEBI:8843, CHEBI:529204
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Formula C17H20N4O6
Net Charge 0
Average Mass 376.36390
Monoisotopic Mass 376.138
InChI 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
SMILES Cc1cc2nc3c(nc(=O)[nH]c3=O)n(C[C@H](O)[C@H](O)[C@H](O)CO)c2cc1C
Metabolite of Species Details
Mus musculus (NCBI:10090) Source: BioModels - MODEL1507180067 See: PubMed
Escherichia coli (NCBI:562) See: PubMed
Roles Classification
Biological Role(s): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
food colouring
A food additive that imparts colour to food. In European countries, E-numbers for permitted food colours are from E 100 to E 199, divided into yellows (E 100-109), oranges (E 110-119), reds (E 120-129), blues and violets (E 130-139), greens (E 140-149), browns and blacks (E 150-159), and others (E 160-199).
B vitamin
Any of the group of eight water-soluble vitamins originally thought to be a single compound (vitamin B) that play important roles in cell metabolism. The group comprises vitamin B1, B2, B3, B5, B6, B7, B9, and B12. (Around 20 other compounds were once thought to be B vitamins but are no longer classified as such.)
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): photosensitizing agent
A chemical compound that can be excited by light of a specific wavelength and subsequently transfer energy to a chosen reactant. This is commonly molecular oxygen within a cancer tissue, which is converted to (highly rective) singlet state oxygen. This rapidly reacts with any nearby biomolecules, ultimately killing the cancer cells.
food colouring
A food additive that imparts colour to food. In European countries, E-numbers for permitted food colours are from E 100 to E 199, divided into yellows (E 100-109), oranges (E 110-119), reds (E 120-129), blues and violets (E 130-139), greens (E 140-149), browns and blacks (E 150-159), and others (E 160-199).
B vitamin
Any of the group of eight water-soluble vitamins originally thought to be a single compound (vitamin B) that play important roles in cell metabolism. The group comprises vitamin B1, B2, B3, B5, B6, B7, B9, and B12. (Around 20 other compounds were once thought to be B vitamins but are no longer classified as such.)
View more via ChEBI Ontology
ChEBI Ontology
Outgoing riboflavin (CHEBI:17015) has role Escherichia coli metabolite (CHEBI:76971)
riboflavin (CHEBI:17015) has role B vitamin (CHEBI:75769)
riboflavin (CHEBI:17015) has role food colouring (CHEBI:77182)
riboflavin (CHEBI:17015) has role metabolite (CHEBI:25212)
riboflavin (CHEBI:17015) has role mouse metabolite (CHEBI:75771)
riboflavin (CHEBI:17015) has role photosensitizing agent (CHEBI:47868)
riboflavin (CHEBI:17015) is a flavin (CHEBI:30527)
riboflavin (CHEBI:17015) is conjugate acid of riboflavin(1−) (CHEBI:57986)
Incoming 7,8-didemethyl-8-hydroxy-5-deazariboflavin (CHEBI:43034) has functional parent riboflavin (CHEBI:17015)
dihydroriboflavins (CHEBI:15031) has functional parent riboflavin (CHEBI:17015)
riboflavin cyclic 4',5'-phosphate (CHEBI:15045) has functional parent riboflavin (CHEBI:17015)
riboflavin sodium phosphate (CHEBI:32098) has functional parent riboflavin (CHEBI:17015)
roseoflavin (CHEBI:72346) has functional parent riboflavin (CHEBI:17015)
vitamin B complex (CHEBI:75782) has part riboflavin (CHEBI:17015)
riboflavin(1−) (CHEBI:57986) is conjugate base of riboflavin (CHEBI:17015)
IUPAC Name
5-deoxy-5-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)-D-ribitol
INNs Sources
riboflavin ChemIDplus
riboflavina ChemIDplus
riboflavine ChemIDplus
riboflavinum ChemIDplus
Synonyms Sources
1-deoxy-1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)pentitol NIST Chemistry WebBook
6,7-dimethyl-9-D-ribitylisoalloxazine
Note: (2004-06-30) Uses obsolete isoalloxazine skeletal numbering system.
ChemIDplus
7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)benzo[g]pteridine-2,4(3H,10H)-dione ChEBI
7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)isoalloxazine ChemIDplus
7,8-Dimethyl-10-ribitylisoalloxazine KEGG COMPOUND
E101 ChEBI
Lactoflavin KEGG COMPOUND
riboflavin ChEMBL
Riboflavin KEGG COMPOUND
RIBOFLAVINE PDBeChem
Vitamin B2 KEGG COMPOUND
vitamin B2 ChEBI
vitamin G DrugBank
Database Links Databases
C00001552 KNApSAcK
C00255 KEGG COMPOUND
D00050 KEGG DRUG
DB00140 DrugBank
HMDB00244 HMDB
LSM-4084 LINCS
RBF PDBeChem
Riboflavin Wikipedia
RIBOFLAVIN MetaCyc
US2807611 Patent
US2876169 Patent
View more database links
Registry Numbers Types Sources
83-88-5 CAS Registry Number KEGG COMPOUND
83-88-5 CAS Registry Number NIST Chemistry WebBook
83-88-5 CAS Registry Number ChemIDplus
97831 Reaxys Registry Number Reaxys
97831 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
16658098 PubMed citation Europe PMC
22770225 PubMed citation Europe PMC
24643482 PubMed citation Europe PMC
25108762 PubMed citation Europe PMC
Last Modified
17 January 2017