Benzoyl-Arginine-Alanine-Methyl Ketone

Identification

Name
Benzoyl-Arginine-Alanine-Methyl Ketone
Accession Number
DB03536  (EXPT03294)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 397.4444
Monoisotopic: 397.212532614
Chemical Formula
C18H28FN5O4
InChI Key
FAAPWXRBXXSQNJ-JSGCOSHPSA-N
InChI
InChI=1S/C18H28FN5O4/c1-12(15(25)10-19)23-16(26)14(8-5-9-22-17(20)21)24-18(27)28-11-13-6-3-2-4-7-13/h2-4,6-7,12,14,17,22H,5,8-11,20-21H2,1H3,(H,23,26)(H,24,27)/t12-,14-/m0/s1
IUPAC Name
(2S)-2-{[(benzyloxy)(hydroxy)methylidene]amino}-5-[(diaminomethyl)amino]-N-[(2S)-4-fluoro-3-oxobutan-2-yl]pentanimidic acid
SMILES
[H][[email protected]@](C)(N=C(O)[[email protected]]([H])(CCCNC(N)N)N=C(O)OCC1=CC=CC=C1)C(=O)CF

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCruzipainNot AvailableTrypanosoma cruzi
UCathepsin FNot 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
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
131704251
PubChem Substance
46504937
ChemSpider
59051958
HET
ZRA
PDB Entries
2aim

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
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0904 mg/mLALOGPS
logP0.19ALOGPS
logP0.63ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)5.49ChemAxon
pKa (Strongest Basic)6.73ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area155.55 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity101.97 m3·mol-1ChemAxon
Polarizability40.91 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8823
Blood Brain Barrier+0.646
Caco-2 permeable-0.734
P-glycoprotein substrateSubstrate0.7215
P-glycoprotein inhibitor INon-inhibitor0.8707
P-glycoprotein inhibitor IINon-inhibitor0.9594
Renal organic cation transporterNon-inhibitor0.858
CYP450 2C9 substrateNon-substrate0.8364
CYP450 2D6 substrateNon-substrate0.791
CYP450 3A4 substrateNon-substrate0.6603
CYP450 1A2 substrateNon-inhibitor0.7599
CYP450 2C9 inhibitorNon-inhibitor0.8548
CYP450 2D6 inhibitorNon-inhibitor0.9092
CYP450 2C19 inhibitorNon-inhibitor0.6548
CYP450 3A4 inhibitorNon-inhibitor0.6264
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8116
Ames testNon AMES toxic0.6651
CarcinogenicityNon-carcinogens0.9189
BiodegradationReady biodegradable0.7217
Rat acute toxicity2.1716 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9654
hERG inhibition (predictor II)Non-inhibitor0.9003
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

Taxonomy

Classification
Not classified

Targets

Kind
Protein
Organism
Trypanosoma cruzi
Pharmacological action
Unknown
General Function
Cysteine-type endopeptidase activity
Specific Function
Hydrolyzes chromogenic peptides at the carboxyl Arg or Lys; requires at least one more amino acid, preferably Arg, Phe, Val or Leu, between the terminal Arg or Lys and the amino-blocking group.The ...
Gene Name
Not Available
Uniprot ID
P25779
Uniprot Name
Cruzipain
Molecular Weight
49835.59 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Cysteine-type endopeptidase activity
Specific Function
Thiol protease which is believed to participate in intracellular degradation and turnover of proteins. Has also been implicated in tumor invasion and metastasis.
Gene Name
CTSF
Uniprot ID
Q9UBX1
Uniprot Name
Cathepsin F
Molecular Weight
53365.455 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. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:15