Cycloleucine
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Identification
- Generic Name
- Cycloleucine
- DrugBank Accession Number
- DB04620
- Background
Cycloleucine is non-metabolisable amino acid formed by cyclization of leucine. It is also a specific and reversible inhibitor of nucleic acid methylation and widely used in biochemical experiments.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 129.157
Monoisotopic: 129.078978601 - Chemical Formula
- C6H11NO2
- Synonyms
- 1-amino-1-cyclopentanecarboxylic acid
- 1-aminocyclopentane-1-carboxylic acid
- 1-aminocyclopentanecarboxylic acid
- Cyclo-leucine
- Cycloleucin
- External IDs
- CB-1639
- WR 14,997
- X 201
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Cycloleucine has cytostatic, immunosuppressive and antineoplastic activities.
- Mechanism of action
Target Actions Organism UGlutamate receptor ionotropic, NMDA 1 Not Available Humans - 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
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Oral, mouse: LD50 = 309 mg/kg; oral, rat: LD50 = 290 mg/kg
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Cycloleucine hydrochloride Z72HVF4L7V 92398-48-6 ONNMHNDIUIHULO-UHFFFAOYSA-N
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- Aliphatic homomonocyclic compound / Amine / Amino acid / Carbonyl group / Carboxylic acid / D-alpha-amino acid / Hydrocarbon derivative / L-alpha-amino acid / Monocarboxylic acid or derivatives / Organic nitrogen compound
- Molecular Framework
- Aliphatic homomonocyclic compounds
- External Descriptors
- non-proteinogenic alpha-amino acid (CHEBI:40547)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 0TQU7668EI
- CAS number
- 52-52-8
- 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
References
- General 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. [Article]
- External Links
- Human Metabolome Database
- HMDB0062225
- KEGG Compound
- C03969
- PubChem Compound
- 2901
- PubChem Substance
- 46505671
- ChemSpider
- 2798
- BindingDB
- 50070638
- ChEBI
- 40547
- ChEMBL
- CHEMBL295830
- ZINC
- ZINC000000001234
- PDBe Ligand
- AC5
- Wikipedia
- Cycloleucine
- PDB Entries
- 1y1m / 3s8n / 4gm3 / 4gm8 / 6fce / 6fj3 / 7yv1
- MSDS
- Download (69.9 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 330 dec °C PhysProp water solubility 5E+004 mg/L (at 25 °C) MERCK INDEX (1996) logP -2.28 TSAI,RS ET AL. (1991) pKa 2.62 TSAI,RS ET AL. (1991) - Predicted Properties
Property Value Source Water Solubility 171.0 mg/mL ALOGPS logP -2.3 ALOGPS logP -1.8 Chemaxon logS 0.12 ALOGPS pKa (Strongest Acidic) 2.48 Chemaxon pKa (Strongest Basic) 9.83 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 63.32 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 32.46 m3·mol-1 Chemaxon Polarizability 13.23 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - 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 inhibitor Non-inhibitor 0.9441 CYP450 2D6 inhibitor Non-inhibitor 0.9774 CYP450 2C19 inhibitor Non-inhibitor 0.9499 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Download (8.04 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 123.5889955 predictedDarkChem Lite v0.1.0 [M-H]- 123.5010955 predictedDarkChem Lite v0.1.0 [M-H]- 124.03179 predictedDeepCCS 1.0 (2019) [M+H]+ 123.9067955 predictedDarkChem Lite v0.1.0 [M+H]+ 123.9381955 predictedDarkChem Lite v0.1.0 [M+H]+ 126.87373 predictedDeepCCS 1.0 (2019) [M+Na]+ 123.7584955 predictedDarkChem Lite v0.1.0 [M+Na]+ 123.7578955 predictedDarkChem Lite v0.1.0 [M+Na]+ 135.44719 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsGlutamate receptor ionotropic, NMDA 1
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- 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. [Article]
- Snell LD, Johnson KM: Cycloleucine competitively antagonizes the strychnine-insensitive glycine receptor. Eur J Pharmacol. 1988 Jun 22;151(1):165-6. [Article]
- 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. [Article]
Drug created at September 11, 2007 17:49 / Updated at January 07, 2021 03:11