N-{[4-(but-2-yn-1-yloxy)phenyl]sulfonyl}-5-methyl-D-tryptophan

Identification

Generic Name
N-{[4-(but-2-yn-1-yloxy)phenyl]sulfonyl}-5-methyl-D-tryptophan
DrugBank Accession Number
DB07233
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 426.485
Monoisotopic: 426.124942514
Chemical Formula
C22H22N2O5S
Synonyms
Not Available

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
UDisintegrin and metalloproteinase domain-containing protein 17Not 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
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. These are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Indolyl carboxylic acids and derivatives
Direct Parent
Indolyl carboxylic acids and derivatives
Alternative Parents
3-alkylindoles / Alpha amino acids and derivatives / Benzenesulfonamides / Benzenesulfonyl compounds / Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Substituted pyrroles / Organosulfonamides / Aminosulfonyl compounds
show 9 more
Substituents
3-alkylindole / Alkyl aryl ether / Alpha-amino acid or derivatives / Aminosulfonyl compound / Aromatic heteropolycyclic compound / Azacycle / Benzenesulfonamide / Benzenesulfonyl group / Benzenoid / Carbonyl group
show 24 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
SFVPXERGVLDWIS-OAQYLSRUSA-N
InChI
InChI=1S/C22H22N2O5S/c1-3-4-11-29-17-6-8-18(9-7-17)30(27,28)24-21(22(25)26)13-16-14-23-20-10-5-15(2)12-19(16)20/h5-10,12,14,21,23-24H,11,13H2,1-2H3,(H,25,26)/t21-/m1/s1
IUPAC Name
(2R)-2-[4-(but-2-yn-1-yloxy)benzenesulfonamido]-3-(5-methyl-1H-indol-3-yl)propanoic acid
SMILES
[H][C@](CC1=CNC2=C1C=C(C)C=C2)(NS(=O)(=O)C1=CC=C(OCC#CC)C=C1)C(O)=O

References

General References
Not Available
PubChem Compound
42627769
PubChem Substance
99443704
ChemSpider
24720685
BindingDB
50279256
ChEMBL
CHEMBL527018
ZINC
ZINC000038225899
PDBe Ligand
792
PDB Entries
3g42

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 Solubility0.00229 mg/mLALOGPS
logP2.77ALOGPS
logP4.03ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)3.27ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area108.49 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity113.98 m3·mol-1ChemAxon
Polarizability44.81 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9752
Blood Brain Barrier+0.6166
Caco-2 permeable-0.674
P-glycoprotein substrateSubstrate0.5226
P-glycoprotein inhibitor INon-inhibitor0.9203
P-glycoprotein inhibitor IINon-inhibitor0.9411
Renal organic cation transporterNon-inhibitor0.8528
CYP450 2C9 substrateNon-substrate0.6033
CYP450 2D6 substrateNon-substrate0.7897
CYP450 3A4 substrateSubstrate0.521
CYP450 1A2 substrateNon-inhibitor0.5695
CYP450 2C9 inhibitorInhibitor0.5
CYP450 2D6 inhibitorNon-inhibitor0.8603
CYP450 2C19 inhibitorNon-inhibitor0.5983
CYP450 3A4 inhibitorInhibitor0.8228
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6647
Ames testNon AMES toxic0.6333
CarcinogenicityNon-carcinogens0.7462
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4181 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9805
hERG inhibition (predictor II)Non-inhibitor0.6689
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
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. [Article]

Drug created on September 15, 2010 21:19 / Updated on June 12, 2020 16:52