Common NameFad
DescriptionFlavin adenine dinucleotide (FAD) is a redox-active coenzyme associated with various proteins, which is involved with several enzymatic reactions in metabolism. 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 drug which is used to treat eye diseases caused by vitamin b2 deficiency, such as keratitis and blepharitis. FAD exists in all living species, ranging from bacteria to humans. In humans, FAD is involved in the metabolic disorder called the medium chain acyl-coa dehydrogenase deficiency (mcad) pathway. Outside of the human body, FAD has been detected, but not quantified in several different foods, such as other bread, passion fruits, asparagus, kelps, and green bell peppers. It is a flavoprotein in which the substituent at position 10 of the flavin nucleus is a 5'-adenosyldiphosphoribityl group.
Structure
Molecular FormulaC27H33N9O15P2
Average Mass785.54970
Monoisotopic Mass785.15713
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 Name[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy({[(2r,3s,4s)-5-{7,8-dimethyl-2,4-dioxo-3h-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy(hydroxy)phosphoryl}oxy)phosphinic acid
CAS Registry Number146-14-5
SMILESCc1cc2nc3c(=O)[n-]c(=O)nc-3n(C[C@H](O)[C@H](O)[C@H](O)COP(=O)([O-])OP(=O)([O-])OC[C@H]3O[C@@H](n4cnc5c(N)ncnc54)[C@H](O)[C@@H]3O)c2cc1C
InChI IdentifierInChI=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
InChI KeyVWWQXMAJTJZDQX-UYBVJOGSSA-N
CHEBI IDCHEBI:57692
HMDB IDHMDB0001248
Pathways
NameSMPDB/PathBank
Glutathione metabolism
Arginine and proline metabolism
beta-Alanine metabolism
One carbon pool by folate
Lysine degradation
Valine, leucine and isoleucine degradation
Pyruvate metabolism
Purine metabolism
Tyrosine metabolism
Glycine, serine and threonine metabolism
Pyrimidine metabolism
Primary bile acid biosynthesis
Tryptophan metabolism
Oxidative phosphorylation
Nicotinate and nicotinamide metabolism
Propanoate metabolism
Glycine, serine and threonine metabolism
Nitrogen metabolism
Phenylalanine and Tyrosine Metabolism
Vitamin B6 Metabolism
Steroid Biosynthesis
Porphyrin Metabolism
Phospholipid Biosynthesis
Caffeine Metabolism
Methionine Metabolism
D-Arginine and D-Ornithine Metabolism
Glycerolipid Metabolism
Histidine metabolism
Fatty acid Metabolism
Citric Acid Cycle
Aspartate Metabolism
Riboflavin Metabolism
Glutamate Metabolism
Butyrate Metabolism
Ibandronate Action Pathway
Simvastatin Action Pathway
Pravastatin Action Pathway
Rosuvastatin Action Pathway
Alendronate Action Pathway
Lovastatin Action Pathway
Zoledronate Action Pathway
Cerivastatin Action Pathway
Risedronate Action Pathway
Pamidronate Action Pathway
Fluvastatin Action Pathway
Glycerol Phosphate Shuttle
Atorvastatin Action Pathway
2-Hydroxyglutric Aciduria (D And L Form)
2-Methyl-3-Hydroxybutryl CoA Dehydrogenase Deficiency
3-Hydroxy-3-Methylglutaryl-CoA Lyase Deficiency
3-Methylglutaconic Aciduria Type I
3-Methylglutaconic Aciduria Type III
3-Methylglutaconic Aciduria Type IV
5-Oxoprolinuria
Adenosine Deaminase Deficiency
Adenylosuccinate Lyase Deficiency
AICA-Ribosiduria
Alkaptonuria
Beta Ureidopropionase Deficiency
Beta-Ketothiolase Deficiency
Canavan Disease
Cystathionine Beta-Synthase Deficiency
Dihydropyrimidinase Deficiency
Dihydropyrimidine Dehydrogenase Deficiency (DHPD)
Ethylmalonic Encephalopathy
Gamma-Glutamyltransferase Deficiency
Glutaric Aciduria Type I
Glutaric Aciduria Type I
Glycerol Kinase Deficiency
Guanidinoacetate Methyltransferase Deficiency (GAMT Deficiency)
Hawkinsinuria
Histidinemia
Hypoacetylaspartia
Leigh Syndrome
Malonic Aciduria
Maple Syrup Urine Disease
Methylmalonic Aciduria
Methylmalonic Aciduria Due to Cobalamin-Related Disorders
MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy)
Molybdenum Cofactor Deficiency
Phenylketonuria
Prolidase Deficiency (PD)
Prolinemia Type II
Hypercholesterolemia
Purine Nucleoside Phosphorylase Deficiency
Pyruvate Dehydrogenase Complex Deficiency
S-Adenosylhomocysteine (SAH) Hydrolase Deficiency
Tyrosinemia Type I
UMP Synthase Deficiency (Orotic Aciduria)
Xanthine Dehydrogenase Deficiency (Xanthinuria)
Methionine Adenosyltransferase Deficiency
Glycine N-methyltransferase Deficiency
Non Ketotic Hyperglycinemia
Short Chain Acyl CoA Dehydrogenase Deficiency (SCAD Deficiency)
Propionic Acidemia
3-Methylcrotonyl Coa Carboxylase Deficiency Type I
Isovaleric Aciduria
Saccharopinuria/Hyperlysinemia II
Dimethylglycine Dehydrogenase Deficiency
4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase Deficiency
Sarcosinemia
Congenital Bile Acid Synthesis Defect Type II
Cerebrotendinous Xanthomatosis (CTX)
