NAV

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

Identification

Generic Name
N-({6-[(4-CYANO-2-FLUOROBENZYL)OXY]NAPHTHALEN-2-YL}SULFONYL)-D-GLUTAMIC ACID
DrugBank Accession Number
DB08112
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 486.47
Monoisotopic: 486.089699867
Chemical Formula
C23H19FN2O7S
Synonyms
Not Available
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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 sulfonamides / 2-naphthalene sulfonic acids and derivatives / Benzonitriles / Alkyl aryl ethers / Fluorobenzenes / Organosulfonamides / Aryl fluorides / Dicarboxylic acids and derivatives / Aminosulfonyl compounds / Carboxylic acids
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Substituents
2-naphthalene sulfonamide / 2-naphthalene sulfonic acid or derivatives / Alkyl aryl ether / Aminosulfonyl compound / Aromatic homopolycyclic compound / Aryl fluoride / Aryl halide / Benzenoid / Benzonitrile / Carbonitrile
show 26 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
IRJUSGUHNFMVCK-OAQYLSRUSA-N
InChI
InChI=1S/C23H19FN2O7S/c24-20-9-14(12-25)1-2-17(20)13-33-18-5-3-16-11-19(6-4-15(16)10-18)34(31,32)26-21(23(29)30)7-8-22(27)28/h1-6,9-11,21,26H,7-8,13H2,(H,27,28)(H,29,30)/t21-/m1/s1
IUPAC Name
(2R)-2-{6-[(4-cyano-2-fluorophenyl)methoxy]naphthalene-2-sulfonamido}pentanedioic acid
SMILES
[H][C@](CCC(O)=O)(NS(=O)(=O)C1=CC2=C(C=C1)C=C(OCC1=C(F)C=C(C=C1)C#N)C=C2)C(O)=O

References

General References
Not Available
PubChem Compound
25058128
PubChem Substance
99444583
ChemSpider
24689802
BindingDB
26455
ChEMBL
CHEMBL457526
ZINC
ZINC000040848762
PDBe Ligand
LKM
PDB Entries
2vtd

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 Solubility0.00453 mg/mLALOGPS
logP1.71ALOGPS
logP3.05Chemaxon
logS-5ALOGPS
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
Refractivity117.95 m3·mol-1Chemaxon
Polarizability47.36 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9315
Blood Brain Barrier+0.5063
Caco-2 permeable-0.6478
P-glycoprotein substrateNon-substrate0.6044
P-glycoprotein inhibitor INon-inhibitor0.7417
P-glycoprotein inhibitor IINon-inhibitor0.931
Renal organic cation transporterNon-inhibitor0.8654
CYP450 2C9 substrateNon-substrate0.6982
CYP450 2D6 substrateNon-substrate0.8066
CYP450 3A4 substrateSubstrate0.539
CYP450 1A2 substrateInhibitor0.5717
CYP450 2C9 inhibitorNon-inhibitor0.5552
CYP450 2D6 inhibitorNon-inhibitor0.8694
CYP450 2C19 inhibitorNon-inhibitor0.5277
CYP450 3A4 inhibitorInhibitor0.615
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5435
Ames testNon AMES toxic0.624
CarcinogenicityNon-carcinogens0.8158
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.3902 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9221
hERG inhibition (predictor II)Non-inhibitor0.5444
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/MSsplash10-014u-0215900000-2ce246c0444dd913544c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0024900000-e61c2f9bb176b9d859c8
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004l-1293200000-153a8dba0178d2156353
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f6x-1918100000-79ed495e9ef8c5c8dcaa
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-2960000000-9efadd1d88a1a744f704
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0zfr-7968300000-056f553ac190b60b62ed
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]-195.10176
predicted
DeepCCS 1.0 (2019)
[M+H]+197.49733
predicted
DeepCCS 1.0 (2019)
[M+Na]+203.40987
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. UDP-N-acetylmuramoylalanine--D-glutamate ligase
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