FMN (CHEBI:17621)

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CHEBI:17621 - FMN

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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	ZINC000003831425

Download	Molfile XML SDF

more structures >>

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Marvin 09020811533D

52 54 0 0 1 0 999 V2000

2.4433 -1.5288 -0.7521 C 0 0 0 0 0 0 0 0 0 0 0 0

2.9264 -2.5910 -1.5169 C 0 0 0 0 0 0 0 0 0 0 0 0

1.1190 -1.2944 -0.7250 N 0 0 0 0 0 0 0 0 0 0 0 0

2.1189 -3.2139 -2.3030 N 0 0 0 0 0 0 0 0 0 0 0 0

0.3072 -1.8141 -1.7126 C 0 0 0 0 0 0 0 0 0 0 0 0

0.8369 -2.8958 -2.4668 C 0 0 0 0 0 0 0 0 0 0 0 0

3.3167 -0.8607 -0.0606 N 0 0 0 0 0 0 0 0 0 0 0 0

5.0425 -2.1766 -0.6530 N 0 0 0 0 0 0 0 0 0 0 0 0

4.2555 -2.9221 -1.3968 C 0 0 0 0 0 0 0 0 0 0 0 0

4.5976 -1.1256 -0.0081 C 0 0 0 0 0 0 0 0 0 0 0 0

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0.0489 -3.6295 -3.3661 C 0 0 0 0 0 0 0 0 0 0 0 0

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5.3450 -0.4208 0.6502 O 0 0 0 0 0 0 0 0 0 0 0 0

-3.2527 -1.6855 -3.0783 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.1009 -4.1682 -4.4853 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.0319 2.8717 2.1571 C 0 0 2 0 0 0 0 0 0 0 0 0

-0.2816 1.4383 1.6026 C 0 0 2 0 0 0 0 0 0 0 0 0

0.8639 0.7680 0.8000 C 0 0 2 0 0 0 0 0 0 0 0 0

0.5517 -0.7224 0.4510 C 0 0 0 0 0 0 0 0 0 0 0 0

1.1097 2.9155 3.0162 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.4544 1.4368 0.7814 O 0 0 0 0 0 0 0 0 0 0 0 0

2.0514 0.8402 1.5896 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.2708 3.3313 2.9609 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.1701 4.5679 3.4589 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.3894 4.4616 5.4738 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.7237 6.5610 4.6070 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.1736 5.2363 4.2751 P 0 0 1 0 0 0 0 0 0 0 0 0

-3.4120 5.3400 3.5439 O 0 0 0 0 0 0 0 0 0 0 0 0

5.9467 -2.4028 -0.5756 H 0 0 0 0 0 0 0 0 0 0 0 0

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0.4794 -4.4197 -3.8543 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.7628 -1.7060 -2.1128 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.8591 -2.2797 -3.7610 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.2676 -0.6611 -3.4550 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.4788 -3.5892 -5.3289 H 0 0 0 0 0 0 0 0 0 0 0 0

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0.1550 3.5557 1.3245 H 0 0 0 0 0 0 0 0 0 0 0 0

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1.8485 0.3361 2.4071 H 0 0 0 0 0 0 0 0 0 0 0 0

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7 1 2 0 0 0 0

2 1 1 0 0 0 0

9 2 1 0 0 0 0

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5 3 1 0 0 0 0

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30 28 1 0 0 0 0

30 29 1 0 0 0 0

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8 32 1 0 0 0 0

11 33 1 0 0 0 0

12 34 1 0 0 0 0

17 35 1 0 0 0 0

17 36 1 0 0 0 0

17 37 1 0 0 0 0

18 38 1 0 0 0 0

18 39 1 0 0 0 0

18 40 1 0 0 0 0

19 41 1 0 0 0 0

20 42 1 0 0 0 0

21 43 1 0 0 0 0

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25 48 1 0 0 0 0

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M END): 16 ms

reading 52 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

52 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

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Wikipedia	License
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, various oxidoreductases induce reversible interconversions between the oxidized (FMN), semiquinone (FMNH•), and reduced (FMNH2) forms of the isoalloxazine core. 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.
Read full article at Wikipedia

Formula

C17H21N4O9P

Net Charge

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

Ravi G, Venkatesh YP (2014)
Recognition of riboflavin and the capsular polysaccharide of Haemophilus influenzae type b by antibodies generated to the haptenic epitope D-ribitol.
Glycoconjugate journal 31, 247-258 [PubMed:24643482]
[show Abstract]

Ravi G, Venkatesh YP (2014)
Recognition of flavin mononucleotide, Haemophilus influenzae type b and its capsular polysaccharide vaccines by antibodies specific to D-ribitol-5-phosphate.
Glycoconjugate journal 31, 573-585 [PubMed:25108762]
[show Abstract]

Lienhart WD, Gudipati V, Macheroux P (2013)
The human flavoproteome.
Archives of biochemistry and biophysics 535, 150-162 [PubMed:23500531]
[show Abstract]

Li W, Chen L, Lu C, Elmore BO, Astashkin AV, Rousseau DL, Yeh SR, Feng C (2013)
Regulatory role of Glu546 in flavin mononucleotide-heme electron transfer in human inducible nitric oxide synthase.
Inorganic chemistry 52, 4795-4801 [PubMed:23570607]
[show Abstract]

RAO NA, FELTON SP, HUENNEKENS FM, MACKLER B (1963)
Flavin mononucleotide: the coenzyme of reduced diphosphopyridine nucleotide dehydrogenase.
The Journal of biological chemistry 238, 449-455 [PubMed:13973054]

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.

CHEBI:17621 - FMN

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