Record Information |
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Version | 1.0 |
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Creation date | 2015-05-07 20:19:11 UTC |
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Update date | 2019-11-26 03:21:55 UTC |
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Primary ID | FDB030862 |
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Secondary Accession Numbers | |
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Chemical Information |
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FooDB Name | FMN |
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Description | Flavin mononucleotide, also known as riboflavin 5'-monophosphate or riboflavine dihydrogen phosphate, is a member of the class of compounds known as flavin nucleotides. Flavin nucleotides are nucleotides containing a flavin moiety. Flavin is a compound that contains the tricyclic isoalloxazine ring system, which bears 2 oxo groups at the 2- and 4-positions. Flavin mononucleotide is practically insoluble (in water) and a moderately acidic compound (based on its pKa). Flavin mononucleotide can be found in a number of food items such as spinach, elliott's blueberry, tea leaf willow, and black mulberry, which makes flavin mononucleotide a potential biomarker for the consumption of these food products. Flavin mononucleotide can be found primarily in blood, as well as throughout most human tissues. Flavin mononucleotide exists in all living species, ranging from bacteria to humans. In humans, flavin mononucleotide is involved in several metabolic pathways, some of which include riboflavin metabolism, pyrimidine metabolism, beta-alanine metabolism, and doxorubicin metabolism pathway. Flavin mononucleotide is also involved in several metabolic disorders, some of which include beta ureidopropionase deficiency, UMP synthase deficiency (orotic aciduria), carnosinuria, carnosinemia, and hypophosphatasia. Moreover, flavin mononucleotide is found to be associated with anorexia nervosa. Flavin mononucleotide (FMN), or riboflavin-5′-phosphate, is a biomolecule produced from riboflavin (vitamin B2) by the enzyme riboflavin kinase and functions as prosthetic group of various oxidoreductases including NADH dehydrogenase as well as cofactor in biological blue-light photo receptors. During the catalytic cycle, a reversible interconversion of the oxidized (FMN), semiquinone (FMNH•) and reduced (FMNH2) forms occurs in the various oxidoreductases. FMN is a stronger oxidizing agent than NAD and is particularly useful because it can take part in both one- and two-electron transfers. In its role as blue-light photo receptor, (oxidized) FMN stands out from the 'conventional' photo receptors as the signaling state and not an E/Z isomerization . |
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CAS Number | 146-17-8 |
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Structure | |
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Synonyms | Synonym | Source |
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Riboflavin 5'-(dihydrogen phosphate) | ChEBI | Riboflavin 5'-monophosphate | ChEBI | Riboflavin 5'-phosphate | ChEBI | Riboflavin monophosphate | ChEBI | Riboflavin-5-phosphate | ChEBI | Riboflavine dihydrogen phosphate | ChEBI | Riboflavin 5'-(dihydrogen phosphoric acid) | Generator | Riboflavin 5'-monophosphoric acid | Generator | Riboflavin 5'-phosphoric acid | Generator | Riboflavin monophosphoric acid | Generator | Riboflavin-5-phosphoric acid | Generator | Riboflavine dihydrogen phosphoric acid | Generator | Flanin | HMDB | Flavine mononucleotide | HMDB | Flavol | HMDB | FMN | HMDB | Riboflavin | HMDB | Riboflavin mononucleotide | HMDB | Riboflavin phosphate | HMDB | Riboflavin-5'-phosphate na | HMDB | Riboflavine 5'-monophosphate | HMDB | Riboflavine 5'-phosphate | HMDB | Riboflavine monophosphate | HMDB | Riboflavine phosphate | HMDB | Riboflavine-5'-phosphate | HMDB | Vitamin b2 phosphate | HMDB | 5'-monoPhosphate, riboflavin | HMDB | 5'-Phosphate, riboflavin | HMDB | Flavin mononucleotide sodium salt | HMDB | Mononucleotide, riboflavin | HMDB | Flavin mononucleotide monosodium salt | HMDB | Flavin mononucleotide monosodium salt, dihydrate | HMDB | Phosphate, sodium riboflavin | HMDB | Riboflavin 5' phosphate | HMDB | Riboflavin phosphate, sodium | HMDB | Mononucleotide, flavin | HMDB | Riboflavin 5' monophosphate | HMDB | Flavin mononucleotide disodium salt | HMDB | Sodium riboflavin phosphate | HMDB |
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Predicted Properties | |
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Chemical Formula | C17H21N4O9P |
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IUPAC name | {[(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-2H,3H,4H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy}phosphonic acid |
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InChI Identifier | InChI=1S/C17H21N4O9P/c1-7-3-9-10(4-8(7)2)21(15-13(18-9)16(25)20-17(26)19-15)5-11(22)14(24)12(23)6-30-31(27,28)29/h3-4,11-12,14,22-24H,5-6H2,1-2H3,(H,20,25,26)(H2,27,28,29)/t11-,12+,14-/m0/s1 |
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InChI Key | FVTCRASFADXXNN-SCRDCRAPSA-N |
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Isomeric SMILES | CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(O)=O)C1=NC(=O)NC(=O)C1=N2 |
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Average Molecular Weight | 456.3438 |