Zellweger Syndrome
Familial Hypercholanemia (FHCA)
Congenital Bile Acid Synthesis Defect Type III
Lysosomal Acid Lipase Deficiency (Wolman Disease)
Phenytoin (Antiarrhythmic) Action Pathway
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency)
Glutathione Synthetase Deficiency
Hyperinsulinism-Hyperammonemia Syndrome
Methylenetetrahydrofolate Reductase Deficiency (MTHFRD)
Hypermethioninemia
Hereditary Coproporphyria (HCP)
Acute Intermittent Porphyria
Congenital Erythropoietic Porphyria (CEP) or Gunther Disease
Porphyria Variegata (PV)
GABA-Transaminase Deficiency
Hyperprolinemia Type II
Hyperprolinemia Type I
Arginine: Glycine Amidinotransferase Deficiency (AGAT Deficiency)
Ornithine Aminotransferase Deficiency (OAT Deficiency)
Lesch-Nyhan Syndrome (LNS)
Gout or Kelley-Seegmiller Syndrome
Tyrosinemia Type 2 (or Richner-Hanhart syndrome)
Tyrosinemia Type 3 (TYRO3)
Methylmalonate Semialdehyde Dehydrogenase Deficiency
Homocarnosinosis
Desmosterolosis
CHILD Syndrome
Chondrodysplasia Punctata II, X Linked Dominant (CDPX2)
Smith-Lemli-Opitz Syndrome (SLOS)
Citalopram Action Pathway
Azathioprine Action Pathway
Mercaptopurine Action Pathway
Disulfiram Action Pathway
Thioguanine Action Pathway
Nicotine Action Pathway
Methotrexate Action Pathway
Threonine and 2-Oxobutanoate Degradation
Pyruvaldehyde Degradation
Vitamin K Metabolism
Capecitabine Action Pathway
Tamoxifen Action Pathway
Plasmalogen Synthesis
Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids
Mitochondrial Beta-Oxidation of Medium Chain Saturated Fatty Acids
Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty Acids
Dimethylglycine Dehydrogenase Deficiency
Hyperglycinemia, non-ketotic
Ureidopropionase Deficiency
Carnosinuria, carnosinemia
Tyrosinemia, transient, of the newborn
Dopamine beta-hydroxylase deficiency
5-oxoprolinase deficiency
Gamma-glutamyl-transpeptidase deficiency
Malonyl-coa decarboxylase deficiency
Hypophosphatasia
Creatine deficiency, guanidinoacetate methyltransferase deficiency
Hyperornithinemia with gyrate atrophy (HOGA)
Hyperornithinemia-hyperammonemia-homocitrullinuria [HHH-syndrome]
L-arginine:glycine amidinotransferase deficiency
Cholesteryl ester storage disease
Hyper-IgD syndrome
Mevalonic aciduria
Wolman disease
Xanthinuria type I
Xanthinuria type II
3-hydroxyisobutyric acid dehydrogenase deficiency
3-hydroxyisobutyric aciduria
Isobutyryl-coa dehydrogenase deficiency
Isovaleric acidemia
Hyperlysinemia I, Familial
Hyperlysinemia II or Saccharopinuria
D-glyceric acidura
Familial lipoprotein lipase deficiency
Monoamine oxidase-a deficiency (MAO-A)
Adenine phosphoribosyltransferase deficiency (APRT)
Mitochondrial DNA depletion syndrome
Myoadenylate deaminase deficiency
Carnitine palmitoyl transferase deficiency (I)
Long chain acyl-CoA dehydrogenase deficiency (LCAD)
Very-long-chain acyl coa dehydrogenase deficiency (VLCAD)
Carnitine palmitoyl transferase deficiency (II)
Medium chain acyl-coa dehydrogenase deficiency (MCAD)
Methylenetetrahydrofolate Reductase Deficiency (MTHFRD)
Trifunctional protein deficiency
Congenital lactic acidosis
Fumarase deficiency
Mitochondrial complex II deficiency
2-ketoglutarate dehydrogenase complex deficiency
Pyruvate dehydrogenase deficiency (E3)
Pyruvate dehydrogenase deficiency (E2)
Primary hyperoxaluria II, PH2
Pyruvate kinase deficiency
Succinic semialdehyde dehydrogenase deficiency
Short-chain 3-hydroxyacyl-CoA dehydrogenase deficiency (SCHAD)
Homocystinuria-megaloblastic anemia due to defect in cobalamin metabolism, cblG complementation type
Pyridoxine dependency with seizures
Tamoxifen Metabolism Pathway
Capecitabine Metabolism Pathway
Mercaptopurine Metabolism Pathway
Citalopram Metabolism Pathway
Nicotine Metabolism Pathway
Valproic Acid Metabolism Pathway
Doxorubicin Metabolism Pathway
Warburg Effect
Thyroid hormone synthesis
2-aminoadipic 2-oxoadipic aciduria
27-Hydroxylase Deficiency
3-Phosphoglycerate dehydrogenase deficiency
Folate malabsorption, hereditary
The oncogenic action of 2-hydroxyglutarate
The Oncogenic Action of Succinate
The Oncogenic Action of Fumarate
Glutaminolysis and Cancer
Sarcosine Oncometabolite Pathway
The oncogenic action of L-2-hydroxyglutarate in Hydroxygluaricaciduria
The oncogenic action of D-2-hydroxyglutarate in Hydroxygluaricaciduria
StateSolid
Water Solubility4.25e+00 g/l
logP-0.78
logS-2.27
pKa (Strongest Acidic)1.86
pKa (Strongest Basic)4.99
Hydrogen Acceptor Count19
Hydrogen Donor Count9
Polar Surface Area356.42 Ų
Rotatable Bond Count13
Physiological Charge-3
Formal Charge0
Refractivity177.43 m³·mol⁻¹
Polarizability70.11

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