1-aminocyclopentane-1-carboxylic acid

• ChemBase ID: 4183
• Molecular Formular: C6H11NO2
• Molecular Mass: 129.15704
• Monoisotopic Mass: 129.0789786
• SMILES: NC1(CCCC1)C(=O)O
• Canonical SMILES: OC(=O)C1(N)CCCC1
• InChI: InChI=1S/C6H11NO2/c7-6(5(8)9)3-1-2-4-6/h1-4,7H2,(H,8,9)
• InChIKey: NILQLFBWTXNUOE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-aminocyclopentane-1-carboxylic acid
• IUPAC Traditional name: cycloleucine
• Synonyms: Cycloleucine; 1-Aminocyclopentanecarboxylic acid; NSC 1026; NSC 112194; NSC 112195; NSC 112197; 1-aminocyclopentane-1-carboxylic acid; Cyclo-leucine; Cycloleucin; 1-Amino-1-cyclopentanecarboxylic acid; 1-Amino-cyclopentanecarboxylic acid; 1-Aminocyclopentane-1-carboxylic acid; 1-Aminocyclopentanecarboxylate; 1-Aminocyclopentanecarboxylic acid; ACP; ACPC; Amino-1-cyclopentanecarboxylic acid; Cycloleucine; Cycloleucine; 1-Amino-1-cyclopentanecarboxylic acid; 1-Aminocyclopentanecarboxylic acid; 1-氨基环戊烷羧酸; 环亮氨酸; 1-氨基环戊烷甲酸

Database IDs

• CAS Number: 52-52-8
• EC Number: 200-144-6
• MDL Number: MFCD00001381
• Beilstein Number: 636626
• Merck Index: 142734
• PubChem SID: 24890914; 46505671; 160967615; 24846087
• PubChem CID: 2901
• CHEMBL: 295830
• Chemspider ID: 2798
• DrugBank ID: DB04620
• KEGG ID: C03969
• Wikipedia Title: Cycloleucine

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.476825
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.8272533
• LogD (pH = 7.4): -1.8284363
• Log P: -1.8270618
• Molar Refractivity: 32.4564 cm^3
• Polarizability: 13.120767 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.3
• LOG S: 0.12
• Solubility (Water): 1.71e+02 g/l

PROPERTIES

Physical Property

• Solubility: 50 mg/mL at 25 oC [MERCK INDEX (1996)]; 50 mg/mL in water
• Apperance: white of beige crystalline flakes or powder
• Melting Point: 320 °C (dec.)(lit.); 320°C; 328-335°C; 328-335°C; ca 320°C dec.
• Boiling Point: 256.1°C
• Density: 1.207 g/mL
• Hydrophobicity(logP): -2.254; -2.28 [TSAI,RS ET AL. (1991)]

Safety Information

• Storage Warning: IRRITANT
• RTECS: GY2625000
• European Hazard Symbols: X; Harmful (Xn)
• UN Number: 2811; UN2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Risk Statements: 22; 22-36/37/38
• Safety Statements: 22-24/25; 26-36/37
• TSCA Listed: false; 是
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Danger
• Main Hazard: Irritant
• GHS Hazard statements: H301; H302-H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A; P301 + P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3

Product Information

• Purity: ≥97.0% (NT); 95%; 95+%; 97%; 97+%
• Grade: purum
• Linear Formula: H2NC5H8CO2H

DETAILS

MP Biomedicals - 05214420

MP Biomedicals Rare Chemical collection

DrugBank - DB04620

• Drug Groups: experimental
• Description: Cycloleucine is an amino acid formed by cyclization of leucine. Cycloleucine is a non-metabolisable amino acid and is a specific and reversible inhibitor of nucleic acid methylation, and as such is widely used in biochemical experiments. [Wikipedia]
• Pharmacology: Cycloleucine has cytostatic, immunosuppressive and antineoplastic activities.
• Toxicity: Oral, mouse: LD₅₀ = 309 mg/kg; oral, rat: LD₅₀ = 290 mg/kg
• Affected Organisms: Humans and other mammals
• References: Herberg LJ, Rose IC: Effects of D-cycloserine and cycloleucine, ligands for the NMDA-associated strychnine-insensitive glycine site, on brain-stimulation reward and spontaneous locomotion. Pharmacol Biochem Behav. 1990 Aug;36(4):735-8. [Pubmed]
• External Links: Wikipedia

Apollo Scientific Ltd - OR0354T

A synthetic amino acid used in biochemical transportstudies.

Sigma Aldrich - A48105

Packaging
5, 10 g in glass bottle

Toronto Research Chemicals - A603540

A synthetic amino acid used in numerous biochemical transport studies.

REFERENCES

• Herberg LJ, Rose IC: Effects of D-cycloserine and cycloleucine, ligands for the NMDA-associated strychnine-insensitive glycine site, on brain-stimulation reward and spontaneous locomotion. Pharmacol Biochem Behav. 1990 Aug;36(4):735-8. Pubmed
• Rabito, C.A., et al.: J. Biol. Chem., 257, 6802 (1982)