Cycloleucine

Identification

Name
Cycloleucine
Accession Number
DB04620
Type
Small Molecule
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]

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 IDs
CB-1639
Product Ingredients
IngredientUNIICASInChI Key
Cycloleucine hydrochlorideZ72HVF4L7V92398-48-6ONNMHNDIUIHULO-UHFFFAOYSA-N
Categories
UNII
0TQU7668EI
CAS number
52-52-8
Weight
Average: 129.157
Monoisotopic: 129.078978601
Chemical Formula
C6H11NO2
InChI Key
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

Pharmacology

Indication
Not Available
Pharmacodynamics

Cycloleucine has cytostatic, immunosuppressive and antineoplastic activities.

Mechanism of action
TargetActionsOrganism
UGlutamate receptor ionotropic, NMDA 1Not AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

Oral, mouse: LD50 = 309 mg/kg; oral, rat: LD50 = 290 mg/kg

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

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
Human Metabolome Database
HMDB0062225
KEGG Compound
C03969
PubChem Compound
2901
PubChem Substance
46505671
ChemSpider
2798
BindingDB
50070638
ChEBI
40547
ChEMBL
CHEMBL295830
HET
AC5
Wikipedia
Cycloleucine
PDB Entries
1y1m / 3s8n / 4gm3 / 4gm8 / 6fce
MSDS
Download (69.9 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)330 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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Download (8.04 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-001i-9100000000-4370c60fab0924acb87d
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-0a4i-0900000000-e532ba4a94b2b9502e92
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0ab9-8900000000-281b59b0ef8c6d49ce2d
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0a4i-0900000000-20f20c6883a8b8010b49
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00kr-5900000000-2bb3a657eb5efefae425
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-0900000000-ff6cd44aca7edab8662d
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-0900000000-02e40c784dcfc166858b
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-1900000000-e3776623b288605d7c79
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0002-9000000000-5a62167bd787768808f7
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0005-9000000000-aeccad5bab6f0ac80882
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-3900000000-167f80bd9598dfc42c67
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-9000000000-601f3c8c19e0adfb4935
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-9000000000-88d32a35b4754114c1d5
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00lr-9000000000-8b24020ad515f02ccc62
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-9000000000-dd53af4c6a332683ed94
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001i-0900000000-1fb29c634b3071a0a6eb
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001i-9200000000-66ef4b7f543f8bf1eba4

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
L-alpha-amino acids
Alternative Parents
D-alpha-amino acids / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives / Carbonyl compounds
Substituents
D-alpha-amino acid / L-alpha-amino acid / Amino acid / Carboxylic acid / Monocarboxylic acid or derivatives / Amine / Hydrocarbon derivative / Organic oxide / Organopnictogen compound / Primary amine
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
non-proteinogenic alpha-amino acid (CHEBI:40547)

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 p...
Gene Name
GRIN1
Uniprot ID
Q05586
Uniprot Name
Glutamate receptor ionotropic, NMDA 1
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]

Drug created on September 11, 2007 11:49 / Updated on November 02, 2018 09:05