KG-501 (2-naphthol-AS-E-phosphate) - ≥98% , CAS No.18228-17-6

CAS: 18228-17-6 Cat. No.: K414004 Molecular Weight: 377.72

GRADE & PURITY ≥98%

Synonyms

C73512 | FT-0712758 | Naphtholas-ephosphate | KG-501 (2-naphthol-AS-E-phosphate) | [3-[(4-chlorophenyl)carbamoyl]naphthalen-2-yl] dihydrogen phosphate | (2z)-2-Indol-3-Ylidene-3h-1,3-Thiazole | UNII-H6R6B93QFC | AC-35586 | EINECS 242-106-1 | Naphthol AS-E

Storage

Protected from light,Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

Information

KG-501 (2-naphthol-AS-E-phosphate) KG-501 (2-naphthol-AS-E-phosphate) is a cAMP response element-binding protein (CREB) inhibitor that disrupts CREB-dependent transcription (Ki = 10 μM) and CREB:CBP interaction (Ki = 50 μM). It also disrupts phospho (Ser-133) CREB binding to KIX with a Ki of ≈90 μM, using concentrations of CREB that were within the linear range of the binding assay.

Targets

CREB

In vitro

KG-501 inhibits induction of cAMP-responsive genes, at least in part, by blocking the CREB:CBP interaction. The inhibition of the CREB pathway using KG-501, induces an inhibition of neurite outgrowth and synaptogenesis, as well as a decrease of MAP2+ neuronal cells.

In vivo

KG-501 inhibits CREB, CCL2 expression and ERK phosphorylation, also significantly lowers the cAMP level. CREB might contribute to the neuroprotection opposed neuroinflammation through cAMP/ERK adjustment pathway. KG-501 significantly promots the neurological outcomes of AOM-treated mice, reduces phosphorylation of ERK and the concentration of cAMP in cortex.

Cell Research(from reference)

Cell lines：HEK293T cells 

Concentrations：5, 10, 25 μM 

Incubation Time：20 min 

Specifications

Synonyms

C73512 | FT-0712758 | Naphtholas-ephosphate | KG-501 (2-naphthol-AS-E-phosphate) | [3-[(4-chlorophenyl)carbamoyl]naphthalen-2-yl] dihydrogen phosphate | (2z)-2-Indol-3-Ylidene-3h-1, 3-Thiazole | UNII-H6R6B93QFC | AC-35586 | EINECS 242-106-1 | Naphthol AS-E

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

KG-501 (2-naphthol-AS-E-phosphate) is a cAMP response element-binding protein (CREB) inhibitor that disrupts CREB-dependent transcription (Ki = 10 μM) and CREB:CBP interaction (Ki = 50 μM). It also disrupts phospho (Ser-133) CREB binding to KIX with a Ki

Storage

Protected from light, Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

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

Purity

≥98%

Product Properties

• ALogP: 3.691
• hba_count: 2
• HBD Count: 1
• Rotatable Bond: 4

Names and Identifiers

• Pubchem Sid: 504755888
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504755888
• Canonical Smiles: C1=CC=C2C=C(C(=CC2=C1)C(=O)NC3=CC=C(C=C3)Cl)OP(=O)(O)O
• IUPAC Name: [3-[(4-chlorophenyl)carbamoyl]naphthalen-2-yl] dihydrogen phosphate
• InChIKey: RQAQWBFHPMSXKR-UHFFFAOYSA-N
• INCHI: 1S/C17H13ClNO5P/c18-13-5-7-14(8-6-13)19-17(20)15-9-11-3-1-2-4-12(11)10-16(15)24-25(21,22)23/h1-10H,(H,19,20)(H2,21,22,23)
• Isomeric SMILES: C1=CC=C2C=C(C(=CC2=C1)C(=O)NC3=CC=C(C=C3)Cl)OP(=O)(O)O
• Molecular Weight: 377.72
• Reaxy-Rn: 6664478
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=6664478&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Naphthalenes
      • Subclass Naphthalenecarboxylic acids and derivatives
        • Level5 Naphthalenecarboxamides
          • Level6 Naphthalene-2-carboxanilides

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Naphthalenes
• Subclass: Naphthalenecarboxylic acids and derivatives
• Intermediate Tree Nodes: Naphthalenecarboxamides
• Direct Parent: Naphthalene-2-carboxanilides
• Alternative Parents: Aromatic anilides Aryl phosphomonoesters Chlorobenzenes Aryl chlorides Secondary carboxylic acid amides Organopnictogen compounds Organooxygen compounds Organonitrogen compounds Organochlorides Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: Naphthalene-2-carboxanilide - Aromatic anilide - Aryl phosphate - Aryl phosphomonoester - Chlorobenzene - Halobenzene - Aryl chloride - Aryl halide - Monocyclic benzene moiety - Phosphoric acid ester - Organic phosphoric acid derivative - Carboxamide group - Secondary carboxylic acid amide - Carboxylic acid derivative - Organic nitrogen compound - Organochloride - Organohalogen compound - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Aromatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as naphthalene-2-carboxanilides. These are naphthalene-2-carboxamides, where the carboxamide group is substituted with an aniline.
• 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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solubility (25°C) In vitro DMSO: 20 mg/mL (52.94 mM); Water: Insoluble; Ethanol: Insoluble
• Sensitivity: Sensitive to light；sensitive to humidity
• DMSO(mg / mL) Max Solubility: 20
• DMSO(mM) Max Solubility: 52.949274594938
• Water(mg / mL) Max Solubility: ＜1
• Molecular Weight: 377.700 g/mol
• XLogP3: 3.000
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 377.022 Da
• Monoisotopic Mass: 377.022 Da
• Topological Polar Surface Area: 95.900 Ų
• Heavy Atom Count: 25
• Formal Charge: 0
• Complexity: 519.000
• 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: 1