CAS 146-14-5: Flavin adenine dinucleotide
Description:Flavin adenine dinucleotide (FAD) is a redox-active coenzyme associated with various biological reactions, particularly in cellular respiration and metabolism. It is a derivative of riboflavin (vitamin B2) and consists of an adenine nucleotide linked to a flavin mononucleotide. FAD plays a crucial role in the electron transport chain, facilitating the transfer of electrons in oxidative phosphorylation, and acts as a cofactor for several enzymes, including flavoproteins. Its structure allows it to exist in oxidized (FAD) and reduced (FADH2) forms, enabling it to participate in oxidation-reduction reactions. FAD is soluble in water and exhibits a yellow color, which is characteristic of flavins. It is essential for the proper functioning of various metabolic pathways, including the citric acid cycle and fatty acid oxidation. Additionally, FAD is involved in the synthesis of certain neurotransmitters and the metabolism of amino acids. Its CAS number, 146-14-5, is used for identification in chemical databases and regulatory contexts.
Formula:C27H33N9O15P2
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
InChI key:InChIKey=VWWQXMAJTJZDQX-UYBVJOGSSA-N
SMILES:O=C1N=C2C(=NC=3C=C(C(=CC3N2CC(O)C(O)C(O)COP(=O)(O)OP(=O)(O)OCC4OC(N5C=NC=6C(=NC=NC65)N)C(O)C4O)C)C)C(=O)N1
- 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
- Adenosine 5'-(trihydrogen pyrophosphate), 5'-5'-ester with riboflavine
- Benzo[g]pteridine, riboflavin 5′-(trihydrogen diphosphate) deriv.
- Brn 0078150
- See more synonyms
- FAD
- Fademin
- Flamitajin B
- Flanin F
- Flavin adenin dinucleotide
- Flavin adenin dinucleotide [JAN]
- Flavin-adenin-dinucleotid
- Flavina-Adenina-Dinucleotido
- Flavinat
- Flavine adenosine diphosphate
- Flavine-adenine dinucleotide
- Flavitan
- Flaziren (free acid)
- Isoalloxazine-adenine dinucleotide
- Nsc 112207
- Riboflavin 5'-(trihydrogen diphosphate), 5'-5'-ester with adenosine
- Riboflavin 5'-(trihydrogen diphosphate), P'-5'-ester with adenosine
- Riboflavin 5'-(trihydrogen diphosphate), P'.fwdarw.5'-ester with adenosine
- Riboflavin 5'-adenosine diphosphate
- Riboflavin-adenine dinucleotide
- Riboflavine, 5′-ester with adenosine 5′-diphosphate
- Riboflavine-adenine dinucleotide
- Unii-Zc44Yti8Kk
- [(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl (2R,3S,4S)-5-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)-2,3,4-trihydroxypentyl dihydrogen diphosphate (non-preferred name)
- [(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl (2S,3R,4R)-5-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)-2,3,4-trihydroxypentyl dihydrogen diphosphate (non-preferred name)
- [(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl 5-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)-2,3,4-trihydroxypentyl dihydrogen diphosphate (non-preferred name)
- [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl [[(2R,3S,4S)-5-(7,8-dimethyl-2,4-dioxo-benzo[g]pteridin-10-yl)-2,3,4-trihydroxy-pentoxy]-oxido-phosphoryl] phosphate
- [5-(6-Aminopurin-9-Yl)-3,4-Dihydroxy-Tetrahydrofuran-2-Yl]Methyl [[5-(7,8-Dimethyl-2,4-Dioxo-Benzo[G]Pteridin-10-Yl)-2,3,4-Trihydroxy-Pentoxy]-Hydroxy-Phosphoryl] Hydrogen Phosphate
- Flavin-Adenine Dinucleotide
- 4-26-00-03632 (Beilstein Handbook Reference)
