N-[(benzyloxy)carbonyl]-L-leucyl-N-[(1S)-3-fluoro-1-(4-hydroxybenzyl)-2-oxopropyl]-L-leucinamide
Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- N-[(benzyloxy)carbonyl]-L-leucyl-N-[(1S)-3-fluoro-1-(4-hydroxybenzyl)-2-oxopropyl]-L-leucinamide
- DrugBank Accession Number
- DB04653
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for N-[(benzyloxy)carbonyl]-L-leucyl-N-[(1S)-3-fluoro-1-(4-hydroxybenzyl)-2-oxopropyl]-L-leucinamide (DB04653)
- Weight
- Average: 557.6535
Monoisotopic: 557.290114232 - Chemical Formula
- C30H40FN3O6
- Synonyms
- Calpain inhibitor IV
- CBZ-LEU-LEU-TYR-CH2F
- N-[(benzyloxy)carbonyl]leucyl-N(1)-[3-fluoro-1-(4-hydroxybenzyl)-2-oxopropyl]leucinamide
Pharmacology
- Indication
Not Available
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Not Available
- Mechanism of action
Target Actions Organism UCalpain-1 catalytic subunit 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
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Not Available
- 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
Categories
- Drug Categories
- Not Available
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Dipeptides
- Alternative Parents
- Leucine and derivatives / N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Benzyloxycarbonyls / Amphetamines and derivatives / 1-hydroxy-2-unsubstituted benzenoids / N-acyl amines / Carbamate esters / Alpha-haloketones / Secondary carboxylic acid amides show 5 more
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / Alkyl fluoride / Alkyl halide / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-dipeptide / Alpha-haloketone / Amphetamine or derivatives / Aromatic homomonocyclic compound / Benzenoid show 22 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 55GY047QB0
- CAS number
- 133410-84-1
- InChI Key
- JCRSHQCFRMCMOC-GSDHBNRESA-N
- InChI
- InChI=1S/C30H40FN3O6/c1-19(2)14-25(28(37)32-24(27(36)17-31)16-21-10-12-23(35)13-11-21)33-29(38)26(15-20(3)4)34-30(39)40-18-22-8-6-5-7-9-22/h5-13,19-20,24-26,35H,14-18H2,1-4H3,(H,32,37)(H,33,38)(H,34,39)/t24-,25-,26-/m0/s1
- IUPAC Name
- benzyl N-[(1S)-1-{[(1S)-1-{[(2S)-4-fluoro-1-(4-hydroxyphenyl)-3-oxobutan-2-yl]carbamoyl}-3-methylbutyl]carbamoyl}-3-methylbutyl]carbamate
- SMILES
- [H]N([C@@H](CC(C)C)C(=O)N([H])[C@@H](CC(C)C)C(=O)N([H])[C@@H](CC1=CC=C(O)C=C1)C(=O)CF)C(=O)OCC1=CC=CC=C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 11505008
- PubChem Substance
- 46507912
- ChemSpider
- 9679808
- ChEMBL
- CHEMBL72006
- ZINC
- ZINC000026289134
- PDBe Ligand
- C1N
- PDB Entries
- 1zcm
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00384 mg/mL ALOGPS logP 3.84 ALOGPS logP 4.78 Chemaxon logS -5.2 ALOGPS pKa (Strongest Acidic) 9.5 Chemaxon pKa (Strongest Basic) -3.1 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 133.83 Å2 Chemaxon Rotatable Bond Count 16 Chemaxon Refractivity 148.28 m3·mol-1 Chemaxon Polarizability 59.42 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.8774 Blood Brain Barrier - 0.7493 Caco-2 permeable - 0.7693 P-glycoprotein substrate Substrate 0.7795 P-glycoprotein inhibitor I Non-inhibitor 0.7683 P-glycoprotein inhibitor II Non-inhibitor 0.874 Renal organic cation transporter Non-inhibitor 0.9234 CYP450 2C9 substrate Non-substrate 0.6536 CYP450 2D6 substrate Non-substrate 0.7682 CYP450 3A4 substrate Substrate 0.5591 CYP450 1A2 substrate Non-inhibitor 0.5997 CYP450 2C9 inhibitor Non-inhibitor 0.7022 CYP450 2D6 inhibitor Non-inhibitor 0.8203 CYP450 2C19 inhibitor Inhibitor 0.6096 CYP450 3A4 inhibitor Non-inhibitor 0.5923 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7581 Ames test Non AMES toxic 0.8052 Carcinogenicity Non-carcinogens 0.8901 Biodegradation Not ready biodegradable 0.9605 Rat acute toxicity 2.5586 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9928 hERG inhibition (predictor II) Non-inhibitor 0.9206
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 229.59181 predictedDeepCCS 1.0 (2019) [M+H]+ 231.4167 predictedDeepCCS 1.0 (2019) [M+Na]+ 237.02252 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Calcium-regulated non-lysosomal thiol-protease which catalyzes limited proteolysis of substrates involved in cytoskeletal remodeling and signal transduction (PubMed:19617626, PubMed:21531719, PubMed:2400579). Proteolytically cleaves CTBP1 at 'Asn-375', 'Gly-387' and 'His-409' (PubMed:23707407). Cleaves and activates caspase-7 (CASP7) (PubMed:19617626)
- Specific Function
- Calcium ion binding
- Gene Name
- CAPN1
- Uniprot ID
- P07384
- Uniprot Name
- Calpain-1 catalytic subunit
- Molecular Weight
- 81889.325 Da
Drug created at September 11, 2007 17:49 / Updated at June 12, 2020 16:52