Compound: riboflavin
SMILES: O=c1nc-2n(c3c(cc(C)c(c3)C)nc2c([nH]1)=O)C[C@H](O)[C@H](O)[C@H](O)CO
InChIKey: AUNGANRZJHBGPY-SCRDCRAPSA-N
Synonyms: riboflavin, vitamin B2, 83-88-5, Riboflavine, Lactoflavin, Vitamin G, Lactoflavine, Flavaxin, Beflavine, Beflavin, Riboderm, Ribipca, Lactobene, Ribocrisina, Riboflavina, Riboflavinum, Ribotone, Vitaflavine, Flaxain, Ribosyn, Ribovel, Vitamin Bi, Flavin BB, Russupteridine Yellow III, Vitasan B2, HYRE, Bisulase, Riboflavinequinone, 6,7-Dimethyl-9-D-ribitylisoalloxazine, 7,8-Dimethyl-10-ribitylisoalloxazine, Lacto-flavin, Fiboflavin, Dermadram, vitamin-b2, Aqua-Flave, C.I. Food Yellow 15, Vitamin B-2, E101, Ins no.101(iii), DTXSID8021777, Ins-101(iii), E-101(iii), TLM2976OFR, Vitamin b2 (as riboflavin), 7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]benzo[g]pteridine-2,4-dione, CHEBI:17015, 7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)isoalloxazine, INS NO. 101(I), Isoalloxazine, 7,8-dimethyl-10-D-ribityl-, C.I. 50900, 7,8-dimethyl-10-((2S,3S,4R)-2,3,4,5-tetrahydroxypentyl)benzo[g]pteridine-2,4(3H,10H)-dione, NSC-33298, NCI-0033298, DTXCID401777, Isoalloxazine, 7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)-, 7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione, Benzo(g)pteridine-2,4(3H,10H)-dione, 7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)-, Vitamin B 2, Freeda, vitaminum b2, 7,8-dimethyl-10-((2S,3S,4R)-2,3,4,5-tetrahydroxypentyl)benzo(g)pteridine-2,4-dione, 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)benzo[g]pteridine-2,4(3H,10H)-dione, 7,8-dimethyl-10-((2S,3S,4R)-2,3,4,5-tetrahydroxypentyl)-2H,3H,4H,10H-benzo(g)pteridine-2,4-dione, 7,8-dimethyl-10-((2S,3S,4R)-2,3,4,5-tetrahydroxypentyl)benzo(g)pteridine-2,4(3H,10H)-dione, PureVita Vitamin B2, RefChem:6201, A11HA04, S01XA26, 7,8-dimethyl-10-((2R,3R,4S)-2,3,4,5-tetrahydroxypentyl)benzo(g)pteridine-2,4-dione, CHEBI:176838, 201-507-1, NSC33298, (-)-riboflavin, Riboflavin (Vitamin B2), MFCD00005022, 1-Deoxy-1-(3,4-dihydro-7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10(2H)-yl)-D-ribitol, C17H20N4O6, 1-deoxy-1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)-D-ribitol, D-Ribitol, 1-deoxy-1-(3,4-dihydro-7,8-dimethyl-2,4-dioxobenzo(g)pteridin-10(2H)-yl)-, NSC 33298, Riboflavine [INN-French], Riboflavinum [INN-Latin], Riboflavina [INN-Spanish], HSDB 817, (?)-Riboflavin, Riboflavin (B2), CCRIS 1904, Riboflavin galactoside, Riboflavin (Vit B2), EINECS 201-507-1, UNII-TLM2976OFR, Riboflavin [USP:INN:BAN], AI3-14697, Riboflavin RS, Riboflavin CRS, 1kyv, 2ccb, 2vxa, ()-Riboflavin, San Yellow B, CAS-83-88-5, NCGC00017291-05, Bisulase (TN), Food Yellow 15, Prestwick_442, Riboflavin (Standard), Vitamin B2-Riboflavin, 2fl5, 2vx9, 4d1y, RIBOFLAVIN [II], RIBOFLAVIN [MI], RIBOFLAVIN [FCC], RIBOFLAVIN [INN], RIBOFLAVIN [JAN], Vitamin B2; E101, Prestwick3_000634, RIBOFLAVIN [HSDB], RIBOFLAVIN [VANDF], Epitope ID:161730, RIBOFLAVINUM [HPUS], RIBOFLAVIN [MART.], SCHEMBL7706, CHEMBL1534, RIBOFLAVIN [USP-RS], RIBOFLAVIN [WHO-DD], RIBOFLAVIN [WHO-IP], Riboflavin(vitamin B2)80%, VITAMIN B2 [VANDF], BSPBio_000628, MLS001066391, BPBio1_000692, GTPL6578, Riboflavin (JP18/USP/INN), RIBOFLAVINE; VITAMIN B2, RIBOFLAVIN [ORANGE BOOK], SCHEMBL29374783, HY-B0456R, MSK1505, RIBOFLAVIN [EP MONOGRAPH], VITAMIN B2 [GREEN BOOK], (-)-Riboflavin, 97-103%, GLXC-22603, HMS2096P10, RIBOFLAVIN [USP MONOGRAPH], ALBB-038639, Benzo[g]pteridine riboflavin deriv., HY-B0456, Riboflavin(B2);7,8-Dimethyl-10-((2S,3S,4R)-2,3,4,5-tetrahydroxypentyl)benzo[g]pteridine-2,4(3H,10H)-dione, RIBOFLAVINUM [WHO-IP LATIN], Tox21_110813, Tox21_111714, Tox21_201633, Tox21_302980, 6,7-Dimethyl-9-ribitylisoalloxazine, BDBM50362895, EBC-26847, s2540, Riboflavin (B2), analytical standard, Riboflavin for peak identification CRS, Tox21_111714_1, DB00140, FR15743, MR10472, NCGC00091288-01, NCGC00091288-02, NCGC00091288-03, NCGC00091288-04, NCGC00091288-05, NCGC00179498-01, NCGC00256408-01, NCGC00259182-01, AS-15936, SMR000112236, SY012957, R0020, (-)-Riboflavin, tested according to Ph.Eur., C00255, D00050, EN300-6477227, (-)-Riboflavin, meets USP testing specifications, Q130365, (-)-Riboflavin, from Eremothecium ashbyii, >=98%, W-104132, 