Flavitan

Base Information

• Chemical Name: Flavitan
• CAS No.: 146-14-5
• Molecular Formula: C27H33 N9 O15 P2
• Molecular Weight: 785.558
• Hs Code.: 29349990
• NSC Number: 112207
• DSSTox Substance ID: DTXSID70859284
• Wikidata: Q32039181
• ChEMBL ID: CHEMBL3580425
• Mol file: 146-14-5.mol

Synonyms:Dinucleotide, Flavin-Adenine;FAD;Flavin Adenine Dinucleotide;Flavin-Adenine Dinucleotide;Flavitan

Chemical Property of Flavitan

Chemical Property:

• Appearance/Colour: solid
• Boiling Point: °Cat760mmHg
• PKA: 1.13±0.50(Predicted)
• Flash Point: °C
• PSA: 382.55000
• Density: 2.08g/cm³
• LogP: -1.79440
• Storage Temp.: −20°C
• XLogP3: -5
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 20
• Rotatable Bond Count: 13
• Exact Mass: 785.15713538
• Heavy Atom Count: 53
• Complexity: 1560

Purity/Quality:

98% ^*data from raw suppliers

FlavineAdenineDinucleotide ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC2=C(C=C1C)N(C3=NC(=O)NC(=O)C3=N2)CC(C(C(COP(=O)(O)OP(=O)(O)OCC4C(C(C(O4)N5C=NC6=C(N=CN=C65)N)O)O)O)O)O
• Uses: The prosthetic group of certain flavoproteins including D-amino acid oxidase, glucose oxidase, glycine oxidase, fumaric hydrogenase, histaminase, and xanthine oxidase. Riboflavin kinase tumor necrosis factor receptor 1 NADPH oxidase Labelled Flavine Adenine xidase. Riboflavin kinase tumor necrosis factor receptor 1 NADPH oxidase The prosthetic group of certain flavoproteins including D-amino acid oxidase, glucose oxidase, glycine oxidase, fumaric hydrogenase, histaminase, and xanthine oxidase. Riboflavin kinase tumor necrosis factor receptor 1 NADPH oxidase.

Technology Process of Flavitan

There total 9 articles about Flavitan which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

5'-adenosine monophosphate (61-19-8,24937-83-5,67583-85-1) → flavin adenine dinucleotide (146-14-5,887565-61-9)

Guidance literature:

With pyridine; di-p-tolylcarbodiimide;

DOI:10.1021/ja01629a136

Reference yield:

flavin adenine dinucleotide fully reduced neutral (1910-41-4) → flavin adenine dinucleotide (146-14-5,887565-61-9)

Guidance literature:

With Artemisone; In acetonitrile;

DOI:10.1002/cmdc.201000508

Reference yield:

→ flavin adenine dinucleotide (146-14-5,887565-61-9)

Guidance literature:

With pyridine; 2-monochlorophenol; beim Behandeln unter Lichtausschluss;

DOI:10.1021/ja01547a073

upstream raw materials:

Flavin mononucleotide

ATP

5'-adenosine monophosphate

flavin adenine dinucleotide fully reduced neutral

Downstream raw materials:

flavin adenine dinucleotide fully reduced neutral

lumiflavin

dihydrogen peroxide

5'-adenosine monophosphate

Refernces

Facile oxidation of leucomethylene blue and dihydroflavins by artemisinins: Relationship with flavoenzyme function and antimalarial mechanism of action

10.1002/cmdc.201000225

The research investigates the interaction between artemisinins, a class of compounds derived from the plant Artemisia annua and used in the treatment of malaria, and redox-active substrates such as leucomethylene blue and dihydroflavins. The study aims to understand the molecular mechanism by which artemisinins exert their antimalarial effects, particularly their ability to generate reactive oxygen species (ROS) and interfere with the redox balance within the malaria parasite. The researchers found that artemisinins can act as both one-electron transfer agents and two-electron acceptors, potentially disrupting the function of flavin cofactors in redox-active enzymes within the parasite. The chemicals used in the study include artemisinins, methylene blue, ascorbic acid, N-benzyldihydronicotinamide (BNAH), riboflavin, flavin mononucleotide (FMN), and flavin adenine dinucleotide (FAD), among others. The conclusions suggest that artemisinins may act as antimalarial drugs by perturbing the redox balance within the malaria parasite, and their selective potency may be due to differences in sensitivity between parasite and human glutathione reductase. This research provides insights into the potential mechanisms of artemisinin resistance in malaria parasites and could inform the development of new antimalarial drugs.

Iron Uptake Oxidoreductase (IruO) Uses a Flavin Adenine Dinucleotide Semiquinone Intermediate for Iron-Siderophore Reduction

10.1021/acschembio.7b00203

This research investigates the role of IruO, an FAD-containing NADPH-dependent reductase from Staphylococcus aureus, in iron-siderophore reduction. The study demonstrates that IruO binds and reduces hydroxamate-type siderophores desferrioxamine B and ferrichrome A with low micromolar affinity, releasing Fe(II) in the presence of NADPH. The crystal structures of IruO were solved in two distinct conformational states mediated by the formation of an intramolecular disulfide bond, revealing a putative siderophore binding site adjacent to the FAD cofactor. Visible spectroscopy of anaerobically reduced IruO showed that the reaction proceeds by a single electron transfer mechanism through an FAD semiquinone intermediate. FAD (flavin adenine dinucleotide) cofactor in IruO is involved in electron transfer during the reduction of Fe(III) siderophores. The study proposes a model for single electron siderophore reduction by IruO using NADPH and suggests that the intramolecular disulfide bond in IruO may have a physiological role to limit iron release under oxidative stress conditions.