SecinH3
Basic information
- CAS
853625-60-2- Standard SMILES
COc1nc(-c2ccc3c(c2)OCO3)n(-c2ccc(NC(=O)CSc3ccccc3)cc2)n1- InChIKey
QPGYAMIHXLCFTJ-UHFFFAOYSA-N- Molecular formula
- C24H20N4O4S
- Average molar mass
- 460.5 g/mol
- Monoisotopic mass
- 460.12052631
Overview
N-[4-[5-(1,3-benzodioxol-5-yl)-3-methoxy-1,2,4-triazol-1-yl]phenyl]-2-(phenylthio)acetamide is a member of triazoles.
Names & identifiers
- Preferred name
- SecinH3
- IUPAC
- N-[4-[5-(1,3-benzodioxol-5-yl)-3-methoxy-1,2,4-triazol-1-yl]phenyl]-2-phenylsulfanylacetamide
- English name
- N-[4-[5-(1,3-BENZODIOXOL-5-YL)-3-METHOXY-1H-1,2,4-TRIAZOL-1-YL]PHENYL]-2-(PHENYLTHIO)ACETAMIDE
- Molecular formula
- C24H20N4O4S
- Molecular weight
- 460.51
Names & synonyms
SecinH3853625-60-2DTXSID80359866RefChem:182138DTXCID00310919N-[4-[5-(1,3-Benzodioxol-5-yl)-3-methoxy-1H-1,2,4-triazol-1-yl]phenyl]-2-(phenylthio)acetamideSecin H3N-[4-[5-(1,3-benzodioxol-5-yl)-3-methoxy-1,2,4-triazol-1-yl]phenyl]-2-phenylsulfanylacetamideN-(4-(5-(benzo[d][1,3]dioxol-5-yl)-3-methoxy-1H-1,2,4-triazol-1-yl)phenyl)-2-(phenylthio)acetamideN-{4-[5-(2H-1,3-benzodioxol-5-yl)-3-methoxy-1H-1,2,4-triazol-1-yl]phenyl}-2-(phenylsulfanyl)acetamideMFCD10687099MLS001065919
Show more names
CS-2379N-(4-(5-(benzo[d][1SecinH3, 10 mM in DMSOSecinH3, Sec7-GEF inhibitor3]dioxol-5-yl)-3-methoxy-1H-14-triazol-1-yl)phenyl)-2-(phenylthio)acetamideAcetamide, N-[4-[5-(1,3-benzodioxol-5-yl)-3-methoxy-1H-1,2,4-triazol-1-yl]phenyl]-2-(phenylthio)-
orb1223028orb1300576SCHEMBL7899934CHEMBL1731533SCHEMBL29384341C24H20N4O4SCHEBI:92787QPGYAMIHXLCFTJ-UHFFFAOYSA-N
Properties
Computed structural properties
- XLogP
- 4.9
- Topological polar surface area
- 113 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 7
- Heavy atoms
- 33
- Formal charge
- 0
- Complexity
- 644
Physicochemical properties
- storage temp.
- 2 · Inert atmosphere,2-8°C
- solubility
- 30 mg/ml; · DMF: 30 mg/ml; DMF:PBS (pH 7.2)(1:3): 0.25 mg/ml; DMSO: 25 mg/ml; Ethanol: 0.3 mg/ml
- form
- White powder solid.
- color
- White to off-white
- InChI
- 1S/C24H20N4O4S/c1-30-24-26-23(16-7-12-20-21(13-16)32-15-31-20)28(27-24)18-10-8-17(9-11-18)25-22(29)14-33-19-5-3-2-4-6-19/h2-13H,14-15H2,1H3,(H,25,29)
- InChIKey
- QPGYAMIHXLCFTJ-UHFFFAOYSA-N
- SMILES
- S(CC(=O)Nc2ccc(cc2)[n]3nc(nc3c4cc5c(cc4)OCO5)OC)c1ccccc1
- UNSPSC Code
- 12352202 · 12352202
- NACRES
- 77 · NA.77
- WGK Germany
- 1 · WGK 1
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Regulatory InformationREACH registered substance: CS-8203 (EC: 418-180-8)
Safety data
- wgk
- WGK 1
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Applications
UsesSecinH3 is a Sec7 cytohesin inhibitor.
General DescriptionA cell-permeable triazolo compound that acts as a Sec7 domain-binding (Kd ≤250 nM for Sec7 from human cytohesins 1-3), selective antagonist against cytohesin family small GEFs (IC50 ≤5.6 μM in ARF1 GDP/GTP exchange assays using human cytohesin 3, as well as murine and Drosophila homologues). It inhibits large GEFs only at much higher concentrations (IC50 ≥65 μM in GDP/GTP exchange assays using hEFA6-S7 and yGea2-S7) and exhibits little activity against a panel of 10 commonly studied kinases or hSosII. Shown to effectively inhibit insulin signaling both in HepG2 cells in vitro and in Drosophila and mice in vivo.
Additional notes
DefinitionChEBI: N-[4-[5-(1,3-benzodioxol-5-yl)-3-methoxy-1,2,4-triazol-1-yl]phenyl]-2-(phenylthio)acetamide is a member of triazoles.
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