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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
1-Amino-1-cyclopentanecarboxylic acid
1-Amino-cyclopentanecarboxylic acid
1-Aminocyclopentane-1-carboxylic acid
1-Aminocyclopentanecarboxylate
1-Aminocyclopentanecarboxylic acid
Amino-1-cyclopentanecarboxylic acid
Cyclo-leucine
Cycloleucin
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII0TQU7668EI
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
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
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
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 inhibitorNon-inhibitor0.9441
CYP450 2D6 inhibitorNon-inhibitor0.9774
CYP450 2C19 inhibitorNon-inhibitor0.9499
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
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)
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-001i-9100000000-4370c60fab0924acb87dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0a4i-0900000000-e532ba4a94b2b9502e92View in MoNA
References
Synthesis ReferenceNot Available
General 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:2170997 ]
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

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Voltage-gated cation channel activity
Specific Function:
NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine. This protein plays a key role in synaptic plasticity, synaptogenesis, excitotoxicity, memory acquisition and learning. It mediates neuronal functions in glutamate neurotransmission. Is involved in the cell surface targeting of NMDA receptors (...
Gene Name:
GRIN1
Uniprot ID:
Q05586
Molecular Weight:
105371.945 Da
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:2170997 ]
  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:2556198 ]
  3. Snell LD, Johnson KM: Cycloleucine competitively antagonizes the strychnine-insensitive glycine receptor. Eur J Pharmacol. 1988 Jun 22;151(1):165-6. [PubMed:2843389 ]
  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:10592235 ]
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Drug created on September 11, 2007 11:49 / Updated on August 17, 2016 12:24