RIBOFLAVIN
Relevant Data
Food Additives Approved in the United States
Food Additives Approved by European Union:
General Information
| Chemical Names: | RIBOFLAVIN; 7,8-DIMETHYL-10-(1'-D-RIBITYL)ISOALLOXAZINE |
| CAS number: | 83-88-5 |
| INS: | 101(i) |
| Functional Class: |
Food Additives COLOUR |
From apps.who.int
Evaluations
| Evaluation year: | 1981 |
| ADI: | 0-0.5 mg/kg bw |
| Meeting: | 25 |
| Specs Code: | R (1987) |
| Comments: | Group ADI for riboflavin and riboflavin-5'-phosphate |
| Report: | TRS 669-JECFA 25/20 |
| Tox Monograph: | FAS 16-JECFA 25/181 |
| Specification: | COMPENDIUM ADDENDUM 10/FNP 52 Add.10/34 (METALS LIMITS) (2002). R; FAO JECFA Monographs 1 vol.3/243 |
From apps.who.int
GSFA Provisions for RIBOFLAVIN
| Number | Food Category | Max Level | Notes |
|---|---|---|---|
| 05.2 | Confectionery including hard and soft candy, nougats, etc. other than food categories 05.1, 05.3 and 05.4 |
1,000 mg/kg | Note XS309R |
| 09.2.4.1 | Cooked fish and fish products |
300 mg/kg | Note 95 |
| 08.4 | Edible casings (e.g. sausage casings) |
1,000 mg/kg | Note 16 |
| 09.3.1 | Fish and fish products, including mollusks, crustaceans, and echinoderms, marinated and/or in jelly |
300 mg/kg | Note 16 |
| 09.3.2 | Fish and fish products, including mollusks, crustaceans, and echinoderms, pickled and/or in brine |
300 mg/kg | Note 16 |
| 01.1.4 | Flavoured fluid milk drinks |
300 mg/kg | Note 52 |
| 10.1 | Fresh eggs |
300 mg/kg | Note 4 |
| 09.2.4.3 | Fried fish and fish products, including mollusks, crustaceans, and echinoderms |
300 mg/kg | Note 16 |
| 09.2.2 | Frozen battered fish, fish fillets, and fish products, including mollusks, crustaceans, and echinoderms |
300 mg/kg | Note XS166,Note 16 |
| 09.2.1 | Frozen fish, fish fillets, and fish products, including mollusks, crustaceans, and echinoderms |
1,000 mg/kg | Note XS315,Note XS165,Note XS95,Note XS36,Note 95,Note XS292,Note XS92,Note XS312,Note XS191,Note XS190 |
| 09.2.3 | Frozen minced and creamed fish products, including mollusks, crustaceans, and echinoderms |
300 mg/kg | Note 16 |
| 04.1.2.8 | Fruit preparations, including pulp, purees, fruit toppings and coconut milk |
300 mg/kg | Note 182 |
| 09.4 | Fully preserved, including canned or fermented fish and fish products, including mollusks, crustaceans, and echinoderms |
500 mg/kg | Note 95 |
| 06.4.3 | Pre-cooked pastas and noodles and like products |
300 mg/kg | Note 153 |
| 08.3 | Processed comminuted meat, poultry, and game products |
1,000 mg/kg | Note XS89,Note XS88,Note XS98,Note 16 |
| 08.2 | Processed meat, poultry, and game products in whole pieces or cuts |
1,000 mg/kg | Note XS97,Note XS96,Note 16 |
| 09.2.5 | Smoked, dried, fermented, and/or salted fish and fish products, including mollusks, crustaceans, and echinoderms |
300 mg/kg | Note XS311,Note 22 |
| 12.5 | Soups and broths |
200 mg/kg | Note 344 |
| 04.1.1.2 | Surface-treated fresh fruit |
300 mg/kg | Note 4,Note 16 |
| 04.2.1.2 | Surface-treated fresh vegetables (including mushrooms and fungi, roots and tubers, pulses and legumes, and aloe vera), seaweeds, and nuts and seeds |
300 mg/kg | Note 4,Note 16 |
| 04.2.2.6 | Vegetable (including mushrooms and fungi, roots and tubers, pulses and legumes, and aloe vera), seaweed, and nut and seed pulps and preparations (e.g. vegetable desserts and sauces, candied vegetables) other than food category 04.2.2.5 |
300 mg/kg | Note 92 |
From www.fao.org
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 493570 |
| IUPAC Name | 7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]benzo[g]pteridine-2,4-dione |
| 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 |
| InChI Key | AUNGANRZJHBGPY-SCRDCRAPSA-N |
| Canonical SMILES | CC1=CC2=C(C=C1C)N(C3=NC(=O)NC(=O)C3=N2)CC(C(C(CO)O)O)O |
| Molecular Formula | C17H20N4O6 |
| Wikipedia | riboflavin |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 376.369 |
| Hydrogen Bond Donor Count | 5 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 5 |
| Complexity | 680.0 |
| CACTVS Substructure Key Fingerprint | A A A D c e B 7 u A A A A A A A A A A A A A A A A A A A A A A A A A A w Q I A A A A A A A A C B A A A A H g A Q C A A A D B z h m A Y z w I P A A g C o A y d y d A C C A A E h A g A B i A E o d I i L c C r A 2 Z G U Y A h n h S L Z y A f w k I I O i A A A Q A A Q A C A Q A A C A A C A A Q A A A A A A A A A = = |
| Topological Polar Surface Area | 155.0 |
