Flavin Mononucleotide (YMDB00085)

Identification

YMDB ID

YMDB00085

Name

Flavin Mononucleotide

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Flavin mononucleotide, also known as riboflavin 5'-phosphate or flanin, 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. Flavin mononucleotide is an extremely weak basic (essentially neutral) compound (based on its pKa). Flavin mononucleotide exists in all living species, ranging from bacteria to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Flanin
Flavine mononucleotide
Flavol
FMN
Riboflavin
Riboflavin 5'-monophosphate
Riboflavin 5'-phosphate
Riboflavin Mononucleotide
Riboflavin monophosphate
Riboflavin phosphate
Riboflavin-5-phosphate
Riboflavin-5'-phosphate na
Riboflavine 5'-monophosphate
Riboflavine 5'-phosphate
Riboflavine dihydrogen phosphate
Riboflavine monophosphate
Riboflavine phosphate
Riboflavine-5'-phosphate
Vitamin B2 phosphate
Riboflavin 5'-(dihydrogen phosphate)
Riboflavin 5'-(dihydrogen phosphoric acid)
Riboflavin 5'-monophosphoric acid
Riboflavin 5'-phosphoric acid
Riboflavin monophosphoric acid
Riboflavin-5-phosphoric acid
Riboflavine dihydrogen phosphoric acid
5'-monoPhosphate, riboflavin
5'-Phosphate, riboflavin
Flavin mononucleotide sodium salt
Mononucleotide, riboflavin
Flavin mononucleotide monosodium salt
Flavin mononucleotide monosodium salt, dihydrate
Phosphate, sodium riboflavin
Riboflavin 5' phosphate
Riboflavin phosphate, sodium
Mononucleotide, flavin
Riboflavin 5' monophosphate
Flavin mononucleotide disodium salt
Sodium riboflavin phosphate

CAS number

146-17-8

Weight

Average: 456.3438
Monoisotopic: 456.104614802

InChI Key

FVTCRASFADXXNN-SCRDCRAPSA-N

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

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

Traditional IUPAC Name

riboflavin 5'-phosphate

Chemical Formula

C₁₇H₂₁N₄O₉P

SMILES

[H]O[C@]([H])(C([H])([H])OP(=O)(O[H])O[H])[C@@]([H])(O[H])[C@@]([H])(O[H])C([H])([H])N1C2=NC(=O)N([H])C(=O)C2=NC2=C1C([H])=C(C(=C2[H])C([H])([H])[H])C([H])([H])[H]

Chemical Taxonomy

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.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Flavin nucleotides

Sub Class

Not Available

Direct Parent

Flavin nucleotides

Alternative Parents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

flavin mononucleotide (CHEBI:17621 )

Physical Properties

State

Solid

Charge

Melting point

290 °C

Experimental Properties

Property	Value	Reference
Water Solubility	92 mg/mL [HMP experimental]	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.67 g/L	ALOGPS
logP	-0.78	ALOGPS
logP	-1	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	1.49	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	201.58 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	107.14 m³·mol⁻¹	ChemAxon
Polarizability	42.19 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

mitochondrion
extracellular
cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

Oxidative phosphorylation	PW002461
Pyrimidine metabolism	PW002469
Riboflavin metabolism	PW002443
Sulfur metabolism	PW002483

KEGG Pathways

Oxidative phosphorylation	ec00190
Pyrimidine metabolism	ec00240
Riboflavin metabolism	ec00740
Sulfur metabolism	ec00920

SMPDB Reactions

Adenosine triphosphate + Riboflavin → ADP + Flavin Mononucleotide

Adenosine triphosphate + Flavin Mononucleotide → Pyrophosphate + FAD

alkylsulfonate + FMNH2 + oxygen → Betaine aldehyde + Sulfite + Flavin Mononucleotide + water + hydron

