(3S)-1-{[4-(but-2-yn-1-yloxy)phenyl]sulfonyl}pyrrolidine-3-thiol

Identification

Name
(3S)-1-{[4-(but-2-yn-1-yloxy)phenyl]sulfonyl}pyrrolidine-3-thiol
Accession Number
DB06943
Type
Small Molecule
Groups
Experimental
Description

(3S)-1-{[4-(but-2-yn-1-yloxy)phenyl]sulfonyl}pyrrolidine-3-thiol is a solid. This compound belongs to the benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring. This substance is known to target disintegrin and metalloproteinase domain-containing protein 17.

Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 311.42
Monoisotopic: 311.064984795
Chemical Formula
C14H17NO3S2
InChI Key
BLIQFUCBRCDFAI-ZDUSSCGKSA-N
InChI
InChI=1S/C14H17NO3S2/c1-2-3-10-18-12-4-6-14(7-5-12)20(16,17)15-9-8-13(19)11-15/h4-7,13,19H,8-11H2,1H3/t13-/m0/s1
IUPAC Name
(3S)-1-[4-(but-2-yn-1-yloxy)benzenesulfonyl]pyrrolidine-3-thiol
SMILES
[H][[email protected]]1(S)CCN(C1)S(=O)(=O)C1=CC=C(OCC#CC)C=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UDisintegrin and metalloproteinase domain-containing protein 17Not 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
9861547
PubChem Substance
99443414
ChemSpider
8037243
BindingDB
26544
ChEMBL
CHEMBL243024
HET
283
PDB Entries
2oi0

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 Solubility0.0177 mg/mLALOGPS
logP3ALOGPS
logP2.26ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)9.92ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.61 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity82.57 m3·mol-1ChemAxon
Polarizability32.65 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9801
Caco-2 permeable-0.6127
P-glycoprotein substrateSubstrate0.5706
P-glycoprotein inhibitor INon-inhibitor0.5635
P-glycoprotein inhibitor IINon-inhibitor0.9038
Renal organic cation transporterNon-inhibitor0.5799
CYP450 2C9 substrateNon-substrate0.5745
CYP450 2D6 substrateNon-substrate0.7608
CYP450 3A4 substrateSubstrate0.5249
CYP450 1A2 substrateNon-inhibitor0.7337
CYP450 2C9 inhibitorNon-inhibitor0.6527
CYP450 2D6 inhibitorNon-inhibitor0.8162
CYP450 2C19 inhibitorInhibitor0.5352
CYP450 3A4 inhibitorNon-inhibitor0.6913
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5651
Ames testNon AMES toxic0.6135
CarcinogenicityNon-carcinogens0.8301
BiodegradationNot ready biodegradable0.6625
Rat acute toxicity2.5141 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5844
hERG inhibition (predictor II)Non-inhibitor0.6449
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 GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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 benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzenesulfonamides
Direct Parent
Benzenesulfonamides
Alternative Parents
Benzenesulfonyl compounds / Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Organosulfonamides / Sulfonyls / Pyrrolidines / Azacyclic compounds / Alkylthiols / Organopnictogen compounds
show 3 more
Substituents
Benzenesulfonamide / Benzenesulfonyl group / Phenoxy compound / Phenol ether / Alkyl aryl ether / Organosulfonic acid amide / Sulfonyl / Organosulfonic acid or derivatives / Organic sulfonic acid or derivatives / Pyrrolidine
show 13 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Cleaves the membrane-bound precursor of TNF-alpha to its mature soluble form. Responsible for the proteolytical release of soluble JAM3 from endothelial cells surface. Responsible for the proteolyt...
Gene Name
ADAM17
Uniprot ID
P78536
Uniprot Name
Disintegrin and metalloproteinase domain-containing protein 17
Molecular Weight
93020.165 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 15:17 / Updated on December 01, 2017 15:43