NAV

4-({4-[(4-AMINOBUT-2-YNYL)OXY]PHENYL}SULFONYL)-N-HYDROXY-2,2-DIMETHYLTHIOMORPHOLINE-3-CARBOXAMIDE

Identification

Generic Name
4-({4-[(4-AMINOBUT-2-YNYL)OXY]PHENYL}SULFONYL)-N-HYDROXY-2,2-DIMETHYLTHIOMORPHOLINE-3-CARBOXAMIDE
DrugBank Accession Number
DB07121
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 413.512
Monoisotopic: 413.107912241
Chemical Formula
C17H23N3O5S2
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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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
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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 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
Alpha amino acids and derivatives / Benzenesulfonyl compounds / Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Thiomorpholines / Organosulfonamides / Sulfonyls / Hydroxamic acids / Azacyclic compounds
show 6 more
Substituents
1,4-thiazinane / Alkyl aryl ether / Alpha-amino acid or derivatives / Amine / Amino acid or derivatives / Aromatic heteromonocyclic compound / Azacycle / Benzenesulfonamide / Benzenesulfonyl group / Carbonyl group
show 22 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
sulfonamide, thiomorpholines, hydroxamic acid (CHEBI:40107)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
AANXPIMDONQTQF-HNNXBMFYSA-N
InChI
InChI=1S/C17H23N3O5S2/c1-17(2)15(16(21)19-22)20(10-12-26-17)27(23,24)14-7-5-13(6-8-14)25-11-4-3-9-18/h5-8,15,22H,9-12,18H2,1-2H3,(H,19,21)/t15-/m0/s1
IUPAC Name
(3S)-4-{4-[(4-aminobut-2-yn-1-yl)oxy]benzenesulfonyl}-N-hydroxy-2,2-dimethylthiomorpholine-3-carboxamide
SMILES
[H][C@]1(N(CCSC1(C)C)S(=O)(=O)C1=CC=C(OCC#CCN)C=C1)C(=O)NO

References

General References
Not Available
PubChem Compound
6102708
PubChem Substance
99443592
ChemSpider
4810225
BindingDB
50180995
ChEMBL
CHEMBL202839
ZINC
ZINC000016051763
PDBe Ligand
4NH
PDB Entries
2a8h

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 Solubility0.035 mg/mLALOGPS
logP1.03ALOGPS
logP-0.21Chemaxon
logS-4.1ALOGPS
pKa (Strongest Acidic)8.45Chemaxon
pKa (Strongest Basic)9.06Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area121.96 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity104.76 m3·mol-1Chemaxon
Polarizability41.51 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.6754
Blood Brain Barrier-0.7132
Caco-2 permeable-0.6435
P-glycoprotein substrateSubstrate0.8185
P-glycoprotein inhibitor INon-inhibitor0.6157
P-glycoprotein inhibitor IINon-inhibitor0.6344
Renal organic cation transporterNon-inhibitor0.7954
CYP450 2C9 substrateNon-substrate0.6209
CYP450 2D6 substrateNon-substrate0.7962
CYP450 3A4 substrateSubstrate0.5541
CYP450 1A2 substrateNon-inhibitor0.8047
CYP450 2C9 inhibitorNon-inhibitor0.6723
CYP450 2D6 inhibitorNon-inhibitor0.8577
CYP450 2C19 inhibitorNon-inhibitor0.6437
CYP450 3A4 inhibitorInhibitor0.7552
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8294
Ames testNon AMES toxic0.5822
CarcinogenicityNon-carcinogens0.6543
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4981 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9843
hERG inhibition (predictor II)Non-inhibitor0.5423
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/MSsplash10-03di-0101900000-8c32f85704299637d066
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0006900000-8dd470cbfb761fb293a6
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0419200000-74b49f1c4dd27b2e3b72
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-06s7-4129200000-9d2cc7063e93a66b54ad
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-015d-1912000000-6a1c0bb79f3471c72476
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0g59-4928100000-28a6110b31063a965ee1
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-179.83188
predicted
DeepCCS 1.0 (2019)
[M+H]+182.18987
predicted
DeepCCS 1.0 (2019)
[M+Na]+188.56236
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Disintegrin and metalloproteinase domain-containing protein 17
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 at September 15, 2010 21:19 / Updated at June 12, 2020 16:52