KEGG Reactions

Flavin Mononucleotide + water Riboflavin + phosphate

Flavin Mononucleotide + Adenosine triphosphate + hydron → Pyrophosphate + FAD

NADH + Flavin Mononucleotide + hydron → NAD + FMNH2

Flavin Mononucleotide + NADPH + hydron → NADP + FMNH2

Fumaric acid + FMNH2 ↔ Flavin Mononucleotide + Succinic acid

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-007d-6931400000-cad44822b1dfefb25732	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0592-6901126000-2ec87848003ebe8e438d	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0002-9000200000-bc07cc2b3950f70a9db3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0002-9000200000-bc07cc2b3950f70a9db3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 10V, positive	splash10-0a4i-0000900000-6e5ca4123f461d0e208d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 16V, positive	splash10-0a4i-0000900000-f1a0fdd1328522519b91	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 24V, positive	splash10-0a4r-2028900000-899e2dcd3bfb217b5766	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 32V, positive	splash10-052f-7289200000-ebb8d8c94ce8d3a5fb86	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 41V, positive	splash10-0006-9782000000-786258c7a5f6feda99e2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 53V, positive	splash10-00dj-4910000000-e978502607653ec51659	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 66V, positive	splash10-006t-3900000000-cd1a65145bae541f2919	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 78V, positive	splash10-0002-3900000000-9be5fed1e1eb535085f6	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 91V, positive	splash10-0fr2-4900000000-d58071130f19cd6bc833	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 107V, positive	splash10-0ktb-7900000000-c3b2300acb88daf0d14f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 124V, positive	splash10-052b-9700000000-e2c1ef96f28d92a23db4	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 149V, positive	splash10-0kbb-9300000000-91cbf6b5c1f4e37d016a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 31V, positive	splash10-000i-0000900000-b60cf8984dd78397651e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 31V, positive	splash10-00kf-0096000000-9690dc0d4d8c890d6900	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 31V, positive	splash10-0fka-0960000000-6d860483a67d4bd784ab	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 31V, positive	splash10-0002-0019000000-60cf80bbeab6e68f82d5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 31V, positive	splash10-004i-0009000000-eea6861c71c50e5ce846	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0134900000-c3ae39f771e510a09ae6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-2391100000-1b8212d4ae35c1e1f1f2	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-1090000000-8948e075f379e327a852	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03kc-9251600000-e0759dcc125b6178b7f2	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004l-9120000000-656647e95148b2404066	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-4778caa348b1cda5e72c	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Wu, M., Repetto, B., Glerum, D. M., Tzagoloff, A. (1995). "Cloning and characterization of FAD1, the structural gene for flavin adenine dinucleotide synthetase of Saccharomyces cerevisiae." Mol Cell Biol 15:264-271.7799934
KEARNEY, E. B., ENGLARD, S. (1951). "The enzymatic phosphorylation of riboflavin." J Biol Chem 193:821-834.14907770
TSUBOI, K. K., WIENER, G., HUDSON, P. B. (1957). "Acid phosphatase. VII. Yeast phosphomonoesterase; isolation procedure and stability characteristics." J Biol Chem 224:621-635.13405892
Liger, D., Graille, M., Zhou, C. Z., Leulliot, N., Quevillon-Cheruel, S., Blondeau, K., Janin, J., van Tilbeurgh, H. (2004). "Crystal structure and functional characterization of yeast YLR011wp, an enzyme with NAD(P)H-FMN and ferric iron reductase activities." J Biol Chem 279:34890-34897.15184374

Synthesis Reference:

Ono, Shigeru; Hirano, Hiroko; Sato, Yoshiyuki. Formation of flavin adenine dinucleotide and flavin mononucleotide by lens homogenate. Experimental Eye Research (1982), 34(2), 297-301.

External Links:

Resource	Link
CHEBI ID	17621
HMDB ID	HMDB01520
Pubchem Compound ID	710
Kegg ID	C00061
ChemSpider ID	24608082
FOODB ID	FDB030862
Wikipedia	Flavin_mononucleotide
BioCyc ID	FMN

Enzymes

Protein Details

1. Putative nitronate monooxygenase

General function:: Involved in nitronate monooxygenase activity
Specific function:: Catalyzes the oxidation of alkyl nitronates to produce the corresponding carbonyl compounds and nitrites
Gene Name:: Not Available
Uniprot ID:: P47177
Molecular weight:: 45142.60156

Reactions

Ethylnitronate + O(2) + FMNH(2) → acetaldehyde + nitrite + FMN + H(2)O.

