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Identification
YMDB IDYMDB00296
NameFAD
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionFAD, 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
Thumb
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 number146-14-5
WeightAverage: 785.5497
Monoisotopic: 785.157134455
InChI KeyVWWQXMAJTJZDQX-UYBVJOGSSA-N
InChIInChI=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 Nameflavine-adenine dinucleotide
Chemical FormulaC27H33N9O15P2
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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassFlavin nucleotides
Sub ClassNot Available
Direct ParentFlavin 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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water Solubility5 mg/mL [HMP experimental]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility4.25 g/LALOGPS
logP-0.78ALOGPS
logP-4.7ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)1.85ChemAxon
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area356.42 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity177.43 m³·mol⁻¹ChemAxon
Polarizability70.53 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Citric Acid CyclePW000952 ThumbThumb?image type=greyscaleThumb?image type=simple
Citric Acid Cycle 1434561204PW000970 ThumbThumb?image type=greyscaleThumb?image type=simple
Fatty acid metabolismPW002460 ThumbThumb?image type=greyscaleThumb?image type=simple
Oxidative phosphorylationPW002461 ThumbThumb?image type=greyscaleThumb?image type=simple
Porphyrin MetabolismPW002462 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Fatty acid metabolismec00071 Map00071
Oxidative phosphorylationec00190 Map00190
Riboflavin metabolismec00740 Map00740
Steroid biosynthesisec00100 Map00100
Sulfur metabolismec00920 Map00920
SMPDB Reactions
Succinic acid + Coenzyme Q10 + FADFumaric acid + QH2 + FADH2
Adenosine triphosphate + Flavin MononucleotidePyrophosphate + FAD
KEGG Reactions
L-Aspartic acid + FADFADH2 + Iminoaspartic acid + hydron
Flavin Mononucleotide + Adenosine triphosphate + hydronPyrophosphate + FAD
Fumaric acid + FADH2FAD + Succinic acid
Glycerol 3-phosphate + FADFADH2 + Dihydroxyacetone phosphate
Ubiquinone-6 + FADH2FAD + Ubiquinol-6
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
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:
ResourceLink
CHEBI ID16238
HMDB IDHMDB01248
Pubchem Compound ID439154
Kegg IDC00016
ChemSpider ID25059042
FOODB IDFDB022511
WikipediaFAD
BioCyc IDFAD

Enzymes

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.
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.
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
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.
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

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