7,8-DIMETHYL-10-(1'-D-RIBITYL)ISOALLOXAZINE, BRD-K92760278-001-06-5, BRD-K92760278-001-07-3, Riboflavin; Riboflavin Sodium Phosphate EP Impurity D, Z2216887959, RIBOFLAVIN SODIUM PHOSPHATE IMPURITY D [EP IMPURITY], Riboflavin, European Pharmacopoeia (EP) Reference Standard, Riboflavin, United States Pharmacopeia (USP) Reference Standard, benzo[g]pteridine-2,4(3H,10H)-dione, 7,8-dimethyl-10-ribityl-, Riboflavin, Pharmaceutical Secondary Standard; Certified Reference Material, 1-Deoxy-1-(4-hydroxy-7,8-dimethyl-2-oxobenzo[g]pteridin-10(2H)-yl)-D-ribitol, 5-deoxy-5-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)-D-ribitol, 7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)-Benzo[g]pteridine-2,4(3H,10H)-dione, Riboflavin for peak identification, European Pharmacopoeia (EP) Reference Standard, (-)-Riboflavin, 100 mug/mL (1% ammonium acetate in 50:50 methanol:water), certified reference material, ampule of 1 mL, (-)-Riboflavin, BioReagent, suitable for cell culture, suitable for insect cell culture, >=98%, 7,8-dimethyl-2,4-dioxo-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl](2,4a,10a-C,1,3-)-2H,3H,4H,10H-benzo[g]pteridin-3-yl, InChI=1/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/s
Theoretical properties:
molecular_formula: C17H20N4O6
molecular_weight: 376.4 g/mol
exact_mass: 376.13828437 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 5
hydrogen_bond_acceptor_count: 7
rotatable_bond_count: 5
heavy_atom_count: 27
topological_polar_surface_area: 155 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Fine orange-yellow needles from 2N acetic acid, alcohol, water, or pyridine ... three different crystal forms
color: Fine orange-yellow needles from 2N acetic acid, alcohol, water, or pyridine ... three different crystal forms
odor: Slight odor
Descriptions:
{"pubchem": "Riboflavin is 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. It has a role as an antioxidant, a cofactor, a photosensitizing agent, an anti-inflammatory agent, a mouse metabolite, a plant metabolite, an Escherichia coli metabolite, a food colouring, a fundamental metabolite and a human urinary metabolite. It is a vitamin B2 and a flavin. It is a conjugate acid of a riboflavin(1-).", "chebi": "<small>D</small>-Ribitol in which the hydroxy group at position 5 is substituted by a 7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[<em>g</em>]pteridin-10(2<em>H</em>)-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.", "chembl": "RIBOFLAVIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Riboflavin, also known as vitamin B2, is a vitamin found in food and sold as a dietary supplement. It is essential to the formation of two major coenzymes, flavin mononucleotide and flavin adenine dinucleotide. These coenzymes are involved in energy metabolism, cellular respiration, and antibody production, as well as normal growth and development. The coenzymes are also required for the metabolism of niacin, vitamin B6, and folate. Riboflavin is prescribed to treat corneal thinning, and taken orally, may reduce the incidence of migraine headaches in adults.\nRiboflavin deficiency is rare and is usually accompanied by deficiencies of other vitamins and nutrients. It may be prevented or treated by oral supplements or by injections. As a water-soluble vitamin, any riboflavin consumed in excess of nutritional requirements is not stored; it is either not absorbed or is absorbed and quickly excreted in urine, causing the urine to have a bright yellow tint. Natural sources of riboflavin include meat, fish and fowl, eggs, dairy products, green vegetables, mushrooms, and almonds. Some countries require its addition to grains.\nIn its purified, solid form, it is a water-soluble yellow-orange crystalline powder. In addition to its function as a vitamin, it is used as a food coloring agent. Biosynthesis takes place in bacteria, fungi and plants, but not animals. Industrial synthesis of riboflavin was initially achieved using a chemical process, but current commercial manufacturing relies on fermentation methods using strains of fungi and genetically modified bacteria.\nIn 2023, riboflavin was the 294th most commonly prescribed medication in the United States, with more than 400,000 prescriptions.\n\n"}