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

Identification

Name
N-Hydroxy-1-(4-Methoxyphenyl)Sulfonyl-4-Benzyloxycarbonyl-Piperazine-2-Carboxamide
Accession Number
DB04232  (EXPT02946)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 449.478
Monoisotopic: 449.125670795
Chemical Formula
C20H23N3O7S
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][[email protected]@]1(CN(CCN1S(=O)(=O)C1=CC=C(OC)C=C1)C(=O)OCC1=CC=CC=C1)C(=O)NO

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UStromelysin-1Not 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
5289389
PubChem Substance
46506933
ChemSpider
4451373
HET
SPI
PDB Entries
1d8f

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 Solubility0.145 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

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
Alpha amino acids and derivatives / Benzyloxycarbonyls / Piperazine carboxylic acids / Piperazine carboxamides / Benzenesulfonyl compounds / Anisoles / Phenoxy compounds / Methoxybenzenes / Alkyl aryl ethers / Organosulfonamides
show 10 more
Substituents
Alpha-amino acid or derivatives / Benzenesulfonamide / Benzyloxycarbonyl / Piperazine-2-carboxamide / Piperazine-1-carboxylic acid / Benzenesulfonyl group / Anisole / Phenoxy compound / Phenol ether / Methoxybenzene
show 24 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
hydroxamic acid, N-sulfonylpiperazine, piperazinecarboxylate ester (CHEBI:45648)

Targets

Details
1. Stromelysin-1
Kind
Protein
Organism
Human
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. [PubMed:17139284]
  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. [PubMed:17016423]
  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. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:25