Z-Val-Ala-Asp fluoromethyl ketone

Identification

Generic Name
Z-Val-Ala-Asp fluoromethyl ketone
DrugBank Accession Number
DB07744
Background

Non-methylated, competitive, and irreversible inhibitor of caspase 1, as well as other caspases,1 which can be used directly with purified enzymes. It does not require an esterase to hydrolyze the O-methyl ester like the cell-permeable form, Z-Val-Ala-Asp(O-Me) fluoromethyl ketone.

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 453.467
Monoisotopic: 453.191128417
Chemical Formula
C21H28FN3O7
Synonyms
  • N-[(Benzyloxy)carbonyl]-L-valyl-N-[(2S)-1-carboxy-4-fluoro-3-oxo-2-butanyl]-L-alaninamide
  • Z-VAD-FMK

Pharmacology

Indication

Not Available

Pharmacology
Reduce drug development failure rates
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Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
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Avoid life-threatening adverse drug events & improve clinical decision support.
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UCaspase-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
Adverseeffects
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Toxicity

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
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as hybrid peptides. These are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Peptidomimetics
Sub Class
Hybrid peptides
Direct Parent
Hybrid peptides
Alternative Parents
Dipeptides / Valine and derivatives / N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Alanine and derivatives / Beta amino acids and derivatives / Benzyloxycarbonyls / Gamma-keto acids and derivatives / N-acyl amines / Alpha-haloketones
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Substituents
Alanine or derivatives / Alkyl fluoride / Alkyl halide / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-dipeptide / Alpha-haloketone / Aromatic homomonocyclic compound / Benzenoid / Benzyloxycarbonyl
show 29 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
161401-82-7
InChI Key
SUUHZYLYARUNIA-YEWWUXTCSA-N
InChI
InChI=1S/C21H28FN3O7/c1-12(2)18(25-21(31)32-11-14-7-5-4-6-8-14)20(30)23-13(3)19(29)24-15(9-17(27)28)16(26)10-22/h4-8,12-13,15,18H,9-11H2,1-3H3,(H,23,30)(H,24,29)(H,25,31)(H,27,28)/t13-,15-,18-/m0/s1
IUPAC Name
(3S)-3-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-methylbutanamido]propanamido]-5-fluoro-4-oxopentanoic acid
SMILES
CC(C)[C@H](NC(=O)OCC1=CC=CC=C1)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(O)=O)C(=O)CF

References

General References
Not Available
PubChem Compound
5497171
PubChem Substance
99444215
ChemSpider
4593739
ChEMBL
CHEMBL205821
ZINC
ZINC000025668028

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
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0358 mg/mLALOGPS
logP1.12ALOGPS
logP1.16ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)4.13ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area150.9 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity109.36 m3·mol-1ChemAxon
Polarizability44.69 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.7761
Blood Brain Barrier-0.7676
Caco-2 permeable-0.784
P-glycoprotein substrateSubstrate0.5932
P-glycoprotein inhibitor INon-inhibitor0.6455
P-glycoprotein inhibitor IINon-inhibitor0.9201
Renal organic cation transporterNon-inhibitor0.9549
CYP450 2C9 substrateNon-substrate0.7854
CYP450 2D6 substrateNon-substrate0.7948
CYP450 3A4 substrateNon-substrate0.5648
CYP450 1A2 substrateNon-inhibitor0.7601
CYP450 2C9 inhibitorNon-inhibitor0.8935
CYP450 2D6 inhibitorNon-inhibitor0.9282
CYP450 2C19 inhibitorNon-inhibitor0.6948
CYP450 3A4 inhibitorNon-inhibitor0.6306
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.913
Ames testNon AMES toxic0.8032
CarcinogenicityNon-carcinogens0.878
BiodegradationNot ready biodegradable0.7344
Rat acute toxicity2.2208 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.989
hERG inhibition (predictor II)Non-inhibitor0.9409
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
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

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Endopeptidase activity
Specific Function
Thiol protease that cleaves IL-1 beta between an Asp and an Ala, releasing the mature cytokine which is involved in a variety of inflammatory processes. Important for defense against pathogens. Cle...
Gene Name
CASP1
Uniprot ID
P29466
Uniprot Name
Caspase-1
Molecular Weight
45158.215 Da
References
  1. 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 on September 15, 2010 21:25 / Updated on June 12, 2020 16:52