FMNH2 (YMDB00686)

Identification

YMDB ID

YMDB00686

Name

FMNH2

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

FMNH2, also known as FMNH or reduced FMN, 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. FMNH2 exists in all living species, ranging from bacteria to plants to humans. Based on a literature review a significant number of articles have been published on FMNH2.

Structure

MOL SDF PDB SMILES InChI

Synonyms

1,5-dihydroriboflavin 5'-(dihydrogen phosphate)
flavin mononucleotide (reduced)
FMNH2
Reduced FMN
FMNH
1,5-Dihydroriboflavin 5'-(dihydrogen phosphoric acid)
Reduced flavin mononucleotide
Flavin mononucleotide hydroquinone

CAS number

Not Available

Weight

Average: 458.3597
Monoisotopic: 458.120264866

InChI Key

YTNIXZGTHTVJBW-SCRDCRAPSA-N

InChI

InChI=1S/C17H23N4O9P/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/h3-4,11-12,14,18,22-24H,5-6H2,1-2H3,(H2,27,28,29)(H2,19,20,25,26)/t11-,12+,14-/m0/s1

IUPAC Name

{[(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-1H,2H,3H,4H,5H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy}phosphonic acid

Traditional IUPAC Name

fmnh(.)

Chemical Formula

C₁₇H₂₃N₄O₉P

SMILES

CC1=C(C)C=C2N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(O)=O)C3=C(NC2=C1)C(=O)NC(=O)N3

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
Alkyldiarylamine
Monosaccharide phosphate
Pteridine
Pyrimidone
Monoalkyl phosphate
Monosaccharide
Organic phosphoric acid derivative
Phosphoric acid ester
Pyrimidine
Alkyl phosphate
Benzenoid
Vinylogous amide
Heteroaromatic compound
Urea
Secondary alcohol
Lactam
Secondary amine
Azacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Organonitrogen compound
Amine
Alcohol
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organic oxide
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

flavin mononucleotide (CHEBI:16048 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.64 g/L	ALOGPS
logP	-0.17	ALOGPS
logP	-1.1	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	1.5	ChemAxon
pKa (Strongest Basic)	-0.52	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	200.92 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	118.51 m³·mol⁻¹	ChemAxon
Polarizability	41.65 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
cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

Riboflavin metabolism

PW002443

KEGG Pathways

Riboflavin metabolism

ec00740

SMPDB Reactions

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

KEGG Reactions

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	splash10-0007-8985500000-75b16c96ea0f481a249b	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0a4i-3097008000-4a68372916e7237f45d3	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4l-0134900000-c067efd0cfc36a1e948b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-2391000000-d074adaacd074db90166	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-1290000000-c7e71e5446c90cf0229b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-06fr-9686800000-5cbc632057bde5fb7731	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002f-9130000000-c711ab545300e0d990b8	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-b1fb1fadd3de6e9ce4bb	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0003900000-159698f8e2f51a77a650	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01oy-2039100000-3d12d69e3f37a5d16d9d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4m-1091000000-4227f41a22b0e7dc3bdc	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-056r-9000800000-adceeefc6ce022df6b41	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-92fea992d3a941dc7202	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
1D NMR	1H 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
Sharp, R. E., Chapman, S. K., Reid, G. A. (1996). "Modulation of flavocytochrome b2 intraprotein electron transfer via an interdomain hinge region." Biochem J 316 ( Pt 2):507-513.8687394
Hazzard, J. T., McDonough, C. A., Tollin, G. (1994). "Intramolecular electron transfer in yeast flavocytochrome b2 upon one-electron photooxidation of the fully reduced enzyme: evidence for redox state control of heme-flavin communication." Biochemistry 33:13445-13454.7947753
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:

Not Available

External Links:

Resource	Link
CHEBI ID	16048
HMDB ID	HMDB0001142
Pubchem Compound ID	44229161
Kegg ID	C01847
ChemSpider ID	393046
FOODB ID	FDB022449
Wikipedia	Flavin_mononucleotide
BioCyc ID	FMNH2

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. 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.

Structure for #<Compound:0xa93bb63c>

Enzymes

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