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クレアチンリン酸

N-methyl-N-(N-phosphonocarbamimidoyl)glycine

HCID 587
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
67-07-2
標準SMILES
CN(CC(=O)O)C(N)=NP(=O)(O)O
InChIKey
DRBBFCLWYRJSJZ-UHFFFAOYSA-N
分子式
C4H10N3O5P
平均分子量
211.11 g/mol
単同位体質量
211.03580743

概要

Phosphocreatine - or creatine phosphate - is the phosphorylated form of creatine. It is primarily found endogenously in the skeletal muscles of vertebrates where it serves a critical role as a rapidly acting energy buffer for muscle cell actions like contractions via its ability to regenerate adenosine triphosphate (ATP) from adenosine diphosphate (ADP).

名称と識別子

優先名称
N-methyl-N-(N-phosphonocarbamimidoyl)glycine
IUPAC
2-[methyl-(N'-phosphonocarbamimidoyl)amino]acetic acid
現地名
クレアチンリン酸
英語名
Creatine phosphate
分子式
C4H10N3O5P
分子量
211.11

名称と別名

Creatine Phosphate (Phosphocreatine), >85%N-methyl-N-(N-phosphonocarbamimidoyl)glycine2-(3-methyl-1-phosphonocarbamimidamido)acetic acid2-(1-Methyl-3-phosphonoguanidino)acetic acidC4H10N3O5PCreatinephosphateMFCD00152044Creatine phosphate; Creatinephosphoric acidSCHEMBL65424SCHEMBL65425SCHEMBL2124030SCHEMBL24116748
名称をさらに表示
N-ホスホロクレアチンクレアチンホスファートネオトンN-(N-ホスホノアミジノ)-N-メチルグリシンN-(ホスホルアミド)サルコシンN-[イミノ(ホスホノアミノ)メチル]-N-メチルグリシンりん酸クレアチンホスホクレアチンクレアチンリン酸ホスファゲンphosphocreatineGlycine, N-[imino(phosphonoamino)methyl]-N-methyl-Neotonphosphagenn-phosphocreatineCREATINE PHOSPHATEN-PhosphorocreatineCreatine phosphate 90%Creatine phosphoric acid
Creatine Phosphate; PhosphocreatineFC149077NS00041187H57884Q1984607

物性

構造計算による物性

XLogP
-2.6
極性表面積
136 Ų
水素結合供与体数
4
水素結合受容体数
6
回転可能結合数
4
重原子数
13
形式電荷
0
複雑度
271

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15
Boiling Point449.1±47.0 °C at 760 mmHg
Melting Point194-195 °C
Physical DescriptionSolid
Collision Cross Section · 4 件

142.8 Ų [M+Na-2H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

153.77 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]

144.4 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

144.8 Ų [M+H]+

物理化学的性質

融点
175 oC · >175oC (dec.)
沸点
449.1 · 449.1±47.0 °C(Predicted)
比重(密度)
1.83 · 1.83±0.1 g/cm3(Predicted)
貯蔵温度
-20 °C · Hygroscopic, -20°C Freezer, Under inert atmosphere
溶解性
水
酸解離定数(Pka)
4.7 · pKa 4.7± 0.01(H2O,t =25)(Approximate)
外見
個体
色
ホワイトからオフホワイト

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。

安全データ

tsca
TSCA listed

化学と産業

薬理情報

Pharmacodynamics · 1 件

Creatine is a naturally occurring chemical within the body and is primarily stored in skeletal muscle in both free and phosphorylated forms. Phosphocreatine is the name given to the phosphorylated form of creatine. Additionally, phosphocreatine can also be found in other areas of the body like the kidneys, liver, and brain. In fact, most *in vivo* synthesis of creatine occurs in the liver where amidine groups from arginine are transfered to glycine with the help of the glycine transaminidase enzyme to form guanidinoacetic acid. This acid is then methylated with the methyl group of S-adenosylmethionine via guanidinoacetate methyltransferase to generate creatine. The synthesized creatine is transported to storage sites in skeletal muscle via the bloodstream. The phosphorylation of creatine is reversible in both a forwards and backwards reaction. That is, while phosphocreatine is capable of anaerobically donating a phosphate group to adenosine diphosphate (ADP) to regenerate ATP, at the same time excess ATP can be dephosphorylated during periods of low muscle activity to convert creatine to phosphocreatine. This dual activity in synthesizing phosphocreatine from excess levels of ATP during rest and use of phosphocreatine to regenerate ATP during high activity demonstrates the crucial utility of phosphocreatine in acting as an energy buffer in body mucle cells. Phosphocreatine's fast regeneration of ATP is considered a coupled reaction - in essence, the energy released from transferring a donating a phosphate group from phosphocreatine is used to regenerate ATP. Phosphocreatine consequently plays an essential role in body tissues that have high, fluctuating energy requirments like muscle and brain tissues.

Mechanism of Action · 1 件

Adenosine triphosphate (ATP) is the primary source of chemical energy that body muscles use to perform contractions. During such contraction processes, ATP molecules are depleted as they undergo hydrolysis reactions and become adenosine diphosphate (ADP). To maintain homeostasis in muscle activity, the ATP supply of muscles must be regenerated regularly. Phosphocreatine occurs naturally within the body and is capable of regenerating ATP by transferring a high-energy phosphate from itself to ADP, resulting in the formation of ATP and creatine. This kind of regeneration of ATP with phosphocreatine typically occurs within seconds of intense muscular or neuronal effort, acting as a quickly accessible reserve of high-energy phosphates for the recycling of ATP in body muscle tissues. ATP recycling from phosphocreatine is in fact known as the quickest form of ATP regeneration.

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化合物ノート

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このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート

データベース識別子

CAS
67-07-2
PubChem CID
587
安定性
吸湿性
InChI
InChI=1S/C4H10N3O5P/c1-7(2-3(8)9)4(5)6-13(10,11)12/h2H2,1H3,(H,8,9)(H4,5,6,10,11,12)
InChIKey
DRBBFCLWYRJSJZ-UHFFFAOYSA-N
SMILES
C(O)(=O)CN(C(=N)NP(O)(O)=O)C
CAS データベース
67 · 67-07-2(CAS DataBase Reference)
EPAの化学物質情報
Glycine, N-[imino(phosphonoamino)methyl]-N-methyl- (67-07-2)
Absorption, Distribution and Excretion · 1 件

Phosphocreatine is eliminated renally. The end result of creatine degredation is the product creatinine, which enters the bloodstream from its storage sites in body muscle. When creatinine enters the renal parenchyma it is filtered in the renal glomerulus to be excreted in the urine.

Tissue LocationsAdipose Tissue
Cellular LocationsMitochondria
Metabolite PathwaysArginine and proline metabolism
応用分野 · 2 件

解説クレアチンリン酸は,ホスホクレアチンとも呼ばれ,ホスファゲンの一つである。1920年代にエグルトンP.Eggletonらがネコ筋から発見した。脊椎動物の筋に広く分布しているが,無脊椎動物でもウニ類に見られ,個体発生においてアルギニンリン酸と置き換わる。無色,水溶性。ATPと並んで高エネルギーリン酸エステルとして知られ,筋肉の収縮運動のエネルギー源として重要である(高エネルギー結合)。酸性では不安定で加水分解されてリン酸を遊離するが,中性では比較的安定である。株式会社平凡社 世界大百科事典 第2版について 情報

使用Phosphocreatine used in the synthesis of hydroxypatite nanorod/nanosheets. Phosphocreatine is used in the treatment of heart and brain ischemia.

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