NAV

Cycloleucine

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
3D
Similar Structures
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
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Cycloleucine has cytostatic, immunosuppressive and antineoplastic activities.

Mechanism of action
TargetActionsOrganism
UGlutamate receptor ionotropic, NMDA 1Not AvailableHumans
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
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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

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Product Ingredients
IngredientUNIICASInChI Key
Cycloleucine hydrochlorideZ72HVF4L7V92398-48-6ONNMHNDIUIHULO-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
  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. [Article]
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

Clinical Trials
PhaseStatusPurposeConditionsCount

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-MSsplash10-000x-9100000000-f2d294f6a1983364287d
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
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00lr-9000000000-ee6b0fd1eadb6c57e2c6
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0900000000-12cf6b28b1e48bfd117d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0900000000-81bba5ddc261be8c9591
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-9000000000-d359f87ab8a52d40826e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001l-9200000000-10cdeb2345e8f4b54dcb
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a5c-9000000000-638506055cbea730f46c
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-123.5889955
predicted
DarkChem Lite v0.1.0
[M-H]-123.5010955
predicted
DarkChem Lite v0.1.0
[M-H]-124.03179
predicted
DeepCCS 1.0 (2019)
[M+H]+123.9067955
predicted
DarkChem Lite v0.1.0
[M+H]+123.9381955
predicted
DarkChem Lite v0.1.0
[M+H]+126.87373
predicted
DeepCCS 1.0 (2019)
[M+Na]+123.7584955
predicted
DarkChem Lite v0.1.0
[M+Na]+123.7578955
predicted
DarkChem Lite v0.1.0
[M+Na]+135.44719
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Details1. Glutamate 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
  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. [Article]
  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. [Article]
  3. Snell LD, Johnson KM: Cycloleucine competitively antagonizes the strychnine-insensitive glycine receptor. Eur J Pharmacol. 1988 Jun 22;151(1):165-6. [Article]
  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. [Article]

Drug created at September 11, 2007 17:49 / Updated at January 07, 2021 03:11