1-アミノシクロペンタンカルボン酸

Cycloleucine

HCID 2901CAS 52-52-8

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

cycloleucine52-52-81-Aminocyclopentanecarboxylic acid1-Aminocyclopentane-1-carboxylic acidCycloleucin1-Amino-1-cyclopentanecarboxylic acidCYCLO-LEUCINE1-Amino-1-carboxycyclopentane1-Amino-cyclopentanecarboxylic acidCyclopentanecarboxylic acid, 1-amino-NSC 1026CB 1639
名称をさらに表示
1-アミノシクロペンタンカルボン酸1-アミノ-1-シクロペンタンカルボン酸1-アミノシクロペンタン-1-カルボン酸1-アミノ-シクロペンタン-1-カルボン酸シクロロイシン1‐アミノ‐1‐シクロペンタンカルボン酸1-Carboxycyclopentylaminex201cb1639CYCLEU
1-AminocyclopentanecarboxylateX 201NSC1026WR 14,997NSC-1026aminocyclopentanecarboxylic acid0TQU7668EIAcid, aminocyclopentanecarboxylic

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

実験および物理化学的性質

Chemical ClassesNitrogen Compounds -> Amino Carboxylic Acids
DrugsPharmaceuticals -> Listed in ZINC15
Color/FormCRYSTALS FROM ETHANOL & WATER
SolubilitySOL IN WATER APPROX 5 G/100 ML
Melting Point330 °C, DECOMP
Physical DescriptionSolid; [Merck Index] Crystalline powder; [Alfa Aesar MSDS]

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)

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 · 4 件

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 · 1 件

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]

Hazard Classes and CategoriesAcute Tox. 3 (94.2%)

毒性情報

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Non-Human Toxicity Excerpts · 5 件

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

化学と産業

薬理情報

PharmacodynamicsCycloleucine has cytostatic, immunosuppressive and antineoplastic activities.
Mechanism of ActionSYNTHETIC AMINO ACID THOUGHT TO ACT AS VALINE ANTAGONIST.
Biological Half-LifeAT 0.4-0.5 MG/G PLASMA LEVEL AT 24 DAYS WAS NOT SIGNIFICANTLY DIFFERENT FROM THAT AT 1 DAY. HIGHEST DOSES (1-3 MG/G) RESULTED IN NEARLY SIMILAR PLASMA LEVELS BY 4TH DAY. T/2 IN PLASMA WAS EXTREMELY LONG.
Absorption, Distribution and Excretion · 2 件

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 · 4 件

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 · 1 件

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).

General Manufacturing InformationCyclopentanecarboxylic acid, 1-amino-: ACTIVE

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 · 1 件

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.]

サプライヤー50 社

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INTATRADE GmbH+49 3493/605464 · [email protected]

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

43 件

関連ノート

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