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Identification
NameCycloleucine
Accession NumberDB04620
Typesmall molecule
Groupsexperimental
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]

Structure
Thumb
Synonyms
SynonymLanguageCode
1-Amino-1-cyclopentanecarboxylic acidNot AvailableNot Available
1-Amino-cyclopentanecarboxylic acidNot AvailableNot Available
1-Aminocyclopentane-1-carboxylic acidNot AvailableNot Available
1-AminocyclopentanecarboxylateNot AvailableNot Available
1-Aminocyclopentanecarboxylic acidNot AvailableNot Available
Amino-1-cyclopentanecarboxylic acidNot AvailableNot Available
Cyclo-leucineNot AvailableNot Available
CycloleucinNot AvailableNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number52-52-8
WeightAverage: 129.157
Monoisotopic: 129.078978601
Chemical FormulaC6H11NO2
InChI KeyInChIKey=NILQLFBWTXNUOE-UHFFFAOYSA-N
InChI
InChI=1S/C6H11NO2/c7-6(5(8)9)3-1-2-4-6/h1-4,7H2,(H,8,9)
IUPAC Name
1-aminocyclopentane-1-carboxylic acid
SMILES
NC1(CCCC1)C(O)=O
Mass Specshow(8.04 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassOrganic Acids and Derivatives
ClassCarboxylic Acids and Derivatives
SubclassAmino Acids, Peptides, and Analogues
Direct parentAlpha Amino Acids and Derivatives
Alternative parentsPolyamines; Enolates; Carboxylic Acids; Monoalkylamines
Substituentscarboxylic acid; enolate; polyamine; primary amine; amine; primary aliphatic amine; organonitrogen compound
Classification descriptionThis compound belongs to the alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
Pharmacology
IndicationNot Available
PharmacodynamicsCycloleucine has cytostatic, immunosuppressive and antineoplastic activities.
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityOral, mouse: LD50 = 309 mg/kg; oral, rat: LD50 = 290 mg/kg
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.8584
Blood Brain Barrier + 0.9122
Caco-2 permeable - 0.6482
P-glycoprotein substrate Non-substrate 0.6827
P-glycoprotein inhibitor I Non-inhibitor 0.9922
P-glycoprotein inhibitor II Non-inhibitor 0.9898
Renal organic cation transporter Non-inhibitor 0.9258
CYP450 2C9 substrate Non-substrate 0.8455
CYP450 2D6 substrate Non-substrate 0.8418
CYP450 3A4 substrate Non-substrate 0.7144
CYP450 1A2 substrate Non-inhibitor 0.9375
CYP450 2C9 substrate Non-inhibitor 0.9441
CYP450 2D6 substrate Non-inhibitor 0.9774
CYP450 2C19 substrate Non-inhibitor 0.9499
CYP450 3A4 substrate Non-inhibitor 0.9522
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9865
Ames test Non AMES toxic 0.9132
Carcinogenicity Non-carcinogens 0.885
Biodegradation Ready biodegradable 0.7678
Rat acute toxicity 2.6179 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9904
hERG inhibition (predictor II) Non-inhibitor 0.9601
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point330 dec °CPhysProp
water solubility5E+004 mg/L (at 25 °C)MERCK INDEX (1996)
logP-2.28TSAI,RS ET AL. (1991)
pKa2.62TSAI,RS ET AL. (1991)
Predicted Properties
PropertyValueSource
water solubility1.71e+02 g/lALOGPS
logP-2.3ALOGPS
logP-1.8ChemAxon
logS0.12ALOGPS
pKa (strongest acidic)2.48ChemAxon
pKa (strongest basic)9.83ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count2ChemAxon
polar surface area63.32ChemAxon
rotatable bond count1ChemAxon
refractivity32.46ChemAxon
polarizability13.23ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
Spectra
References
Synthesis ReferenceNot Available
General Reference
  1. 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
ResourceLink
KEGG CompoundC03969
PubChem Compound2901
PubChem Substance46505671
HETAC5
WikipediaCycloleucine
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(69.9 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

1. Glutamate receptor ionotropic, NMDA 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Glutamate receptor ionotropic, NMDA 1 Q05586 Details

References:

  1. 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
  2. Hershkowitz N, Rogawski MA: Cycloleucine blocks NMDA responses in cultured hippocampal neurones under voltage clamp: antagonism at the strychnine-insensitive glycine receptor. Br J Pharmacol. 1989 Nov;98(3):1005-13. Pubmed
  3. Snell LD, Johnson KM: Cycloleucine competitively antagonizes the strychnine-insensitive glycine receptor. Eur J Pharmacol. 1988 Jun 22;151(1):165-6. Pubmed
  4. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

Comments
Drug created on September 11, 2007 11:49 / Updated on September 16, 2013 17:25