(2R)-N-hydroxy-3-naphthalen-2-yl-2-[(naphthalen-2-ylsulfonyl)amino]propanamide

Identification

Name
(2R)-N-hydroxy-3-naphthalen-2-yl-2-[(naphthalen-2-ylsulfonyl)amino]propanamide
Accession Number
DB07861
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: 420.481
Monoisotopic: 420.114377828
Chemical Formula
C23H20N2O4S
InChI Key
MMOUXLMPQFMDRD-JOCHJYFZSA-N
InChI
InChI=1S/C23H20N2O4S/c26-23(24-27)22(14-16-9-10-17-5-1-3-7-19(17)13-16)25-30(28,29)21-12-11-18-6-2-4-8-20(18)15-21/h1-13,15,22,25,27H,14H2,(H,24,26)/t22-/m1/s1
IUPAC Name
(2R)-N-hydroxy-3-(naphthalen-2-yl)-2-(naphthalene-2-sulfonamido)propanamide
SMILES
[H][C@](CC1=CC2=C(C=CC=C2)C=C1)(NS(=O)(=O)C1=CC2=C(C=CC=C2)C=C1)C(=O)NO

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UUDP-3-O-[3-hydroxymyristoyl] N-acetylglucosamine deacetylaseNot AvailablePseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
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
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

References

General References
Not Available
External Links
PubChem Compound
9823454
PubChem Substance
99444332
ChemSpider
7999201
ChEMBL
CHEMBL261713
ZINC
ZINC000000594749
PDBe Ligand
GVR
PDB Entries
2ves / 4isa

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 Solubility0.000431 mg/mLALOGPS
logP3.14ALOGPS
logP3.67ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)8.69ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area95.5 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity114.8 m3·mol-1ChemAxon
Polarizability43.4 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8505
Blood Brain Barrier+0.6629
Caco-2 permeable-0.6419
P-glycoprotein substrateNon-substrate0.5549
P-glycoprotein inhibitor INon-inhibitor0.8916
P-glycoprotein inhibitor IINon-inhibitor0.8709
Renal organic cation transporterNon-inhibitor0.9359
CYP450 2C9 substrateNon-substrate0.5908
CYP450 2D6 substrateNon-substrate0.826
CYP450 3A4 substrateNon-substrate0.6417
CYP450 1A2 substrateNon-inhibitor0.7707
CYP450 2C9 inhibitorNon-inhibitor0.711
CYP450 2D6 inhibitorNon-inhibitor0.8779
CYP450 2C19 inhibitorNon-inhibitor0.6661
CYP450 3A4 inhibitorNon-inhibitor0.8251
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7963
Ames testNon AMES toxic0.6056
CarcinogenicityNon-carcinogens0.7352
BiodegradationNot ready biodegradable0.9965
Rat acute toxicity2.3532 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9931
hERG inhibition (predictor II)Non-inhibitor0.8742
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 2-naphthalene sulfonic acids and derivatives. These are organic aromatic compounds that contain a naphthalene moiety that carries a sulfonic acid group (or a derivative thereof) at the 2-position. Naphthalene is a bicyclic compound that is made up of two fused benzene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Naphthalenes
Sub Class
Naphthalene sulfonic acids and derivatives
Direct Parent
2-naphthalene sulfonic acids and derivatives
Alternative Parents
2-naphthalene sulfonamides / Alpha amino acids and derivatives / Organosulfonamides / Aminosulfonyl compounds / Hydroxamic acids / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
2-naphthalene sulfonamide / Naphthalene sulfonamide / 2-naphthalene sulfonic acid or derivatives / N-substituted-alpha-amino acid / Alpha-amino acid or derivatives / Organosulfonic acid amide / Aminosulfonyl compound / Sulfonyl / Organosulfonic acid or derivatives / Organic sulfonic acid or derivatives
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Pharmacological action
Unknown
General Function
Udp-3-o-[3-hydroxymyristoyl] n-acetylglucosamine deacetylase activity
Specific Function
Involved in the biosynthesis of lipid A, a phosphorylated glycolipid that anchors the lipopolysaccharide to the outer membrane of the cell.
Gene Name
lpxC
Uniprot ID
P47205
Uniprot Name
UDP-3-O-[3-hydroxymyristoyl] N-acetylglucosamine deacetylase
Molecular Weight
33434.81 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. [PubMed:10592235]

Drug created on September 15, 2010 15:26 / Updated on March 01, 2020 20:06

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