C188-9 - Moligand™, ≥98% , Inhibitor of signal transducer and activator of transcription 3, CAS No.432001-19-9, Inhibitor of signal transducer and activator of transcription 3

CAS: 432001-19-9 Cat. No.: C414081 Molecular Weight: 471.52 EC Number: 836-653-0

GRADE & PURITY Moligand™, ≥98%

Synonyms

GTPL12268 | N-(4-hydroxy-3-(2-hydroxynaphthalen-1-yl)naphthalen-1-yl)-4-methoxybenzenesulfonamide | EX-A1961 | C 188-9 | C75162 | BCP28881 | N-(1',2-dihydroxy-[1,2'-binaphthalen]-4'-yl)-4-methoxybenzenesulfonamide | UNII-KZ3DLD11RQ | NCGC00262829-02 | Ben

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Information

C188-9 (TTI 101) is a potent inhibitor ofSTAT3that binds to STAT3 with high affinity (KD=4.7±0.4 nM). C188-9 is well tolerated in mice, shows good oral bioavailability, and is concentrated in tumors.

Targets

STAT3 (Cell-free) 4.7 nM(Kd)

In vitro

C188-9 is a small-molecule inhibitor of Stat3 that targets the phosphotyrosyl peptide binding site within the Stat3 Src homology 2 (SH2) domain with Ki 136 nM. It does not inhibit upstream Jak or Src kinases.

In vivo

Treatment of nude mice bearing xenografts of UM-SCC-17B, a radioresistant HNSCC line, with C188-9, but not C188, prevented tumor xenograft growth. C188-9 was well tolerated in mice, showed good oral bioavailability, and was concentrated in tumors.

Cell Research(from reference)

Cell lines：HNSCC cell line, UM-SCC-17B 

Concentrations：0, 0.1, 0.3, 1, 3, 10, 30 μM 

Incubation Time：24 h 

Specifications

Synonyms

GTPL12268 | N-(4-hydroxy-3-(2-hydroxynaphthalen-1-yl)naphthalen-1-yl)-4-methoxybenzenesulfonamide | EX-A1961 | C 188-9 | C75162 | BCP28881 | N-(1', 2-dihydroxy-[1, 2'-binaphthalen]-4'-yl)-4-methoxybenzenesulfonamide | UNII-KZ3DLD11RQ | NCGC00262829-02 | Ben

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

C188-9 (TTI 101) is a potent inhibitor of STAT3 that binds to STAT3 with high affinity (KD=4.7±0.4 nM). C188-9 is well tolerated in mice, shows good oral bioavailability, and is concentrated in tumors.

Storage

Protected from light, Store at -20°C

Shipped In

Ice chest + Ice pads

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

Grade

Moligand™

Action Type

INHIBITOR

Mechanism of action

Inhibitor of signal transducer and activator of transcription 3

Purity

≥98%

Product Properties

• ALogP: 5.152
• hba_count: 3
• HBD Count: 3
• Rotatable Bond: 5

Names and Identifiers

• Pubchem Sid: 504760464
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504760464
• Canonical Smiles: COC1=CC=C(C=C1)S(=O)(=O)NC2=CC(=C(C3=CC=CC=C32)O)C4=C(C=CC5=CC=CC=C54)O
• IUPAC Name: N-[4-hydroxy-3-(2-hydroxynaphthalen-1-yl)naphthalen-1-yl]-4-methoxybenzenesulfonamide
• InChIKey: QDCJDYWGYVPBDO-UHFFFAOYSA-N
• INCHI: 1S/C27H21NO5S/c1-33-18-11-13-19(14-12-18)34(31,32)28-24-16-23(27(30)22-9-5-4-8-21(22)24)26-20-7-3-2-6-17(20)10-15-25(26)29/h2-16,28-30H,1H3
• Isomeric SMILES: COC1=CC=C(C=C1)S(=O)(=O)NC2=CC(=C(C3=CC=CC=C32)O)C4=C(C=CC5=CC=CC=C54)O
• Alternate CAS: 432001-19-9
• MeSH Entry Terms: C188-9 compound;N-(4-hydroxy-3-(2-hydroxynaphthalen-1-yl)naphthalen-1-yl)-4-methoxybenzenesulfonamide;STAT3 inhibitor TTI-101;TTI-101
• Molecular Weight: 471.52
• Reaxy-Rn: 23997464
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=23997464&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Naphthalenes
      • Subclass Naphthols and derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Naphthalenes
• Subclass: Naphthols and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Naphthols and derivatives
• Alternative Parents: Sulfanilides Benzenesulfonamides Benzenesulfonyl compounds Phenoxy compounds Methoxybenzenes Anisoles Alkyl aryl ethers 1-hydroxy-2-unsubstituted benzenoids Organosulfonamides Aminosulfonyl compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: 2-naphthol - 1-naphthol - Benzenesulfonamide - Sulfanilide - Benzenesulfonyl group - Phenoxy compound - Anisole - Methoxybenzene - Phenol ether - Alkyl aryl ether - 1-hydroxy-2-unsubstituted benzenoid - Monocyclic benzene moiety - Organosulfonic acid amide - Aminosulfonyl compound - Sulfonyl - Organosulfonic acid or derivatives - Organic sulfonic acid or derivatives - Ether - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Organosulfur compound - Organic oxygen compound - Organopnictogen compound - Aromatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position.
• 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)

STAT3 Tchem Signal transducer and activator of transcription 3 (0 Activities)

Discover Target: STAT3

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

STAT3 Tchem Signal transducer and activator of transcription 3 (3313 Activities)

Discover Target: STAT3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AGS (1999 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MCF7 (126967 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MKN-1 (175 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MKN-28 (466 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Kasumi 1 (420 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MDA-MB-231 (73002 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GDM-1 (82 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solubility (25°C) In vitro DMSO: 94 mg/mL (199.35 mM); Ethanol: 6 mg/mL (12.72 mM); Water: Insoluble
• Sensitivity: Light sensitive
• DMSO(mg / mL) Max Solubility: 94
• DMSO(mM) Max Solubility: 199.3552766
• Water(mg / mL) Max Solubility: ＜1
• Molecular Weight: 471.500 g/mol
• XLogP3: 5.800
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 471.114 Da
• Monoisotopic Mass: 471.114 Da
• Topological Polar Surface Area: 104.000 Ų
• Heavy Atom Count: 34
• Formal Charge: 0
• Complexity: 776.000
• 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