| Monoisotopic Mass | 376.138 |
| Exact Mass | 376.138 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 27 |
| Defined Atom Stereocenter Count | 3 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
From Pubchem
Food Additives Biosynthesis/Degradation
ADMET Predicted Profile --- Classification
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB- | 0.8495 |
| Human Intestinal Absorption | HIA+ | 0.9156 |
| Caco-2 Permeability | Caco2- | 0.7122 |
| P-glycoprotein Substrate | Substrate | 0.7414 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8708 |
| Non-inhibitor | 0.9466 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9279 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.3960 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7819 |
| CYP450 2D6 Substrate | Non-substrate | 0.8435 |
| CYP450 3A4 Substrate | Non-substrate | 0.5220 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.8531 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9071 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9516 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.7302 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8309 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9203 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9395 |
| Non-inhibitor | 0.5362 | |
| AMES Toxicity | Non AMES toxic | 0.8040 |
| Carcinogens | Non-carcinogens | 0.7954 |
| Fish Toxicity | Low FHMT | 0.5410 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9697 |
| Honey Bee Toxicity | Low HBT | 0.7948 |
| Biodegradation | Not ready biodegradable | 0.9641 |
| Acute Oral Toxicity | IV | 0.6176 |
| Carcinogenicity (Three-class) | Non-required | 0.6445 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.6043 | LogS |
| Caco-2 Permeability | 0.2634 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.6067 | LD50, mol/kg |
| Fish Toxicity | 1.7396 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.3393 | pIGC50, ug/L |
From admetSAR
Toxicity Profile
| Route of Exposure | Vitamin B2 is readily absorbed from the upper gastrointestinal tract. |
|---|---|
| Mechanism of Toxicity | Binds to riboflavin hydrogenase, riboflavin kinase, and riboflavin synthase. Riboflavin is the precursor of flavin mononucleotide (FMN, riboflavin monophosphate) and flavin adenine dinucleotide (FAD). The antioxidant activity of riboflavin is principally derived from its role as a precursor of FAD and the role of this cofactor in the production of the antioxidant reduced glutathione. Reduced glutathione is the cofactor of the selenium-containing glutathione peroxidases among other things. The glutathione peroxidases are major antioxidant enzymes. Reduced glutathione is generated by the FAD-containing enzyme glutathione reductase. |
| Metabolism | Hepatic. Half Life: 66-84 minutes |
| Toxicity Values | None |
| Lethal Dose | None |
| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
| Minimum Risk Level | None |
| Health Effects | None |
| Treatment | None |
| Reference |
|
From T3DB
Taxonomic Classification
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organoheterocyclic compounds |
| Class | Pteridines and derivatives |
| Subclass | Alloxazines and isoalloxazines |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Flavins |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Flavin - Diazanaphthalene - Quinoxaline - Pyrimidone - Pyrazine - Pyrimidine - Benzenoid - Heteroaromatic compound - Vinylogous amide - Secondary alcohol - Lactam - Polyol - Azacycle - Alcohol - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Primary alcohol - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as flavins. These are compounds containing a flavin (7,8-dimethyl-benzo[g]pteridine-2,4-dione) moiety, with a structure characterized by an isoalloaxzine tricyclic ring. |
From ClassyFire
Targets
- General Function:
- Riboflavin kinase activity
- Specific Function:
- Catalyzes the phosphorylation of riboflavin (vitamin B2) to form flavin-mononucleotide (FMN), hence rate-limiting enzyme in the synthesis of FAD. Essential for TNF-induced reactive oxygen species (ROS) production. Through its interaction with both TNFRSF1A and CYBA, physically and functionally couples TNFRSF1A to NADPH oxidase. TNF-activation of RFK may enhance the incorporation of FAD in NADPH oxidase, a critical step for the assembly and activation of NADPH oxidase.
