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
Show more names
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
- Formal charge
- 0
- Complexity
- 127
Experimental & physicochemical properties
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)
- pka
- 2.38 · 2.38±0.20(Predicted)
- form
- Crystalline Flakes or Powder
- color
- White to beige
- Water Solubility
- 5 g/100 · 5 g/100 mL
- Merck
- 14 · 14,2734
- BRN
- 636626 · 636626
- Major Application
- peptide synthesis
- 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 DataBase Reference
- 52 · 52-52-8(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 0 TQU7668EI · 0TQU7668EI
- NCI Drug Dictionary
- cycloleucine
- NIST Chemistry Reference
- 1 · Cyclopentanecarboxylic acid, 1-amino-(52-52-8)
- EPA Substance Registry System
- 1 · Cyclopentanecarboxylic acid, 1-amino- (52-52-8)
- UNSPSC Code
- 12352209 · 12352209
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 301 · H301
- Precautionary statements
- 301 · P301+P310+P330
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- Hazard Codes
- Xn,Xi
- Risk Statements
- 22 · 22
- Safety Statements
- 22 · 22-24/25
- RIDADR
- 2811 · UN 2811 6.1/PG 3
- WGK Germany
- 3 · 3
- RTECS
- 2625000 · GY2625000
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1
- PackingGroup
- III
- HS Code
- 29224999 · 29224999
- Storage Class
- 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- 3 Oral · Acute Tox. 3 Oral
- Hazardous Substances Data
- 52 · 52-52-8(Hazardous Substances Data)
- Toxicity
- 50 oral · LD50 oral in rat: 290mg/kg
- Limited Quantities
- 5 kg · 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Safety & regulation
GHS classification
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.
Hazard information
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]
Toxicology
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.
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
- Toxicity
- LD50 oral in rat: 290mg/kg
- risk_code
- 22
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- Xn,Xi
- safety_code
- 22-24/25
- hazard_class
- 6.1
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- packing_group
- III
- Hazard statements
- H301
- Limited Quantities
- 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
- Hazard Classifications
- Acute Tox. 3 Oral
- Precautionary statements
- P301+P310+P330
- Hazardous Substances Data
- 52-52-8(Hazardous Substances Data)
Chemistry & industry
Pharmacology
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.
Uses & manufacturing
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).
Applications
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.
Upstream & downstream products
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: A non-proteinogenic alpha-amino acid that is cyclopentane substituted at position 1 by amino and carboxy groups.
Related reactions
Linked notes
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