(1n)-4-N-Butoxyphenylsulfonyl-(2r)-N-Hydroxycarboxamido-(4s)-Methanesulfonylamino-Pyrrolidine

Identification

Generic Name
(1n)-4-N-Butoxyphenylsulfonyl-(2r)-N-Hydroxycarboxamido-(4s)-Methanesulfonylamino-Pyrrolidine
DrugBank Accession Number
DB02367
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 435.516
Monoisotopic: 435.113391549
Chemical Formula
C16H25N3O7S2
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UStromelysin-1Not 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 proline and derivatives. These are compounds containing proline or a derivative thereof resulting from reaction of proline 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
Proline and derivatives
Alternative Parents
Alpha amino acid amides / Benzenesulfonamides / Benzenesulfonyl compounds / Pyrrolidinecarboxamides / Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Organosulfonamides / Organic sulfonamides / Aminosulfonyl compounds
show 7 more
Substituents
Alkyl aryl ether / Alpha-amino acid amide / Aminosulfonyl compound / Aromatic heteromonocyclic compound / Azacycle / Benzenesulfonamide / Benzenesulfonyl group / Benzenoid / Carbonyl group / Ether
show 22 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
sulfonamide, N-acylpyrrolidine, D-proline derivative, pyrrolidinehydroxamic acid (CHEBI:39531)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
ULDXUWXTVRRUND-SWLSCSKDSA-N
InChI
InChI=1S/C16H25N3O7S2/c1-3-4-9-26-13-5-7-14(8-6-13)28(24,25)19-11-12(18-27(2,22)23)10-15(19)16(20)17-21/h5-8,12,15,18,21H,3-4,9-11H2,1-2H3,(H,17,20)/t12-,15+/m0/s1
IUPAC Name
(2R,4S)-1-(4-butoxybenzenesulfonyl)-N-hydroxy-4-methanesulfonamidopyrrolidine-2-carboxamide
SMILES
CCCCOC1=CC=C(C=C1)S(=O)(=O)N1C[C@H](C[C@@H]1C(=O)NO)NS(C)(=O)=O

References

General References
Not Available
PubChem Compound
5287415
PubChem Substance
46506803
ChemSpider
4449804
BindingDB
50095567
ChEMBL
CHEMBL358064
ZINC
ZINC000003870354
PDBe Ligand
111
PDB Entries
1g49

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 Solubility0.459 mg/mLALOGPS
logP0.2ALOGPS
logP-0.46Chemaxon
logS-3ALOGPS
pKa (Strongest Acidic)8.71Chemaxon
pKa (Strongest Basic)-4.9Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area142.11 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity101.32 m3·mol-1Chemaxon
Polarizability43.62 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9756
Blood Brain Barrier-0.6509
Caco-2 permeable-0.6781
P-glycoprotein substrateSubstrate0.7046
P-glycoprotein inhibitor INon-inhibitor0.6823
P-glycoprotein inhibitor IINon-inhibitor0.6311
Renal organic cation transporterNon-inhibitor0.8827
CYP450 2C9 substrateNon-substrate0.6024
CYP450 2D6 substrateNon-substrate0.7768
CYP450 3A4 substrateSubstrate0.588
CYP450 1A2 substrateNon-inhibitor0.8116
CYP450 2C9 inhibitorNon-inhibitor0.6106
CYP450 2D6 inhibitorNon-inhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.6442
CYP450 3A4 inhibitorNon-inhibitor0.6055
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8307
Ames testNon AMES toxic0.5939
CarcinogenicityNon-carcinogens0.7229
BiodegradationNot ready biodegradable0.9762
Rat acute toxicity2.4873 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9719
hERG inhibition (predictor II)Non-inhibitor0.5641
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/MSsplash10-000i-0000900000-e1a101a6e0af50b2c48f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0001900000-7d081e3afce45ca786a2
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0102900000-f3ff46e21aa88ea0aeb1
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-1319300000-60ed4592d28a2666af9e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0kwo-2449100000-7574b7ede3139ff8e9b8
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-003l-0911000000-907f2a3aebc7f1151853
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]-194.01591
predicted
DeepCCS 1.0 (2019)
[M+H]+196.4115
predicted
DeepCCS 1.0 (2019)
[M+Na]+202.32402
predicted
DeepCCS 1.0 (2019)

Targets

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Details
1. Stromelysin-1
Kind
Protein
Organism
Humans
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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at July 02, 2020 13:15