NAV

{4-[(CARBOXYMETHOXY)CARBONYL]-3,3-DIOXIDO-1-OXONAPHTHO[1,2-D]ISOTHIAZOL-2(1H)-YL}ACETIC ACID

Identification

Generic Name
{4-[(CARBOXYMETHOXY)CARBONYL]-3,3-DIOXIDO-1-OXONAPHTHO[1,2-D]ISOTHIAZOL-2(1H)-YL}ACETIC ACID
DrugBank Accession Number
DB07999
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 393.325
Monoisotopic: 393.015451645
Chemical Formula
C16H11NO9S
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UAldose reductaseNot AvailableHumans
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 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 / Naphthothiazoles / Naphthalenecarboxylic acids / Alpha amino acids and derivatives / Tricarboxylic acids and derivatives / Benzothiazoles / Organosulfonic acids and derivatives / Carboxylic acid esters / Carboxylic acids / Azacyclic compounds
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Substituents
1,2-benzothiazole / 2-naphthalene sulfonamide / 2-naphthalene sulfonic acid or derivatives / 2-naphthalenecarboxylic acid / 2-naphthalenecarboxylic acid or derivatives / Alpha-amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Carbonyl group / Carboxylic acid
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
dicarboxylic acid, mixed diacylamine, naphthothiazole (CHEBI:43485)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
IXLBOIRSEDMRPI-UHFFFAOYSA-N
InChI
InChI=1S/C16H11NO9S/c18-11(19)6-17-15(22)13-9-4-2-1-3-8(9)5-10(14(13)27(17,24)25)16(23)26-7-12(20)21/h1-5H,6-7H2,(H,18,19)(H,20,21)
IUPAC Name
2-[2-(carboxymethyl)-1,3,3-trioxo-1H,2H-3lambda6-naphtho[1,2-d][1,2]thiazole-4-carbonyloxy]acetic acid
SMILES
OC(=O)COC(=O)C1=C2C(C(=O)N(CC(O)=O)S2(=O)=O)=C2C=CC=CC2=C1

References

General References
Not Available
PubChem Compound
11494891
PubChem Substance
99444470
ChemSpider
9669697
BindingDB
16242
ZINC
ZINC000011536145
PDBe Ligand
ITA
PDB Entries
2nvc

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 Solubility0.0925 mg/mLALOGPS
logP0.69ALOGPS
logP0.62Chemaxon
logS-3.6ALOGPS
pKa (Strongest Acidic)2.5Chemaxon
pKa (Strongest Basic)-7Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area155.35 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity87.94 m3·mol-1Chemaxon
Polarizability35.36 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9881
Blood Brain Barrier+0.7299
Caco-2 permeable-0.6654
P-glycoprotein substrateNon-substrate0.5566
P-glycoprotein inhibitor INon-inhibitor0.8096
P-glycoprotein inhibitor IINon-inhibitor0.8152
Renal organic cation transporterNon-inhibitor0.8843
CYP450 2C9 substrateNon-substrate0.563
CYP450 2D6 substrateNon-substrate0.8157
CYP450 3A4 substrateNon-substrate0.5794
CYP450 1A2 substrateNon-inhibitor0.7822
CYP450 2C9 inhibitorNon-inhibitor0.6472
CYP450 2D6 inhibitorNon-inhibitor0.8373
CYP450 2C19 inhibitorNon-inhibitor0.806
CYP450 3A4 inhibitorNon-inhibitor0.9017
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8194
Ames testNon AMES toxic0.5971
CarcinogenicityNon-carcinogens0.7409
BiodegradationNot ready biodegradable0.8967
Rat acute toxicity2.2723 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.996
hERG inhibition (predictor II)Non-inhibitor0.7874
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 GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-014i-1029000000-bbc25996e0c7e1b27f08
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0009000000-0a91731e32109fc7785f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0009000000-e522cafa1ca7ff6f85f7
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0009000000-246da7463161a2a6cf83
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0007-0019000000-dc35af0bcee0f9c9b981
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0090000000-d420d80f2e1a36b9786d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dl-5490000000-f0ab2f4749181aee59c7
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]-180.77528
predicted
DeepCCS 1.0 (2019)
[M+H]+183.13329
predicted
DeepCCS 1.0 (2019)
[M+Na]+190.74275
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Aldose reductase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Glyceraldehyde oxidoreductase activity
Specific Function
Catalyzes the NADPH-dependent reduction of a wide variety of carbonyl-containing compounds to their corresponding alcohols with a broad range of catalytic efficiencies.
Gene Name
AKR1B1
Uniprot ID
P15121
Uniprot Name
Aldose reductase
Molecular Weight
35853.125 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 21:27 / Updated at June 12, 2020 16:52