CHEBI:17621 - FMN

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name FMN
ChEBI ID CHEBI:17621
Definition A flavin mononucleotide that is riboflavin (vitamin B2) in which the primary hydroxy group has been converted to its dihydrogen phosphate ester.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:42587, CHEBI:4960, CHEBI:13317, CHEBI:21127
Supplier Information ChemicalBook:CB8186041, eMolecules:525723, ZINC000003831040
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Flavin mononucleotide (FMN), or riboflavin-5′-phosphate, is a biomolecule produced from riboflavin (vitamin B2) by the enzyme riboflavin kinase and functions as the prosthetic group of various oxidoreductases, including NADH dehydrogenase, as well as a 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. It is the principal form in which riboflavin is found in cells and tissues. It requires more energy to produce, but is more soluble than riboflavin. In cells, FMN occurs freely circulating but also in several covalently bound forms. Covalently or non-covalently bound FMN is a cofactor of many enzymes playing an important pathophysiological role in cellular metabolism. For example dissociation of flavin mononucleotide from mitochondrial complex I has been shown to occur during ischemia/reperfusion brain injury during stroke.
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Formula C17H21N4O9P
Net Charge 0
Average Mass 456.344
Monoisotopic Mass 456.10462
InChI 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
InChIKey FVTCRASFADXXNN-SCRDCRAPSA-N
SMILES C12=NC(NC(C1=NC=3C(N2C[C@@H]([C@@H]([C@@H](COP(=O)(O)O)O)O)O)=CC(=C(C3)C)C)=O)=O
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Homo sapiens (NCBI:txid9606) See: PubMed
Roles Classification
Biological Role(s): coenzyme
A low-molecular-weight, non-protein organic compound participating in enzymatic reactions as dissociable acceptor or donor of chemical groups or electrons.
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).
(via flavin mononucleotide )
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
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): 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 FMN (CHEBI:17621) has role bacterial metabolite (CHEBI:76969)
FMN (CHEBI:17621) has role coenzyme (CHEBI:23354)
FMN (CHEBI:17621) has role cofactor (CHEBI:23357)
FMN (CHEBI:17621) has role human metabolite (CHEBI:77746)
FMN (CHEBI:17621) has role mouse metabolite (CHEBI:75771)
FMN (CHEBI:17621) is a flavin mononucleotide (CHEBI:24041)
FMN (CHEBI:17621) is a vitamin B2 (CHEBI:176838)
FMN (CHEBI:17621) is conjugate acid of FMN(3−) (CHEBI:58210)
Incoming 8-carboxy-8-demethylriboflavin 5'-phosphate (CHEBI:140157) has functional parent FMN (CHEBI:17621)
8-formyl-8-demethylriboflavin 5'-phosphate (CHEBI:140156) has functional parent FMN (CHEBI:17621)
FMN-N5-peroxide(2−) (CHEBI:176498) has functional parent FMN (CHEBI:17621)
FMN-L-threonine (CHEBI:74347) has functional parent FMN (CHEBI:17621)
prenyl-FMN (CHEBI:87749) has functional parent FMN (CHEBI:17621)
FMN(3−) (CHEBI:58210) is conjugate base of FMN (CHEBI:17621)
IUPAC Name
1-deoxy-1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)-5-O-phosphono-D-ribitol
Synonyms Sources
Flavin mononucleotide KEGG COMPOUND
FLAVIN MONONUCLEOTIDE PDBeChem
FMN KEGG COMPOUND
riboflavin 5'-(dihydrogen phosphate) ChemIDplus
riboflavin 5'-monophosphate ChemIDplus
riboflavin 5'-phosphate ChemIDplus
riboflavin monophosphate ChemIDplus
Riboflavin-5-phosphate KEGG COMPOUND
riboflavine dihydrogen phosphate ChemIDplus
Manual Xrefs Databases
2374 DrugCentral
C00019686 KNApSAcK
C00061 KEGG COMPOUND
DB03247 DrugBank
Flavin_mononucleotide Wikipedia
FMN PDBeChem
HMDB0001520 HMDB
MOL000043 COMe
US2535385 Patent
US2610179 Patent
US2740775 Patent
US3118876 Patent
View more database links
Registry Numbers Types Sources
146-17-8 CAS Registry Number KEGG COMPOUND
146-17-8 CAS Registry Number ChemIDplus
477717 Gmelin Registry Number Gmelin
68086 Reaxys Registry Number Reaxys
Citations Types Sources
13973054 PubMed citation Europe PMC
23500531 PubMed citation Europe PMC
23570607 PubMed citation Europe PMC
24643482 PubMed citation Europe PMC
25108762 PubMed citation Europe PMC
Last Modified
20 July 2021
General Comment
2011-03-18 A coenzyme for a number of oxidative enzymes including NADH dehydrogenase, FMN is the principal form in which riboflavin is found in cells and tissues.