基本情報
- CAS
352-97-6- 標準SMILES
NC(N)=NCC(=O)O- InChIKey
BPMFZUMJYQTVII-UHFFFAOYSA-N- 分子式
- C3H7N3O2
- 平均分子量
- 117.11 g/mol
概要
Guanidinoacetic acid is the N-amidino derivative of glycine. It has a role as a nutraceutical, a mouse metabolite, a bacterial metabolite, a human metabolite and a rat metabolite. It is a conjugate acid of a guanidinoacetate. It is a tautomer of a guanidinoacetic acid zwitterion.
名称と識別子
- 優先名称
- Guanidinoacetic Acid
- IUPAC
- 2-(diaminomethylideneamino)acetic acid
- 現地名
- グアニジノ酢酸
- 英語名
- Guanidineacetic acid
- 分子式
- C3H7N3O2
- 分子量
- 117.11
名称と別名
glycocyamineguanidinoacetic acid352-97-6Guanidineacetic acidGuanidoacetic acidN-amidinoglycineGuanyl glycineBetacyamineBetasyamineguanidinoacetateGuanidylacetic acidglycine, N-(aminoiminomethyl)-
名称をさらに表示
グリコシアミンN-グアニルグリシンN-アミジノグリシン2-グアニジノ酢酸(アミノイミノメチル)アミノ酢酸グアニド酢酸グリコシアミン(グアニジノ酢酸)グアニジン酢酸グアニジノ酢酸2-カルバムイミドアミド酢酸NSC 1901NSC 26360NSC 227847GLYCOYAMINEGlycocyaminglucocyamine
GLYCINE, N-AMIDINO-Guanidine, (carboxymethyl)-amidinoglycine2-(diaminomethylideneamino)acetic acid2-carbamimidamidoacetic acidAcetic acid, ((aminoiminomethyl)amino)-N-(aminoiminomethyl)-glycineGO52O1A04E
データベース識別子
- CAS
352-97-6
物性
構造計算による物性
- XLogP
- -1.6
- 極性表面積
- 102 Ų
- 水素結合供与体数
- 3
- 水素結合受容体数
- 3
- 回転可能結合数
- 2
- 重原子数
- 8
- 形式電荷
- 0
- 複雑度
- 116
実験および物理化学的性質
DrugsPharmaceuticals -> Listed in ZINC15
Solubility3.6 mg/mL at 15 °C
Physical DescriptionSolid
Collision Cross Section
134.6 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
124.8 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
126.88 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]
134.4 Ų [M+Na]+
物理化学的性質
- 融点
- 300 °C · 300 °C(lit.)
- 沸点
- 218.88 °C · 218.88°C (rough estimate)
- 比重(密度)
- 1.402 · 1.4020 (rough estimate)
- 屈折率
- 1.49 · 1.4900 (estimate)
- 貯蔵温度
- Keep in dark place,Inert atmosphere,Room temperature
- 溶解性
- 6 M · 6 M NaOH : 50 mg/mL 無色透明
- 酸解離定数(Pka)
- 2.82 · 2.82(at 25℃)
- 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。
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 2.2% (1 of 46) of reports.
Warning
H315 (97.8%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 46 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Regulatory InformationRegulation (EC) No 1831/2003 (amended)
Hazard Classes and CategoriesSkin Irrit. 2 (97.8%)
毒性情報
Treatment
Chronic Exposure: Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored. Acute Exposure: EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice.
Health Effects
Acute exposure to guanidoacetic acid can lead to some mild skin and eye irritation. Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. Chronically high levels of guanidoacetic acid are associated with at least 4 inborn errors of metabolism including: Argininemia, Guanidinoacetate methyltransferase deficiency, Guanidinoacetate Methyltransferase Deficiency (GAMT Deficiency) and S-Adenosylhomocysteine (SAH) Hydrolase Deficiency.
化学と産業
薬理情報
Metabolism/Metabolites
Guanidino acetic acid (GAA) is synthesized in the liver and kidney from Arg and Gly and subsequently methylated by S-adenosylmethionine to form creatine. The conversion of guaniodacetate to creatinine in the liver causes a depletion of methyl groups. This causes homocysteine levels to rise, which has been shown to produce cardiovascular and skeletal problems.
MeSH Pharmacological Classification
Analogs of those substrates or compounds which bind naturally at the active sites of proteins, enzymes, antibodies, steroids, or physiological receptors. These analogs form a stable covalent bond at the binding site, thereby acting as inhibitors of the proteins or steroids.
Tissue LocationsBrain
Cellular LocationsCytoplasm
Metabolite Pathways3-Phosphoglycerate dehydrogenase deficiency
用途と製造
UsesNaturally produced by the body (endogenous). Is used as a supplement to enhance athletic performance.
応用分野
解説グリコシアミン,針状結晶．分解点270～280 ℃．熱湯に易溶，エタノール，エーテルに不溶．坂口反応は陽性を示す．酸と加熱すると分子内でアミド結合をつくり，グリコシアミジンに環化する．生体内でメチル化されて，クレアチンやクレアチニンに変化する．森北出版「化学辞典（第2版）
用途生化学研究用。
調製方法
純化方法Recrystallise it from 15 parts of hot H2O, or by dissolving it in slightly more than the calculated amount of 2N HCl and precipitating it by adding an equivalent of 2N NaOH, filtering, washing with cold H2O and drying first in vacuo, then at 60o in vacuo. The hydrochloride has m 200o(dec) after recrystallisation from aqueous HCl as plates. The picrate forms needles from hot H2O with m 210o(dec). [Brand & Brand Org Synth Coll Vol III 440 1955, Failey & Brand J Biol Chem 102 768 1933, King J Chem Soc 2375 1930, Beilstein 4 H 359, 4 I 477, 4 II 793, 4 III 1165.]
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