(S)-2-{Methyl-[2-(Naphthalene-2-Sulfonylamino)-5-(Naphthalene-2-Sulfonyloxy)-Benzoyl]-Amino}-Succinicacid

Identification

Generic Name
(S)-2-{Methyl-[2-(Naphthalene-2-Sulfonylamino)-5-(Naphthalene-2-Sulfonyloxy)-Benzoyl]-Amino}-Succinicacid
DrugBank Accession Number
DB01879
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 662.686
Monoisotopic: 662.102886442
Chemical Formula
C32H26N2O10S2
Synonyms
Not Available

Pharmacology

Indication

Not Available

Pharmacology
Reduce drug development failure rates
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UUDP-N-acetylglucosamine 1-carboxyvinyltransferaseNot AvailableEnterobacter cloacae subsp. cloacae (strain ATCC 13047 / DSM 30054 / NBRC 13535 / NCDC 279-56)
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
Adverseeffects
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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 aspartic acid and derivatives. These are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic 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
Aspartic acid and derivatives
Alternative Parents
2-naphthalene sulfonamides / 2-naphthalene sulfonates / 2-naphthalene sulfonic acids and derivatives / Hippuric acids / N-acyl-alpha amino acids / Sulfanilides / Arylsulfonic acids and derivatives / Phenoxy compounds / Benzoyl derivatives / Organosulfonic acid esters
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Substituents
2-naphthalene sulfonamide / 2-naphthalene sulfonate / 2-naphthalene sulfonic acid or derivatives / Aminosulfonyl compound / Aromatic homopolycyclic compound / Arylsulfonic acid or derivatives / Aspartic acid or derivatives / Benzamide / Benzenoid / Benzoic acid or derivatives
show 31 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
JOAALZBSMWLOPQ-LJAQVGFWSA-N
InChI
InChI=1S/C32H26N2O10S2/c1-34(29(32(38)39)19-30(35)36)31(37)27-18-24(44-46(42,43)26-14-11-21-7-3-5-9-23(21)17-26)12-15-28(27)33-45(40,41)25-13-10-20-6-2-4-8-22(20)16-25/h2-18,29,33H,19H2,1H3,(H,35,36)(H,38,39)/t29-/m0/s1
IUPAC Name
(2S)-2-{N-methyl-1-[2-(naphthalene-2-sulfonamido)-5-[(naphthalene-2-sulfonyl)oxy]phenyl]formamido}butanedioic acid
SMILES
[H][C@@](CC(O)=O)(N(C)C(=O)C1=C(NS(=O)(=O)C2=CC3=CC=CC=C3C=C2)C=CC(OS(=O)(=O)C2=CC3=CC=CC=C3C=C2)=C1)C(O)=O

References

General References
Not Available
PubChem Compound
656973
PubChem Substance
46504961
ChemSpider
571209
ZINC
ZINC000058661194
PDBe Ligand
TAV
PDB Entries
1ybg

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 Solubility0.000444 mg/mLALOGPS
logP3.6ALOGPS
logP4.36ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)2.38ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area184.45 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity166.16 m3·mol-1ChemAxon
Polarizability66.21 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8453
Blood Brain Barrier+0.5311
Caco-2 permeable-0.6597
P-glycoprotein substrateNon-substrate0.6877
P-glycoprotein inhibitor INon-inhibitor0.7617
P-glycoprotein inhibitor IINon-inhibitor0.6267
Renal organic cation transporterNon-inhibitor0.9097
CYP450 2C9 substrateNon-substrate0.5488
CYP450 2D6 substrateNon-substrate0.8204
CYP450 3A4 substrateNon-substrate0.528
CYP450 1A2 substrateNon-inhibitor0.6031
CYP450 2C9 inhibitorNon-inhibitor0.524
CYP450 2D6 inhibitorNon-inhibitor0.8966
CYP450 2C19 inhibitorNon-inhibitor0.5288
CYP450 3A4 inhibitorInhibitor0.5498
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6251
Ames testNon AMES toxic0.6134
CarcinogenicityCarcinogens 0.565
BiodegradationNot ready biodegradable0.9923
Rat acute toxicity2.3284 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9607
hERG inhibition (predictor II)Non-inhibitor0.7182
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

Targets

Drugtargets2
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Kind
Protein
Organism
Enterobacter cloacae subsp. cloacae (strain ATCC 13047 / DSM 30054 / NBRC 13535 / NCDC 279-56)
Pharmacological action
Unknown
General Function
Udp-n-acetylglucosamine 1-carboxyvinyltransferase activity
Specific Function
Cell wall formation. Adds enolpyruvyl to UDP-N-acetylglucosamine. Target for the antibiotic fosfomycin.
Gene Name
murA
Uniprot ID
P33038
Uniprot Name
UDP-N-acetylglucosamine 1-carboxyvinyltransferase
Molecular Weight
44776.16 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. [Article]
  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. [Article]

Drug created on June 13, 2005 13:24 / Updated on June 12, 2020 16:52