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

Identification

Generic Name
N-({6-[(4-CYANOBENZYL)OXY]NAPHTHALEN-2-YL}SULFONYL)-D-GLUTAMIC ACID
DrugBank Accession Number
DB08108
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 468.479
Monoisotopic: 468.099121694
Chemical Formula
C23H20N2O7S
Synonyms
Not Available

Pharmacology

Indication

Not Available

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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

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 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
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Substituents
2-naphthalene sulfonamide / 2-naphthalene sulfonic acid or derivatives / Alkyl aryl ether / Aminosulfonyl compound / Aromatic homopolycyclic compound / Benzenoid / Benzonitrile / Carbonitrile / Carbonyl group / Carboxylic acid
show 20 more
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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

References

General References
Not Available
PubChem Compound
24755471
PubChem Substance
99444579
ChemSpider
24690845
BindingDB
26453
ChEMBL
CHEMBL458966
ZINC
ZINC000016052548
PDBe Ligand
LK4
PDB Entries
2uup

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 Solubility0.00825 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/MSsplash10-0gi0-0419800000-ad7920e3985bf2fce3c2
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0gdi-0068900000-b6b2647547c7fc0d8a91
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0avi-3494200000-b8fe68113e97ee7936b0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0pb9-0269000000-65f285d9effbde514219
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ar0-3950000000-d035179a1704326e6d87
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0zfr-2279100000-da7989be729847523fc7
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]-190.08783
predicted
DeepCCS 1.0 (2019)
[M+H]+192.48338
predicted
DeepCCS 1.0 (2019)
[M+Na]+198.39592
predicted
DeepCCS 1.0 (2019)

Targets

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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. [Article]

Drug created at September 15, 2010 21:28 / Updated at June 12, 2020 16:52