2-[3-(5-MERCAPTO-[1,3,4]THIADIAZOL-2YL)-UREIDO]-N-METHYL-3-PENTAFLUOROPHENYL-PROPIONAMIDE

Identification

Name
2-[3-(5-MERCAPTO-[1,3,4]THIADIAZOL-2YL)-UREIDO]-N-METHYL-3-PENTAFLUOROPHENYL-PROPIONAMIDE
Accession Number
DB07988
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: 427.373
Monoisotopic: 427.019606994
Chemical Formula
C13H10F5N5O2S2
InChI Key
HZAXNPDJVFUGDS-BYPYZUCNSA-N
InChI
InChI=1S/C13H10F5N5O2S2/c1-19-10(24)4(20-11(25)21-12-22-23-13(26)27-12)2-3-5(14)7(16)9(18)8(17)6(3)15/h4H,2H2,1H3,(H,19,24)(H,23,26)(H2,20,21,22,25)/t4-/m0/s1
IUPAC Name
(2S)-N-methyl-3-(pentafluorophenyl)-2-{[(5-sulfanyl-1,3,4-thiadiazol-2-yl)carbamoyl]amino}propanamide
SMILES
[H][[email protected]@](CC1=C(F)C(F)=C(F)C(F)=C1F)(NC(=O)NC1=NN=C(S)S1)C(=O)NC

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UStromelysin-1Not 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
4369080
PubChem Substance
99444459
ChemSpider
3571804
BindingDB
50076341
ChEMBL
CHEMBL290140
HET
IN9
PDB Entries
1usn

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 Solubility0.0126 mg/mLALOGPS
logP2.78ALOGPS
logP2.17ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)6.45ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area96.01 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity89.78 m3·mol-1ChemAxon
Polarizability34.27 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5682
Blood Brain Barrier+0.8684
Caco-2 permeable-0.6009
P-glycoprotein substrateNon-substrate0.5642
P-glycoprotein inhibitor INon-inhibitor0.6967
P-glycoprotein inhibitor IINon-inhibitor0.9707
Renal organic cation transporterNon-inhibitor0.8855
CYP450 2C9 substrateNon-substrate0.7297
CYP450 2D6 substrateNon-substrate0.8206
CYP450 3A4 substrateNon-substrate0.5962
CYP450 1A2 substrateNon-inhibitor0.5661
CYP450 2C9 inhibitorInhibitor0.5808
CYP450 2D6 inhibitorNon-inhibitor0.8957
CYP450 2C19 inhibitorNon-inhibitor0.5815
CYP450 3A4 inhibitorNon-inhibitor0.7444
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6693
Ames testNon AMES toxic0.6204
CarcinogenicityNon-carcinogens0.8496
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4746 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.977
hERG inhibition (predictor II)Non-inhibitor0.712
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

Description
This compound belongs to the class of organic compounds known as phenylalanine and derivatives. These are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Phenylalanine and derivatives
Alternative Parents
N-carbamoyl-alpha amino acids and derivatives / Alpha amino acid amides / Amphetamines and derivatives / 1,3,4-thiadiazol-2-ylureas / Fluorobenzenes / Aryl fluorides / Fatty amides / Heteroaromatic compounds / Ureas / Secondary carboxylic acid amides
show 8 more
Substituents
Phenylalanine or derivatives / N-carbamoyl-alpha-amino acid or derivatives / Alpha-amino acid amide / Amphetamine or derivatives / 1,3,4-thiadiazol-2-ylurea / Halobenzene / Fluorobenzene / Aryl fluoride / Aryl halide / Fatty amide
show 24 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
organofluorine compound, ureas, thiadiazoles, L-phenylalanine derivative (CHEBI:43536)

Targets

Details
1. Stromelysin-1
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Can degrade fibronectin, laminin, gelatins of type I, III, IV, and V; collagens III, IV, X, and IX, and cartilage proteoglycans. Activates procollagenase.
Gene Name
MMP3
Uniprot ID
P08254
Uniprot Name
Stromelysin-1
Molecular Weight
53976.84 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 September 15, 2010 15:27 / Updated on December 01, 2017 15:58