(2S)-2-アミノ-4-メチルホスホニルブタン酸

Phosphinothricin

HCID 91619CAS 35597-44-5

基本情報

標準SMILES: CP(=O)(O)CC[C@H](N)C(=O)O
InChIKey: IAJOBQBIJHVGMQ-BYPYZUCNSA-N
分子式: C5H12NO4P
平均分子量: 181.13 g/mol
単同位体質量: 181.05039449

概要

Glufosinate-P is a 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid that has S configuration at position 2. A glutamine synthetase inhibitor, it is used (generally as the corresponding ammonium or sodium salts, known as glufosinate-P-ammonium and glufosinate-P-sodium, respectively) as a herbicide to control annual weeds and grasses. It has a role as an EC 6.3.1.2 (glutamate--ammonia ligase) inhibitor, a herbicide and an agrochemical. It is an enantiomer of a (2R)-glufosinate. It is a tautomer of a glufosinate-P zwitterion.

名称と識別子

優先名称: Phosphinothricin
IUPAC: (2S)-2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid
現地名: (2S)-2-アミノ-4-メチルホスホニルブタン酸
英語名: Glufosinate-P
分子式: C5H12NO4P
分子量: 181.13

名称と別名

phosphinothricin35597-44-5RefChem:6631642-amino-4-methylphosphinobutyric acidGlufosinate-PL-GlufosinateL-PHOSPHINOTHRICIN(S)-Phosphinothricin(2S)-2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acidButanoic acid, 2-amino-4-(hydroxymethylphosphinyl)-, (2S)-CHEMBL145114(S)-Glufosinate

名称をさらに表示

(2S)-2-アミノ-4-[ヒドロキシ(メチル)ホスフィニル]ブタン酸(S)-2-アミノ-4-(メチルホスホニル)ブタン酸(S)-4-[ヒドロキシ(メチル)ホスフィニル]-2-アミノ酪酸L-ホスフィノトリシンL-グルホシナートL-グルホシネートホスフィノトリシン(S)-ホスフィノトリシン(2S)-2-アミノ-4-メチルホスホニルブタン酸グルホシネートP(2S)-2-アミノ-4-(メチルホスホニル)ブタン酸(2S)-2-アミノ-4-[ヒドロキシ(メチル)ホスホリル]ブタン酸L-Glufosinate ammoniumGlufosinate Impurity 5L-GlufositePhosphinothricine(S)-2-Amino-4-(hydroxymethylphosphinyl)butyric acid(S)-4-[Hydroxy(methyl)phosphinyl]-2-aminobutyric acid

DTXSID401020544(2S)-2-amino-4-(hydroxymethylphosphinyl)butanoic acid(2S)-2-Amino-4-(hydroxy(methyl)phosphoryl)butanoic acidGlufosinate-P [ISO](2S)-2-amino-4-(hydroxy(methyl)phosphinoyl)butyric acidCHEMBL53515315766-01-5(2S)-2-azaniumyl-4-[hydroxy(methyl)phosphoryl]butanoate

データベース識別子

CAS: 35597-44-5、51276-47-2
PubChem CID: 91619
DTXSID: DTXSID401020544
ChEMBL: CHEMBL145114、CHEMBL535153
ChEBI: CHEBI:142852
UNII: 72P470U27C
EC Number: 690-077-2
Nikkaji: J391.973K

物性

構造計算による物性

XLogP: -5
極性表面積: 101 Å²
水素結合供与体数: 3
水素結合受容体数: 5
回転可能結合数: 4
重原子数: 11
形式電荷: 0
複雑度: 193

物理化学的性質

融点: 209 · 209-210 °C
沸点: 519.1 · 519.1±45.0 °C(Predicted)
比旋光度: 25 · D25 +13.4° (c = 1 in water)
比重(密度): 1.378 · 1.378±0.06 g/cm3(Predicted)
酸解離定数(Pka): 2.22 · 2.22±0.10(Predicted)
InChI: InChI=1S/C5H12NO4P/c1-11(9,10)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)(H,9,10)/t4-/m0/s1
InChIKey: IAJOBQBIJHVGMQ-BYPYZUCNSA-N
SMILES: C(CP(O)(=O)C)[C@H](N)C(=O)O

安全と法規制

GHS分類

GHS Classification · 4 件

Danger

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P271, P301+P317, P304+P340, P316, P321, P330, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 28 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory InformationButanoic acid, 2-amino-4-(hydroxymethylphosphinyl)-, (2S)-: 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.

Hazard Classes and CategoriesAcute Tox. 4 (100%)

毒性情報

Health EffectsSeizures; muscle weakness (post-status epileptic myopathy); convulsions; and even death. (T10)

Toxicity SummaryGlufosinate irreversibly inhibits the enzyme glutamine synthetase, which decreases ammonia detoxification. Increased ammonia levels lead to impairment of photorespiration and photosynthesis in plants. (T10)

Signs and SymptomsNausea, vomiting, and diarrhea that is followed in 24h by impaired respiration. (T10)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

安全データ

危険有害性情報: コード危険有害性情報危険有害性クラス区分注意喚起語シンボル P コード H302

化学と産業

薬理情報

MeSH Pharmacological Classification · 2 件

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.

Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE.

上流・下流製品情報

上流原料

Butanoic acid, 2-amino-4-(ethoxymethylphosphinyl)-, (2S)- (9CI)L-glufosinate hydrochloride

サプライヤー25 社

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