NAV

N-Hydroxy-1-(4-Methoxyphenyl)Sulfonyl-4-Benzyloxycarbonyl-Piperazine-2-Carboxamide

Identification

Generic Name
N-Hydroxy-1-(4-Methoxyphenyl)Sulfonyl-4-Benzyloxycarbonyl-Piperazine-2-Carboxamide
DrugBank Accession Number
DB04232
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 449.478
Monoisotopic: 449.125670795
Chemical Formula
C20H23N3O7S
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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 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 / Benzyloxycarbonyls / Piperazine carboxylic acids / Piperazine carboxamides / Benzenesulfonyl compounds / Anisoles / Phenoxy compounds / Methoxybenzenes / Alkyl aryl ethers / Organosulfonamides
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Substituents
1,4-diazinane / Alkyl aryl ether / Alpha-amino acid or derivatives / Anisole / Aromatic heteromonocyclic compound / Azacycle / Benzenesulfonamide / Benzenesulfonyl group / Benzyloxycarbonyl / Carbamic acid ester
show 24 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
hydroxamic acid, N-sulfonylpiperazine, piperazinecarboxylate ester (CHEBI:45648)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
DNGGPLKVDUPXFN-GOSISDBHSA-N
InChI
InChI=1S/C20H23N3O7S/c1-29-16-7-9-17(10-8-16)31(27,28)23-12-11-22(13-18(23)19(24)21-26)20(25)30-14-15-5-3-2-4-6-15/h2-10,18,26H,11-14H2,1H3,(H,21,24)/t18-/m1/s1
IUPAC Name
benzyl (3R)-3-(hydroxycarbamoyl)-4-(4-methoxybenzenesulfonyl)piperazine-1-carboxylate
SMILES
[H][C@@]1(CN(CCN1S(=O)(=O)C1=CC=C(OC)C=C1)C(=O)OCC1=CC=CC=C1)C(=O)NO

References

General References
Not Available
PubChem Compound
5289389
PubChem Substance
46506933
ChemSpider
4451373
ZINC
ZINC000000580494
PDBe Ligand
SPI
PDB Entries
1d8f

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 Solubility0.145 mg/mLALOGPS
logP1.27ALOGPS
logP1.17Chemaxon
logS-3.5ALOGPS
pKa (Strongest Acidic)8.7Chemaxon
pKa (Strongest Basic)-4.8Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area125.48 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity110.45 m3·mol-1Chemaxon
Polarizability44.74 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8519
Blood Brain Barrier-0.7249
Caco-2 permeable-0.6889
P-glycoprotein substrateSubstrate0.7095
P-glycoprotein inhibitor IInhibitor0.6953
P-glycoprotein inhibitor IINon-inhibitor0.5495
Renal organic cation transporterNon-inhibitor0.7384
CYP450 2C9 substrateNon-substrate0.6039
CYP450 2D6 substrateNon-substrate0.7887
CYP450 3A4 substrateSubstrate0.5417
CYP450 1A2 substrateNon-inhibitor0.8337
CYP450 2C9 inhibitorNon-inhibitor0.7136
CYP450 2D6 inhibitorNon-inhibitor0.868
CYP450 2C19 inhibitorNon-inhibitor0.6868
CYP450 3A4 inhibitorNon-inhibitor0.6157
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9392
Ames testNon AMES toxic0.603
CarcinogenicityNon-carcinogens0.7778
BiodegradationNot ready biodegradable0.9901
Rat acute toxicity2.4577 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9089
hERG inhibition (predictor II)Inhibitor0.6866
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

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Details1. 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]
  3. 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 June 13, 2005 13:24 / Updated at June 12, 2020 16:52