FAD (YMDB00296)

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Identification

YMDB ID

YMDB00296

Name

FAD

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

FAD, also known as adeflavin or flamitajin b, 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. FAD is a strong basic compound (based on its pKa). FAD exists in all living species, ranging from bacteria to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

1H-Purin-6-amine flavin dinucleotide
1H-Purin-6-amine flavine dinucleotide
Adenine-flavin dinucleotide
Adenine-flavine dinucleotide
Adenine-riboflavin dinuceotide
Adenine-riboflavin dinucleotide
Adenine-riboflavine dinucleotide
FAD
Flamitajin B
Flanin F
Flavin adenine dinucleotide
flavin adenine dinucleotide oxidized
Flavin-adenine dinucleotide
Flavine adenosine diphosphate
Flavine-adenine dinucleotide
Flavitan
Flaziren
Isoalloxazine-adenine dinucleotide
Riboflavin 5'-adenosine diphosphate
Riboflavin-adenine dinucleotide
Riboflavine-adenine dinucleotide
Adenosine 5'-(trihydrogen pyrophosphate), 5'-5'-ester with riboflavine
Adenosine 5'-[3-(riboflavin-5'-yl) dihydrogen diphosphate]
Riboflavin 5'-(trihydrogen diphosphate), 5'-5'-ester with adenosine
Adeflavin
Adenosine 5'-(trihydrogen pyrophosphoric acid), 5'-5'-ester with riboflavine
Adenosine 5'-[3-(riboflavin-5'-yl) dihydrogen diphosphoric acid]
Riboflavin 5'-(trihydrogen diphosphoric acid), 5'-5'-ester with adenosine
Riboflavin 5'-adenosine diphosphoric acid
Dinucleotide, flavin-adenine

CAS number

146-14-5

Weight

Average: 785.5497
Monoisotopic: 785.157134455

InChI Key

VWWQXMAJTJZDQX-UYBVJOGSSA-N

InChI

InChI=1S/C27H33N9O15P2/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/h3-4,8-9,14-16,19-21,26,37-41H,5-7H2,1-2H3,(H,44,45)(H,46,47)(H2,28,29,30)(H,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-2H,3H,4H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid

Traditional IUPAC Name

flavine-adenine dinucleotide

Chemical Formula

C₂₇H₃₃N₉O₁₅P₂

SMILES

[H]O[C@]([H])(C([H])([H])OP(=O)(O[H])OP(=O)(O[H])OC([H])([H])[C@@]1([H])O[C@@]([H])(N2C([H])=NC3=C2N=C([H])N=C3N([H])[H])[C@]([H])(O[H])[C@]1([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
(3'->5')-dinucleotide
(3'->5')-dinucleotide or analogue
Purine ribonucleoside diphosphate
Purine ribonucleoside monophosphate
Flavin
Isoalloxazine
Pentose-5-phosphate
Pentose phosphate
Glycosyl compound
N-glycosyl compound
Diazanaphthalene
Pentose monosaccharide
Pteridine
6-aminopurine
Quinoxaline
Organic pyrophosphate
Monosaccharide phosphate
Imidazopyrimidine
Purine
Monoalkyl phosphate
Aminopyrimidine
Pyrimidone
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Imidolactam
Benzenoid
Alkyl phosphate
Phosphoric acid ester
Pyrimidine
Pyrazine
Tetrahydrofuran
Azole
Vinylogous amide
Heteroaromatic compound
Imidazole
Secondary alcohol
Lactam
Polyol
Oxacycle
Azacycle
Organoheterocyclic compound
Organic oxide
Organic oxygen compound
Organopnictogen compound
Organonitrogen compound
Hydrocarbon derivative
Primary amine
Alcohol
Amine
Organic nitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

flavin adenine dinucleotide (CHEBI:16238 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	5 mg/mL [HMP experimental]	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	4.25 g/L	ALOGPS
logP	-0.78	ALOGPS
logP	-4.7	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	1.85	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	356.42 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	177.43 m³·mol⁻¹	ChemAxon
Polarizability	70.53 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

Citric Acid Cycle	PW000952
Citric Acid Cycle 1434561204	PW000970
Fatty acid metabolism	PW002460
Oxidative phosphorylation	PW002461
Porphyrin Metabolism	PW002462

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

Adenosine triphosphate + Flavin Mononucleotide → Pyrophosphate + FAD

KEGG Reactions

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

Flavin Mononucleotide + Adenosine triphosphate + hydron → Pyrophosphate + FAD

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	splash10-0170-1032960400-cdd3286ebb1dea7c4f54	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 (TBDMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_5) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_6) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_7) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_8) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_9) - 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
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000j-0908600300-b1eccda8ebae8b9e4cc1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-bdb826f9c3cbc09eff9b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0019800000-00ad56b6b6a3bb4516e6	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000b-0009400000-667064ca470a5c341974	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000j-0509700500-8766cb874f927ed5a795	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-3125e04c09a14c62f22a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0019700000-78c46ea4b4f562757e56	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000b-0009400000-94b845d2c8d082b9484c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0000100900-6bac7b7f631dfc074a0c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0920000000-49c9d4fb9b57a59f45a5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-000i-0003900000-572f0b1bd59f71ab3c5f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-000i-0003900000-d2ede6a2e7183f1c32a3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0000100900-78554afbc26abe26af35	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0930000000-274da0a01c651b791733	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-000i-0003900000-55939cda9e14fc582757	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-000i-0003900000-db784762434fac3d351f	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0932110400-f05626487523221c34de	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0930000000-86c3d6490bc3a27e053a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052r-0980000000-58a46c839e0e520474d7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-8482400900-2c4839849821d2807c57	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001l-5920100000-b38889aa3d09576e2f3e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a7l-3900000000-f7144f6355fab252a516	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
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:

Not Available

External Links:

Resource	Link
CHEBI ID	16238
HMDB ID	HMDB01248
Pubchem Compound ID	439154
Kegg ID	C00016
ChemSpider ID	25059042
FOODB ID	FDB022511
Wikipedia	FAD
BioCyc ID	FAD

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. 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.

Protein Details

5. 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:0xaf6d3dc8>

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Transporters