Flavin Adenine Dinucleotide
Grundinformationen
- CAS
146-14-5- Standard-SMILES
Cc1cc2nc3c(=O)[nH]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- InChIKey
VWWQXMAJTJZDQX-UYBVJOGSSA-N- Summenformel
- C27H33N9O15P2
- Durchschnittliche Molmasse
- 785,5 g/mol
- Monoisotopische Masse
- 785,15713538
Überblick
FAD is a flavin adenine dinucleotide in which the substituent at position 10 of the flavin nucleus is a 5'-adenosyldiphosphoribityl group. It has a role as a cofactor, a prosthetic group, a mouse metabolite, an Escherichia coli metabolite and a human metabolite. It is a vitamin B2 and a flavin adenine dinucleotide. It is a conjugate acid of a FAD(3-).
Namen und Bezeichner
- Bevorzugter Name
- Flavin Adenine Dinucleotide
- IUPAC
- [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4S)-5-(7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10-yl)-2,3,4-trihydroxypentyl] hydrogen phosphate
- Englischer Name
- Flavin adenine dinucleotide
- Summenformel
- C27H33N9O15P2
- Molmasse
- 785.55
Namen und Synonyme
flavin adenine dinucleotide146-14-5Flavin-adenine dinucleotideFlavine-adenine dinucleotideFlavine adenosine diphosphateAdenine-riboflavin dinucleotideRiboflavin 5'-adenosine diphosphateFlavin adenin dinucleotideFlavine adenine dinucleotideZC44YTI8KKCHEBI:16238NSC-112207
Weitere Namen anzeigen
DISODIUM FLAVINE ADENINE DINUCLEOTIDEFademinflavitanflavinatFlavininWakadeninNSC 112207FAD PowderFlavine Adenine5'-ester with adenosine
ADENOSINE 5'-(TRIHYDROGEN PYROPHOSPHATE), 5'-5'-ESTER with RIBOFLAVINE[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4S)-5-(7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10-yl)-2,3,4-trihydroxypentyl] hydrogen phosphateDTXSID4048307Riboflavin 5'-(trihydrogen diphosphate), 5'-5'-ester with adenosineRiboflavin 5'-(trihydrogen diphosphate), P'->5'-ester with adenosineRiboflavin 5'-(trihydrogen diphosphate), P'-5'-ester with adenosineRIBOFLAVINE 5'-(TRIHYDROGEN DIPHOSPHATE) 5'->5'-ESTER WITH ADENOSINE(((((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl)methoxy)(hydroxy)phosphoryl)oxy)((((2R,3S,4S)-5-(7,8-dimethyl-2,4-dioxo-2H,3H,4H,10H-benzo(g)pteridin-10-yl)-2,3,4-trihydroxypentyl)oxy))phosphinic acid
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -5
- Polarare Oberfläche (TPSA)
- 356 Ų
- H-Brücken-Donoren
- 9
- H-Brücken-Akzeptoren
- 20
- Frei drehbare Bindungen
- 13
- Schwere Atome
- 53
- Formalladung
- 0
- Komplexität
- 1.560
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
Solubility5 mg/mL
Physical DescriptionSolid
Collision Cross Section
259.22 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
247.3 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
250.3 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
249.2 Ų [M+H]+
Physikochemische Eigenschaften
- Density
- 2.08 · 2.08±0.1 g/cm3(Predicted)
- storage temp.
- 20 °C · −20°C
- solubility
- Methanol (Slightly, Heated), Water (Slightly)
- pka
- 1.13 · 1.13±0.50(Predicted)
- form
- powder
- color
- orange
- ex/em
- 441 nm; · λex 441 nm; λem 530 nm
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Gefahrenhinweise
Regulatory InformationRiboflavin 5'-(trihydrogen diphosphate), P'â5'-ester with adenosine: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Sicherheitsdaten
- F
- 8-10-21
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- AU7470000
- hs_code
- 29349990
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 24/25
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P280-P302+P352-P362+P364
Chemie und Industrie
Pharmakologische Informationen
Tissue LocationsErythrocyte
Cellular LocationsCytoplasm
Metabolite Pathways2-aminoadipic 2-oxoadipic aciduria
Verwendung und Herstellung
General Manufacturing InformationRiboflavin 5'-(trihydrogen diphosphate), P'.fwdarw.5'-ester with adenosine: ACTIVE
Anwendungen
DescriptionFlavin adenine dinucleotide (FAD) is a cofactor for cytochrome-b5 reductase, the enzyme that maintains hemoglobin in its functional reduced state, and for glutathione reductase. This enzyme also protects erythrocytes from oxidative damage. FAD is a redox cofactor of several essential reactions in metabolism. This cofactor exists in two redox states, with FAD and FADH2 being the oxidized and reduced forms, respectively. FAD is formed of a riboflavin moiety (vitamin B2) coupled to a phosphate group of an ADP molecule. The reaction starts with the conversion of riboflavin into flavin mononucleotide catalyzed by riboflavin kinase. Flavin mononucleotide is subsequently transformed into FAD by adding an AMP moiety from ATP catalyzed by FAD-synthase. Therefore, FAD availability is tightly dependent on vitamin B2 and energy metabolism[1].
UsesLabelled Flavine Adenine xidase. Riboflavin kinase tumor necrosis factor receptor 1 NADPH oxidase
UsesThe 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.
Anbieter100 Anbieter
Zugehörige Reaktionen
1
Notizen zur Verbindung
Wird geladen…