基本情報
- 標準SMILES
NC1(C(=O)O)CCCC1- InChIKey
NILQLFBWTXNUOE-UHFFFAOYSA-N- 分子式
- C6H11NO2
- 平均分子量
- 129.16 g/mol
- 単同位体質量
- 129.07897859
概要
1-aminocyclopentanecarboxylic acid is a non-proteinogenic alpha-amino acid that is cyclopentane substituted at position 1 by amino and carboxy groups. It has a role as an EC 2.5.1.6 (methionine adenosyltransferase) inhibitor.
名称と識別子
- 優先名称
- Cycloleucine
- IUPAC
- 1-aminocyclopentane-1-carboxylic acid
- 現地名
- 1-アミノシクロペンタンカルボン酸
- 英語名
- Cycloleucine
- 分子式
- C6H11NO2
- 分子量
- 129.16
名称と別名
名称をさらに表示
データベース識別子
- CAS
52-52-8- PubChem CID
- 2901
- DTXSID
DTXSID5024475- ChEMBL
CHEMBL295830- ChEBI
CHEBI:40547- UNII
- 0TQU7668EI
- EC Number
- 200-144-6
- Nikkaji
- J4.131I
物性
構造計算による物性
- XLogP
- -2.6
- 極性表面積
- 63.3 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 3
- 回転可能結合数
- 1
- 重原子数
- 9
- 形式電荷
- 0
- 複雑度
- 127
実験および物理化学的性質
物理化学的性質
- 融点
- 320 °C · 320 °C (dec.) (lit.)
- 沸点
- 239.22 °C · 239.22°C (rough estimate)
- 比重(密度)
- 1.1426 · 1.1426 (rough estimate)
- 屈折率
- 1.4827 · 1.4827 (estimate)
- 貯蔵温度
- Keep in dark place,Inert atmosphere,Room temperature
- 溶解性
- 1 mg/mL · DMSO: < 1 mg/mL (ultrasonic) (insoluble or slightly soluble)
- 酸解離定数(Pka)
- 2.38 · 2.38±0.20(Predicted)
- 外見
- 結晶フレークまたは粉末
- 色
- 白からベージュ
- 水溶解度
- 5 g/100mL · 5g/100mL
- Merck
- 14 · 14,2734
- BRN
- 636626 · 636626
- 主な用途
- ペプチド合成
- InChI
- 1S/C6H11NO2/c7-6(5(8)9)3-1-2-4-6/h1-4,7H2,(H,8,9)
- InChIKey
- NILQLFBWTXNUOE-UHFFFAOYSA-N
- SMILES
- NC1(CCCC1)C(O)=O
- CAS データベース
- 52 · 52-52-8(CAS DataBase Reference)
- NISTの化学物質情報
- 1 · Cyclopentanecarboxylic acid, 1-amino-(52-52-8)
- EPAの化学物質情報
- 1 · Cyclopentanecarboxylic acid, 1-amino- (52-52-8)
化学的性質
化学的特性WHITE TO BEIGE CRYSTALLINE FLAKES OR POWDER
安全と法規制
GHS分類
GHS Classification
Danger
H301 (94.2%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 52 reports by companies from 5 notifications to the ECHA C&L Inventory.
危険有害性情報
Hazards Summary
Possesses cytostatic, immunosuppressive, and antineoplastic properties; [ChemIDplus] Evidence of neurotoxicity in experimental animals; [HSDB] Causes urine changes in 3-day intermittent intraperitoneal studies of rats; Causes muscle weakness and hemorrhage in 15-day intermittent intravenous studies of dogs; Oral administration in humans causes anorexia and nausea or vomiting; [RTECS] An irritant; Harmful by ingestion; [Alfa Aesar MSDS]
毒性情報
Non-Human Toxicity Excerpts
WHEN ADDED TO CHICK EMBRYO FIBROBLAST CULTURES WHICH HAD BEEN INFECTED WITH AVIAN SARCOMA VIRUS, CYCLOLEUCINE DID NOT SIGNIFICANTLY AFFECT VIRUS YIELDS BUT INHIBITED METHYLATION OF VIRAL RNA AT 5'-TERMINAL STRUCTURES.
IN BHK CELLS INFECTED WITH VESICULAR STOMATITIS VIRUS (VSV), CYCLOLEUCINE INHIBITED VIRUS SYNTHESIS BY 99% & REDUCED SIGNIFICANTLY THE SIZE OF VSV MESSENGER RNA SPECIES.
TREATMENT OF DEVELOPING RATS RESULTED IN CHANGES OF BRAIN & SPINAL CORD PHOSPHOLIPID CONTENT & FATTY ACIDS. DECR IN ETHANOLAMINE PHOSPHOLIPID CONTENT & INCR IN SATURATED FATTY ACIDS OF ETHANOLAMINE PHOSPHOLIPID. MINOR FATTY ACIDS CHANGES IN PHOSPHATIDYL CHOLINE.
