N-({6-[(4-CYANOBENZYL)OXY]NAPHTHALEN-2-YL}SULFONYL)-D-GLUTAMIC ACID

Identification

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Name
N-({6-[(4-CYANOBENZYL)OXY]NAPHTHALEN-2-YL}SULFONYL)-D-GLUTAMIC ACID
Accession Number
DB08108
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: 468.479
Monoisotopic: 468.099121694
Chemical Formula
C23H20N2O7S
InChI Key
PUHRQSFXADUGJW-OAQYLSRUSA-N
InChI
InChI=1S/C23H20N2O7S/c24-13-15-1-3-16(4-2-15)14-32-19-7-5-18-12-20(8-6-17(18)11-19)33(30,31)25-21(23(28)29)9-10-22(26)27/h1-8,11-12,21,25H,9-10,14H2,(H,26,27)(H,28,29)/t21-/m1/s1
IUPAC Name
(2R)-2-{6-[(4-cyanophenyl)methoxy]naphthalene-2-sulfonamido}pentanedioic acid
SMILES
[H][C@](CCC(O)=O)(NS(=O)(=O)C1=CC2=C(C=C1)C=C(OCC1=CC=C(C=C1)C#N)C=C2)C(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UUDP-N-acetylmuramoylalanine--D-glutamate ligaseNot AvailableEscherichia coli (strain K12)
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
24755471
PubChem Substance
99444579
ChemSpider
24690845
BindingDB
26453
ChEMBL
CHEMBL458966
HET
LK4
PDB Entries
2uup

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 Solubility0.00825 mg/mLALOGPS
logP1.53ALOGPS
logP2.91ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)2.97ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area153.79 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity117.73 m3·mol-1ChemAxon
Polarizability47.14 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9243
Blood Brain Barrier+0.6625
Caco-2 permeable-0.6704
P-glycoprotein substrateNon-substrate0.6248
P-glycoprotein inhibitor INon-inhibitor0.8259
P-glycoprotein inhibitor IINon-inhibitor0.89
Renal organic cation transporterNon-inhibitor0.8463
CYP450 2C9 substrateNon-substrate0.656
CYP450 2D6 substrateNon-substrate0.8009
CYP450 3A4 substrateSubstrate0.5101
CYP450 1A2 substrateNon-inhibitor0.5107
CYP450 2C9 inhibitorNon-inhibitor0.5299
CYP450 2D6 inhibitorNon-inhibitor0.9173
CYP450 2C19 inhibitorNon-inhibitor0.6057
CYP450 3A4 inhibitorInhibitor0.5861
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5894
Ames testNon AMES toxic0.6188
CarcinogenicityNon-carcinogens0.8396
BiodegradationNot ready biodegradable0.9769
Rat acute toxicity2.2561 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9039
hERG inhibition (predictor II)Non-inhibitor0.6155
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 glutamic acid and derivatives. These are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid 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
Glutamic acid and derivatives
Alternative Parents
2-naphthalene sulfonic acids and derivatives / 2-naphthalene sulfonamides / Benzonitriles / Alkyl aryl ethers / Organosulfonamides / Dicarboxylic acids and derivatives / Aminosulfonyl compounds / Nitriles / Carboxylic acids / Organopnictogen compounds
show 3 more
Substituents
Glutamic acid or derivatives / Naphthalene sulfonic acid or derivatives / 2-naphthalene sulfonic acid or derivatives / Naphthalene sulfonamide / 2-naphthalene sulfonamide / Naphthalene / Benzonitrile / Alkyl aryl ether / Monocyclic benzene moiety / Dicarboxylic acid or derivatives
show 20 more
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Udp-n-acetylmuramoylalanine-d-glutamate ligase activity
Specific Function
Cell wall formation. Catalyzes the addition of glutamate to the nucleotide precursor UDP-N-acetylmuramoyl-L-alanine (UMA).
Gene Name
murD
Uniprot ID
P14900
Uniprot Name
UDP-N-acetylmuramoylalanine--D-glutamate ligase
Molecular Weight
46973.185 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 15:28 / Updated on June 04, 2019 06:52