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 376.369
Monoisotopic Mass 376.13828
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 CC1=C(C)C=C2N(C[C@H](O)[C@H](O)[C@H](O)CO)C3=NC(=O)NC(=O)C3=NC2=C1
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Mangifera indica (NCBI:txid29780) See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Homo sapiens (NCBI:txid9606) Found in blood (UBERON:0000178). See: Geigy Scientific Tables, 8th Rev edition, pp. 165-177. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp., Basel, Switzerland c1981-1992.
Homo sapiens (NCBI:txid9606) Found in saliva (UBERON:0001836). See: Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Homo sapiens (NCBI:txid9606) Found in urine (BTO:0001419). See: Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Homo sapiens (NCBI:txid9606) Found in cerebrospinal fluid (UBERON:0001359). See: PubMed
Homo sapiens (NCBI:txid9606) From MetaboLights See: MetaboLights Study
Homo sapiens (NCBI:txid9606) From MetaboLights See: MetaboLights Study
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
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).
cofactor
An organic molecule or ion (usually a metal ion) that is required by an enzyme for its activity. It may be attached either loosely (coenzyme) or tightly (prosthetic group).
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).
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
human urinary metabolite
Any metabolite (endogenous or exogenous) found in human urine samples.
fundamental metabolite
Any metabolite produced by all living cells.
water-soluble vitamin (role)
Any vitamin that dissolves in water and readily absorbed into tissues for immediate use. Unlike the fat-soluble vitamins, they are not stored in the body and need to be replenished regularly in the diet and will rarely accumulate to toxic levels since they are quickly excreted from the body via urine.
(via B vitamin )
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).
anti-inflammatory agent
Any compound that has anti-inflammatory effects.
nutraceutical
A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.
(via B vitamin )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing riboflavin (CHEBI:17015) has role Escherichia coli metabolite (CHEBI:76971)
riboflavin (CHEBI:17015) has role anti-inflammatory agent (CHEBI:67079)
riboflavin (CHEBI:17015) has role antioxidant (CHEBI:22586)
riboflavin (CHEBI:17015) has role cofactor (CHEBI:23357)
riboflavin (CHEBI:17015) has role food colouring (CHEBI:77182)
riboflavin (CHEBI:17015) has role fundamental metabolite (CHEBI:78675)
riboflavin (CHEBI:17015) has role human urinary metabolite (CHEBI:84087)
riboflavin (CHEBI:17015) has role mouse metabolite (CHEBI:75771)
riboflavin (CHEBI:17015) has role photosensitizing agent (CHEBI:47868)
riboflavin (CHEBI:17015) has role plant metabolite (CHEBI:76924)
riboflavin (CHEBI:17015) is a flavin (CHEBI:30527)
riboflavin (CHEBI:17015) is a vitamin B2 (CHEBI:176838)
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)
8-amino-8-demethylriboflavin (CHEBI:137336) has functional parent riboflavin (CHEBI:17015)
8-demethyl-8-(methylamino)riboflavin (CHEBI:137340) 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
1-deoxy-1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)-D-ribitol
INNs Sources
riboflavin WHO MedNet
riboflavina WHO MedNet
riboflavine WHO MedNet
riboflavinum WHO MedNet
Synonyms Sources
1-deoxy-1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)pentitol NIST Chemistry WebBook
5-deoxy-5-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)-D-ribitol ChEBI
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-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]benzo[g]pteridine-2,4(3H,10H)-dione IUPAC
7,8-dimethyl-10-ribitylisoalloxazine KEGG COMPOUND
E101 ChEBI
lactoflavin KEGG COMPOUND
riboflavin (vit B2) DrugCentral
Vitamin B2 KEGG COMPOUND
vitamin B2 ChEBI
vitamin G DrugBank
vitasan B2 ChemIDplus
Brand Names Sources
Aqua-Flave ChemIDplus
Beflavin ChemIDplus
Beflavine ChemIDplus
Bisulase KEGG DRUG
Dermadram ChemIDplus
Fiboflavin ChemIDplus
Flavaxin ChemIDplus
Flavin Bb ChemIDplus
Flaxain ChemIDplus
Hyflavin ChemIDplus
Manual Xrefs Databases
2834 DrugCentral
431981 ChemSpider
C00001552 KNApSAcK
C00255 KEGG COMPOUND
D00050 KEGG DRUG
DB00140 DrugBank
FDB012160 FooDB
HMDB0000244 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
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Last Modified
20 July 2021