CONSIDERABLE MYELIN SPLITTING WAS SHOWN BY ELECTRON MICROSCOPIC EXAMINATION OF THE SPINAL CORDS OF CYCLOLEUCINE-AFFECTED RATS.
For more Non-Human Toxicity Excerpts (Complete) data for CYCLOLEUCINE (10 total), please visit the HSDB record page.
安全データ
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- GY2625000
- ridadr
- UN 2811 6.1/PG 3
- 毒性
- LD50 oral in rat: 290mg/kg
- hs_code
- 29224999
- risk_code
- 22
- hazard_code
- Xn,Xi
- safety_code
- 22-24/25
- hazard_class
- 6.1
- packing_group
- III
- Hazard Classifications
- Acute Tox. 3 Oral
- ストレージクラス
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- 有毒物質データの
- 52-52-8(Hazardous Substances Data)
化学と産業
薬理情報
Absorption, Distribution and Excretion
LEVELS OF (14)C IN LIVER & PANCREAS WERE RESPECTIVELY EIGHTFOLD & TWOFOLD THOSE IN BLOOD, 15 MIN AFTER IV DOSE OF [(14)C]-1-AMINOCYCLOPENTANECARBOXYLIC ACID TO RHESUS MONKEYS. (14)C LEVELS IN THESE TISSUES WERE SIMILAR TO THOSE IN BLOOD AFTER 24 HR.
WHEN ADMIN TO MICE CYCLOLEUCINE ACCUM IN TISSUES AT LEVELS BETWEEN 0.02 & 1.29 MG/ML. MOST OF REMAINING 2% WAS ASSOC WITH PROTEIN. ACCUM AGAINST CONCN GRADIENT OCCURRED IN KIDNEY, IN SPLEEN TO GREATER EXTENT & TO MUCH GREATER DEGREE IN PANCREAS. THE DISTRIBUTION RATIOS FOR CNS TISSUE, KIDNEY & SPLEEN DID NOT CHANGE AS FUNCTION OF PLASMA CYCLOLEUCINE CONCN OR OF TIME BETWEEN 4 & 40 DAYS AFTER ADMIN TO MICE. 5 DAYS AFTER ADMIN OF CYCLOLEUCINE TO MICE, HEPATIC CYCLOLEUCINE DISTRIBUTION RATIO WAS CONSIDERABLY GREATER THAN UNITY AT THE LOWEST DOSES & INCR VARIABLY WITH INCR CYCLOLEUCINE PLASMA LEVELS.
用途と製造
Uses
A synthetic amino acid used in amino acid transport studies and in testing for immunosuppression in mice; [Merck Index] Used as experimental tumor screening agent; [HSDB]
BIOLOGICAL TESTING MATERIALS FOR IMMUNOSUPPRESSIVE PROPERTIES IN MICE; FOR AMINO ACID TRANSPORT STUDIES
AS EXPTL TUMOR SCREENING AGENT
MEDICATION (VET)
Methods of Manufacturing
ZELINSKY, STADNIKOFF, Z PHYSIOL CHEM 75, 350 (1911); CONNORS, ROSS, J CHEM SOC 1960, 2119; CREMLYN, J CHEM SOC 1962, 3977; SUDO, ICHIHARA, BULL CHEM SOC JAPAN 36, 34 (1963). MFR: NETHERLAND PATENT APPLICATION 6,607,754 (1966 TO ROHM & HAAS), CA 67, 73159B (1967).
応用分野
使用Cycloleucine is a synthetic amino acid used in numerous biochemical transport studies
一般的な説明Cycloleucine is a nonmetabolizable amino acid widely used as a building block in peptide synthesis.
調製方法
純化方法Any Cl -or other anions are removed by stirring with a strong cation exchange resin (Amberlite IR-120), filtering, and washing with distilled H2O until the filtrate is free from the anion. The resin is then stirred overnight with 6N NH4OH, filtered, the filtrate is decolourised (charcoal) and evaporated to dryness in a vacuum. The residue is recrystallised from H2O/EtOH. Also crystallise it from aqueous EtOH. The hydrochloride has m 222-224o(dec). [Neelakantan & Hartung J Org Chem 23 967 1958, Connors & Ross J Chem Soc 2119 1960. O’Donnell et al. Synthesis 127 1984, Beilstein 14 IV 974.]
上流・下流製品情報
下流製品
サプライヤー50 社
補足説明
定義ChEBI: A non-proteinogenic alpha-amino acid that is cyclopentane substituted at position 1 by amino and carboxy groups.
関連反応
関連ノート
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