基本情報
- CAS
146-14-5- 標準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- 分子式
- C27H33N9O15P2
- 平均分子量
- 785.5 g/mol
- 単同位体質量
- 785.15713538
概要
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-).
名称と識別子
- 優先名称
- 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
- 英語名
- Flavin adenine dinucleotide
- 分子式
- C27H33N9O15P2
- 分子量
- 785.55
名称と別名
flavin adenine dinucleotide146-14-5Flavin-adenine dinucleotideFlavine-adenine dinucleotideFlavine adenosine diphosphateAdenine-riboflavin dinucleotideRiboflavin 5'-adenosine diphosphateFlavin adenin dinucleotideFlavine adenine dinucleotideZC44YTI8KKCHEBI:16238NSC-112207
名称をさらに表示
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
物性
構造計算による物性
- XLogP
- -5
- 極性表面積
- 356 Ų
- 水素結合供与体数
- 9
- 水素結合受容体数
- 20
- 回転可能結合数
- 13
- 重原子数
- 53
- 形式電荷
- 0
- 複雑度
- 1,560
実験および物理化学的性質
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]+
物理化学的性質
- 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
- Merck
- 4091 · 4091
- Stability
- Stable. Incompatible with strong oxidizing agents.
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
危険有害性情報
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.
安全データ
- 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
化学と産業
薬理情報
Tissue LocationsErythrocyte
Cellular LocationsCytoplasm
Metabolite Pathways2-aminoadipic 2-oxoadipic aciduria
用途と製造
General Manufacturing InformationRiboflavin 5'-(trihydrogen diphosphate), P'.fwdarw.5'-ester with adenosine: ACTIVE
応用分野
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.
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