Showing Metabocard for FADH2 (BASm0003360)

Common NameFadh2
DescriptionFADH is the reduced form of flavin adenine dinucleotide (FAD). FAD is synthesized from riboflavin and two molecules of ATP. Riboflavin is phosphorylated by ATP to give riboflavin 5-phosphate (FMN). FAD is then formed from FMN by the transfer of an AMP moiety from a second molecule of ATP. FADH is generated in each round of fatty acid oxidation, and the fatty acyl chain is shortened by two carbon atoms as a result of these reactions; because oxidation is on the beta carbon, this series of reactions is called the beta-oxidation pathway. In the citric acid cycle, FADH is involved in the harvesting of high-energy electrons from carbon fuels; the citric acid cycle itself neither generates a large amount of ATP nor includes oxygen as a reactant. Instead, the citric acid cycle removes electrons from acetyl CoA and uses these electrons to form FADH.
Structure
Molecular FormulaC27H35N9O15P2
Average Mass787.56560
Monoisotopic Mass787.17278
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 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-1h,3h,5h-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy(hydroxy)phosphoryl}oxy)phosphinic acid
CAS Registry Number1910-41-4
SMILESCc1cc2c(cc1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(=O)([O-])OP(=O)([O-])OC[C@H]1O[C@@H](n3cnc4c(N)ncnc43)[C@H](O)[C@@H]1O)c1[nH]c(=O)[nH]c(=O)c1N2
InChI IdentifierInChI=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
InChI KeyYPZRHBJKEMOYQH-UYBVJOGSSA-N
CHEBI IDCHEBI:58307
HMDB IDHMDB0001197
Pathways
NameSMPDB/PathBank
Phospholipid Biosynthesis
Citric Acid Cycle
Glycerol Phosphate Shuttle
Congenital lactic acidosis
Fumarase deficiency
Mitochondrial complex II deficiency
2-ketoglutarate dehydrogenase complex deficiency
Pyruvate dehydrogenase deficiency (E3)
Pyruvate dehydrogenase deficiency (E2)
Warburg Effect
The oncogenic action of 2-hydroxyglutarate
The Oncogenic Action of Succinate
The Oncogenic Action of Fumarate
Glutaminolysis and Cancer
The oncogenic action of L-2-hydroxyglutarate in Hydroxygluaricaciduria
The oncogenic action of D-2-hydroxyglutarate in Hydroxygluaricaciduria
StateSolid
Water Solubility2.65e+00 g/l
logP-0.93
logS-2.47
pKa (Strongest Acidic)1.86
pKa (Strongest Basic)5.00
Hydrogen Acceptor Count18
Hydrogen Donor Count11
Polar Surface Area355.76 Ų
Rotatable Bond Count13
Physiological Charge-2
Formal Charge0
Refractivity188.80 m³·mol⁻¹
Polarizability72.42

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