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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
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number52-52-8
WeightAverage: 129.157
Monoisotopic: 129.078978601
Chemical FormulaC6H11NO2
InChI KeyNILQLFBWTXNUOE-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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • D-alpha-amino acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
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
PropertyValueProbability
Human Intestinal Absorption+0.8584
Blood Brain Barrier+0.9122
Caco-2 permeable-0.6482
P-glycoprotein substrateNon-substrate0.6827
P-glycoprotein inhibitor INon-inhibitor0.9922
P-glycoprotein inhibitor IINon-inhibitor0.9898
Renal organic cation transporterNon-inhibitor0.9258
CYP450 2C9 substrateNon-substrate0.8455
CYP450 2D6 substrateNon-substrate0.8418
CYP450 3A4 substrateNon-substrate0.7144
CYP450 1A2 substrateNon-inhibitor0.9375
CYP450 2C9 substrateNon-inhibitor0.9441
CYP450 2D6 substrateNon-inhibitor0.9774
CYP450 2C19 substrateNon-inhibitor0.9499
CYP450 3A4 substrateNon-inhibitor0.9522
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9865
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.885
BiodegradationReady biodegradable0.7678
Rat acute toxicity2.6179 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9904
hERG inhibition (predictor II)Non-inhibitor0.9601
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 Solubility171.0 mg/mLALOGPS
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 Area63.32 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity32.46 m3·mol-1ChemAxon
Polarizability13.23 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (8.04 KB)
SpectraGC-MS
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
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (69.9 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

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

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