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Monoisotopic Molecular Weight | 456.104614802 |
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Classification |
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Description | Belongs to the class of organic compounds known as flavin nucleotides. These are nucleotides containing a flavin moiety. Flavin is a compound that contains the tricyclic isoalloxazine ring system, which bears 2 oxo groups at the 2- and 4-positions. |
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Kingdom | Organic compounds |
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Super Class | Nucleosides, nucleotides, and analogues |
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Class | Flavin nucleotides |
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Sub Class | Not Available |
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Direct Parent | Flavin nucleotides |
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Alternative Parents | |
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Substituents | - Flavin nucleotide
- Flavin
- Isoalloxazine
- Diazanaphthalene
- Pteridine
- Quinoxaline
- Monoalkyl phosphate
- Pyrimidone
- Pyrazine
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Benzenoid
- Alkyl phosphate
- Pyrimidine
- Heteroaromatic compound
- Vinylogous amide
- Secondary alcohol
- Lactam
- Azacycle
- Polyol
- Organoheterocyclic compound
- Organooxygen compound
- Organonitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Alcohol
- Organic nitrogen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Industrial application: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | Not Available | |
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Melting Point | Not Available | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | Riboflavine 5'-(dihydrogen phosphate), non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-007d-6931400000-cad44822b1dfefb25732 | Spectrum | Predicted GC-MS | Riboflavine 5'-(dihydrogen phosphate), 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0592-6901126000-2ec87848003ebe8e438d | Spectrum | Predicted GC-MS | Riboflavine 5'-(dihydrogen phosphate), non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Riboflavine 5'-(dihydrogen phosphate), non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-0002-9000200000-bc07cc2b3950f70a9db3 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0002-9000200000-bc07cc2b3950f70a9db3 | Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 10V, positive | splash10-0a4i-0000900000-6e5ca4123f461d0e208d | Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 16V, positive | splash10-0a4i-0000900000-f1a0fdd1328522519b91 | Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 24V, positive | splash10-0a4r-2028900000-899e2dcd3bfb217b5766 | Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 32V, positive | splash10-052f-7289200000-ebb8d8c94ce8d3a5fb86 | Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 41V, positive | splash10-0006-9782000000-786258c7a5f6feda99e2 | Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 53V, positive | splash10-00dj-4910000000-e978502607653ec51659 | Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 66V, positive | splash10-006t-3900000000-cd1a65145bae541f2919 | Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 78V, positive | splash10-0002-3900000000-9be5fed1e1eb535085f6 | Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 91V, positive | splash10-0fr2-4900000000-d58071130f19cd6bc833 | Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 107V, positive | splash10-0ktb-7900000000-c3b2300acb88daf0d14f | Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 124V, positive | splash10-052b-9700000000-e2c1ef96f28d92a23db4 | Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 149V, positive | splash10-0kbb-9300000000-91cbf6b5c1f4e37d016a | Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 31V, positive | splash10-000i-0000900000-b60cf8984dd78397651e | Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 31V, positive | splash10-00kf-0096000000-9690dc0d4d8c890d6900 | Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 31V, positive | splash10-0fka-0960000000-6d860483a67d4bd784ab | Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 31V, positive | splash10-0002-0019000000-60cf80bbeab6e68f82d5 | Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 31V, positive | splash10-004i-0009000000-eea6861c71c50e5ce846 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-0134900000-c3ae39f771e510a09ae6 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-2391100000-1b8212d4ae35c1e1f1f2 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-1090000000-8948e075f379e327a852 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03kc-9251600000-e0759dcc125b6178b7f2 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004l-9120000000-656647e95148b2404066 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-4778caa348b1cda5e72c | Spectrum |
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NMR | |
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External Links |
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ChemSpider ID | Not Available |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | Not Available |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | Not Available |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | |
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