N-(6-Aminohexyl)-5-chloro-1-naphthalenesulfonamide Hydrochloride - ≥98%(HPLC) , CAS No.61714-27-0

CAS: 61714-27-0 Cat. No.: N136431 Molecular Weight: 377.33 Beilstein Registry Number: 6030170

GRADE & PURITY ≥98%(HPLC)

Synonyms

ALEXIDINE [MART.] | N-(6-aminohexyl)-5-chloronaphthalene-1-sulfonamide;hydrochloride | NCGC00178278-01 | W-7, Hydrochloride - CAS 61714-27-0 | SMR000326845 | C16092 | AKOS024457749 | N-(6-AMINOHEXYL)-5-CHLORO-1-NAPHTHALENESULPHONAMIDE HYDROCHLORIDE | SPEC

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

W-7 has been reported to be a calmodulin (CaM) antagonist that inhibits Ca2+/calmodulin-regulated enzyme activities. Injection of murine tails with W-7 has demonstrated this agents ability to decrease tolerance to antinociceptive effects, therefore, CaM and its dependent pathways have demonstrated the capacity to play a role in antinociceptive agent tolerance processes. This cell permeable compound has been found to inhibit proliferation of hamster ovary K1 cells. W-7 has also been noted to bind troponin C in the presence of Ca2+ and inhibit striated muscle contractions.
A calmodulin (CaM) antagonist and antiproliferative agent.

Application

N-(6-Aminohexyl)-5-chloro-1-naphthalenesulfonamide hydrochloride has been used to study its effect of on coated pit staining.

Specifications

Synonyms

ALEXIDINE [MART.] | N-(6-aminohexyl)-5-chloronaphthalene-1-sulfonamide;hydrochloride | NCGC00178278-01 | W-7, Hydrochloride - CAS 61714-27-0 | SMR000326845 | C16092 | AKOS024457749 | N-(6-AMINOHEXYL)-5-CHLORO-1-NAPHTHALENESULPHONAMIDE HYDROCHLORIDE | SPEC

Specifications & Purity

≥98%(HPLC)

Biochemical and Physiological Mechanisms

CaM and myosin light chain kinase inhibitor (IC 50 values are 28 and 51 μM for CaM-dependent PDE activity and myosin light chain kinase respectively). W-5 , W-12 and W-13 analog. Shows antiproliferative effects.

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%(HPLC)

Names and Identifiers

• Pubchem Sid: 504756967
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504756967
• Canonical Smiles: C1=CC2=C(C=CC=C2Cl)C(=C1)S(=O)(=O)NCCCCCCN.Cl
• IUPAC Name: N-(6-aminohexyl)-5-chloronaphthalene-1-sulfonamide;hydrochloride
• InChIKey: OMMOSRLIFSCDBL-UHFFFAOYSA-N
• INCHI: 1S/C16H21ClN2O2S.ClH/c17-15-9-5-8-14-13(15)7-6-10-16(14)22(20,21)19-12-4-2-1-3-11-18;/h5-10,19H,1-4,11-12,18H2;1H
• Isomeric SMILES: C1=CC2=C(C=CC=C2Cl)C(=C1)S(=O)(=O)NCCCCCCN.Cl
• WGK Germany: 3
• Molecular Weight: 377.33
• Beilstein: 6030170
• Reaxy-Rn: 6030174
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=6030174&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Naphthalenes
      • Subclass Naphthalene sulfonic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Naphthalenes
• Subclass: Naphthalene sulfonic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: 1-naphthalene sulfonic acids and derivatives
• Alternative Parents: 1-naphthalene sulfonamides Chloronaphthalenes Organosulfonamides Aryl chlorides Aminosulfonyl compounds Organopnictogen compounds Organochlorides Organic oxides Monoalkylamines Hydrochlorides Hydrocarbon derivatives
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: 1-naphthalene sulfonic acid or derivatives - Naphthalene sulfonamide - 1-naphthalene sulfonamide - Chloronaphthalene - Aryl chloride - Aryl halide - Organosulfonic acid amide - Organic sulfonic acid or derivatives - Organosulfonic acid or derivatives - Sulfonyl - Aminosulfonyl compound - Amine - Hydrochloride - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Primary amine - Organosulfur compound - Organonitrogen compound - Organochloride - Organohalogen compound - Primary aliphatic amine - Organic oxygen compound - Organic nitrogen compound - Aromatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as 1-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 1-position. Naphthalene is a bicyclic compound that is made up of two fused benzene ring.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

KCNH2 Tclin HERG (29587 Activities)

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THRB Tclin Thyroid hormone receptor beta-1 (7926 Activities)

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ALOX15B Tchem Arachidonate 15-lipoxygenase, type II (7244 Activities)

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GLP1R Tclin Glucagon-like peptide 1 receptor (111429 Activities)

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CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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TP53 Tchem Cellular tumor antigen p53 (48468 Activities)

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HepG2 (196354 Activities)

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APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)

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EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)

Discover Target: EHMT2

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

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LMNA Tbio Prelamin-A/C (36751 Activities)

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GMNN Tbio Geminin (128009 Activities)

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PMP22 Tbio Peripheral myelin protein 22 (699 Activities)

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

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MPHOSPH8 Tbio M-phase phosphoprotein 8 (656 Activities)

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SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

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ATXN2 Tbio Ataxin-2 (54410 Activities)

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USP1 Tchem Ubiquitin carboxyl-terminal hydrolase 1 (22556 Activities)

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IDH1 Tclin Isocitrate dehydrogenase [NADP] cytoplasmic (40980 Activities)

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MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)

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Associated Targets(non-human)

Plasmodium falciparum (966862 Activities)

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Npsr1 Neuropeptide S receptor (260 Activities)

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ffp 4'-phosphopantetheinyl transferase ffp (24982 Activities)

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FTL Ferritin light chain (43324 Activities)

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nfo Endonuclease 4 (425 Activities)

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Scn2a Sodium channel alpha subunits; brain (Types I, II, III) (344 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water (Partly miscible), methanol, 100% ethanol (10 mg/ml)(warm), DMSO (25 mg/ml), DMF, ethylene glycol, and 50% ethanol/water (20 mg/ml).
• Sensitivity: Heat Sensitive
• Melt Point(°C): 222 °C
• Molecular Weight: 377.300 g/mol
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 376.078 Da
• Monoisotopic Mass: 376.078 Da
• Topological Polar Surface Area: 80.600 Ų
• Heavy Atom Count: 23
• Formal Charge: 0
• Complexity: 424.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 2

XLogP3

References

1. Bin Zhang, Xueying Li, Xiuhong Li, Zhigang Lu, Xiaona Cai, Qing Ou Yang, Pengda Ma, Juane Dong.  (2020)  Lipopolysaccharide Enhances Tanshinone Biosynthesis via a Ca2+-Dependent Manner in Salvia miltiorrhiza Hairy Roots.  INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES,  21  (24): (9576).  [PMID:33339149] [10.3390/ijms21249576]