Riboflavin
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Basic Info
| Common Name | Riboflavin(F05527) |
| 2D Structure | |
| Description | Nutritional factor found in milk, eggs, malted barley, liver, kidney, heart, and leafy vegetables. The richest natural source is yeast. It occurs in the free form 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. |
| FRCD ID | F05527 |
| CAS Number | 83-88-5 |
| PubChem CID | 493570 |
| Formula | C17H20N4O6 |
| IUPAC Name | 7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]benzo[g]pteridine-2,4-dione |
| InChI Key | AUNGANRZJHBGPY-SCRDCRAPSA-N |
| 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 |
| Canonical SMILES | CC1=CC2=C(C=C1C)N(C3=NC(=O)NC(=O)C3=N2)CC(C(C(CO)O)O)O |
| Isomeric SMILES | CC1=CC2=C(C=C1C)N(C3=NC(=O)NC(=O)C3=N2)C[C@@H]([C@@H]([C@@H](CO)O)O)O |
| Wikipedia | Riboflavin |
| Synonyms |
Lactoflavine
riboflavin
vitamin B2
Lactoflavin
Riboflavine
Vitamin G
83-88-5
(-)-riboflavin
Beflavin
Beflavine
|
| Classifies |
Plant Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| 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. |
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 |
| Monoisotopic Mass | 376.138 |
| Exact Mass | 376.138 |
| XLogP | -1.5 |
| 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 |
ADMET
| 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 |
| 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 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Transcriptome Analysis of Hepatopancreas from the Cr (VI)-Stimulated Mantis Shrimp ( Oratosquilla oratoria) by Illumina Paired-End Sequencing: Assembly, Annotation, and Expression Analysis. | J Agric Food Chem | 2018 Mar 21 | 29425446 |
| Optimization of Effective Minerals on Riboflavin Production by Bacillus subtilis subsp. subtilis ATCC 6051 Using Statistical Designs. | Avicenna J Med Biotechnol | 2018 Jan-Mar | 29296267 |
| Molecular characterization of an unauthorized genetically modified Bacillussubtilis production strain identified in a vitamin B2 feed additive. | Food Chem | 2017 Sep 1 | 28407967 |
| Influence of protein deficient diet, vitamin B[sub]2[/sub] supplementation andphysical training on serum composition of polyunsaturated fatty acids (PUFAs) in rats. | Ann Agric Environ Med | 2017 May 11 | 28664691 |
| Bioproduction of riboflavin: a bright yellow history. | J Ind Microbiol Biotechnol | 2017 May | 27696023 |
| Usefulness of nutraceuticals in migraine prophylaxis. | Neurol Sci | 2017 May | 28527067 |
| Micronutrient-Fortified Milk and Academic Performance among Chinese Middle School Students: A Cluster-Randomized Controlled Trial. | Nutrients | 2017 Mar 2 | 28257107 |
| Factors stimulating riboflavin produced by Lactobacillus plantarum CRL 725 grown in a semi-defined medium. | J Basic Microbiol | 2017 Mar | 27966212 |
| Evaluation of Nutritional Composition of The Dried Seaweed Ulva lactuca fromPameungpeuk Waters, Indonesia. | Trop Life Sci Res | 2017 Jul | 28890765 |
| Nutrient Profiles and Volatile Odorous Compounds of Raw Milk After Exposure toElectron Beam Pasteurizing Doses. | J Food Sci | 2017 Jul | 28613401 |
| Physiochemical and cytotoxicity study of TPGS stabilized nanoemulsion designed by ultrasonication method. | Ultrason Sonochem | 2017 Jan | 27773233 |
| Electrochemical quantification of some water soluble vitamins in commercial multi-vitamin using poly-amino acid caped by graphene quantum dots nanocomposite as dual signal amplification elements. | Anal Biochem | 2017 Dec 15 | 29056522 |
| Low intakes of carotene, vitamin B2 , pantothenate and calcium predict cognitive decline among elderly patients with diabetes mellitus: The Japanese ElderlyDiabetes Intervention Trial. | Geriatr Gerontol Int | 2017 Aug | 27427336 |
| Bioavailability of Cu, Zn and Mn from Mineral Chelates or Blends of InorganicSalts in Growing Turkeys Fed with Supplemental Riboflavin and/or Pyridoxine. | Biol Trace Elem Res | 2016 Sep | 26781955 |
| Effects of calcium montmorillonite clay and aflatoxin exposure on dry matter intake, milk production, and milk composition. | J Dairy Sci | 2016 Feb | 26709170 |
| Effect of bovine ABCG2 polymorphism Y581S SNP on secretion into milk ofenterolactone, riboflavin and uric acid. | Animal | 2016 Feb | 26510964 |
| Comparative study of in vitro prooxidative properties and genotoxicity induced by aflatoxin B1 and its laccase-mediated detoxification products. | Chemosphere | 2015 Sep | 25876029 |
| Use of next generation sequencing data to develop a qPCR method for specificdetection of EU-unauthorized genetically modified Bacillus subtilis overproducingriboflavin. | BMC Biotechnol | 2015 Nov 11 | 26559764 |
| Effects of nutritional supplementation on fatigue, and autonomic and immunedysfunction in patients with end-stage renal disease: a randomized, double-blind,placebo-controlled, multicenter trial. | PLoS One | 2015 Mar 6 | 25746727 |
| Vitamin B₂ Sensitizes Cancer Cells to Vitamin-C-Induced Cell Death via Modulationof Akt and Bad Phosphorylation. | J Agric Food Chem | 2015 Aug 5 | 26165392 |
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
- Werner R, Manthey KC, Griffin JB, Zempleni J: HepG2 cells develop signs of riboflavin deficiency within 4 days of culture in riboflavin-deficient medium. J Nutr Biochem. 2005 Oct;16(10):617-24. [16081269 ]
- 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
- Russell TR, Demeler B, Tu SC: Kinetic mechanism and quaternary structure of Aminobacter aminovorans NADH:flavin oxidoreductase: an unusual flavin reductase with bound flavin. Biochemistry. 2004 Feb 17;43(6):1580-90. [14769034 ]
- 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 ]