アデノシン-5'-三りん酸
アトリホス · アデトール · アデノシン三りん酸 · トリアデニル · アデニルピロりん酸 · ATP【ヌクレオチド】 · ミオトリホス · ホスホビオン
識別子と物理属性
| CAS No. | 56-65-5 |
|---|---|
| 分子式 | C10H16N5O13P3 |
| 平均分子量 | 507.18 g/mol |
| 単同位体質量 | 506.99574546 g/mol |
| SMILES | Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O |
| InChIKey | ZKHQWZAMYRWXGA-KQYNXXCUSA-N |
| PubChem CID | 5957 |
| ChEMBL | CHEMBL14249 |
| ChEBI | CHEBI:15422 |
| EC No. | 200-283-2 |
| DTXSID | DTXSID6022559 |
| 現地名 | アデノシン-5'-三りん酸 |
化学・物理的性質
| XLogP | -5.7 |
|---|---|
| 極性表面積 | 279 |
| 水素結合供与体数 | 7 |
| 水素結合受容体数 | 17 |
| 回転可能結合数 | 8 |
| 重原子数 | 31 |
| 形式電荷 | 0 |
| 複雑度 | 800 |
| 医薬品 | Pharmaceuticals -> Listed in ZINC15 |
| 化粧品 | Cosmetic ingredients (Adenosine Triphosphate) -> CIR (Cosmetic Ingredient Review)Skin conditioning |
| 溶解度 | 1000.0 mg/mL862 mg/mL (magnesium salt)可溶(水)，Na，K塩は水に易溶，Ba塩は水に不溶Water : ≥ 100 mg/mL (197.17 mM) |
| Physical Description | Solid |
| Collision Cross Section | 198.86 Ų [M-H]- [CCS Type: DTMethod: stepped-field]185.74 Ų [M-H]- [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]196.6 Ų [M+H]+ [CCS Type: DTMethod: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]204.2 Ų [M+Na]+ |
| 融点 | 144°C (rough estimate) |
| 沸点 | 951.4±75.0 °C(Predicted) |
| 比旋光度 | D22 -26.7° (c = 3.095) |
| 密度 | 1.0 g/mL at 20 °C |
| 貯蔵条件 | Keep in dark place,Inert atmosphere,Store in freezer, under -20°C |
| 外観・状態 | 凍結乾燥粉末 |
| pKa（酸解離定数） | pK2: 4.00(-1)pK3: 6.48(-2) (25°C) |
| 色 | White to off-white |
| pH | 7.0 ± 0.1 |
| 化粧品成分の機能 | スキンコンディショニング |
| InChIKey | ZKHQWZAMYRWXGA-KQYNXXCUSA-N |
| SMILES | C(OP(=O)(O)OP(O)(=O)OP(O)(O)=O)[C@H]1O[C@@H](N2C3C(=C(N=CN=3)N)N=C2)[C@H](O)[C@@H]1O |
| LogP（分配係数） | -4.180 (est) |
| CAS データベース | 56-65-5(CAS DataBase Reference) |
| EPAの化学物質情報 | Adenosine triphosphate (56-65-5) |
化学的特性
The structure of Adenosine triphosphate has an ordered carbon compound as a backbone, but the part that is really critical is the phosphorous part - the triphosphate. Three phosphorous groups are connected by oxygens to each other, and there are also side oxygens connected to the phosphorous atoms. Under the normal conditions in the body, each of these oxygens has a negative charge, and therefore repel each other. These bunched up negative charges want to escape - to get away from each other, so there is a lot of potential energy here.If you remove just one of these phosphate groups from the end, so that there are just two phosphate groups, the molecule is much happier. This conversion from ATP to ADP is an extremely crucial reaction for the supplying of energy for life processes. Just the cutting of one bond with the accompanying rearrangement is sufficient to liberate about 7.3 kilocalories per mole = 30.6 kJ/mol. This is about the same as the energy in a single peanut.hyperphysics.phy-astr.gsu.edu
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 100% (2 of 2) of all reports.Not ClassifiedAggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory. |
|---|---|
| 規制情報 | Chemical: Adenosine 5'-(tetrahydrogen triphosphate)Adenosine triphosphate: Does not have an individual approval but may be used under an appropriate group standard |
| その他の安全情報 | IMAP assessments - Adenosine 5'-(tetrahydrogen triphosphate): Environment tier I assessment |
| Hazard Classes and Categories | Not Classified |
| 毒性の概要 | Safe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.orgATP is able to store and transport chemical energy within cells. ATP also plays an important role in the synthesis of nucleic acids. ATP can be produced by various cellular processes, most typically in mitochondria by oxidative phosphorylation under the catalytic influence of ATP synthase. The total quantity of ATP in the human body is about 0.1 mole. The energy used by human cells requires the hydrolysis of 200 to 300 moles of ATP daily. This means that each ATP molecule is recycled 2000 to 3000 times during a single day. ATP cannot be stored, hence its consumption must closely follow its synthesis. |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Toxicity Data | Oral LD<sub>50</sub> in rats is > 2 g/kg. |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| 毒性 | dni-hmn:lym 10 mmol/L CNREA8 42,2092,82 |
| 安全措置（S） | 22-24/25 |
用途
解説
アデノシン三リン酸，すべての生物に存在する化学物質でアデニン、リボース、3分子のリン酸により構成される。ATP（adenosine triphosphate）と略記する。
説明
Adenosine triphosphate, also known as ATP, is a molecule that carries energy within cells. It is one of the most important biological compounds because of its role in supplying energy for life. ATP is the universal energy carrier used by all organisms to supply energy for biological functions. It is often referred to as the energy currency of cells.ATP also functions as a neurotransmitter that is stored and secreted with other neurotransmitters from the pancreas. ATP is a nucleotide consisting of the nucleoside adenosine with three attached phosphate groups (see Adenine). Like other nucleotides, ATP consists of three parts: a sugar, an amine base, and a phosphate group. The central part of the molecule in ATP is the sugar ribose. The amine base adenine is attached to the ribose, forming adenosine. Opposite the adenine on the ribose is attached a chain of three phosphate groups.
来歴
ATP was first isolated by the German chemist Karl Lohmann (1898–1978) from muscle tissue extracts in 1929. Alexander Todd’s (1907–1997) research helped to clarify ATP’s structure, and it was first synthesized by Todd in 1948.
使用
Adenosine triphosphate (ATP) plays a critical role in the transport of macromolecules such as proteins and lipids into and out of the cell. The hydrolysis of ATP provides the required energy for active transport mechanisms to carry such molecules across a concentration gradient.
製法・合成法
純化方法
ATP is purified by precipitating it as the barium salt on adding excess barium acetate solution to a 5% solution of ATP in water. The precipitate is filtered off, washed with distilled water, dissolved in 0.2M HNO3 and again precipitated with barium acetate. The precipitate, after several washings with distilled water, is redissolved in 0.2M HNO3, and slightly more than an equivalent of 0.2M H2SO4 is added to precipitate all the barium as BaSO4 which is filtered off. The ATP is then precipitated by addition of a large excess of 95% ethanol. It is filtered off, washed several times with 100% EtOH and finally with dry diethyl ether. It is dried in vacuo. [Kashiwagi & Rabinovitch J Phys Chem 59 498 1955, Beilstein 26 III/IV 3654.]