- Gene Name:
- RFK
- Uniprot ID:
- Q969G6
- Molecular Weight:
- 17623.08 Da
References
- Hirano G, Izumi H, Yasuniwa Y, Shimajiri S, Ke-Yong W, Sasagiri Y, Kusaba H, Matsumoto K, Hasegawa T, Akimoto M, Akashi K, Kohno K: Involvement of riboflavin kinase expression in cellular sensitivity against cisplatin. Int J Oncol. 2011 Apr;38(4):893-902. doi: 10.3892/ijo.2011.938. Epub 2011 Feb 9. [21308351 ]
- General Function:
- Riboflavin reductase (nadph) activity
- Specific Function:
- Broad specificity oxidoreductase that catalyzes the NADPH-dependent reduction of a variety of flavins, such as riboflavin, FAD or FMN, biliverdins, methemoglobin and PQQ (pyrroloquinoline quinone). Contributes to heme catabolism and metabolizes linear tetrapyrroles. Can also reduce the complexed Fe(3+) iron to Fe(2+) in the presence of FMN and NADPH. In the liver, converts biliverdin to bilirubin.
- Gene Name:
- BLVRB
- Uniprot ID:
- P30043
- Molecular Weight:
- 22119.215 Da
References
- van Pee KH, Patallo EP: Flavin-dependent halogenases involved in secondary metabolism in bacteria. Appl Microbiol Biotechnol. 2006 May;70(6):631-41. Epub 2006 Mar 17. [16544142 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
- Gene Name:
- AR
- Uniprot ID:
- P10275
- Molecular Weight:
- 98987.9 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RXR/RAR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. In the absence of ligand, the RXR-RAR heterodimers associate with a multiprotein complex containing transcription corepressors that induce histone acetylation, chromatin condensation and transcriptional suppression. On ligand binding, the corepressors dissociate from the receptors and associate with the coactivators leading to transcriptional activation. RARA plays an essential role in the regulation of retinoic acid-induced germ cell development during spermatogenesis. Has a role in the survival of early spermatocytes at the beginning prophase of meiosis. In Sertoli cells, may promote the survival and development of early meiotic prophase spermatocytes. In concert with RARG, required for skeletal growth, matrix homeostasis and growth plate function (By similarity). Regulates expression of target genes in a ligand-dependent manner by recruiting chromatin complexes containing KMT2E/MLL5. Mediates retinoic acid-induced granulopoiesis.
- Gene Name:
- RARA
- Uniprot ID:
- P10276
- Molecular Weight:
- 50770.805 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Riboflavin synthase activity
- Specific Function:
- Catalyzes the dismutation of two molecules of 6,7-dimethyl-8-ribityllumazine, resulting in the formation of riboflavin and 5-amino-6-(D-ribitylamino)uracil.
- Gene Name:
- ribC
- Uniprot ID:
- P0AFU8
- Molecular Weight:
- 23444.77 Da
From T3DB