FADH2 (YMDB00597)

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Identification

YMDB ID

YMDB00597

Name

FADH2

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

FADH, also known as 1,5-dihydro-fad or FADH2, 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. FADH is a strong basic compound (based on its pKa). FADH exists in all living species, ranging from bacteria to humans. In yeast, FADH is involved in the metabolic pathway called the tca cycle pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

1,5-dihydro-FAD
1,5-dihydro-P-5-ester with adenosine
Adenosine 5-(trihydrogen pyrophosphate)
Dihydro-FAD
Dihydroflavine-adenine dinucleotide
FAD
FADH2
FDA
flavin adenine dinucleotide (reduced form)
Flavin adenine dinucleotide (reduced)
flavin adenine dinucleotide reduced
Reduced flavine adenine dinucleotide
1,5-Dihydro-riboflavin 5'-(trihydrogen diphosphate) p'->5'-ester with adenosine
Adenosine 5'-(trihydrogen pyrophosphate), 5'-5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine
Adenosine 5'-(trihydrogen pyrophosphate), 5'->5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine
Adenosine 5'-{3-[D-ribo-5-(7,8-dimethyl-2,4-dioxo-1,2,3,4,5,10-tetrahydrobenzo[g]pteridin-10-yl)-2,3,4-trihydroxypentyl] dihydrogen diphosphate}
Adenosine pyrophosphate 5'-5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine
Adenosine pyrophosphate, 5'-5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine
Adenosine pyrophosphate, 5'->5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine
Benzo[GR]pteridine riboflavin 5'-(trihydrogen diphosphate) deriv
Benzo[g]pteridine riboflavin 5'-(trihydrogen diphosphate) deriv

CAS number

1910-41-4

Weight

Average: 787.5656
Monoisotopic: 787.172784519

InChI Key

YPZRHBJKEMOYQH-UYBVJOGSSA-N

InChI

InChI=1S/C27H35N9O15P2/c1-10-3-12-13(4-11(10)2)35(24-18(32-12)25(42)34-27(43)33-24)5-14(37)19(39)15(38)6-48-52(44,45)51-53(46,47)49-7-16-20(40)21(41)26(50-16)36-9-31-17-22(28)29-8-30-23(17)36/h3-4,8-9,14-16,19-21,26,32,37-41H,5-7H2,1-2H3,(H,44,45)(H,46,47)(H2,28,29,30)(H2,33,34,42,43)/t14-,15+,16+,19-,20+,21+,26+/m0/s1

IUPAC Name

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[(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}(hydroxy)phosphoryl)oxy]phosphinic acid

Traditional IUPAC Name

fadh(.)

Chemical Formula

C₂₇H₃₅N₉O₁₅P₂

SMILES

CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC3=C1N=CN=C3N)C1=C(N2)C(=O)NC(=O)N1

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
Purine ribonucleoside diphosphate
Purine ribonucleoside monophosphate
Flavin
Pentose phosphate
Pentose-5-phosphate
Alkyldiarylamine
Glycosyl compound
N-glycosyl compound
6-aminopurine
Organic pyrophosphate
Pentose monosaccharide
Pteridine
Monosaccharide phosphate
Imidazopyrimidine
Purine
Aminopyrimidine
Monoalkyl phosphate
Pyrimidone
Imidolactam
Benzenoid
Phosphoric acid ester
Organic phosphoric acid derivative
N-substituted imidazole
Monosaccharide
Pyrimidine
Alkyl phosphate
Azole
Heteroaromatic compound
Tetrahydrofuran
Imidazole
Vinylogous amide
Urea
Lactam
Secondary alcohol
Secondary amine
Organoheterocyclic compound
Azacycle
Oxacycle
Polyol
Primary amine
Amine
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

flavin adenine dinucleotide (CHEBI:17877 )

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	3.39 g/L	ALOGPS
logP	-0.23	ALOGPS
logP	-4.8	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	1.85	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	355.76 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	188.8 m³·mol⁻¹	ChemAxon
Polarizability	69.69 Å³	ChemAxon
Number of Rings	6	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
Steroid biosynthesis	PW002482
Sulfur metabolism	PW002483
TCA Cycle	PW002377

KEGG Pathways

Fatty acid metabolism	ec00071
Oxidative phosphorylation	ec00190
Riboflavin metabolism	ec00740
Steroid biosynthesis	ec00100
Sulfur metabolism	ec00920

SMPDB Reactions

Succinic acid + Coenzyme Q10 + FAD ↔ Fumaric acid + QH2 + FADH2

KEGG Reactions

L-Aspartic acid + FAD → FADH2 + Iminoaspartic acid + hydron

Fumaric acid + FADH2 → FAD + Succinic acid

Glycerol 3-phosphate + FAD → FADH2 + Dihydroxyacetone phosphate

Ubiquinone-6 + FADH2 ↔ FAD + Ubiquinol-6

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	splash10-0g70-0024960400-5de09e4bdf0187b78529	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_10) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_11) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-0001200900-b0740b3d33d50996ccde	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000m-0105900000-3abff26d5bb35f8527b8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-0931700000-73f360589a13230eea7a	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0932110400-58a2ec43460cf9df1c4d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0930000000-15d7e9b22a8286323cc5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0960000000-64746c5025e9c53c89b3	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0159-1675510900-39158f1ef2e33daa689e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001l-4940100000-64cc07487da7b6c45ba2	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a7i-4900000000-4da9166c58a097f7d7ef	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0104000900-487b1a93da5295026592	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0964110400-9a24ca36f159cc16d182	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052u-0693100000-d2fe9957910ae7607fd3	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0000000900-5c202a395443de89e132	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-005i-9611010700-e3e8cae89c8f03508db4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05r0-9735640500-89a663c6bc64f3d8f9f1	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
1D NMR	1H 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:

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
Muratsubaki, H., Enomoto, K. (1998). "One of the fumarate reductase isoenzymes from Saccharomyces cerevisiae is encoded by the OSM1 gene." Arch Biochem Biophys 352:175-181.9587404

Synthesis Reference:

Kavakli I Halil; Sancar Aziz Analysis of the role of intraprotein electron transfer in photoreactivation by DNA photolyase in vivo. Biochemistry (2004), 43(48), 15103-10.

External Links:

Resource	Link
CHEBI ID	17877
HMDB ID	HMDB01197
Pubchem Compound ID	446013
Kegg ID	C01352
ChemSpider ID	25057974
FOODB ID	FDB030853
Wikipedia	FAD
BioCyc ID	FADH2

Enzymes

Protein Details

1. Glycerol-3-phosphate dehydrogenase, mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: sn-glycerol 3-phosphate + a quinone = glycerone phosphate + a quinol
Gene Name:: GUT2
Uniprot ID:: P32191
Molecular weight:: 72388.29688

Reactions

sn-glycerol 3-phosphate + a quinone → glycerone phosphate + a quinol.

Protein Details

2. 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

3. 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

4. Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial

General function:: Involved in 2 iron, 2 sulfur cluster binding
Specific function:: Subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q). SDH1 and SDH2 form the catalytic dimer. Electrons flow from succinate to the FAD bound to SDH1, and sequentially through the iron-sulfur clusters bound to SDH2 and enter the membrane dimer formed by SDH3 and SDH4
Gene Name:: SDH2
Uniprot ID:: P21801
Molecular weight:: 30230.90039

Reactions

Succinate + ubiquinone → fumarate + ubiquinol.

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:0xb0feaf28>

Enzymes

Reactions

Reactions

Reactions

Reactions

Transporters