1-Aminocyclopentancarbonsäure

Cycloleucine

HCID 2901CAS 52-52-8

Grundinformationen

Standard-SMILES
NC1(C(=O)O)CCCC1
InChIKey
NILQLFBWTXNUOE-UHFFFAOYSA-N
Summenformel
C6H11NO2
Durchschnittliche Molmasse
129,16 g/mol
Monoisotopische Masse
129,07897859

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
Cycloleucine
IUPAC
1-aminocyclopentane-1-carboxylic acid
Lokaler Name
1-Aminocyclopentancarbonsäure
Englischer Name
Cycloleucine
Summenformel
C6H11NO2
Molmasse
129.16

Namen und Synonyme

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
Weitere Namen anzeigen
1-Carboxycyclopentylaminex201cb1639CYCLEU
1-AminocyclopentanecarboxylateX 201NSC1026WR 14,997NSC-1026aminocyclopentanecarboxylic acid0TQU7668EIAcid, aminocyclopentanecarboxylic

Datenbank-Bezeichner

CAS
52-52-8
PubChem CID
2901
DTXSID
DTXSID5024475
ChEMBL
CHEMBL295830
ChEBI
CHEBI:40547
UNII
0TQU7668EI
EC Number
200-144-6
Nikkaji
J4.131I

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-2,6
Polarare Oberfläche (TPSA)
63,3 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
1
Schwere Atome
9

Experimentelle und physikochemische Eigenschaften

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]

Physikochemische Eigenschaften

Schmelzpunkt
320 °C · 320 °C (dec.) (lit.)
Siedepunkt
239.22 °C · 239.22°C (rough estimate)
Dichte
1.1426 · 1.1426 (rough estimate)
Brechungsindex
1.4827 · 1.4827 (estimate)
storage temp.
Keep in dark place,Inert atmosphere,Room temperature
Löslichkeit
1 mg/mL · DMSO: < 1 mg/mL (ultrasonic) (insoluble or slightly soluble)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

Hazards Summary · 1 Eintrag

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%)

Toxikologische Informationen

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

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.

Sicherheitsdaten

wgk
3
tsca
TSCA listed
ridadr
UN 2811 6.1/PG 3
hs_code
29224999
RTECS-Nr.
GY2625000
risk_code
22

Chemie und Industrie

Pharmakologische Informationen

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 Einträge

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.

Verwendung und Herstellung

Uses · 4 Einträge

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 Eintrag

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

Anwendungen

VerwendenCycloleucine is a synthetic amino acid used in numerous biochemical transport studies

Anbieter50 Anbieter

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]

Ergänzende Hinweise

DefinitionChEBI: A non-proteinogenic alpha-amino acid that is cyclopentane substituted at position 1 by amino and carboxy groups.

Zugehörige Reaktionen

43

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