Cycloleucine

HCID 2901CAS 52-52-8

Basic information

Standard SMILES
NC1(C(=O)O)CCCC1
InChIKey
NILQLFBWTXNUOE-UHFFFAOYSA-N
Molecular formula
C6H11NO2
Average molar mass
129.16 g/mol
Monoisotopic mass
129.07897859

Overview

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.

Names & identifiers

Preferred name
Cycloleucine
IUPAC
1-aminocyclopentane-1-carboxylic acid
English name
Cycloleucine
Molecular formula
C6H11NO2
Molecular weight
129.16

Names & synonyms

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
Show more names
1-Carboxycyclopentylaminex201cb1639CYCLEU
1-AminocyclopentanecarboxylateX 201NSC1026WR 14,997NSC-1026aminocyclopentanecarboxylic acid0TQU7668EIAcid, aminocyclopentanecarboxylic

Database identifiers

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

Properties

Computed structural properties

XLogP
-2.6
Topological polar surface area
63.3 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
3
Rotatable bonds
1
Heavy atoms
9

Experimental & physicochemical properties

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]

Physicochemical properties

Melting point
320 °C · 320 °C (dec.) (lit.)
Boiling point
239.22 °C · 239.22°C (rough estimate)
Density
1.1426 · 1.1426 (rough estimate)
refractive index
1.4827 · 1.4827 (estimate)
storage temp.
Keep in dark place,Inert atmosphere,Room temperature
solubility
1 mg/mL · DMSO: < 1 mg/mL (ultrasonic) (insoluble or slightly soluble)

Safety & regulation

GHS classification

GHS Classification · 4 items

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.

Hazard information

Hazards Summary · 1 item

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%)

Toxicology

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

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.

Safety data

PPE
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
wgk
3
tsca
TSCA listed
rtecs
GY2625000
ridadr
UN 2811 6.1/PG 3
hs_code
29224999

Chemistry & industry

Pharmacology

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 items

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.

Uses & manufacturing

Uses · 4 items

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 item

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
Applications · 4 items

UsesNMDA receptor antagonist, inhibits nucleic acid methylation; adrenergic agonist

UsesCycloleucine can be used as a building block to synthesize: Phosphonylmethylaminocyclopentane-1-carboxylic acid by reacting with paraformaldehyde and diethylphosphite via Kabachnik-Field′s reaction. Benzo[b]thiophene-2-carboxylic acid {1-[1-(R)-(3-morpholin-4-ylpropylcarbamoyl)-2-phenylethylcarbamoyl]cyclopentyl}-amide, (MEN14268) as potential tachykinin NK2 receptor antagonist.

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

General DescriptionCycloleucine is a nonmetabolizable amino acid widely used as a building block in peptide synthesis.

Suppliers50 total

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]

Additional notes

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

Related reactions

43 records

Linked notes

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