Protein Details

2. Pyridoxamine 5'-phosphate oxidase

General function:: Involved in pyridoxamine-phosphate oxidase activity
Specific function:: Catalyzes the oxidation of either pyridoxine 5'- phosphate (PNP) or pyridoxamine 5'-phosphate (PMP) into pyridoxal 5'-phosphate (PLP)
Gene Name:: PDX3
Uniprot ID:: P38075
Molecular weight:: 26908.0

Reactions

Pyridoxamine 5'-phosphate + H(2)O + O(2) → pyridoxal 5'-phosphate + NH(3) + H(2)O(2).
Pyridoxine 5'-phosphate + O(2) → pyridoxal 5'-phosphate + H(2)O(2).

Protein Details

3. Fumarate reductase

General function:: Involved in electron carrier activity
Specific function:: Could be a fumarate reductase
Gene Name:: Not Available
Uniprot ID:: P32614
Molecular weight:: 50843.69922

Reactions

Succinate + NAD(+) → fumarate + NADH.

Protein Details

4. Osmotic growth protein 1

General function:: Involved in electron carrier activity
Specific function:: Could be a fumarate reductase
Gene Name:: OSM1
Uniprot ID:: P21375
Molecular weight:: 55064.80078

Reactions

Protein Details

5. Acid phosphatase PHO11

General function:: Involved in acid phosphatase activity
Specific function:: A phosphate monoester + H(2)O = an alcohol + phosphate
Gene Name:: PHO11
Uniprot ID:: P35842
Molecular weight:: 52757.39844

Reactions

A phosphate monoester + H(2)O → an alcohol + phosphate.

Protein Details

6. Riboflavin kinase

General function:: Involved in riboflavin kinase activity
Specific function:: Catalyzes the phosphorylation of riboflavin (vitamin B2) to form flavin mononucleotide (FMN) coenzyme
Gene Name:: FMN1
Uniprot ID:: Q03778
Molecular weight:: 24536.90039

Reactions

ATP + riboflavin → ADP + FMN.

Protein Details

7. Repressible acid phosphatase

General function:: Involved in acid phosphatase activity
Specific function:: Partially mediates extracellular nucleotide derived phosphate hydrolysis along with NPP1 and NPP2
Gene Name:: PHO5
Uniprot ID:: P00635
Molecular weight:: 52858.10156

Reactions

A phosphate monoester + H(2)O → an alcohol + phosphate.

Protein Details

8. NAD(P)H-dependent FMN reductase LOT6

General function:: Involved in FMN reductase activity
Specific function:: Has several reductase activities that are NAD(P)H- dependent and involve FMN as a cofactor, ferricyanide being the best substrate for reduction. May be involved in ferric iron assimilation
Gene Name:: LOT6
Uniprot ID:: Q07923
Molecular weight:: 21280.40039

Reactions

FMNH(2) + NAD(P)(+) → FMN + NAD(P)H.

Protein Details

9. FAD synthase

General function:: Involved in catalytic activity
Specific function:: Catalyzes the adenylation of flavin mononucleotide (FMN) to form flavin adenine dinucleotide (FAD) coenzyme
Gene Name:: FAD1
Uniprot ID:: P38913
Molecular weight:: 35545.80078

Reactions

ATP + FMN → diphosphate + FAD.

Transporters

Protein Details

1. Mitochondrial FAD carrier protein FLX1

General function:: Involved in binding
Specific function:: Transport of FAD from the cytosol to the mitochondrial matrix
Gene Name:: FLX1
Uniprot ID:: P40464
Molecular weight:: 34408.89844

Structure for #<Compound:0xaf2d35e8>

Enzymes

Reactions

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Transporters